15849-86-2

Basic information

• Product Name: METHYLPHENYLCHLOROPHOSPHINE
• Synonyms: METHYLPHENYLCHLOROPHOSPHINE
• CAS NO: 15849-86-2
• Molecular Formula: C₇H₈ClP
• Molecular Weight: 158.565181
• Mol File: 15849-86-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 167 °C(Press: 22 Torr)
• Appearance: /
• Density: 1.2683 g/cm3
• CAS DataBase Reference: METHYLPHENYLCHLOROPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLPHENYLCHLOROPHOSPHINE(15849-86-2)
• EPA Substance Registry System: METHYLPHENYLCHLOROPHOSPHINE(15849-86-2)

Safety Data

• Hazardous Substances Data: 15849-86-2(Hazardous Substances Data)

Upstream product

• 102099-45-6 (dichloroacetyl)methylphenylphosphane 
• 4073-31-8 (diethylamino)phenylchlorophosphine 
• 644-97-3 Dichlorophenylphosphine 
• 20684-97-3 chloro(diisopropylamino)(phenyl)phosphine 
• 506-82-1 dimethylcadmium 
• 3676-96-8 1,2-dimethyl-1,2-diphenyldiphosphine 
• 708-90-7 (N,N-diethylamino)(methyl)(phenyl)phosphine 
• 13639-62-8 chloromethylphenylphosphine sulfide 
• 59877-21-3 methyl(phenyl)(trimethylsilyl)phosphine 

Downstream Products

• 19432-40-7 Benzylmethyl(1-naphthyl)phenylphosphonium-chlorid 
• 220925-09-7 dimethyl-[2-(methyl-phenyl-phosphanyl)-benzyl]-amine 
• 146071-60-5 r-2--t-4,t-6-dimethyl-1,3-dithiane 
• 1271313-62-2 (Me₃Si)2N-N(SiMe₃)-P(Me)(C₆H₅) 
• 165268-22-4 (RS,SR)/(RR,SS)-pentacarbonyl[(α-chlorobenzyl)(methyl)phenylphosphine]tungsten 

Relevant articles and documents

A simple resolution procedure using the Staudinger reaction for the preparation of P-stereogenic phosphine oxides

The resolution of a variety of (±)-P-stereogenic phosphines is achieved by exploiting the Staudinger reaction of a (±)-phosphine with enantiopure (1S,2R)-O-(tert-butyldimethylsilyl)isobornyl-10-sulfonyl azide. The resulting mixtures of diastereomeric phosphinimines are generally separable by fractional crystallization or flash chromatography. Subsequent acid-catalyzed hydrolysis provides the corresponding optically pure phosphine oxides in high yields.

Synthesis and Properties of Mixed Substituted (Chloroacetyl)organylphenylphosphanes

The mono-, di- and trichloroacetylorganylphenylphosphanes X1X2CClC(O)PPhR (3av-cz) are obtained by reaction of Me3SiPPhR (2v-z) with the azid chlorides X1X2CClC(O)Cl (1a-c).Increasing content of chlorine results in a shift of the >C=O band and the 31P signal to higher wavelengths and fields, respectively, in the IR and 31P NMR spectra of 3av-cz.Due to the centre of chirality at the phosphorus atom in the 1H NMR spectra one observes diastereotopic protons in the chloroacetyl moiety of 3av-az and of the P-adjacent CH2 protons of 3aw-cw and 3ay-cy.The magnetic inequivalence of both methyl substituents in the isopropyl groups of 3ax-cx is observable also in the 13C and 1H NMR spectra.Because of steric reasons the free rotation about the P-isopropyl axis is hindered up to 355 K.From the coalescence temperature the free activation energy ΔG* is calculated to give 74.7 kJ/mole.The degradation of the thermolabile compounds 3av-cz results in the formation of the chlorophosphanes 5v-z.Individual investigations on 3bv, 3bw and 3by indicate the formation of mono- and dichloroacetyl chloride.The appearance of ClCH2C(O)Cl proceeds via the chloroketene 4b.

SYNTHESE DIRECTE DE PHOSPHINES TERTIARIES RACEMIQUES ET DE CHLOROPHOSPHINES DISSYMETRIQUES

Racemic tertiary phosphines are obtained from dichlorophenylphosphine by a "one pot" synthesis in two steps: (1) condensation of one equivalent of an organocadmium, and (2) substitution of the second chlorine by another organometallic compound.The phosphines liberated from the resulting complexes can be stabilised by direct complexation with cuprous salts.The monochlorophosphines can be isolated in the first stage when their cadmium complexes are submitted to ligand exchange with pyridine.