230299-05-5

Basic information

• Product Name: Bis[(-)pinanediolato]diboron
• Synonyms: BIS[(1S,2S,3R,5S-PINANEDOLATO)]DIBORON;Bis[(-)pinanediolato]diboron;Bis[(1R,2R,3S,5R)-pinanediolato]diboron;(+)-Bis(pinanediolato)diborane, (3aS,3'aS,4S,4'S,6S,6'S,7aR,7'aR)-(+)-Dodecahydro-3a,3'a,5,5,5',5'-hexamethyl-2,2'-bi-4,6-methano-1,3,2-benzodioxaborole;Bis[(-)pinediolato]diboron
• CAS NO: 230299-05-5
• Molecular Formula: C20H32B2O4
• Molecular Weight: 358.09
• Product Categories: CHIRAL COMPOUNDS
• Mol File: 230299-05-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 147-151 °C(lit.)
• Boiling Point: 360.606 °C at 760 mmHg
• Flash Point: 171.888 °C
• Appearance: /
• Density: 1.126 g/cm³
• Vapor Pressure: 4.56E-05mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Bis[(-)pinanediolato]diboron(CAS DataBase Reference)
• NIST Chemistry Reference: Bis[(-)pinanediolato]diboron(230299-05-5)
• EPA Substance Registry System: Bis[(-)pinanediolato]diboron(230299-05-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37-60
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 230299-05-5(Hazardous Substances Data)

Usage

General Description

Bis[(-)pinanediolato]diboron, also known as B2pin2, is a chemical compound with the molecular formula C20H30B2O4. It is a boron-containing compound that is commonly used in organic synthesis as a reagent for cross-coupling reactions. B2pin2 is a stable, air-stable, and moisture-stable solid that is soluble in common organic solvents. It is known for its ability to undergo facile reactions with various organic electrophiles, making it a valuable building block for the synthesis of a wide range of organic compounds. Additionally, B2pin2 has been shown to be a versatile precursor for the preparation of other useful boron-containing compounds, further expanding its potential applications in organic chemistry.

InChI:InChI=1/C20H32B2O4/c1-17(2)11-7-13(17)15-19(5,9-11)25-21(23-15)22-24-16-14-8-12(18(14,3)4)10-20(16,6)26-22/h11-16H,7-10H2,1-6H3/t11?,12?,13?,14?,15-,16-,19+,20+/m0/s1

Upstream product

• 13675-18-8 tetrahydroxydiboron 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 

Downstream Products

• 132488-71-2 (3aS,7aR)-3a,5,5-trimethyl-2-vinylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 1536530-76-3 C₂₁H₃₁BClNO₃S 
• 1536530-75-2 C₂₂H₃₄BNO₃S 
• 186906-12-7 C₁₈H₂₆BNO₂ 
• 1536530-77-4 C₂₂H₃₄BNO₃S 
• 1536530-73-0 C₂₁H₃₂BNO₃S 
• 1448440-98-9 (2R)-2-((3aS,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)pyrrolidine hydrochloride 

Relevant articles and documents

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.