| Identification | Back Directory | [Name]
BIS(TRIMETHYLSILYL)CHLOROMETHANE | [CAS]
5926-35-2 | [Synonyms]
BIS(TRIMETHYLSILYL)CHLOROMETHANE
Chloro-bis(trimethylsilyl)methane
BIS(TRIMETHYLSILYL)METHYL CHLORIDE
Chloro-bis-trimethylsilanyl-methane
Chlorobis(trimethylsilyl)methane 97%
(Chloromethylene)bis(trimethylsilane)
chloro(trimethylsilyl)methyl]-trimethylsilane
Silane, 1,1'-(chloromethylene)bis[1,1,1-trimethyl- | [Molecular Formula]
C7H19ClSi2 | [MDL Number]
MFCD00054866 | [MOL File]
5926-35-2.mol | [Molecular Weight]
194.85 |
| Chemical Properties | Back Directory | [Boiling point ]
57-60 °C/15 mmHg (lit.) | [density ]
0.892 g/mL at 25 °C (lit.) | [refractive index ]
n20/D 1.449(lit.) | [Fp ]
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 |
| Hazard Information | Back Directory | [Physical properties]
bp 57–60°C(15 mmHg); flash point 48 °C;
d 0.892 gmL?1 (25 °C). | [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.
| [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. | [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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