136735-95-0

Basic information

• Product Name: (+)-1,2-BIS[(2S,5S)-2,5-DIMETHYLPHOSPHOLANO]BENZENE
• Synonyms: (+)-1,2-Bis((2S,5S)-2,5-diMethylphospholano)benzene (S,S)-Me-DUPHOS;(+)-1,2-Bis[(2S,5S)-2,5-diMethylphospholano]benzene kanata purity;(S,S)-ME-DUPHOS;(S,S)-METHYL-DUPHOS;(+)-1,2-BIS[(2S,5S)-2,5-DIMETHYLPHOSPHOLANO]BENZENE;(2S,2'S,5S,5'S)-2,2',5,5'-TETRAMETHYL-1,1'-(1,2-PHENYLENE)DIPHOSPHOLANE;(2S,2'S,5S,5'S)-2,2',5,5'-TETRAMETHYL-1,1'-(O-PHENYLENE)DIPHOSPHOLANE;(+)-1,2-Bis((2S,5S)-2,5-dimethylphospholano)benzene,98+%(S,S)-Me-DUPHOS
• CAS NO: 136735-95-0
• Molecular Formula: C₁₈H₂₈P₂
• Molecular Weight: 306.36
• Product Categories: organophosphine ligand
• Mol File: 136735-95-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67-76 °C
• Boiling Point: 415°C at 760 mmHg
• Flash Point: 216.3°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[(2S,5S)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1,2-BIS[(2S,5S)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(136735-95-0)
• EPA Substance Registry System: (+)-1,2-BIS[(2S,5S)-2,5-DIMETHYLPHOSPHOLANO]BENZENE(136735-95-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 136735-95-0(Hazardous Substances Data)

Usage

Reaction

The DUPHOS family of catalysts is highly efficient for the asymmetric hydrogenation of various substituted acetamidoacrylates 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. Palladium-catalyzed asymmetric phosphination. Palladium-catalyzed asymmetric hydrogenation of carbonyls. Palladium-catalyzed 1,4 arylation of α, β-unsaturated ketones. Asymmetric, Ir-catalyzed, [2+2+2] cycloaddition. Asymmertric palladium-catalyzed synthesis of 2-methyl-indolines via C–H activation. Copper-catalyzed monoborylation of 1,3-Dienes. Rhodium-catalyzed enantioselective transmetalation. CuH-catalyzed hydroamination of styrenes.

Uses

It is a DuPhos and BPE ligands which are highly efficient privileged ligands.

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-/m0/s1

Upstream product

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

Relevant articles and documents

General and selective copper-catalyzed reduction of tertiary and secondary phosphine oxides: Convenient synthesis of phosphines

Novel catalytic reductions of tertiary and secondary phosphine oxides to phosphines have been developed. Using tetramethyldisiloxane (TMDS) as a mild reducing agent in the presence of copper complexes, PO bonds are selectively reduced in the presence of other reducible functional groups (FGs) such as ketones, esters, and olefins. Based on this transformation, an efficient one pot reduction/phosphination domino sequence allows for the synthesis of a variety of functionalized aromatic and aliphatic phosphines in good yields.

Method for Producing Polyhydroxyalkanoates

The invention relates to a process for preparing polyhydroxyalkanoates by polymerization of lactones of the general formula I, where the substituents and the index n have the meanings given in the description, in the presence of at least one catalyst of the formula (II) LIMaXam, where the substituents and indices have the meanings given in the description. The invention further relates to poly-3-hydroxybutyrates which have a novel property profile and are obtainable for the first time by means of this process, and also biodegradable polyester mixtures based on these poly-3-hydroxybutyrates.

C2-symmetric bis(phospholanes) and their use in highly enantioselective hydrogenation reactions

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