8
N H Si N H N Scavenging of Nucleophiles and Basic Reacvity with SiliaBond® Guanidine Applicaon Note : SiliaBond Guanidine PN: R68230B Scavenger Name : Si-Guanidine, (E)-1,2-diisopropyl-3- propylguanidine, Dimethylpyrazole guanidino silica Chemical Formula : Si-C 10 H 21 N 3 Descripon : Organic Scavenger for Nucleophiles & Strong Base Parcle Size*: 40 - 63 µm Pore Diameter*: 60 Å Surface Area : 480 - 550 m 2 /g Pore Volume : 0.70 - 0.85 g/mL Molecular Loading : ≥ 0.80 mmol/g Typical Tap Density: 732 g/L Appearance : Light yellow Solvent Compability : All solvents, organic and aqueous Prolonged Storage : Keep dry under argon Shelf-Life : 1 year Abstract Effecvely eliminates organic acids and may be used as a strong base SiliaBond Guanidine is a silica-supported diisopropylguanidine ligand. It is a very powerful scavenger for the chelang of organic acids in general, especially boronic acids and phenolic acids. It may also be used as a very strong base. It is sufficiently basic to deprotonate moderately acidic hydrogens, as in the alkylaon of amines and phenols (Williamson ether synthesis) and the esterificaon of carboxylic acids using alkyl halides. *Other silica matrices available on request

Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

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Page 1: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

NH

Si NH

NScavenging of Nucleophiles and Basic Reactivity

with SiliaBond® Guanidine

Application Note :

SiliaBond GuanidinePN: R68230BScavenger Name : Si-Guanidine, (E)-1,2-diisopropyl-3-propylguanidine, Dimethylpyrazole guanidino silica

Chemical Formula : Si-C10H21N3

Description : Organic Scavenger for Nucleophiles & Strong Base

Particle Size*: 40 - 63 µm

Pore Diameter*: 60 Å

Surface Area : 480 - 550 m2/g

Pore Volume : 0.70 - 0.85 g/mL

Molecular Loading : ≥ 0.80 mmol/g

Typical Tap Density : 732 g/L

Appearance : Light yellow

Solvent Compatibility : All solvents, organic and aqueous

Prolonged Storage : Keep dry under argon

Shelf-Life : 1 year

AbstractEffectively eliminates organic acids and may be used as a strong base

SiliaBond Guanidine is a silica-supported diisopropylguanidine ligand.

It is a very powerful scavenger for the chelating of organic acids in general, especially boronic acids and phenolic acids.

It may also be used as a very strong base. It is sufficiently basic to deprotonate moderately acidic hydrogens, as in the alkylation of amines and phenols (Williamson ether synthesis) and the esterification of carboxylic acids using alkyl halides.

*Other silica matrices available on request

Page 2: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

Analyte

Impurities

Conditioning Loading Washing Step 1 Washing Step 2 Elution

SiliCycle Application Noteswww.SiliCycle.com | [email protected]

Description • Scavengers are our class of functionalized silica that exhibit

ability to bond (that is, to “scavenge”) various metal compounds or organic molecules dissolved in solution.

• Recently, the need to carry out more challenging coupling reactions has resulted in the development of more advanced catalysts. New options are hence necessary for the removal of organic fragments in fine and speciality chemistry.

• SiliaBond Guanidine is a silica-supported diisopropylguanidine ligand.

• SiliaBond Guanidine has a dual-purpose : it is a powerful scavenger for the chelating of acidic species in general-especially boronic acids and phenolic acids- from reaction mixtures, reaction intermediates or final APIs.

• It is also a very strong base, sufficiently basic to deprotonate moderately acidic hydrogens as in the alkylation of amines and phenols (Williamson ether synthesis), and the esterification of carboxylic acids using alkyl halides.

Typical Applications and Uses• New product that replaces SiliCycle SiliaBond TBD.

• New cost-effective option for the purification of high value products from organic mixtures.

• Si-Guanidine is able to stabilize intermediate anions via hydrogen-bonding or hydrophobic interactions.

• A very potent scavenger for acidic species in particular phenolic acids and boronic acids. The latter are used extensively in organic chemistry as chemical building blocks and intermediates, but not limited to this function. Their unique and versatile reactivity and stability have led to uses in numerous areas, including:

□ C-C bond formation □ Acid catalysis □ Asymmetric synthesis □ Carbohydrate analysis □ Metal-catalysis □ Molecular sensing □ Enzyme inhibitors □ Novel materials □ Chemical biology □ Medicinal chemistry

• Benefits of acidic phenols’ as antiseptics and disinfectants are unchallenged. However, their impact on human health and toxicology is controversial and the EPA (United State Environment Protection Agency) has reported them as “quite toxic to humans”. There is now a severe pressure on the chemical industry to strongly limit their concentration. Si-Guanidine are specially developped to achieve this goal.

• Can be used as a heterogeneous catalyst or reagent for carbon-carbon bond formation reactions, and other reactions known to be catalysed by guanidine moieties :

□ Williamson etherifications (ether formation from an organohalide and an alcohol)

□ Alkylations of activated methylene compounds □ Esterifications of carboxylic acids □ Dehalogenations of organic halides

□ High throughtput synthesis of aryl triflates and aryl nonaflates

□ Micheal additions (1,4-conjugate addition of resonance-stabilized carbanions)

□ Aldol condensations (synthesis of a conjugated enone by the reaction of an enolate with a carbonyl compound and subsequent dehydration).

□ Strecker reactions (preparation of α-aminonitriles)• SiliaBond Guanidine is an excellent strategy toward green

chemistry, as an alternative to homogeneous catalysts that are effective but raise serious environmental issues as well as contamination problems. Heterogeneous catalysis offers many advantages such as :

□ No reduction in activity compared to homogeneous equivalent

□ Ease of isolation □ Improved sustainability □ Reduced environmental impact □ No undesired catalyst-derived contamination □ Suitable for either batch or continuous flow processes □ No laborious purifications

• SiliaBond Guanine has shown exceptional performance notably for Williamson ether synthesis. The Williamson reaction is a general method useful for the synthesis of ethers, both asymmetric and symmetrical (scheme 1). The traditional method is treatment of an alkoxide (prepared from primary and secondary alcohols or phenols and a base) in the presence of a primary alkyl halide (secondary halide give low yields and tertiary halide yield the elimination product)

R’-X + R-OH R’-O-R + Base.HXSi-Guanidine

Scheme 1 : Williamson Ether Synthesis

• It can be very useful in parallel synthesis for libraries of asymmetric ethers from phenolic compounds.

• SiliaBond Guanidine can be used in a “catch and release” strategy, where the product can be released into a solution. In this purification technique, a molecule is temporarily bound, either ionically or covalently, to functionalized silica and subsequently released.

• Common reactions that may produce organic waste to be best scavenged by SiliaBond Guanidine are summarized in Table 1.

Page 3: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

RT: 20.06 - 42.65

22 24 26 28 30 32 34 36 38 40 42Time (min)

0

20

40

60

80

1000

20

40

60

80

1000

20

40

60

80

1000

20

40

60

80

100 39.05

36.5341.9035.7931.30 38.43

25.18 29.74 33.7122.64 29.4027.6526.1923.42 32.3520.5740.0237.6834.3721.04

30.54

30.16 39.0536.5829.94 35.84 41.9324.34 31.6720.61 38.3833.87

22.69 27.71 32.5525.22 29.4826.2440.1437.6921.93

36.5424.32 38.3820.60 35.8041.8931.32 38.98

29.8025.18 26.5322.66 33.7227.65 29.40

32.3623.72

40.1021.2836.90 37.16 40.0336.61 41.31

35.7835.53

35.2434.9821.38 21.48 34.6122.67 24.51 26.91 27.10 28.57 30.32 31.97 34.02

NL:3.40E7TIC F: MS 141205_02_no_silica_01

NL:4.96E7TIC F: MS 141205_04_si-tbd_01

NL:2.44E7TIC F: MS 141205_03_si-gua_01

NL:1.12E6TIC F: MS 141205_01_Blk_01

No silica gel

Si-TBD

Si-Guanidine

System blank

3

Reaction Organic impurity to be scavenged

Suzuki coupling

Boronic acidChan-Lam coupling

Liebeskind-Srogl coupling

Conjugate addition

Table 1 : Scavenging activity for metals by SiliaBond Guanidine

STRENGTH AS A CATALYSTComparison of SiliaBond Guanidine with Discontinued SiliaBond TBD for the Conversion of Amines Into AmidesTypically, a base is needed to catalyze and achieve complete conversion of primary and secondary amines to their corresponding amides. It was shown that SiliaBond TBD provided the clean amide, whereas attempts to use other bases such as hydroxides and tertiary amines produced a mixture of by-products, incomplete reactions or contaminated samples with primary amines.

As shown by the gas chromatography mass spectrometer (GC/MS) chromatograms of the derivatization of aliphatic amines using Si-TBD and Si-Guanidine. Si-Guanidine gave higher yields and less by-products compared to Si-TBD (scheme 2).

Scheme 2 : GC/MS chromatograms of the derivatization of aliphatic amines using no base, Si-TBD and Si-Guanidine. 25 aliphatic amines were screened, and compounds were identified by comparison with elution time and mass spectra of standards.

Our SiliaBond Guanidine is the first silica-supported Guanidine on the market, and it is produced in large scale at our state-of-the-art facility.

Page 4: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

SiliCycle Application Noteswww.SiliCycle.com | [email protected]

Typical Experimental Procedure in Batch Reactor Mode (Bulk) for the Scavenging of NucleophilesFor initial screening, start with 2 - 4 molar equivalents of SiliaBond in respect to the residual organic impurity concentration

1. Directly use the crude reaction mixture

2. Directly add the SiliaBond to your reaction mixture. 1

3. For initial tests, stir the solution for at least one hour at room temperature.

4.

Scavenging progress can be followed by normal analytical techniques. If scavenging seems incomplete or very slow, reaction time or temperature can be increased, or more equivalents of the scavenger can be added.

5. At the end of the scavenging, filter off the SiliaBond using a fritted funnel or filtration device.

6. Wash thoroughly with solvent to afford impurity-free solution. Concentrate under vaccum.

7. Direct scale-up is now possible. Otherwise, scavenging optimization can be examined

Typical Experimental Procedure for the Williamson Etherification

1.To a solution of acetonitrile (MeCN) (4 mL) and the alcohol was added 0.3 molar equivalent of SiliaBond Guanidine, in regard to the alcohol.

2. The solution was stirred for 1 h at room temperature (22°C).

3.0,8 molar equivalent of the alkyl halide in regard to the alcohol was then added to the reaction mixture, which was again stirred tfor 16h at 60°C.

4.

Catalysis progress can be followed by normal analytical techniques.

Conversion can be optimized trying longer reaction time ; more equivalents of the SiliaBond, increased temperature, etc.

5. At the end of the reaction, SiliaBond was filtered using a fritted funnel or filtration device and washed with acetonitrile (MeCN)

8. Direct scale-up is now possible. Otherwise, optimization options can be further be examined.

Please keep in mind that the above procedures are standard and introductory, and that optimization of conditions is key to optimal results.

This screening, as well as the reactions in our case studies were all successfully conducted using SiliCycle MiniBlock®, a unique and powerful tool designed for parallel synthesis, quick screenings and optimization studies.

1 Note : no pre - wetting of the SiliaBond is required.

Page 5: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

5

Ordering Information

SiliaBond Guanidine Bulk Ordering Information

Product Number Formats

R68230B 5 g, 10 g, 25 g, 50 g, 100 g, 250 g, 500 g, 1 kg, 5 kg, 10 kg, 25 kg, …up to multi - ton scale.

SiliaBond Guanidine Scavengers is Also Available in Fixed Bed Mode (SPE or Flash Cartridges)

SiliaSep™ Guanidine Flash Cartridges Ordering Information

PN Sorbent weight Qty / box PN Sorbent weight Qty / box

FLH-R68230B-ISO04 4 g 2 FLH-R68230B-IS120 120 g 1

FLH-R68230B-ISO12 12 g 1 FLH-R68230B-IS220 220 g 1

FLH-R68230B-ISO25 25 g 1 FLH-R68230B-IS330 330 g 1

FLH-R68230B-ISO40 40 g 1 FLH-R68230B-IS750 800 g 1

FLH-R68230B-ISO80 80 g 1 FLH-R68230B-I1500 1600 g 1

SiliaSep™ OT (Open Top) Guanidine Cartridges Ordering Information

PN Sorbent weight Volume Qty / box PN Sorbent weight Volume Qty / box

FLH-R68230B-15U 2 g 12 mL 20 FLH-R68230B-95K 25 g 150 mL 10

FLH-R68230B-70Y 10 g 70 mL 16 FLH-R68230B-95M 50 g 150 mL 10

FLH-R68230B-70i 15 g 70 mL 16 FLH-R68230B-95N 70 g 150 mL 10

FLH-R68230B-70Z 20 g 70 mL 16 FLH-R68230B-276F 100 g 276 mL 12

SiliaPrep™ Guanidine SPE Cartridges Ordering Information

PN Sorbent weight Volume Qty / box PN Sorbent weight Volume Qty / box

SPE-R68230B-03G 200 mg 3 mL 50 SPE-R68230B-06S 1 g 6 mL 50

SPE-R68230B-03P 500 mg 3 mL 50 SPE-R68230B-06U 2 g 6 mL 50

SPE-R68230B-06P 500 mg 6 mL 50 SPE-R68230B-20X 5 g 25 mL 20

New to this Technology ? Our Kits Have Specially Been Designed for New UsersIf you wish to try this technology for the first time, we strongly suggest to first try a Scavenger Kit for screening purposes, since most sample matrices have different functionalities and affinities.

NOVEL Scavengers Kit Ordering Information

Product Number List of Scavengers included in kit Formats

K34530B AMPA , DEAM , DMT : Guanidine and Thiol 5 g, 10 g, 25 g, 50 g, 100 g (custom - made format available)

Page 6: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

SiliCycle Application Noteswww.SiliCycle.com | [email protected]

Organic Scavengers Portfolio

SiliaBond Organic Scavengers Portfolio

SiliaBond / SiliaMetS Structure Nature Molecules RemovedSiliaBond Amine

PN : R52030B Loading : ≥ 1.20 mmol/g Endcapping : Yes

NH2Si

Scavenger for Electrophiles (Covalent Bonding) Acid Chlorides, Aldehydes, Anhydrides, Chloroformates, Isocyanates, Ketones & Sulfonyl Chlorides

Scavenger for Nucleophiles (Acids) (Ionic Bonding) Acids & Acidic Phenols

SiliaBond Carbonate

PN : R66030B Loading : ≥ 0.46 mmol/g Endcapping : Yes

N+Si(CO3

2-)0.5Scavenger for Nucleophiles (Acids) (Covalent & Ionic Bonding) Acids, Acidic Phenols & Boronic Acids

SiliaBond Carboxylic Acid

PN : R70030B Loading : ≥ 0.92 mmol/g Endcapping : Yes

OHSi

O

Scavenger for Electrophiles (Bases) (Covalent Bonding) Primary & Secondary Amines & Anilines

SiliaMetS DEAM

PN : R54430B Loading : ≥ 0.85 mmol/g Endcapping : Yes

Si

NOH

OH

Scavenger for Nucleophiles (Lewis Acids) (Covalent Bonding) Boronic Acids

SiliaMetS Diamine

PN : R49030B Loading : ≥ 1.28 mmol/g Endcapping : Yes

NH

SiNH2

Scavenger for Electrophiles (Covalent Bonding) Acid Chlorides, Aldehydes, Anhydrides, Chloroformates, Isocyanates, Ketones & Sulfonyl Chlorides

Scavenger for Nucleophiles (Acids) (Ionic Bonding) Acids & Acidic phenols

SiliaBond Diol

PN : R35030B Loading : ≥ 0.97 mmol/g Endcapping : No

OSi OH

OH

Scavenger for Nucleophiles (Lewis Acids) (Covalent Bonding)

Catch & ReleaseBoronic Acids

SiliaBond DMAP

PN : R75530B Loading : ≥ 0.53 mmol/g Endcapping : Yes

NSi

N

Scavenger for Electrophiles (Covalent Bonding) Acid Chlorides & Sulfonyl Chlorides

SiliaBond Guanidine

PN : R68230B Loading : ≥ 0.80 mmol/g Endcapping : Yes N

HSi N

H

NScavenger for Nucleophiles (Acids) (Covalent & Ionic Bonding) Acids, Acidic Phenols & Boronic Acids

SiliaBond Isocyanate

PN : R50030B Loading : ≥ 1.16 mmol/g Endcapping : Yes

NSi C O Scavenger for Nucleophiles (Covalent Bonding) Alcohols, Alkoxides, Amines, Anilines, Hydrazines, Organometallics, Thiols & Thiolates

SiliaBond Maleimide

PN : R71030B Loading : ≥ 0.64 mmol/g Endcapping : Yes

NSi

O

O

Scavenger for Nucleophiles (Covalent Bonding) Thiols & Thiolates

SiliaBond Piperazine

PN : R60030B Loading : ≥ 0.83 mmol/g Endcapping : Yes

NSi

NHScavenger for Electrophiles (Acids) (Covalent Bonding) Acids & Acidic Phenols

SiliaBond Propylsulfonic Acid

PN : R51230B Loading : ≥ 0.63 mmol/g Endcapping : Yes

SSiOH

O

O

Scavenger for Nucleophiles (Bases) (Covalent Bonding)

Catch & ReleaseAmines & Anilines

SiliaBond Tosic Acid

PN : R60530B Loading : ≥ 0.54 mmol/g Endcapping : Yes

SiS OH

O

O

SiliaBond TMA Acetate

PN : R66430B Loading : ≥ 0.71 mmol/g Endcapping : No

N+SiCH3C00-

Scavenger for Electrophiles (Acids) (Covalent Bonding)

Catch & ReleaseCarboxylic Acids

SiliaBond Tosyl Chloride

PN : R44030B Loading : ≥ 0.88 mmol/g Endcapping : Yes

SiS Cl

O

O

Scavenger for Nucleophiles (Covalent Bonding) Alcohols, Alkoxydes, Amines, Anilines, Hydrazines & Organometallics

SiliaMetS Triamine

PN : R48030B Loading : ≥ 1.11 mmol/g Endcapping : Yes

NH

SiHN

NH2

Scavenger for Electrophiles (Covalent Bonding) Acid Chlorides, Aldehydes, Anhydrides, Chloroformates, Isocyanates, Ketones & Sulfonyl Chlorides

Scavenger for Nucleophiles (Acids) (Ionic Bonding) Acids & Acidic Phenols

New Product

New Product

Potentially Genotoxic Impurities (PGI ) Scavenger  - Contact Us for More Information

Page 7: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

NewNew

NewNew

SiliCycle Inc. Worldwide Headquarters2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADATel. : 1 418 874.0054 Toll Free : 1 877 745.4292 (North America only) Fax : 1 418 874.0355 www.SiliCycle.com [email protected]

Search by metalScavenger

SiliaMetS Thiol (Si-Thiol) PN : R51030B

SiliaMetS DMT (Si-DMT) PN : R79030B

SiliaBond Amine (Si-WAX) PN : R52030B

SiliaMetS AMPA (Si-AMPA) PN : R85130B

SiliaMetS Cysteine (Si-Cys) PN : R80530B

SiliaMetS DEAM (Si-DEAM) PN : R54430B

SiliaMetS Diamine (Si-DIA) PN : R49030B

SiliaMetS Imidazole (Si-IMI) PN : R79230B

SiliaMetS TAAcOH (Si-TAAcOH) PN : R69030B

SiliaMetS TAAcONa (Si-TAAcONa) PN : R69230B

SiliaMetS Thiourea (Si-THU) PN : R69530B

SiliaMetS Triamine (Si-TRI) PN : R48030B

Structure SHSi

NH

Si N

NN

SH

SH

NH2SiNSi P

PHO

HO

OH

OH

O

ONH

SiONa

SH

O

Si

NOH

OH

NH

SiNH2 NSi

N NSiN

N

OH (ONa)

OH (ONa)

OH (ONa)OH (ONa)

O

O

O

O

NH

Si NH

S

NH

SiHN

NH2

Loading mmol/g ≥ 1.20 ≥ 0.50 ≥ 1.20 ≥ 0.80 ≥ 0.30 ≥ 0.85 ≥ 1.28 ≥ 0.96 ≥ 0.41 ≥ 0.41 ≥ 1.07 ≥ 1.11

Met

als t

o be

scav

enge

d

AgAlCaCdCeCoCrCsCuFeHgIrLaLiMgMnNiOsPbPd (II)Pd (0)PtRh (I)Rh (II)Rh (III)Ru (II)ScSnTiWZn

A newcomer ? Our kits have been designed for maximum flexibility

PNK30730B Universal

Metal Scavengers Kit

K34530B Novel

Scavengers Kit

K34630B Palladium

Metal Scavengers Kit

Com

posi

tion

Si-Cysteine Si-DMT Si-Imidazole Si-TAAcOH Si-TAAcONa Si-Thiol Si-Thiourea Si-Triamine

Si-AMPA Si-DEAM Si-DMT Si-Guanidine Si-Thiol

Si-DMT Si-Diamine Si-Thiol Si-Thiourea Si-Triamine

PNK34730B

Tin Metal Scavengers Kit

K35230B Electrophile

Scavengers Kit

K32630B Nucleophile

Scavengers Kit

Com

posi

tion

Si-Cysteine Si-DEAM Si-DMT Si-TAAcOH Si-TAAcONa Si-Thiourea Si-Thiol

Si-Amine Si-Carboxylic Acid Si-DMAP Si-Diamine Si-Piperazine Si-TMA Acetate Si-Tosyl Chloride Si-Triamine

Si-Carbonate Si-DEAM Si-Diol Si-Guanidine Si-Isocyanate Si-Maleimide Si-Propylsulfonic Acid Si-Tosic Acid

Remember  : All Kits are available in 5 g, 10 g, 25 g, 50 g, 100 g, and up to 1 kg formats Kits can easily be customized for any specific needs, contact us for more information.

SiliCycle offers an unparalleled range of Metal and Organic Scavengers, SiliaMetS®and SiliaBond®, to significantly facilitate any purification processes.

Typical procedure to be followed • Use 4-8 molar equivalent of Scavenger

• At room temperature up to 50°C

• Optimal pH range is from 2 to 10

• Typical solvents are THF, DMF, Ethyl Acetate, MeOH, PhMe, Ethers & Chlorinated solvents

• Stir one hour (1h) at moderate agitation (or more followed by ICP analysis)

TIP : Solution’s color might be a good indication of the scavenging progressDon’t forget to optimize via temperature, solvents, times, etc.

Could need some help ?Having a problem scavenging a product ?

Take advantage of SiliCycle’s expertise in scavenging. Our experienced R&D team can find the optimal conditions for you!

Our scavenging screening services are innovative as they provide an on-hand solution to quickly develop the most efficient metal or organic scavenging process for both time and cost savings.

Confidentiality is assured, as in most cases the solution involves working with API and other patented materials, and easy technology transfers are guaranteed.

Our team comprises passion driven scientists with various university levels in various specialities :

• Analytical, Inorganic, Organic & Organometallic Chemistry

• Biology & Biochemistry

• Catalysis

• Chemical Engineering

• Mesostructured Material

• Physical & Petrochemistry

22%

22% B.Sc.

Ph.D.

M.Sc.

R&DServices

Why are Potentially Genotoxic Impurities (PGI) Scavengers so important ?Genotoxic compounds induce genetic mutations and/or chromosomal rearrangements and can therefore act as carcinogenic compounds.

Whatever the nature of the impurity you might encounter, you can rely on our family of genotoxic Scavengers in order to eliminate tedious post-reaction purifications.

Search by chemicalScavenger

SiliaBond Amine (Si-WAX) PN : R52030B

SiliaBond Carbonate (Si-CO3) PN : R66030B

SiliaBond Carboxylic Acid (Si-WCX) PN : R70030B

SiliaMetS DEAM (Si-DEAM) PN : R54430B

SiliaMetS Diamine (Si-DIA) PN : R49030B

SiliaBond Diol (Si-Diol) PN : R35030B

SiliaBond DMAP (Si-DMAP) PN : R75530B

SiliaBond Guanidine (Si-GUA) PN : R68230B

SiliaBond Isocyanate (Si-ISO) PN : R50030B

SiliaBond Maleimide (Si-MAL) PN : R71030B

SiliaBond Piperazine (Si-PPZ) PN : R60030B

SiliaBond Propylsulfonic Acid (Si-SCX-2) PN : R51230B Tosic Acid (Si-SCX) PN : R60530B

SiliaBond TMA Acetate (Si-SAX2) PN : R66430B

SiliaBond Tosyl Chloride (Si-TsCl) PN : R44030B

SiliaMetS Triamine (Si-TRI) PN : R48030B

Structure NH2Si N+Si(CO3

2-)0.5 OHSi

OSi

NOH

OH

NH

SiNH2 OSi OH

OH NSi

N

NH

Si NH

N NSi C O NSi

O

O

NSi

NH

SSiOH

O

O

SiS OH

O

O

N+SiC3HC00-

SiS Cl

O

ONH

SiHN

NH2

Loading mmol/g ≥ 1.20 ≥ 0.46 ≥ 0.92 ≥ 0.85 ≥ 1.28 ≥ 0.97 ≥ 0.53 ≥ 0.80 ≥ 1.16 ≥ 0.64 ≥ 0.83 SCX-2 : ≥ 0.63 | SCX : ≥ 0.54 ≥ 0.71 ≥ 0.88 ≥ 1.11

Elec

trop

hile

s & N

ucle

ophi

les

to b

e sc

aven

ged

AcidAcid chlorideAcidic phenol

AlcoholAldehydeAlkoxideAmine

AnhydrideAniline

Boronic acid Carboxylic acid Chloroformate

HydrazineIsocyanate

KetoneOrganometallic

Sulfonyl chlorideThiol / Thiolate

ELECTROPHILE SCAVENGER : | NUCLEOPHILE SCAVENGER : | IONIC BONDING : | CATCH & RELEASE:

http ://www.silicycle.com/products/metal-scavengers

http ://www.silicycle.com/products/functionalized-silica-gels/siliabond-scavengers

Give our scavengers a try with SiliCycle MiniBlock® for mistake-proof parallel screeningsThe SiliCycle MiniBlock® platform offers full internal «flow-through» parallel processing of chemical reactions. The MiniBlock is unique in that reactions do not have to be removed from the apparatus for full processing but instead are run, partially purified and isolated in semi-crude form within the platform using a vertical flow design that is completely intuitive. Which is ideal for scavengers screening.

With our extensive experience in many niche areas, you are assured of a partner who is a leader in your domain.

BEST SCAVENGER : | GOOD SCAVENGER :

(COVALENT BONDING) (COVALENT BONDING)POS-001 v.1.2 02/15

© 2015, SiliCycle Inc.

Choosing your metal & organic scavenging solution

Why Silica outperforms Polymer-based resins ?• No Swelling

• Faster Kinetics

• Solvent Independent

• Easy to Use

• Mechanically Stable

• Thermally Stable

• Easily Scalable

• Flexible Formats

• Controlled Loading

SCX-2

SCX

7

All our Scavenging Solutions at a Quick GlanceWhich SiliaMetS Metal or SiliaBond Organic Scavenger will best suit your needs? Find out by ordering your FREE copy of our Scavenging Solution poster (PN : POS-001).

Call us to order your poster or for more information about our R&D Services : 1 877 745.4292 (North America only) +1 418 874.0054 (Worldwide)

R & D Services: Having a Problem with Your Scavenging or Metal Removal? We Can Help!Take advantage of SiliCycle’s expertise in scavenging. Our experienced R&D team can find the optimal conditions for you!

Our scavenging screening services are innovative as they provide an on - hand solution to quickly develop the most efficient metal or organic scavenging process for both time and cost savings.

Confidentiality is assured, as in most cases the solution involves working with API and other patented materials, and easy technology transfers are guaranteed.

Our team comprises passion driven scientists with various university levels in various specialities :

• Analytical, Inorganic, Organic & Organometallic Chemistry

• Biology & Biochemistry

• Catalysis

• Chemical Engineering

• Mesostructured Material

• Physical & Petrochemistry

With our extensive experience in many niche areas, you are assured of a partner who is a leader in your domain.

Page 8: Application Note - SiliCycle · Application Note : SiliaBond Guanidine PN: ... • New cost-effective option for the purification of high value ... of a primary alkyl halide

Custom R&D Services• Scavenging Screening• Catalysis Services• Organic Services• Chromatography, Purification &

Analytical Services• Material Science Services• Custom Packing Services

Heterogeneous Catalysis• Coupling (Suzuki,

Stille, Heck, Sonogashira, Kumada)

• Debenzylation• Hydrosilylation• Hydrogenation• Oxydation• Etc.

Scavenging Technology (Silica-Based)• Metal Scavengers• Electrophile Scavengers• Nucleophile Scavengers• Potential Genotoxic

Impurities (PGI)• Etc.

Sample Preparation• SPE Cartridges

and Well-Plates• Micro-SPE Tips• QuEChERS• Accesssories

(Vacuum Manifold, Collection Plates, …)

• Etc.

Organic Synthesis• Amide Coupling• Oxydation• Reductive Amination• Other Reagents Available

Analytical Chromatography• Spherical Silica Gels• HPLC and Guard Columns• HPLC Column Distributions

for Different Manufacturers• Etc.

Equipments• SiliCycle MiniBlock®

• TLC Scanner• Vacuum Manifold• Other Equipments

on Our Website

Chromatography• Irregular Silica Gels• Spherical Silica Gels for

Preparative Chromatography• Chromatographic Phases

(C18, NH2 …)

• Flash Cartridges and Accessories

• TLC Plates• Etc.

Consumables• Syringe Filters• Membrane Filters• Vials & Caps• Etc.

Other services available

WE PROVIDE SOLUTIONS TO THE GLOBAL CHEMICAL INDUSTRY.Founded in 1995, SiliCycle® Inc. is a worldwide leader in the development, the manufacturing and the commercialization of high value silica-based and specialty products for chromatography, analytical and organic chemistry. Our business extends to more than fifty countries and our customer portfolio includes companies in a wide range of markets.

At SiliCycle, we are at the forefront of the chromatography industry, owing to the extraordinary purity of our silica gels and polymeric sorbents, combined with our capacity to rapidly adapt our products to meet the specific requirements of scientists worldwide.

We lead the way in offering innovative first-rate UltraPure products. Our automated manufacturing processes are continuously optimized to ensure high purity and a low percentage of fine particles, thereby guaranteeing optimal performance. With our multi-ton manufacturing capacity, we are your partner of choice for all your analysis, metal removal, catalysis, synthesis, and purification requirements.

SiliCycle is also a leading service provider, offering turnkey solutions based on its expertise in organic chemistry, material science, analytical chemistry to name only a few. With state-of-the-art instrumentation in the areas of chromatography, spectroscopy, and manufacturing combined to an applications support laboratory, we are devoted to extend your R&D and make your project a success.

SiliCycle has several sales offices in many countries such as China, India, European Union (France & Germany) just to name a few. All products are available worldwide through SiliCycle or via distributors.

We are committed to providing you with the highest quality products and services in the industry

Information about SiliCycle is available at www.SiliCycle.com

SiliCycle Inc. Worldwide Headquarters2500, Parc-Technologique Blvd Quebec City (Quebec) G1P 4S6 CANADA Tel. : 1 418 874.0054 Toll Free : 1 877 745.4292 (North America only) Fax : 1 418 874.0355 www.SiliCycle.com [email protected]

SiliCycle China Chinese [email protected]

SiliCycle India Indian [email protected]

SiliCycle Europe European [email protected]

© 2015, SiliCycle Inc. Printed in Canada

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