86392-93-0

Basic information

• Product Name: (+/-)-(α-hydroxybenzyl)triethylsilane
• Synonyms: (+/-)-(α-hydroxybenzyl)triethylsilane
• CAS NO: 86392-93-0
• Molecular Weight: 222.403
• Mol File: 86392-93-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+/-)-(α-hydroxybenzyl)triethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-(α-hydroxybenzyl)triethylsilane(86392-93-0)
• EPA Substance Registry System: (+/-)-(α-hydroxybenzyl)triethylsilane(86392-93-0)

Safety Data

• Hazardous Substances Data: 86392-93-0(Hazardous Substances Data)

Upstream product

• 13959-92-7 benzyl triethylsilyl ether 
• 125950-75-6 ((triethylsilyl)oxy)(phenyl(CH))tributylstannane 
• 745783-97-5 triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 
• 100-52-7 benzaldehyde 
• 5425-44-5 2-Phenyl-[1,3]dithiane 
• 461051-82-1 2-phenyl-2-triethylsilyl-1,3-dithiane 
• 994-30-9 triethylsilyl chloride 
• 100-51-6 benzyl alcohol 
• 648428-83-5 (α,α-dibromobenzyl)triethylsilane 
• 100-44-7 benzyl chloride 
• 18412-74-3 benzyltriethylsilane 
• 63935-93-3 benzoyltriethylsilane 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 648428-52-8 (Triethylsilanyl-trimethylsilanyloxy-methyl)-benzene 

Downstream Products

• 86393-01-3 (-)-(α-chlorobenzyl)triethylsilane 
• 86392-90-7 (+)-(α-chlorobenzyl)triethylsilane 
• 86393-02-4 (-)-(α-hydroxybenzyl)triethylsilane 
• 86393-08-0 (+)-(α-hydroxybenzyl)triethylsilane 

Relevant articles and documents

Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles

A reductive cross-coupling reaction between aromatic aldehydes and arylnitriles using a copper catalyst and a silylboronate as a reductant is reported. This protocol represents an unprecedented approach to the chemoselective synthesis of α-hydroxy ketones by electrophile–electrophile cross-coupling.

A Lewis acid-promoted reduction of acylsilanes to α-hydroxysilanes by diethylzinc

We report here the first example of the reduction of acylsilanes to α-hydroxysilanes, in which diethylzinc was used as a highly reactive agent in the presence of Ti(OiPr)4 or other Lewis acids. The reduction typically proceeds to give synthetically useful α-hydroxysilanes in good yields.

Synthesis of Optically Pure Arylsilylcarbinols and Their Use as Chiral Auxiliaries in Oxacarbenium Ion Reactions

A family of arylsilylcarbinols was synthesized and investigated as chiral auxiliaries for oxacarbenium ion reactions. The optically pure arylsilylcarbinols were prepared using Noyori's transfer hydrogenation catalyst 11. The transfer hydrogenation shows very good enantioselectivities and turnover efficiency for the aryl silyl ketones and is the method of choice for preparing these optically pure alcohols. The diastereoselective addition of allyltrimethylsilane to an in situ generated oxacarbenium ion was explored using Marko's conditions. The selectivity for a representative aliphatic aldehyde was very good, but the selectivity was significantly reduced with unsaturated and aromatic aldehydes. The range of selectivities with different auxiliaries was narrow, and the most practical auxiliary is the phenylsilylcarbinol 2.