85116-37-6

Basic information

• Product Name: (-)-Diisopinocampheyl chloroborane
• Synonyms: (-)-B-Chlorodiisopinocampheylborane (60% in Heptane, ca. 1.7mol/L);(-)-B-Chlorodiisopinocampheylborane, (-)-Ipc2BCl;(-)B-chloro-diisopinocamphenyl borane [(-)-DIP-Cl];()-DIP-Chloride solution;(-)-DiisopincaMpheyl chloroborane;(-)-B- DiisopinocaMphenylchloroborane;(-)-DiisopinocaMpheylchloroborane in hexanes;(-)-B-ChlorodiisopinocaMpheylborane, 60 wt.% solution in heptane, ca.1.7 M, J&KSeal
• CAS NO: 85116-37-6
• Molecular Formula: C₂₀H₃₄BCl
• Molecular Weight: 320.75
• Product Categories: Asymmetric Synthesis;B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry;Asymmetric Synthesis;Chiral Catalysts, Ligands, and Reagents
• Mol File: 85116-37-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 52-56 °C(lit.)
• Boiling Point: 66-69°C
• Flash Point: 82 °F
• Appearance: /
• Density: 0.954 g/mL at 25 °C
• Vapor Pressure: 2.63E-06mmHg at 25°C
• Refractive Index: -51 ° (C=neat)
• Storage Temp.: 2-8°C
• BRN: 5937756
• CAS DataBase Reference: (-)-Diisopinocampheyl chloroborane(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Diisopinocampheyl chloroborane(85116-37-6)
• EPA Substance Registry System: (-)-Diisopinocampheyl chloroborane(85116-37-6)

Safety Data

• Hazard Codes: C,F+,N,F
• Statements: 34-20/22-12-10-67-65-62-51/53-48/20-50/53-11-37
• Safety Statements: 9-16-29-33-36/37-61-62-45-36/37/39-26
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 3/8
• PackingGroup: II
• Hazardous Substances Data: 85116-37-6(Hazardous Substances Data)

Usage

Chemical Properties

solutio

InChI:InChI=1/C22H38BCl/c1-13-17-9-7-15(21(17,3)4)11-19(13)23(24)20-12-16-8-10-18(14(20)2)22(16,5)6/h13-20H,7-12H2,1-6H3/t13-,14-,15?,16?,17?,18?,19-,20-/m1/s1

Upstream product

• 21932-54-7 diisopinocampheylborane 
• 7647-01-0 hydrogenchloride 
• 80-56-8 Pinene 
• 7785-70-8 (+)-α-pinene 

Downstream Products

• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 185409-83-0 1,13-dibenzyloxy-3,11-di(triethylsilyloxy)-5-tert-butyldimethylsilyloxy-9-hydroxy-tridecan-7-one 
• 185409-71-6 (4S,6S)-8-benzyloxy-4-hydroxy-6-(triethylsiloxy)-2-octanone 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 102692-77-3 B-cinnamyldiisopinocampheylborane 
• 872047-98-8 2,3-diphenylpent-4-en-2-ol 
• 106356-53-0 B-allyldiisopinocampheylborane 
• 931-13-5 (1R,2R)-2-chlorocyclohexanol 
• 127913-43-3 (1R,2R)-(-)-2-chlorocyclo-4-hexen-1-ol 
• 172732-43-3 1-(t-butoxycarbonyl)-4-{3-bromo-4-chloro-5-[1-(S)-hydroxypropyl]}phenylpiperazine 
• 185409-77-2 C₄₇H₈₃BO₄Si₂ 
• 178435-67-1 (1S,2R,3R,6R,8R)-2,9,9-Trimethyl-3-((E)-styryl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.0^2,6]decane 
• 178435-68-2 (1S,2R,3S,6R,8R)-2,9,9-Trimethyl-3-(1-phenyl-vinyl)-5-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-4-oxa-5-bora-tricyclo[6.1.1.0^2,6]decane 
• 69460-11-3 (1R,2R,3R,5S)-(-)-Isopinocampheylamine 

Relevant articles and documents

Kinetic analysis of the asymmetric amplification exhibited by B-chlorodiisopinocampheylborane

A quantitative investigation was undertaken to determine experimentally the relative reaction rates of the heterochiral and homochiral species of B-chlorodiisopinocampheylborane (Dip-Cl), a reagent that exhibits asymmetric amplification. Using the method of flooding to reduce the apparent second-order reaction to pseudo-first-order conditions, rate constants of 3.8 (±1.0) × 10-4 and 1.7 (±0.8) × 10-5 M -1 s-1 (at -15°C) were found for the homochiral and heterochiral species, respectively. The resulting relative reaction rate, the value of g in Kagan and co-workers' model, was 0.04 ± 0.03. Additional experiments were conducted to confirm this value. The deterioration of the chiral purity of the final product was simulated throughout reaction conversion and compared with actual values. Through minimization, a relative reaction rate (g) of 0.08 ± 0.04 was determined. Finally, using 8-hydroxyquinoline complexation, the change in isomeric ratio of the Dip-Cl remaining in the reaction solution was measured. The relative reaction rate (g) required to consume the isomers at the observed rate was determined as 0.08 ± 0.01. Thus, three independent methods have been used to determine the relative reaction rate (g) of the heterochiral to homochiral species with good agreement to give an average value of 0.07 ± 0.03. Copyright

Total Synthesis and Antitrypanosomal Activity of Janadolide and Simplified Analogues

Janadolide is a cyclic depsipeptide natural product isolated from the marine cyanobacterium Okeania sp. Herein, we describe the total synthesis of janadolide, along with eight simplified analogues, via an efficient solid-phase strategy. Crucial to the synthesis of the natural product was the construction of a key polyketide fragment via an enantioselective (-)-B-chlorodiisopinocampheylborane-mediated reduction and a B-alkyl Suzuki reaction. Janadolide and the simplified analogues exhibited antitrypanosomal activity against pathogenic Trypanosoma brucei rhodesiense and Trypanosoma cruzi parasites.

A convenient and economical method for the preparation of DIP-chloride(TM) and its application in the asymmetric reduction of aralkyl ketones

A convenient and economical in situ preparation of DIP-chloride(TM) from NaBH4, BCl3 and α-pinene is described. Its application in the asymmetric reduction of representative aralkyl ketones is presented.