848618-13-3

Basic information

• Product Name: N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine
• Synonyms: (+)-9-(1S, 2S-Pseudoephedrinyl)-(10R)-(trimethylsilyl)-9-borabicyclo[3.3.2]decane;N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine
• CAS NO: 848618-13-3
• Molecular Formula: C₂₂H₃₈BNOSi
• Molecular Weight: 371.44
• Mol File: 848618-13-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 130-134 °C
• Boiling Point: 452.1°C at 760 mmHg
• Flash Point: 227.2°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 2.31E-08mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine(848618-13-3)
• EPA Substance Registry System: N,α-Dimethyl-β-[[(10R)-10-(trimethylsilyl)-9-borabicyclo[3.3.2]dec-9-yl]oxy]-(αS,βS)-benzeneethanamine(848618-13-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 848618-13-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H38BNOSi/c1-17(24-2)21(18-11-7-6-8-12-18)25-23-20-15-9-13-19(14-10-16-20)22(23)26(3,4)5/h6-8,11-12,17,19-22,24H,9-10,13-16H2,1-5H3/t17-,19?,20?,21+,22-/m0/s1

Upstream product

• 90-82-4 pseudoephedrine 
• 872359-67-6 (R)-9-((S)-1-Propyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane 
• 872359-75-6 (R)-9-((S)-1-Phenyl-2-trimethylsilanyl-buta-2,3-dienyloxy)-10-trimethylsilanyl-9-bora-bicyclo[3.3.2]decane 
• 872359-59-6 (R)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane 
• 848617-93-6 (+/-)-B-methoxy-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 
• 38050-71-4 9-methoxy-9-BBN 

Downstream Products

• 872420-37-6 (-)-(1S)-1-phenyl-2-(trimethylsilyl)-2,3-butadien-1-ol 
• 17199-29-0 (S)-Mandelic acid 
• 89682-11-1 C₁₁H₁₆O₃Si 
• 872359-79-0 (S)-2-Hydroxy-2-phenyl-1-trimethylsilanyl-ethanone 
• 872359-59-6 (R)-10-Trimethylsilanyl-9-(3-trimethylsilanyl-prop-2-ynyl)-9-bora-bicyclo[3.3.2]decane 
• 90-82-4 pseudoephedrine 

Relevant articles and documents

Asymmetric γ-methoxyallylation with the robust 10-tms-9- borabicyclo[3.3.2]decanes

The asymmetric γ-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-β-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obta

Nonracemic α-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) The asymmetric propargylboration of aldehydes at -78°C in 98% ee). The reagents 1 are easily prepared in both enantiomeric forms with a simple Grignard procedure and air-stable borinate complexes 2. The ozonolysis of 6 proceeds smoothly through an acylsilane intermediate to give a TMS ester, which is hydrolyzed to the α-hydroxy acid quantitatively with water.