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Merck

386529

Chlorotrimethylsilane

purified by redistillation, ≥99%

Synonym(s):

TMSCl, TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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About This Item

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

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Product Name

Chlorotrimethylsilane, purified by redistillation, ≥99%

InChI key

IJOOHPMOJXWVHK-UHFFFAOYSA-N

InChI

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

SMILES string

C[Si](C)(C)Cl

vapor density

3.7 (vs air)

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.)

Quality Level

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This Item
923608959592361
assay

≥99%

assay

≥99.0% (GC)

assay

≥99.0% (GC)

assay

≥98.0% (GC)

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

density

0.856 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

density

0.856 g/mL at 25 °C (lit.)

mp

−40 °C (lit.)

mp

−40 °C (lit.)

mp

−40 °C (lit.)

mp

−40 °C (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.387 (lit.)

refractive index

n20/D 1.387 (lit.)

form

liquid

form

liquid

form

liquid

form

liquid

Application

Chlorotrimethylsilane (TMSCl) can be used as:       
  • A reagent to protect alcohol and amine groups via the formation of trimethylsilyl ethers and trimethylsilyl amines.[1][2]      
  • A catalyst for the preparation of 1,3-diphenyl-2-propenone derivatives (chalcones) as antimicrobial agents.[2]        
  • A trapping agent for the anions generated during acyloin condensation reaction.[3]       
  • 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.[4]
  •  A catalyst in the transesterification of triglycerides with alcohols to form fatty acid alkyl esters.[5]        
  • A reagent along with lithium bromide for the conversion of alcohols to the corresponding bromides.[6]       
  • A reagent in Fischer glycosidation.[7]       
  • A source of acid catalyst in the reductive benzylation reaction using benzaldehyde and Et3SiH.[8]
  • 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.[9]

General description

Chlorotrimethylsilane is a chloroorganosilane compound mainly used for silylation reactions.[10]

signalword

Danger

Hazard Classifications

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

supp_hazards

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

-18.4 °F - closed cup

flash_point_c

-28 °C - closed cup

ppe

Faceshields, Gloves, Goggles


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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)
Houben-Weyl Methods of Molecular Transformations Vol. 4: Compounds of Groups 15 (As, Sb, Bi) and Silicon Compounds
Sci. Synth., 261-261 (2014)
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)
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)

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/418/501/product-dating-information-06-25-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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