136705-64-1

Basic information

• Product Name: (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE
• Synonyms: (2R,2'R,5R,5'R)-2,2'-5,5'-TETRAETHYL-1,1'-(O-PHENYLENE)DIPHOSPHOLANE;(-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE;(R,R)-ETHYL-DUPHOS;(R,R)-ET-DUPHOS;(-)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene, Kanata purity;(-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene(r,r)-et-duphos;(-)-1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene,98+%(R,R)-Et-DUPHOS;(R,R)-Ethyl-DUPHOS, (2R,2μR,5R,5μR)-2,2μ-5,5μ-Tetraethyl-1,1μ-(o-phenylene)diphospholane
• CAS NO: 136705-64-1
• Molecular Formula: C₂₂H₃₆P₂
• Molecular Weight: 362.47
• Product Categories: organophosphine ligand
• Mol File: 136705-64-1.mol

Chemical Properties

• Boiling Point: bp0.045 138-145°
• Flash Point: >230 °F
• Appearance: /
• Density: 1.01 g/mL at 25 °C
• Vapor Pressure: 1.67E-08mmHg at 25°C
• Refractive Index: n 20/D 1.6
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Air Sensitive
• Merck: 13,3499
• BRN: 4814174
• CAS DataBase Reference: (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE(136705-64-1)
• EPA Substance Registry System: (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE(136705-64-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 136705-64-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE is used as a catalyst for asymmetric hydrogenations, a crucial process in the synthesis of various pharmaceuticals, agrochemicals, and fine chemicals. Its chiral structure allows for the selective formation of desired enantiomers, which is essential for the development of biologically active compounds.
Used in Coordination Chemistry:
In the field of coordination chemistry, (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE serves as a highly efficient privileged ligand, particularly in the development of DuPhos and BPE ligands. These ligands play a vital role in enhancing the performance of transition metal catalysts, leading to improved reaction rates and selectivities in various chemical transformations.
Used in Pharmaceutical Industry:
(-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE is used as a key intermediate in the synthesis of novel pharmaceutical compounds. Its unique structural features enable the development of new drugs with improved potency, selectivity, and reduced side effects.
Used in Material Science:
In the field of material science, (-)-1,2-BIS((2R,5R)-2,5-DIETHYLPHOSPHOLANO)BENZENE can be utilized as a building block for the development of new materials with unique properties, such as advanced polymers, optoelectronic materials, and catalysts for various applications.

Reactions

Ligand used in rhodium catalyzed asymmetric hydrogenation of 2-methylenesuccinamic acid. Cobalt-catalyzed asymmetric hydrogenation.

InChI:InChI=1/C22H36P2/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4/h9-12,17-20H,5-8,13-16H2,1-4H3/t17-,18-,19-,20-/m1/s1

Upstream product

• 136705-66-3 (3S,6S)-octane-3,6-diol 
• 80510-04-9 1,2-bis(phosphino)benzene 
• 136705-67-4 (S,S)-octane-3,6-diol cyclic sulfate 

Relevant articles and documents

Preparation and use of C2-symmetric bis(phospholanes): Production of α-amino acid derivatives via highly enantioselective hydrogenation reactions

A new class of chiral C2-symmetric bis(phospholane) ligands has been prepared and used in rhodium-catalyzed asymmetric hydrogenation reactions. We describe a practical, one-pot procedure which utilizes enantiomerically pure 1,4-diol cyclic sulf