92360

Chlorotrimethylsilane

puriss., ≥99.0% (GC)

• Synonym(s): TMCS, Trimethylchlorosilane, Trimethylsilyl chloride
• 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: 12352101
• PubChem Substance ID: 329770119
• NACRES: NA.22

Properties

• vapor density: 3.7 (vs air)
• Quality Level: 200
• vapor pressure: 100 mmHg ( 25 °C)
• grade: puriss.
• 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: [H][C@@]12CC(C)(C)CC[C@]1(C)CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C; C[Si](C)(C)Cl
• InChI: 1S/C3H9ClSi/c1-5(2,3)4/h1-3H3
• InChI key: IJOOHPMOJXWVHK-UHFFFAOYSA-N

Description

General description

Chlorotrimethylsilane is a chloro-organosilane compound mainly used for silylation reactions.[1]

Application

• Chlorotrimethylsilane can be a non-toxic alternative to mercuric chloride as activator in samarium-promoted cyclopropanation of both allylic and α-allenic alcohols.[2]
• It can be used in combination with hexamethyldisilazane for the protection of alcohols by forming trimethylsilyl ethers via silylation.[3]
• It is employed in chloromethylation of polysulfones (PSUs).[4]
• It activates lithium hydride to convert it into a hydride source for the reductive silylation of carbonyl compounds.[5]
• Chlorotrimethylsilane/lithium bromide forms an effective reagent for the conversion of alcohols to bromides.[6]
• 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.[7]
• 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.[8]
• Chlorotrimethylsilane along with sodium nitrite or nitrate can be used for deoximation reactions.[9]

Other Notes

Silylating agent[10][11]

Safety Information

• Pictograms: GHS02,GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H225,H301 + H331,H312,H314
• Precautionary Statements: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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