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

Description

(-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is a chiral hydroboration reagent, which is an amine-borane complex. It is utilized in various chemical reactions due to its unique properties and ability to act as a polarity-reversal catalyst.

Uses

Used in Chemical Synthesis:
(-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is used as a chiral hydroboration reagent for the asymmetric synthesis of various organic compounds. Its application reason is to facilitate the formation of specific enantiomers, which are crucial in the development of pharmaceuticals and other chiral molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is used as a catalyst for the kinetic resolution of racemic esters and ketones. The application reason is to selectively convert one enantiomer of a racemic mixture into a product, leaving the other enantiomer unreacted. This process is essential for obtaining pure enantiomers, which are often required for the development of effective and safe drugs.
Used in Research and Development:
(-)-ISOPINOCAMPHENYLBORANE TMEDA COMPLEX is also used in research and development for the study of new reaction mechanisms and the development of novel synthetic methods. The application reason is to explore the potential of this complex in various chemical transformations and to expand its utility in the synthesis of complex molecules and materials.

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.