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386529

Sigma-Aldrich

Chlorotrimethylsilane

purified by redistillation, ≥99%

Synonym(s):

TMSCl, TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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25 ML
PLN 129.00
100 ML
PLN 431.00
1 L
PLN 1,830.00

PLN 129.00

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25 ML
PLN 129.00
100 ML
PLN 431.00
1 L
PLN 1,830.00

About This Item

Linear Formula:
(CH3)3SiCl
CAS Number:
75-77-4
Molecular Weight:
108.64
Beilstein:
1209232
EC Number:
200-900-5
MDL number:
MFCD00000502
UNSPSC Code:
12352302
PubChem Substance ID:
24864097
NACRES:
NA.22
form:
liquid
Assay:
≥99%

PLN 129.00

Please contact Customer Service for Availability
Request a Bulk Order

vapor density

3.7 (vs air)

Quality Level

200

vapor pressure

100 mmHg ( 25 °C)

Assay

≥99%

form

liquid

autoignition temp.

752 °F

purified by

glass distillation
redistillation

expl. lim.

6.4 %

impurities

<0.1% dichlorodimethylsilane

refractive index

n20/D 1.387 (lit.)

bp

57 °C (lit.)

mp

−40 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)Cl

InChI

1S/C3H9ClSi/c1-5(2,3)4/h1-3H3

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

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General description

Chlorotrimethylsilane is a chloroorganosilane compound mainly used for silylation reactions.[1]

Application

Chlorotrimethylsilane (TMSCl) can be used as:       
  • A reagent to protect alcohol and amine groups via the formation of trimethylsilyl ethers and trimethylsilyl amines.[2][3]      
  • A catalyst for the preparation of 1,3-diphenyl-2-propenone derivatives (chalcones) as antimicrobial agents.[3]        
  • A trapping agent for the anions generated during acyloin condensation reaction.[4]       
  • A better alternative catalyst to the toxic mercuric chloride for the activation of samarium (Sm) during the cyclopropanation of both allylic and α-allenic alcohols.[5]
  •  A catalyst in the transesterification of triglycerides with alcohols to form fatty acid alkyl esters.[6]        
  • A reagent along with lithium bromide for the conversion of alcohols to the corresponding bromides.[7]       
  • A reagent in Fischer glycosidation.[8]       
  • A source of acid catalyst in the reductive benzylation reaction using benzaldehyde and Et3SiH.[9]
  • A reagent to synthesize sodium trimethylsilanethiolate (Me3SiSNa) by reacting with sodium sulfide, which is an odorless alternative method of synthesizing Me3SiSNa from foul-smelling bis(trimethylsilyl)sulfide and sodium methoxide.[10]

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1A

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-18.4 °F - closed cup

Flash Point(C)

-28 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR0253
SHBS2463
SHBS2106
SHBS2462
SHBR0025

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Acyloin Condensation in which Chlorotrimethylsilane is used as a Trapping Agent: 1, 2-Bis (trimethylsilyloxy) cyclobutene and 2-Hydroxycyclobutanone: Trimethylsilane, 1-cyclobuten-1, 2-ylenedioxybis-and Cyclobutanone, 2-hydroxy-
Bloomfield JJ and Nelke JM
Organic Syntheses, 57, 1-1 (2003)
Jukun Xiong et al.
Environmental pollution (Barking, Essex : 1987), 219, 596-603 (2016-06-29)
To reveal the emission patterns of brominated flame retardants (BFRs) in the Beijiang River, South China, concentrations of polybrominated diphenyl ethers (PBDEs) and phenolic BFRs (2,4,6-tribromophenol (TBP), pentabromophenol (PeBP), tetrabromobisphenol A (TBBPA)), and bisphenol A (BPA) in water and sediments
Chlorotrimethylsilane as a mild and effective source of acid catalyst in reductive benzylation
Izumi M and Fukase K
Chemistry Letters (Jpn), 34(4), 594-595 (2005)
Guozhong Zhao et al.
Frontiers in microbiology, 11, 579808-579808 (2021-01-26)
Japanese soy sauce has become more acceptable by Chinese consumers due to its umami taste. However, the volatile flavor compounds and taste characters have not been fully clarified. This study aimed to explore the flavor characteristics of three kinds of
TMSCl as a mild and effective source of acidic catalysis in Fischer glycosidation and use of propargyl glycoside for anomeric protection
Izumi M, et al.
Bioscience, Biotechnology, and Biochemistry, 66(1), 211-214 (2002)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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