205354
(Chloromethyl)trimethylsilane
98%
Synonym(s):
(Trimethylsilyl)methyl chloride
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About This Item
Linear Formula:
(CH3)3SiCH2Cl
CAS Number:
Molecular Weight:
122.67
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
219-058-5
Beilstein/REAXYS Number:
906705
MDL number:
vapor pressure
~25 mmHg ( 20 °C)
Quality Level
assay
98%
form
liquid
refractive index
n20/D 1.418 (lit.)
bp
98-99 °C (lit.)
density
0.879 g/mL at 25 °C (lit.)
functional group
chloro
SMILES string
C[Si](C)(C)CCl
InChI
1S/C4H11ClSi/c1-6(2,3)4-5/h4H2,1-3H3
InChI key
OOCUOKHIVGWCTJ-UHFFFAOYSA-N
Application
(Chloromethyl)trimethylsilane can be treated with aldehydes or ketones in the presence of triphenylphosphine to synthesize terminal alkenes. It can also be used in the preparation of a reagent, trimethylsilylmethyl magnesium chloride, commonly used in Peterson methylenation.
Packaging
The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
24.8 °F - closed cup
flash_point_c
-4 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Articles
Review SET mechanism in photoredox catalysis for sustainable reactions and rearrangement of oxaziridines.
Methylenation of Perfluoroalkyl Ketones using a Peterson Olefination Approach.
Hamlin T A, et al.
The Journal of Organic Chemistry, 79(3), 1145-1155 (2014)
Direct synthesis of terminal olefins from ketones. Application of (chloromethyl) trimethylsilane to a Wittig reaction.
Sekiguchi A and Ando W
The Journal of Organic Chemistry, 44(3), 413-415 (1979)
Synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. III. Full report and a synthesis of the sex pheromone of gypsy moth.
Chan T H and Chang E
The Journal of Organic Chemistry, 39(22), 3264-3268 (1974)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 205354-100ML | 04061838767653 |
| 205354-4X25ML | 04061838767660 |