88824-38-8

Basic information

• Product Name: C₂₄H₄₂BNO₂Si₂
• CAS NO: 88824-38-8
• Molecular Weight: 443.585
• Mol File: 88824-38-8.mol

Chemical Properties

• CAS DataBase Reference: C₂₄H₄₂BNO₂Si₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₄H₄₂BNO₂Si₂(88824-38-8)
• EPA Substance Registry System: C₂₄H₄₂BNO₂Si₂(88824-38-8)

Safety Data

• Hazardous Substances Data: 88824-38-8(Hazardous Substances Data)

Upstream product

• 88824-37-7 (R)-(1-chloro-2-phenylethyl)boronic acid (1R,2R,3S,5R)-(-)-2,3-pinanediol ester 
• 4039-32-1 lithium hexamethyldisilazane 

Downstream Products

• 88824-39-9 (-)-pinanediol (S)-1-acetamido-2-phenylethane-1-boronate 

Relevant articles and documents

Synthesis of 1-amino-2-phenylethane-1-boronic acid derivatives

The boron analogue of N-acetylphenylalanine, (R)-1-acetamido-2-phenylethane-1-boronic acid (5b), has been synthesized from (+)-pinanediol phenylmethane-1-boronate (1b), which was converted by (dichloromethyl)lithium to the (S)-1-chloro-2-phenylethane-1-boronate (2b), then with N-lithiohexamethyldisilazane to the silylated 1-amino-2-phenylethane-1-boronic ester 3b, which was desilylated and acetylated in situ to (+)-pinanediol (R)-1-acetamido-2-phenylethane-1-boronate (4b) and then cleaved to the free boronic acid 5b with boron trichloride. 1-Amino-2-phenylethane-1-boronic esters (6) were found to be isolable but unstable, deboronating to 2-phenylethylamine under the influence of heat or hydroxylic solvents. 1-Amino-2-phenylethane-1-boronic acid, though not isolable, partially survives for an hour in cold aqueous solution. Attempts to synthesize the stable α-acetamido boronic esters (4) directly by reaction of lithioacetamide with 1-halo-2-phenylethane-1-boronic esters (2) have resulted in a major proportion of O-alkylation to form imino esters. Pinacol 1-acetamidino-2-phenylethane-1-boronate (8) has been obtained from the α-iodo boronic ester 2d and acetamidine.