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95541

Sigma-Aldrich

Chlorotrimethylsilane

produced by Wacker Chemie AG, Burghausen, Germany, ≥99.0% (GC)

Synonym(s):

Silane M3, TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

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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:
57653685
NACRES:
NA.22

grade

produced by Wacker Chemie AG, Burghausen, Germany

Quality Level

200

vapor density

3.7 (vs air)

vapor pressure

100 mmHg ( 25 °C)

Assay

≥99.0% (GC)

form

liquid

autoignition temp.

752 °F

expl. lim.

6.4 %

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 chloro-organosilane compound mainly used for silylation reactions.

Application

Possible usages of chlorotrimethylsilane:
  • Chloromethylation of polysulfones (PSUs).
  • Activation of lithium hydride to convert it into a hydride source for the reductive silylation of carbonyl compounds.
  • Chlorotrimethylsilane/lithium bromide forms an effective reagent for the conversion of alcohols to bromides.
  • Chlorotrimethylsilane is a non-toxic alternative to mercuric chloride in activating in samarium-promoted cyclopropanation of both allylic and α-allenic alcohols.

It is also used in Fisher glycosylation.

Other Notes

Silane M3
prices for bulk quantities on request

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A practical method for activation of commercial lithium hydride: reductive silylation of carbonyl compounds with lithium hydride and chlorotrimethylsilane.
Ohkuma T, et al.
The Journal of Organic Chemistry, 59(1), 217-221 (1994)
Modification of polysulfones by click chemistry: amphiphilic graft copolymers and their protein adsorption and cell adhesion properties.
Yilmaz G, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 49(1), 110-117 (2011)
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 4, 1060-1060 (2014)
Chlorotrimethylsilane as an Activating Reagent in the Samarium-Promoted Cyclopropanation of Allylic and ?-Allenic Alcohols.
Lautens M
The Journal of Organic Chemistry, 61(6), 2210-2214 (1996)
Chlorotrimethylsilane/lithium bromide and hexamethyldisilane/pyridinium bromide perbromide: effective and selective reagents for the conversion of alkyl (cycloalkyl and aralkyl) alcohols into bromides.
Olah GA, et al.
The Journal of Organic Chemistry, 45(9), 1638-1639 (1980)
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