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900258

Sigma-Aldrich

Isopropoxy(phenyl)silane

Synonym(s):

RubenSilane

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About This Item

Empirical Formula (Hill Notation):
C9H14OSi
CAS Number:
910037-63-7
Molecular Weight:
166.29
UNSPSC Code:
12352005
NACRES:
NA.22

form

liquid

Quality Level

100

reaction suitability

reagent type: reductant
reaction type: Reductions

refractive index

n/D 1.4799

density

0.926 g/mL

storage temp.

2-8°C

General description

Isopropoxy(phenyl)silane is used as a stoichiometric reductant that allows for a significant decrease in catalyst loading, lower reaction temperatures, a wide range of functional group tolerance, and more diverse solvents in metal-catalyzed Mukaiyama hydrofunctionalizations.

Application

Isopropoxy(phenyl)silane can be used as a hydride source for alkene hydrofunctionalization reactions in the presence of metal catalysts, particularly under aprotic, nonalcoholic conditions. This reagent is considered as one of the most efficient stoichiometric reductants than phenylsilane because of its ability to exclude alcohol solvent from a series of catalytic reactions. When utilized, it allows the researcher to significantly decrease catalyst loadings, lower reaction temperatures, and employ more diverse solvents in iron- and manganese-catalyzed Mukaiyama hydrofunctionalizations.
It can be used as a reagent in:
  • The hydrogenation of olefins
  • Branch-selective olefin cross-coupling reactions
  • Markovnikov alkene hydration/amination reactions

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

900258-VAR:
900258-BULK:
900258-5G:
900258-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN5621
MKCH4553

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Carla Obradors et al.
Journal of the American Chemical Society, 138(14), 4962-4971 (2016-03-18)
We report the discovery of an outstanding reductant for metal-catalyzed radical hydrofunctionalization reactions. Observations of unexpected silane solvolysis distributions in the HAT-initiated hydrogenation of alkenes reveal that phenylsilane is not the kinetically preferred reductant in many of these transformations. Instead
Isopropoxy (phenyl) silane
Demoret RM and Shenvi RA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)

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