BIS(TRIMETHYLSILYL)CHLOROMETHANE
BIS(TRIMETHYLSILYL)CHLOROMETHANE Basic information
- Product Name:
- BIS(TRIMETHYLSILYL)CHLOROMETHANE
- Synonyms:
-
- BIS(TRIMETHYLSILYL)CHLOROMETHANE
- BIS(TRIMETHYLSILYL)METHYL CHLORIDE
- Chloro-bis(trimethylsilyl)methane
- Chlorobis(trimethylsilyl)methane 97%
- Chloro-bis-trimethylsilanyl-methane
- (Chloromethylene)bis(trimethylsilane)
- Silane, 1,1'-(chloromethylene)bis[1,1,1-trimethyl-
- chloro(trimethylsilyl)methyl]-trimethylsilane
- CAS:
- 5926-35-2
- MF:
- C7H19ClSi2
- MW:
- 194.85
- Mol File:
- 5926-35-2.mol
BIS(TRIMETHYLSILYL)CHLOROMETHANE Chemical Properties
- 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
- Hazard Codes
- Xi
- Risk Statements
- 10-36/37/38
- Safety Statements
- 26-36/37/39
- RIDADR
- UN 1993 3/PG 3
- WGK Germany
- 3
- F
- 21
- TSCA
- No
- HazardClass
- 3.2
- PackingGroup
- III
MSDS
- Language:English Provider:SigmaAldrich
BIS(TRIMETHYLSILYL)CHLOROMETHANE Usage And Synthesis
Physical properties
bp 57–60°C(15 mmHg); flash point 48 °C; d 0.892 gmL?1 (25 °C).
Uses
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.
Uses
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
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