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386529

Sigma-Aldrich

Chlorotrimethylsilane

purified by redistillation, ≥99%

Synonyme(s) :

TMSCl, TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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About This Item

Formule linéaire :
(CH3)3SiCl
Numéro CAS:
75-77-4
Poids moléculaire :
108.64
Beilstein:
1209232
Numéro CE :
200-900-5
Numéro MDL:
MFCD00000502
Code UNSPSC :
12352302
ID de substance PubChem :
24864097
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Densité de vapeur

3.7 (vs air)

Niveau de qualité

200

Pression de vapeur

100 mmHg ( 25 °C)

Essai

≥99%

Forme

liquid

Température d'inflammation spontanée

752 °F

Produit purifié par

glass distillation
redistillation

Limite d'explosivité

6.4 %

Impuretés

<0.1% dichlorodimethylsilane

Indice de réfraction

n20/D 1.387 (lit.)

pb

57 °C (lit.)

Pf

−40 °C (lit.)

Densité

0.856 g/mL at 25 °C (lit.)

Chaîne SMILES 

C[Si](C)(C)Cl

InChI

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

Clé InChI

IJOOHPMOJXWVHK-UHFFFAOYSA-N

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Description générale

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]

Pictogrammes

FlameSkull and crossbonesCorrosion
GHS02,GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H225,H301 + H331,H312,H314

Classification des risques

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

Risques supp

EUH014

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

-18.4 °F - closed cup

Point d'éclair (°C)

-28 °C - closed cup

Équipement de protection individuelle

Faceshields, Gloves, Goggles

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Certificats d'analyse (COA)

Lot/Batch Number
SHBR0253
SHBS2463
SHBS2106
SHBS2462
SHBR0025

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Houben-Weyl Methods of Molecular Transformations Vol. 4: Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds
Sci. Synth., 261-261 (2014)
Chlorotrimethylsilane in combination with sodium sulfide as the equivalent of sodium trimethylsilanethiolate in organic reactions.
Shiao M
The Journal of Organic Chemistry, 58(17), 4742-4744 (1993)
Chlorotrimethylsilane catalyzed synthesis of 1, 3-diphenyl-2-propenones and their antimicrobial activities
Goswami P, et al.
Comptes Rendus Chimie, 16(5), 442-450 (2013)
Acyloin Condensation in which Chlorotrimethylsilane is used as a Trapping Agent: 1, 2?Bis (trimethylsilyloxy) cyclobutene and 2?Hydroxycyclobutanone.
Bloomfield J
Organic Syntheses, 1 (1977)
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
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Questions

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  1. 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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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    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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