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92360 Sigma-Aldrich

Chlorotrimethylsilane

puriss., ≥99.0% (GC)

Synonym: TMCS, Trimethylchlorosilane, Trimethylsilyl chloride

  • CAS Number 75-77-4

  • Linear Formula (CH3)3SiCl

  • Molecular Weight 108.64

  •  Beilstein/REAXYS Number 1209232

  •  EC Number 200-900-5

  •  MDL number MFCD00000502

  •  PubChem Substance ID 329770119

  •  NACRES NA.22

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Properties

Related Categories Analytical Reagents, Analytical/Chromatography, Chemical Synthesis, Derivatization Reagents, Derivatization Reagents GC,
Quality Level   200
vapor density   3.7 (vs air)
vapor pressure   100 mmHg ( 25 °C)
InChI Key   IJOOHPMOJXWVHK-UHFFFAOYSA-N
grade   puriss.
assay   ≥99.0% (GC)
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.)

Description

General description

Chlorotrimethylsilane is a chloro-organosilane compound mainly used for silylation reactions.

Application

• Chlorotrimethylsilane can be a non-toxic alternative to mercuric chloride as activator in samarium-promoted cyclopropanation of both allylic and α-allenic alcohols.
• It can be used in combination with hexamethyldisilazane for the protection of alcohols by forming trimethylsilyl ethers via silylation.
• It is employed in chloromethylation of polysulfones (PSUs).
• It activates 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/sodium iodide in acetonitrile is a better alternative to iodotrimethylsilane for the cleavage of esters, lactones, carbamates, and ethers. It can also be used for the conversion of alcohols to iodides.
• Chlorotrimethylsilane along with silver or ammonium nitrate forms an efficient regioselective nitrating reagent for the ipso-nitration of arylboronic acids to form the corresponding nitroarenes.
• Chlorotrimethylsilane along with sodium nitrite or nitrate can be used for deoximation reactions.

Other Notes

Silylating agent

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
Reacts violently with water.
RIDADR 
UN1298 - class 3 - PG 2 - Trimethylchlorosilane
WGK Germany 
1
RTECS 
VV2710000
Flash Point(F) 
-4 °F
Flash Point(C) 
-20 °C
Protocols & Articles

Articles

Silylating Reagents for GC-MS Compatible Derivatives of NSAIDs

Human and veterinary pharmaceuticals are a group of “emerging” contaminants,1, 2 some of which are produced in increasingly large volumes every year. The amounts produced are reaching quantities simi...
Luis-Alberto Martin
AnalytiX Volume 10 Article 2
Keywords: Anti-inflammatory agents, Derivatizations, Environmental, Gas chromatography, Gas chromatography mass spectrometry, Mass spectrometry, Metabolites, Pesticides, Pharmaceutical, Silylations, Veterinary

Peer-Reviewed Papers
15

References

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