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911208

Sigma-Aldrich

1-Hydrosilatrane

≥95%

Synonym(s):

Hydrosilatrane, Silatrane

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About This Item

Empirical Formula (Hill Notation):
C6H13NO3Si
CAS Number:
283-60-3
Molecular Weight:
175.26
NACRES:
NA.22

Assay

≥95%

form

powder or crystals

reaction suitability

reagent type: reductant

mp

249-256 °C

storage temp.

−20°C

InChI

1S/C6H12NO3Si/c1-4-8-11-9-5-2-7(1)3-6-10-11/h1-6H2

InChI key

XBRVPWBNRAPVCC-UHFFFAOYSA-N

Application

1-Hydrosilatrane is an air- and moisture-stable hydride reducing reagent that exhibits high functional group compatibility. The Adler group has used 1-hydrosilatrane for the reduction of ketones and aldehydes as well as the direct reductive amination of ketones under mild conditions.

Other Notes

Chiral Bronsted Acid-Catalyzed Metal-Free Asymmetric Direct Reductive Amination Using 1-Hydrosilatrane

Silatrane as a Practical and Selective Reagent for the Reduction of Aryl Aldehydes to Benzylic Alcohols

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

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Vladislav Skrypai et al.
The Journal of organic chemistry, 84(9), 5021-5026 (2019-04-12)
The asymmetric direct reductive amination of prochiral ketones with aryl amines using 1-hydrosilatrane with a chiral Brønsted acid catalyst is reported. This is the first known example of chiral Brønsted acid-catalyzed asymmetric reductive amination using a silane as the hydride
1-Hydrosilatrane: A Locomotive for Efficient Ketone Reductions.
Varjosaari E S, et al.
European Journal of Organic Chemistry, 2017(2), 229-232 (2017)
Silatrane as a Practical and Selective Reagent for the Reduction of Aryl Aldehydes to Benzylic Alcohols.
Skrypai V, et al.
European Journal of Organic Chemistry, 2016(12), 2207-2211 (2016)

Articles

1-hydrosilatrane

As a versatile hydride reagent, 1-hydrosilatrane can be used in reduction reactions to synthesize alcohols, amines, their chiral counterparts, and esters from aldehydes/ketones.

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