80510-04-9

Basic information

• Product Name: 1,2-BIS(PHOSPHINO)BENZENE
• Synonyms: 1,2-PHENYLENEBISPHOSPHINE;1,2-BIS(PHOSPHINO)BENZENE;O-BIS(PHOSPHINO)BENZENE;Bisphosphinobenzenecolorlessliq;Bisphosphinobenzeneinhexane;1 2-PHENYLENEBISPHOSPHINE 98%;10wt%inhexane;1,2-Bis(phosphino)benzene,98+%
• CAS NO: 80510-04-9
• Molecular Formula: C₆H₈P₂
• Molecular Weight: 142.08
• Product Categories: Catalysis and Inorganic Chemistry;Phosphorus Compounds;Polydentate Phosphine Ligands;organophosphine ligand
• Mol File: 80510-04-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 53-55°C 0,25mm
• Flash Point: 102.1 °C
• Appearance: colorless/liquid
• Density: 1.101 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0455mmHg at 25°C
• Sensitive: air sensitive
• CAS DataBase Reference: 1,2-BIS(PHOSPHINO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(PHOSPHINO)BENZENE(80510-04-9)
• EPA Substance Registry System: 1,2-BIS(PHOSPHINO)BENZENE(80510-04-9)

Safety Data

• Hazard Codes: F
• Statements: 17-23/24/25-36/37/38
• Safety Statements: 7/8-26-36/37/39-43-27-16
• RIDADR: 2924
• Hazardous Substances Data: 80510-04-9(Hazardous Substances Data)

Usage

Chemical Properties

Liquid

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 1875, 1981 DOI: 10.1016/S0040-4039(01)90465-4

InChI:InChI=1/C6H8P2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2

Upstream product

• 615-42-9 1,2-Diiodobenzene 
• 615-41-8 2-iodochlorobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 15104-46-8 1,2-bis(dimethoxyphosphoryl)benzene 
• 82495-67-8 1,2-bis(dichlorophosphanyl)benzene 
• 71838-15-8 phenylene-1,2-diphosphonic acid tetraethyl ester 

Downstream Products

• 102816-61-5 {[2-(Diethylaminomethyl-phosphanyl)-phenylphosphanyl]-methyl}-diethyl-amine 
• 102816-60-4 1,2-dibenzene 
• 89982-96-7 1,2-Bisbenzol 
• 1151946-61-0 P₄As₂H₂(W(CO)5)4(C₆H₄)2*C₆H₅CH₃ 
• 773810-13-2 1,2,3,4-Tetrahydro-1,4-diphosphorin 
• 111348-46-0 P-(2-Chlorethyl)-o-phenylen-diphosphin 
• 111348-45-9 1,4-Diphospha-2,3-benzo-bicyclo<2.2.2>octan 
• 81510-32-9 C₆H₆P₂^(2-)*2Na⁽¹⁺⁾ 
• 81510-32-9 C₆H₇P₂^(1-)*Na⁽¹⁺⁾ 
• 28255-47-2 1,2-phenylenediphosphonic acid 
• 151073-37-9 1,2-bis((2R,5R)-2,5-dipropylphospholano)benzene 
• 136705-64-1 1,2-bis((2R,5R)-2,5-diethylphosphoranylidene)benzene 
• 136705-65-2 (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene 
• 136779-28-7 (S,S)-Et-DUPHOS 

Relevant articles and documents

A Benzodiphosphaborolediide

The first example of a diphosphaborolediide, the benzo-fused [C6H4P2BPh]2? (12?), is prepared from ortho-bis(phosphino)benzene (C6H4{PH2}) and dichlorophenylborane, via a sequential lithiation approach. The dilithio-salt can be obtained as an oligomeric THF solvate or discrete TMEDA adduct, both of which are fully characterized, including by X-ray diffraction. Alongside NICS calculations, data strongly suggest some aromaticity within 12?, which is further supported by preliminary coordination studies that demonstrate η5-coordination to a zerovalent molybdenum center, as observed crystallographically for the oligomeric [{Mo(CO)3(η5-1)}{μ-η1-Mo(CO)3(TMEDA)}2] ? [μ-Li(THF)][μ-Li(TMEDA)].

Synthesis of chiral hydroxyl phospholanes from D-mannitol and their use in asymmetric catalytic reactions

Chiral hydroxyl monophosphane 3 [(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane] and bisphospholanes 5a [1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethylphospholanyl]benzene] and 5b [1,2-bis[(2S,3S,4S,5S)-2,5-diethyl-3,4-dihydroxyphospholanyl]benzene] were synthesized from readily available D-mannitol in high yields. Strategies for protection and deprotection of OH-groups in the presence of phosphines have been explored. Rate acceleration in the Baylis - Hillman reaction was observed when a hydroxyl phosphine was used as the catalyst. Rhodium complexes with chiral bisphospholanes are highly enantioselective catalysts for the asymmetric hydrogenation of various kinds of functionalized olefins such as dehydroamino acid derivatives, itaconic acid derivatives, and enamides. An interesting feature of the hydroxyl phospholane system is that hydrogenation of some substrates can be carried out in water with >99% ee and 100% conversion (e.g., itaconic acid).

Synthesis of o-Phenylene-bis(dibromophosphane) - Reaction Products of o-Phenylene-bis(dichlorophosphane)

o-Phenylene-bis(dibromophosphane) (1) is prepared by reaction of P,P,P',P'-tetrakis(dimethylamino)-o-phenylenediphosphane with hydrogen bromide in ether.The reaction of o-phenylene-bis(dichlorophosphane) (2) with CH3OH in ether yields o-phenylene-bis(phos