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Chloromethyldimethylsilane

Catalog Number
ACM3121775
Product Name
Chloromethyldimethylsilane
Structure
CAS Number
3121-77-5
IUPAC Name
chloromethyl-ethyl-dimethylsilane
Synonyms
ethyl-chloromethyl-dimethyl-silane; Aethyl-chlormethyl-dimethyl-silan; (Chloromethyl)dimethylethylsilane; chloromethyl(ethyl)dimethylsilane;
Category
Halogen hydroxyl silane
Molecular Weight
108.64
Exact Mass
136.04800
Molecular Formula
C3H9ClSi
Boiling Point
122.5ºC at 760 mmHg
Flash Point
16ºC
Density
0.864 g/cm3
Purity
95%+
Appearance
Transparent liquid
SMILES
CC[Si](C)(C)CCl
InChIKey
BCZCLPJVTSRZLR-UHFFFAOYSA-N
Safty Description
7-16-29-33 23 24 25
Hazard Statements
F: Flammable;
WGK Germany
3
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1Asymmetric Synthesis of N-Boc-(R)-Silaproline via Rh-Catalyzed Intramolecular Hydrosilylation of Dehydroalanine and Continuous Flow N-Alkylation.

Chung JY1, Shevlin M1, Klapars A1, Journet M1.

Org Lett. 2016 Apr 15;18(8):1812-5. doi: 10.1021/acs.orglett.6b00548. Epub 2016 Mar 25.

An asymmetric synthesis of a silicon-containing proline surrogate, N-Boc-(R)-silaproline (1), is described. Starting from N-Boc-dehydroalanine ester, deprotonation, followed by N-alkylation with chloromethyldimethylsilane under flow conditions, afforded the N-alkylated product 8 in 91% yield. An unprecedented enantioselective (NBD)2RhBF4/Josiphos 404-1 catalyzed 5-endo-trig hydrosilylation afforded the silaproline ester in 85-90% yield and >95% ee. Subsequent saponification and salt formation upgraded 1 to >99% ee.

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Email:
Tel:1-201-478-8534
1-516-662-5404
Fax: 1-516-927-0118
Address: 2200 Smithtown Avenue, Room 1 Ronkonkoma, NY 11779-7329 USA