73624-47-2

Basic information

• Product Name: B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE
• Synonyms: R-ALPINE-BORANE(R);B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE;(R)-B-isopinocampheyl-9-borabicyclo[3.3.1]nonane;R-2,7,7-trimethylnorpinanborabicyclo(3.3.1)nonane;R-alpine-borane (0.5M soln. in thf);R-Alpine-Borane? (R)-2,6,6-trimethyl-4-(9-borabicyclo[3.3.1]nonan-9-yl)bicyclo[3.1.1]heptane;R-ALPINE-BORANE;R-ALPINE-BORANE 97%
• CAS NO: 73624-47-2
• Molecular Formula: C18H31B
• Molecular Weight: 258.25
• Product Categories: API intermediates
• Mol File: 73624-47-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: >55 °C(lit.)
• Flash Point: 1 °F
• Appearance: /
• Density: 0.896 g/mL at 25 °C
• Vapor Pressure: 0.00022mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE(CAS DataBase Reference)
• NIST Chemistry Reference: B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE(73624-47-2)
• EPA Substance Registry System: B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE(73624-47-2)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-19-22-36/37/38-17-40-36/37
• Safety Statements: 16-26-27-36/37/39-24-6-36/37
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 4.3
• PackingGroup: III
• Hazardous Substances Data: 73624-47-2(Hazardous Substances Data)

Usage

Description

B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE, also known as R-Alpine-Borane, is a chiral reducing agent synthesized from (+)-α-pinene via hydroboration. It is a valuable compound in the field of organic chemistry, particularly for the synthesis of various complex molecules with high stereoselectivity.

Uses

Used in Pharmaceutical Industry:
B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE is used as a chiral reducing agent for the stereoselective total synthesis of complex molecules. Its application in this industry is crucial for the development of new drugs with improved efficacy and selectivity.
1. Used in Stereoselective Total Synthesis:
B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE is used as a chiral reducing agent for the preparation of (R)-5-(Benzyloxy)pent-3-y-2-ol, an intermediate for the stereoselective total synthesis of (-)-stagonolide D. This application is important for the development of new pharmaceutical compounds with potential therapeutic properties.
2. Used in Enatioselective Synthesis:
B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE is used as a chiral reducing agent for the preparation of (R)-1-(p-Tolyl)-1-pentyn-3-ol, an intermediate for the enatioselective synthesis of (R)-incrustoporin. This application is significant for the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry due to their potential differences in biological activity.
3. Used in Synthesis of Amino Acid Derivatives:
B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONANE is used as a chiral reducing agent for the synthesis of N-(tert-Butyloxycarbonyl)-(4S)-[4-2H]-1-L-homoserine tert-butyl ester, an intermediate for synthesizing (4S)-[4-2H]-L-homoserine. This application is important for the development of novel amino acid derivatives with potential applications in the pharmaceutical industry.

InChI:InChI=1/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1

Upstream product

• 7785-70-8 (+)-α-pinene 
• 22560-16-3 lithium triethylborohydride 
• 10170-69-1 dimanganese decacarbonyl 

Relevant articles and documents

Hydroboration. 94. Rates of Hydroboration of 2-Organylapopinenes with 9-Borabicyclo[3.3.1]nonane, Providing B-(2-Organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes, Potentially Valuable for the Asymmetric Reduction of Prochiral Ketones

Five representative enantiomerically pure, hindered terpenes, derived from α-pinene, namely 2-organylapopinenes (2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr) have been treated with 9-borabicyclo[3.3.1]nonane (9-BBN) in a 1:1 molar ratio in THF at 24 °C and the rate of hydroboration followed. Increasing the bulk of the 2-R group from the 2-methyl of α-pinene (Ipc, 2-methylapopinene) to 2-ethyl- (Eap), to 2-propyl- (Prap), to 2-isobutyl- (i-Bap), to 2-phenyl- (Pap), and to 2-isopropyl- (i-Prap) significantly lowers the rate of hydroboration with 9-BBN. Thus, the rate of hydroboration of α-pinene with 9-BBN is faster than the rates for the 2-R-apopinenes studied. The sterically bulkier 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes reveal a significantly slower rate of hydroboration with 9-BBN. At an elevated temperature, 65 °C, the reaction of 9-BBN (1.0 equiv) with a slight excess of optically pure 2-isobutyl- and 2-phenylapopinenes (1.10-1.20 equiv), under neat conditions, is facilitated to provide the desired B-(2-organylapoisopinocampheyl)-9-borabicyclo[3.3.1]nonanes (2-organyl = isobutyl- and phenyl) in quantitative yield. Unfortunately, this synthesis failed for 2-isopropylapopinene. Fortunately, an indirect synthesis proved satisfactory. Treatment of enantiomerically pure (2-isopropylapoisopinocampheyl)borane, i-PrapBH2, conveniently synthesized from 2-isopropylapopinene, and 1,5-cyclooctadiene (1,5-COD), provided, after thermal isomerization, the desired 1:1 adduct [B-(2-Rap)-9-BBN; 2-Rap = 2-isopropylapoisopinyl skeleton] in quantitative yield. Consequently, five of the 2-R-apopinenes, R = Et, Pr, i-Bu, Ph, and i-Pr, have been successfully converted into the corresponding B-(2-Rap)-9-BBN derivatives.