Product Name
Diphenylsilane
Synonyms
Diphenylsilane, Silane, diphenyl-, 148482_ALDRICH, NSC33013, EINECS 212-271-4, NSC 33013, NSC168693, 775-12-2, 17950-94-6
IUPAC Name
di(phenyl)silicon
Molecular Weight
184.31 g/mol
Molecular Formula
C12H12Si
InChI Key
BPYFPNZHLXDIGA-UHFFFAOYSA-N
Boiling Point
97 °C(12 mmHg)
Appearance
Colorless to Light yellow clear liquid
Application
Diphenylsilane serves as a versatile reagent with a primary purpose centered on facilitating radical reactions for various chemical transformations At room temperature it efficiently reduces thiocarbonyl derivatives of secondary and primary alcohols via a radical chain process using triethylborane-air as an initiator enabling the deoxygenation of alcohols Additionally diphenylsilane is involved in the deamination of alcohols via isonitriles and dehalogenation of bromo- and iodo-compounds It further serves in the reduction of carboxylic acid derivatives such as transforming carboxylic esters into alcohols especially when catalyzed by rhodium complexes achieving yields up to 99% This reagent is also instrumental in sequential C-Si bond formations and is beneficial in the synthesis of silyl-substituted alkylidene tantalum complexes Moreover diphenylsilane participates in ionic reduction of enones to saturated ketones reductive cyclization of unsaturated ketones and asymmetric reduction of methyl ketones as well as other ketones It effectively reduces esters to alcohols with zinc hydride or rhodium catalysis thio esters to ethers and α-halo ketones in the presence of Mo(0) and is capable of reductively cleaving allyl acetates showcasing its broad utility in synthetic chemistry
Storage
Store under inert gas
Hazard Statements
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation °Ccurs: Get medical advice/ attention.
Safety Description
37/39-26
Stability
Stable at room temperature in closed containers under normal storage and handling conditions.