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HomeProduct name listBIS(TRIMETHYLSILYL)CHLOROMETHANE

BIS(TRIMETHYLSILYL)CHLOROMETHANE

Synonym(s):Bis(trimethylsilyl)chloromethane

BIS(TRIMETHYLSILYL)CHLOROMETHANE Structural

What is BIS(TRIMETHYLSILYL)CHLOROMETHANE?

Physical properties

bp 57–60°C(15 mmHg); flash point 48 °C; d 0.892 gmL?1 (25 °C).

The Uses of BIS(TRIMETHYLSILYL)CHLOROMETHANE

Silane, 1,1-(Chloromethylene)bis[1,1,1]- trimethyl- can be used as versatile C1 building block; broad application in Peterson olefination reactions; Grignard reagent participates readily in Kumada cross-coupling reactions with aryl and vinyl halides; useful in synthesis of methylenephosphine analogs and as sterically demanding ligand for a number of main group and transition metal complexes.

The Uses of BIS(TRIMETHYLSILYL)CHLOROMETHANE

Chlorobis(trimethylsilyl)methane can be used as a reagent for the preparation of:

  • Para-bis(trimethylsilyl)ethylstyrene (PBTES) monomer, which is used to synthesize corresponding network polymer of styrene.
  • Bis(trimethylsilyl)methyl magnesium chloride (Grignard reagent), which is used in the synthesis of bis(trimethylsilyl) allyl compounds by reacting with alkenyl bromide via the Kumada coupling reaction.
  • N-[Bis(trimethylsilyl)methyl]heterocumulenes.

Preparation

a convenient one-pot procedure has been developed by Kemp and Cowley in which trimethylsilylchloride reacts with dichloromethane in the presence of nBuLi at ?110°Cto give bis(trimethylsilyl)dichloromethane.1 This intermediate is sequentially treated with nBuLi and ethanol to yield chlorobis(trimethylsilyl)methane. A number of other syntheses have been described

Properties of BIS(TRIMETHYLSILYL)CHLOROMETHANE

Boiling point: 57-60 °C/15 mmHg (lit.)
Density  0.892 g/mL at 25 °C (lit.)
refractive index  n20/D 1.449(lit.)
Flash point: 120 °F
solubility  soluble in common organic solvents (DMF, THF, Et2O, CH2Cl2).
Specific Gravity 0.892
Hydrolytic Sensitivity 4: no reaction with water under neutral conditions
BRN  1736681

Safety information for BIS(TRIMETHYLSILYL)CHLOROMETHANE

Signal word Warning
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H226:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for BIS(TRIMETHYLSILYL)CHLOROMETHANE

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