147253-67-6

Basic information

• Product Name: (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE
• Synonyms: (2R,2'R,5R,5'R)-2,2',5,5'-TETRAMETHYL-1,1'-(1,2-PHENYLENE)DIPHOSPHOLANE;(2R,2'R,5R,5'R)-2,2',5,5'-TETRAMETHYL-1,1'-(O-PHENYLENE)DIPHOSPHOLANE;(-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE;(-)-1,2-BIS((2R,5R)-2,5-DIMETHYLPHOSPHOLANO)BENZENE, KANATA PURITY;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(r,r)-me-duphos;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene,98+%(R,R)-Me-DUPHOS;(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene, (R,R)-Me-DUPHOS,98+%;()-1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene,(2R,2’R,5R,5′R)-2,2′,5,5′-Tetramethyl-1,1′-(o-phenylene)diphospholane, (R,R)-Me-DUPHOS, (R,R)-Methyl-DUPHOS
• CAS NO: 147253-67-6
• Molecular Formula: C₁₈H₂₈P₂
• Molecular Weight: 306.36
• Product Categories: organophosphine ligand
• Mol File: 147253-67-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 66-76 °C
• Boiling Point: 414.958 °C at 760 mmHg
• Flash Point: 216.272 °C
• Appearance: white/crystal
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 4810602
• CAS DataBase Reference: (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(147253-67-6)
• EPA Substance Registry System: (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(147253-67-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 147253-67-6(Hazardous Substances Data)

Usage

Description

(-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE is a complex organic compound with a unique molecular structure, characterized by its phospholano groups and benzene ring. It is known for its significant role as a building block in various chemical syntheses and for its potential applications in different industries.

Uses

Used in Organic Synthesis:
(-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows for the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE is used as a highly efficient privileged ligand. Its ability to form stable complexes with other molecules makes it a valuable tool in the development of new drugs and therapeutic agents.
Used in Agrochemicals:
(-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE is also utilized in the agrochemical industry, where it serves as a vital component in the development of new pesticides and other agricultural chemicals. Its unique properties contribute to the effectiveness and selectivity of these products.
Used in Dyestuff Industry:
In the dyestuff industry, (-)-1,2-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANO]BENZENE is employed as a crucial raw material for the production of various dyes and pigments. Its molecular structure allows for the creation of dyes with specific color properties and stability, making it an essential component in the dye manufacturing process.

Reactions

The DUPHOS family of catalysts is highly efficient for the asymmetric hydrogenation of various substituted cetamidoacrylates and enol acetates yielding products of high enantiomeric excesses. Efficient ligand for the asymmetric hydrogenation of imines, enamines, and enamides. Asymmetric hydrogenation of vinyl alcohols. Catalyst used for the asymmetric hydrogenation of enol phosphonates. Asymmetric hydrogenation of allylic alcohols. Ligand for the catalytic asymmetric [4+1] cycloaddition of vinylallenes with CO. Ligand for the Rh-catalyzed asymmetric enyne cycloisomerization. Catalytic enantioselective addition of dialkylzinc to N-Diphenylphosphinoylimines.

InChI:InChI=1/C18H28P2/c1-13-9-10-14(2)19(13)17-7-5-6-8-18(17)20-15(3)11-12-16(20)4/h5-8,13-16H,9-12H2,1-4H3/t13-,14-,15-,16-/m1/s1

Upstream product

• 80510-04-9 1,2-bis(phosphino)benzene 
• 136779-29-8 (4R,7R)-4,7-dimethyl-[1,3,2]dioxathiepane 2,2-dioxide 
• 5732-44-5 1,3,2-dioxathiepane 2,2-dioxide 
• 220224-82-8 (4S,7S)-4,7-dimethyl-1,3,2-dioxathiepane 2,2-dioxide 
• 1380079-15-1 (S,S)-Me-BozPHOS 
• 17299-07-9 (2R,5R)-2,5-hexanediol 

Relevant articles and documents

2,5-Dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene: First member of the hetero-DuPHOS family

The 2,5-dimethyl-3,4-bis[(2R,5R)-2,5-dimethylphospholano]thiophene (UlluPHOS), a new thiophene-based analogue of (R,R)-1,2-bis(phospholano)benzene (Me-DuPHOS), was synthesized, geometrically and electronically characterized, and employed as ligand of Rh and Ru in some standard hydrogenation reactions of prostereogenic functionalized carbon-carbon and carbon-oxygen double bonds. The synthesis of UlluPHOS is much easier than that provided for Me-DuPHOS. UlluPHOS and Me-DuPHOS display very similar geometries, while the electronic availability of the former is higher than that exhibited by the latter. The Rh and Ru complexes of UlluPHOS produced excellent enantiomeric excesses (98.9-99.5%) in the hydrogenation of N-acetyl-α-enamino acids and reaction rates higher than those found when employing the analogous complexes of Me-DuPHOS.

Highly chemoselective metal-free reduction of phosphine oxides to phosphines

Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Br?nsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)2MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.

Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands

(Chemical Equation Presented) The hemilabile ligand Me-DuPHOS(O) 2 has proven to be a successful ligand for the copper-catalyzed addition of diethylzinc to N-phosphinoylimines. The corresponding α-chiral amines were obtained in high yields (80-98%) and enantiomeric ratios (19.0:1 to 99.0:1 er). Furthermore, this Cu?2 catalytic system has been shown to be effective in the addition of diethylzinc to nitroalkenes and in the reduction of β,β-disubstituted vinyl phenyl sulfones. This paper describes a general structure/selectivity study in which the three ligand subunits (chiral phospholane-linker-labile coordinating group (Z)) are systematically modified and tested in the copper-catalyzed addition of diethylzinc to the N-phosphinoylimine 1 derived from benzaldehyde. This study led to the discovery of a new class of effective chiral ligands that combine a chiral phospholane unit and an achiral phosphine oxide.