67826-92-0

Basic information

• Product Name: (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX
• Synonyms: (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX;(-)-N,N'-BIS(MONOISOPINOCAMPHENYLBORANE)-N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE;N,N'-BIS(MONOISOPINOCAMPHEYL-BORANE)-N,N,N',N'-TETRAMETHYLETHYLENEDIAMINE;R-ALPINE-BORAMINE(TM);R-alpine-boramine;(R)-Alpine-BoramineTM, (-)-N,Nμ-Bis(monoisopinocampheylborane)-N,N,Nμ,Nμ-tetramethylethylenediamine
• CAS NO: 67826-92-0
• Molecular Formula: C26H54B2N2
• Molecular Weight: 416.34
• Mol File: 67826-92-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 139-141 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX(67826-92-0)
• EPA Substance Registry System: (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX(67826-92-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 15-36/38
• Safety Statements: 26-36-43
• RIDADR: 3132
• WGK Germany: 3
• HazardClass: 4.3
• PackingGroup: III
• Hazardous Substances Data: 67826-92-0(Hazardous Substances Data)

Usage

Uses

Chiral hydroboration reagent.This amine-borane complex has been used as a polarity-reversal catalyst for the kinetic resolution of racemic esters and ketones.

InChI:InChI=1/2C10H19B.C6H16N2/c2*1-6-8-4-7(5-9(6)11)10(8,2)3;1-7(2)5-6-8(3)4/h2*6-9H,4-5,11H2,1-3H3;5-6H2,1-4H3/t2*6-,7-,8+,9-;/m11./s1

Upstream product

• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 7785-26-4 (-)-α-pinene 
• 13292-87-0 dimethylsulfide borane complex 

Downstream Products

• 82248-44-0 ((1S,2S)-2-Phenyl-cyclopentyl)-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-borane 

Relevant articles and documents

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.