1019-71-2

Basic information

• Product Name: Chlorodi(p-tolyl)phosphine, 95%
• Synonyms: Chlorodi(p-tolyl)phosphine, 95%;P,P-Bis(4-methylphenyl)-phosphinous chloride, Chlorodi-p-tolylphosphine;chloro-bis(4-methylphenyl)phosphane;Chlorodi(p-tolyl)phosphine
• CAS NO: 1019-71-2
• Molecular Formula: C₁₄H₁₄ClP
• Molecular Weight: 248.69
• Mol File: 1019-71-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 180-184℃/10mm
• Flash Point: 163.6 °C
• Appearance: /
• Density: 1.1 g/mL at 25 °C
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: n20/D1.501
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: Chlorodi(p-tolyl)phosphine, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: Chlorodi(p-tolyl)phosphine, 95%(1019-71-2)
• EPA Substance Registry System: Chlorodi(p-tolyl)phosphine, 95%(1019-71-2)

Safety Data

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8 / PGIII
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1019-71-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1019-71-2 differently. You can refer to the following data:
1. Chlorodi(p-tolyl)phosphine is used as a reactant for synthesis of palladium catalysts for C-C bond forming cross-coupling reactions, ligands for nickel(0)-catalyzed isomerization reactions, phosphinosulfonamide nickel complexes for oligomerization reactions. It is a reactant for phosphinylation reactions.
2. Reactant for synthesis of:Palladium catalysts for C-C bond forming cross-coupling reactionsLigands for nickel(0)-catalyzed isomerization reactionsPhosphinosulfonamide nickel complexes for oligomerization reactionsReactant for:Pd-catalyzed intramolecular asymmetric allylic amination and ring-closing metathesisPhosphinylation reactions

InChI:InChI=1/C14H14ClP/c1-11-3-7-13(8-4-11)16(15)14-9-5-12(2)6-10-14/h3-10H,1-2H3

Upstream product

• 1038-95-5 Tri(p-tolyl)phosphine 
• 2409-61-2 di(p-tolyl)phosphine oxide 
• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 696-61-7 4-tolylmagnesium chloride 
• 108-88-3 toluene 
• 106-38-7 para-bromotoluene 
• 1005-32-9 p-tolyldichlorophosphine 
• 537-64-4 bis(p-tolyl)mercury 

Downstream Products

• 5032-47-3 <1-Phenylmercapto-aethyl>-di-p-tolyl-phosphinoxyd 
• 5032-50-8 <1-Phenylmercapto-aethyl>-di-p-tolyl-phosphinthiooxyd 
• 131151-05-8 (CH₃C₆H₄)2PP(CH₃C₆H₄)2Cl⁽¹⁺⁾*AlCl₄^(1-)=(CH₃C₆H₄)2PP(CH₃C₆H₄)2ClAlCl₄ 
• 55743-56-1 trans-1,2-ethenediylbis[di(4-methylphenyl)phosphine] 
• 1184204-00-9 7-(di(p-methylphenyl)phosphino)-3-(pyridin-2'-yl)-[1,2,3]triazolo[1,5-a]pyridine 
• 1184204-02-1 3-(6'-(di(p-methylphenyl)phosphino)pyridin-2'-yl)-[1,2,3]triazolo[1,5-a]pyridine 
• 1184204-21-4 C₂₅H₂₁N₄PSe 
• 1383658-56-7 (R)-(2-(tert-butylsulfinyl)phenyl)di-p-tolylphosphine 
• 1189197-20-3 bis(4-methylphenyl)(6-methyl-2-pyridyl)phosphine 
• 1231209-34-9 N-methyl-N-[bis(4-methylphenyl)phosphino]-(S)-1-[2-(diphenylphosphino)phenyl]ethylamine 
• 1231209-30-5 N-[bis(4-methylphenyl)phosphino]-(S)-1-[2-(diphenylphosphino)phenyl]ethylamine 
• 959680-45-6 di(p-tolyl)-N,N-bis-((S,S)-1-phenyl-ethyl)phosphinamine 

Relevant articles and documents

Twofold C?H Activation-Based Enantio- and Diastereoselective C?H Arylation Using Diarylacetylenes as Rare Arylating Reagents

C?H bond activation has been established as an attractive strategy to access axially chiral biaryls, and the most straightforward method is direct C?H arylation of arenes. However, the arylating source has been limited to several classes of reactive and bulky reagents. Reported herein is rhodium-catalyzed 1:2 coupling of diarylphosphinic amides and diarylacetylenes for enantio- and diastereoselective construction of biaryls with both central and axial chirality. This twofold C?H activation reaction stays contrast to the previously explored Miura–Satoh type 1:2 coupling of arenes and alkynes in terms of chemoselectivity and proceeded under mild conditions with the alkyne acting as a rare arylating reagent. Both C?H activation events are stereo-determining and are under catalyst control, with the 2nd C?H activation being diastereo-determining in a remote fashion. Analysis of the stereochemistry of the major and side products suggests moderate enantioselectivity of the initial C?H activation–desymmetrization process. However, the minor (R) rhodium vinyl intermediate is consumed more readily in undesired protonolysis, eventually resulting in high enantio- and diastereoselectivity of the major product.

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.