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Merck
CN

205354

(Chloromethyl)trimethylsilane

98%

Synonym(s):

(Trimethylsilyl)methyl chloride

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About This Item

Linear Formula:
(CH3)3SiCH2Cl
CAS Number:
2344-80-1
Molecular Weight:
122.67
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
24852326
EC Number:
219-058-5
Beilstein/REAXYS Number:
906705
MDL number:
MFCD00000878

Key Documents

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InChI key

OOCUOKHIVGWCTJ-UHFFFAOYSA-N

InChI

1S/C4H11ClSi/c1-6(2,3)4-5/h4H2,1-3H3

SMILES string

C[Si](C)(C)CCl

vapor pressure

~25 mmHg ( 20 °C)

assay

98%

form

liquid

Quality Level

100

bp

98-99 °C (lit.)

density

0.879 g/mL at 25 °C (lit.)

functional group

chloro

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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

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBR9948
SHBR7477
27496KJV
35397LJ
39697LJ

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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)
Methylenation of Perfluoroalkyl Ketones using a Peterson Olefination Approach.
Hamlin T A, et al.
The Journal of Organic Chemistry, 79(3), 1145-1155 (2014)
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)

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