Skip to Content
Merck
All Photos(2)

Documents

205354

Sigma-Aldrich

(Chloromethyl)trimethylsilane

98%

Synonym(s):

(Trimethylsilyl)methyl chloride

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
(CH3)3SiCH2Cl
CAS Number:
Molecular Weight:
122.67
Beilstein:
906705
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

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.)

SMILES string

C[Si](C)(C)CCl

InChI

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

InChI key

OOCUOKHIVGWCTJ-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Articles

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service