1005-32-9

Basic information

• Product Name: (4-methylphenyl)phosphonous dichloride
• Synonyms: (4-Methylphenyl)phosphonous dichloride; phosphonous dichloride, P-(4-methylphenyl)-
• CAS NO: 1005-32-9
• Molecular Formula: C₇H₇Cl₂P
• Molecular Weight: 193.0102
• Mol File: 1005-32-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 243.7°C at 760 mmHg
• Flash Point: 101.2°C
• Vapor Pressure: 0.0493mmHg at 25°C
• CAS DataBase Reference: (4-methylphenyl)phosphonous dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: (4-methylphenyl)phosphonous dichloride(1005-32-9)
• EPA Substance Registry System: (4-methylphenyl)phosphonous dichloride(1005-32-9)

Safety Data

• Hazardous Substances Data: 1005-32-9(Hazardous Substances Data)

Usage

General Description

(4-methylphenyl)phosphonous dichloride, also known as 4-methylphenylphosphinous dichloride, is a chemical compound with the molecular formula C7H8Cl2P. It is a white or off-white solid with a strong, unpleasant odor. (4-methylphenyl)phosphonous dichloride is used in organic synthesis as a precursor to various phosphine derivatives, which have applications in pharmaceuticals, agrochemicals, and materials science. It is a highly reactive compound and must be handled with care due to its toxic and corrosive nature. Additionally, it is sensitive to air and moisture, and should be stored and handled in a controlled environment. (4-methylphenyl)phosphonous dichloride is a valuable intermediate in the production of various organic compounds and has important industrial applications.

Upstream product

• 106-38-7 para-bromotoluene 
• 1038-95-5 Tri(p-tolyl)phosphine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 18236-57-2 methyl-4-methylphenyl-dichlorosilane 
• 108-88-3 toluene 
• 537-64-4 bis(p-tolyl)mercury 
• 51303-75-4 tetrachloro-p-tolylphosphorane 
• 90252-89-4 p-tolylzinc(II) chloride 
• 2417-95-0 p-tolyllithium 
• 17566-84-6 p-tolylphosphonic dichloride 

Downstream Products

• 28869-92-3 dipiperidino-p-tolyl-phosphine 
• 63507-03-9 p-tolyl-phosphonous acid dimethyl ester 
• 19031-52-8 diethyl(p-tolyl)phosphine 
• 20676-64-6 dimethyl(4-tolyl)phosphine 
• 20783-50-0 p-tolylphosphinic acid 
• 67653-40-1 dipropyl-p-tolyl-phosphine 
• 1019-71-2 chlorodi-p-tolylphosphane 
• 20355-96-8 p-tolyl-phosphonous acid diethyl ester 
• 1978-58-1 tetrafluoro-p-tolyl-phosphorane 
• 51303-75-4 tetrachloro-p-tolylphosphorane 
• 17566-84-6 p-tolylphosphonic dichloride 
• 1016-80-4 chloro-phenyl-p-tolyl-phosphine 
• 19966-97-3 di(n-butyl)(p-tolyl)phosphine 

Relevant articles and documents

-

-

Hydrogen/Halogen Exchange of Phosphines for the Rapid Formation of Cyclopolyphosphines

The hydrogen/halogen exchange of phosphines has been exploited to establish a truly useable substrate scope and straightforward methodology for the formation of cyclopolyphosphines. Starting from a single dichlorophosphine, a sacrificial proton "donor phosphine"makes the rapid, mild synthesis of cyclopolyphosphines possible: reactions are complete within 10 min at room temperature. Novel (aryl)cyclopentaphosphines (ArP)5 have been formed in good conversion, with the crystal structures presented. The use of catalytic quantities of iron(III) acetylacetonate provides significant improvements in conversion in the context of diphosphine (Ar2P)2 and alkyl-substituted cyclotetra- or cyclopentaphosphine ((AlkylP)n, where n = 4 or 5) formation. Both iron-free and iron-mediated reactions show high levels of selectivity for one specific ring size. Finally, investigations into the reactivity of Fe(acac)3 suggest that the iron species is acting as a sink for the hydrochloric acid byproduct of the reaction.

AlCl3-catalyzed C-H p hosphination of benzene: A mechanistic study

The characteristics of the reaction for the preparation of dichlorophenylphosphine (DCPP) via benzene and PCl3 in the presence of AlCl3 were studied. Some unique characteristics were observed when a catalytic amount of AlCl3 was used. Namely, more than one mole of DCPP was obtained per mole AlCl3, the reaction solution was layered, and DCPP could be directly separated. Our mechanistic study showed that benzene reacted with PCl3 to form DCPP-AlCl3, and DCPP-AlCl3 dissociated into DCPP and AlCl3, continuing to catalyze this reaction. This resulted in the high catalytic efficiency of AlCl3. The layering of the reaction solution was caused by the immiscibility of DCPP-AlCl3 with the raw materials, greatly facilitating the dissociation process of DCPP-AlCl3. The formation of diphenylphosphorus chloride (DPC) was due to a continuous Friedel-Crafts reaction between DCPP and benzene. DPC cooperated with AlCl3 to form the stable coordination compound DPC-AlCl3 that did not dissociate and was responsible for the deactivation of AlCl3.

Base-Induced 1,3-Sigmatropic rearrangement of mesitylphosphonium salts

Attempted synthesis of the ylide dianion [2,4,6-Me3C 6H2P(CHR)3]2- (2,4,6-Me 3C6H2 = mesityl, R = H or Me) by the reaction of mesitylphosphonium iodides [2,4,6-Me3C6H 2PR3]+I- (R = Me, 1; R = Et, 2) with tBuLi at reflux does not result in the anticipated deprotonation of the phosphorus-bonded R groups. Instead, quantitative 1,3-sigmatropic rearrangement occurs to give new benzylic phosphonium salts [(3,5-Me2C 6H3)CH2PR3]+I - (R = Me, 6; R = Et, 7), in which the phosphonium centre, the R 3P group, is transferred to an ortho-CH3 group. In situ 31P NMR spectroscopic studies show that the reaction is base-activated and stoichiometric with respect to tBuLi. DFT calculations support the conclusion that the rearrangement is thermodynamically favourable in the gas phase and in THF and show that the rearrangement is enthalpically driven. Copyright