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205354

Sigma-Aldrich

(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
Beilstein:
906705
EC Number:
219-058-5
MDL number:
MFCD00000878
UNSPSC Code:
12352103
PubChem Substance ID:
24852326
NACRES:
NA.22

vapor pressure

~25 mmHg ( 20 °C)

Quality Level

100

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.)

SMILES string

C[Si](C)(C)CCl

InChI

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

InChI key

OOCUOKHIVGWCTJ-UHFFFAOYSA-N

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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

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

24.8 °F - closed cup

Flash Point(C)

-4 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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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)

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