5510-87-2

Basic information

• Product Name: (2-methylphenyl)phosphonous dichloride
• Synonyms: (2-Methylphenyl)phosphonous dichloride; phosphonous dichloride, P-(2-methylphenyl)-
• CAS NO: 5510-87-2
• Molecular Formula: C₇H₇Cl₂P
• Molecular Weight: 193.0102
• Mol File: 5510-87-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 236.8°C at 760 mmHg
• Flash Point: 97°C
• Vapor Pressure: 0.0714mmHg at 25°C
• CAS DataBase Reference: (2-methylphenyl)phosphonous dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2-methylphenyl)phosphonous dichloride(5510-87-2)
• EPA Substance Registry System: (2-methylphenyl)phosphonous dichloride(5510-87-2)

Safety Data

• Hazardous Substances Data: 5510-87-2(Hazardous Substances Data)

Usage

General Description

(2-methylphenyl)phosphonous dichloride, also known as o-tolylphosphonous dichloride, is a chemical compound with the formula C7H8Cl2P. It is a phosphonic acid derivative and belongs to the class of organophosphorus compounds. The compound is a colorless to pale yellow liquid at room temperature and is highly reactive. It is commonly used as a reagent in organic synthesis to introduce the phosphonous dichloride group to other organic molecules. It is also used as a precursor for the synthesis of various functionalized phosphorus compounds. Due to its reactivity and potential hazard, it should be handled with caution and appropriate safety measures.

Upstream product

• 616-99-9 bis(2-tolyl) mercury 
• 113544-73-3 N,N,N',N'-tetraethyl-P-(2-methylphenyl)phosphonous diamide 
• 95-46-5 2-methylphenyl bromide 
• 108-88-3 toluene 
• 932-31-0 ortho-tolylmagnesium bromide 
• 6699-93-0 (2-methylphenyl)lithium 
• 685-83-6 bis(diethylamino)chlorophosphine 
• 33872-80-9 o-tolyl magnesium chloride 
• 62386-52-1 o-tolyl-phosphonic acid-dichloride 

Downstream Products

• 1064156-80-4 (3,5-dimethylphenyl)-(ortho-tolyl)-methyl phosphine 
• 1619925-50-6 adamantyl hydrogen(o-tolyl)phosphinate 
• 41845-30-1 o-Tolyl-dimethylphosphin 
• 6779-11-9 (2-methylphenyl)phosphonic acid 
• 207905-28-0 bis[(trifluoromethyl)phenyl](methylphenyl)phosphine 
• 137622-07-2 2-methyl-phenylphosphinic acid 

Relevant articles and documents

Stereoselective Synthesis of All Possible Phosferrox Ligand Diastereoisomers Displaying Three Elements of Chirality: Stereochemical Optimization for Asymmetric Catalysis

All four possible diastereoisomers of phosphinoferrocenyloxazoline (Phosferrox type) ligands containing three elements of chirality were synthesized as single enantiomers. The Sc configured oxazoline moiety (R = Me, i-Pr) was used to control th

Synthesis of β-Lactams by Palladium(0)-Catalyzed C(sp3)?H Carbamoylation

A general and user-friendly synthesis of β-lactams is reported that makes use of Pd0-catalyzed carbamoylation of C(sp3)?H bonds, and operates under stoichiometric carbon monoxide in a two-chamber reactor. This reaction is compatible with a range of primary, secondary and activated tertiary C?H bonds, in contrast to previous methods based on C(sp3)?H activation. In addition, the feasibility of an enantioselective version using a chiral phosphonite ligand is demonstrated. Finally, this method can be employed to synthesize valuable enantiopure free β-lactams and β-amino acids.

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