74289-57-9

Basic information

• Product Name: BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE
• Synonyms: BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE;Bis(3,5-dimethylphenyl)chlorophosphine,98%;Chlorobis(3,5-dimethylphenyl)phosphine, tech. 90%;Chlorobis(3,5-dimethylphenyl)phosphine;Bis(3,5-dimethylphenyl)chlorophosphine, tech.;Bis(3,5-dimethylphenyl)phosphine chloride;Bis(3,5-dimethylphenyl)phosphinous chloride;chloro-bis(3,5-dimethylphenyl)phosphane
• CAS NO: 74289-57-9
• Molecular Formula: C₁₆H₁₈ClP
• Molecular Weight: 276.74
• EINECS: -0
• Product Categories: Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors
• Mol File: 74289-57-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 407.2°C at 760 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.102 g/mL at 25 °C
• Vapor Pressure: 1.81E-06mmHg at 25°C
• Refractive Index: n20/D 1.606
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE(74289-57-9)
• EPA Substance Registry System: BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE(74289-57-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-43-45
• RIDADR: UN3261
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 74289-57-9(Hazardous Substances Data)

Usage

Uses

Chlorobis(3,5-dimethylphenyl)phosphine is used in the synthesis of (S)- and (R)-2,2?-Bis[bis(3,5-dimethylphenyl)phosphinoyl]-5,5?,6,6?,7,7?,8,8?-octahydro-1,1?-binaphthyl (Xyl-H 8 -BINAPO).

InChI:InChI=1/C16H18ClP/c1-11-5-12(2)8-15(7-11)18(17)16-9-13(3)6-14(4)10-16/h5-10H,1-4H3

Upstream product

• 194149-25-2 [bis-(3,5-dimethylphenyl)](diethylamino)phosphine 
• 556-96-7 5-bromo-1,3-xylene 
• 34696-73-6 3,5-dimethyphenylmagnesium bromide 
• 1069-08-5 diethylphosphoramidous dichloride 
• 187344-92-9 bis(3,5-dimethylphenyl)phosphine oxide 
• 69227-47-0 tris(3,5-dimethylphenyl)phosphine 
• 109-72-8 n-butyllithium 

Downstream Products

• 926034-96-0 N-(2-butoxycarbonyl-1-methyl-1-phenylethyl)-di(3,5-xylyl)phosphinamide 
• 721446-00-0 (R)-N-(1-(4-trifluoromethylphenyl)ethyl) bis(3,5-dimethylphenyl)phosphinamide 
• 669091-00-3 2-[bis(3,5-dimethylphenyl)phosphino]benzaldehyde 

Relevant articles and documents

Regiocontrolled Reductive Vinylation of Aliphatic 1,3-Dienes with Vinyl Triflates by Nickel Catalysis

The regiocontrolled functionalization of 1,3-dienes has become a powerful tool for divergent synthesis, yet it remains a long-standing challenge for aliphatic substrates. Herein, we report a reductive approach for a branch-selective 1,2-hydrovinylation of aliphatic 1,3-dienes with R-X electrophiles, which represents a new selectivity pattern for diene functionalization. Simple butadiene, aromatic 1,3-dienes, and highly conjugated polyene were also tolerated. The combination of Ni(0) and the phosphine-nitrile ligand generally resulted in >20:1 regioselectivity with the retention of the geometry of the C3-C4 double bonds. This reaction proceeds with a broad substrate scope, and it allows for the conjugation of two biologically active units to form more complex polyene molecules, such as tetraene and pentaene as well as heptaene.

Method for preparing diarylphosphoryl chloride compound

The invention discloses a method for preparing a diarylphosphochlorine compound and belongs to the field of organic synthesis. The method is as follows: the diarylphosphochlorine compound is preparedby reaction of triarylphosphine as a starting material with phosphorus trichloride in the presence of zinc trifluoromethanesulfonate as a catalyst and distillation. Compared with the prior art, the method has the advantages of high reaction yield and simple post-treatment, is particularly suitable for preparation of the diarylphosphochlorine compound with a substituent, and is more suitable for industrial production. The obtained diarylphosphochlorine compound can be used as a ligand for synthesizing metal catalysts, and is applied to the fields such as organic photoelectric materials and medicines.

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.