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

Description

BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE is an organophosphorus compound with the chemical formula Cl(P(C6H2(CH3)2)2). It is a versatile reagent in organic synthesis and has unique properties due to its chlorophosphine structure.

Uses

Used in Chemical Synthesis:
BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE is used as a reagent in the synthesis of various organic compounds, particularly in the preparation of chiral ligands and catalysts.
Used in Pharmaceutical Industry:
BIS(3,5-DIMETHYLPHENYL)CHLOROPHOSPHINE is used as a key intermediate 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), which is a chiral ligand for asymmetric catalysis. This ligand is crucial in the production of enantiomerically pure pharmaceutical compounds, as it helps to control the stereochemistry of the reaction, leading to the desired enantiomer with high selectivity.

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

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

Downstream Products

• 1242052-26-1 8-bis(3,5-dimethylphenyl)phosphino-quinoline 
• 1356851-33-6 2-(bis(3,5-dimethylphenyl)phosphino)benzoic acid 
• 137219-86-4 2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl 
• 1365320-14-4 (3,5-dimethoxyphenyl)bis(3,5-dimethylphenyl)phosphine oxide 
• 358721-84-3 (S(p),S(p))-2,2''-bis[bis(3,5-dimethylphenyl)phosphino]-1,1''-biferrocene 
• 358721-82-1 (S,S(p),S(p))-2-bis(3,5-dimethylphenyl)phosphino-2''-(4-methylphenyl)sulfinyl-biferrocene 
• 400711-25-3 C₃₄H₄₉O₂PSSi 

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.

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented.

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.