82495-67-8

Basic information

• Product Name: 1,2-BIS(DICHLOROPHOSPHINO)BENZENE
• Synonyms: O-BIS(DICHLOROPHOSPHINO)BENZENE;O-PHENYLENBIS(DICHLORPHOSPHAN);1,2-BIS(DICHLOROPHOSPHINO)BENZENE;0-PHENYLENBIS(DICHLORPHOSPHAN);1,2-Bis(dichlorophosphino)benzene, min. 97%;1,2-Bis(dichlorophosphino)benzene, 98+%;1,2-Bis(dichlorophosphino)benzene 96%;dichloro-(2-dichlorophosphanylphenyl)phosphane
• CAS NO: 82495-67-8
• Molecular Formula: C₆H₄Cl₄P₂
• Molecular Weight: 279.86
• Product Categories: organophosphine ligand
• Mol File: 82495-67-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 320.3 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: colorless to pale yellow/liquid
• Density: 1.545 g/mL at 25 °C
• Refractive Index: n20/D1.662
• Sensitive: moisture sensitive
• CAS DataBase Reference: 1,2-BIS(DICHLOROPHOSPHINO)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BIS(DICHLOROPHOSPHINO)BENZENE(82495-67-8)
• EPA Substance Registry System: 1,2-BIS(DICHLOROPHOSPHINO)BENZENE(82495-67-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGII
• WGK Germany: 3
• Hazardous Substances Data: 82495-67-8(Hazardous Substances Data)

Usage

General Description

1,2-Bis(dichlorophosphino)benzene is a chemical compound with the formula C12H8Cl4P2. It is a yellow crystalline solid that is used as a catalyst in various chemical reactions. 1,2-BIS(DICHLOROPHOSPHINO)BENZENE contains two phosphorus atoms bonded to a benzene ring, each of which is also bonded to two chlorine atoms. 1,2-Bis(dichlorophosphino)benzene is often used as a ligand in coordination chemistry, where it can form stable complexes with transition metals, and is particularly effective in catalyzing the hydrogenation of alkenes. It is also used in organic synthesis to form carbon-phosphorus bonds. The compound is toxic and should be handled with care, as exposure can cause irritation to the skin, eyes, and respiratory system.

Upstream product

• 82495-65-6 P,P,P',P'-Tetrakis(dimethylamino)-o-phenylendiphosphan 
• 80510-04-9 1,2-bis(phosphino)benzene 
• 5274-51-1 ortho-dichlorophosphinobromobenzene 
• 882872-08-4 o-C₆H₄(Me₂PO)2 
• 95-50-1 1,2-dichloro-benzene 
• 583-53-9 2,3-dibromobenzene 
• 82495-63-4 ortho-bis(dimethylamino)phosphinobromobenzene 
• 51241-56-6 1,2-dilithiobenzene 

Downstream Products

• 28255-47-2 1,2-phenylenediphosphonic acid 
• 80510-04-9 1,2-bis(phosphino)benzene 
• 220096-34-4 1,2-bis[di[3',5'-bis(dimethoxymethyl)phenyl]phosphanyl]benzene 
• 251982-51-1 1,2-Bis{di[2'-(dimethoxymethyl)phenyl]phosphanyl}benzene 
• 942937-07-7 1,2-bis(di-orthofluorophenylphosphino)benzene 
• 1082028-69-0 C₆₄H₅₂N₄O₆P₂ 
• 1082028-95-2 C₇₈H₇₂N₄O₈P₂ 
• 1082028-97-4 C₈₂H₈₀N₄O₈P₂ 
• 1082028-99-6 C₈₆H₈₈N₄O₈P₂ 
• 1082029-01-3 C₈₆H₈₈N₄O₈P₂ 
• 1082029-03-5 C₉₀H₉₆N₄O₈P₂ 
• 1084910-75-7 C₇₄H₆₀Cl₄N₄O₈P₂ 
• 1084910-76-8 C₇₈H₇₂N₄O₁₂P₂ 
• 1084910-77-9 C₉₀H₉₆N₄O₈P₂ 

Relevant articles and documents

Azadiphosphaindane-1,3-diyls: A Class of Resonance-Stabilized Biradicals

Conversion of 1,2-bis(dichlorophosphino)benzene with sterically demanding primary amines led to the formation of 1,3-dichloro-2-aza-1,3-diphosphaindanes of the type C6H4(μ-PCl)2N-R. Reduction yielded the corresponding 2-az

Modular chiral bidentate phosphonites: Design, synthesis, and application in catalytic asymmetric hydroformylation reactions

A new class of C2-symmetric chiral bidentate phosphonite ligands has been synthesized in moderate to good yields from readily available starting materials. Application of these air-stable chiral phosphonites in the Rh I-catalyzed asymmetric hydroformylation of styrene derivatives, vinyl acetate, and allyl cyanide afforded the corresponding chiral aldehydes with high regio- and enantioselectivities under mild reaction conditions. The modular nature of the ligands allows fine-tuning of the selectivities through judicious modifications of the substituents on the ligand backbone. X-ray structural analysis of the catalyst precursor suggested that the steric hindrance caused by the protruding remote substituents of the ligands into the vicinity of the metal center might be an important factor for the enantio-control of the reaction, whereas the sense of asymmetric induction can be rationalized on the basis of a trigonal-bipyramidal transition state diagram.

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.