20767-40-2

Basic information

• Product Name: [(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester
• Synonyms: [(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester
• CAS NO: 20767-40-2
• Molecular Weight: 250.619
• Mol File: 20767-40-2.mol

Chemical Properties

• CAS DataBase Reference: [(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: [(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester(20767-40-2)
• EPA Substance Registry System: [(3-Chloro-phenyl)-hydroxy-methyl]-phosphonic acid dimethyl ester(20767-40-2)

Safety Data

• Hazardous Substances Data: 20767-40-2(Hazardous Substances Data)

Upstream product

• 2033-24-1 cycl-isopropylidene malonate 
• 587-04-2 m-Chlorobenzaldehyde 
• 121-45-9 phosphorous acid trimethyl ester 
• 868-85-9 Dimethyl phosphite 

Relevant articles and documents

Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions

Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.

Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes

We synthesized substituted benzaldehyde derived α-hydroxyphosphonates (αOHP), α-hydroxyphosphonic acids (αOHPA) and α-phosphinoyloxyphosphonates (αOPP) and characterized their cytotoxicity against a panel of cancer cell lines. A library containing 56 analogues was screened against Mes-Sa parental and Mes-Sa/Dx5 multidrug resistant uterine sarcoma cell lines, using a fluorescence-based cytotoxicity assay. The cytotoxicity screening revealed that dibenzyl-αOHPs and dimethyl-α-diphenyl-OPPs were the most active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure-activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line Mes-Sa/Dx5, suggesting these compounds may overcome P-glycoprotein mediated multidrug resistance by evading the drug transporter.

Phospha-Michael Addition to in Situ Prepared 5-Arylmethylidene Meldrum's Acids

Knoevenagel condensation reaction of an aldehyde and Meldrum's acid produces a 5-arylmethylidene Meldrum's acid, which undergoes Michael addition of a trialkyl phosphite under solvent-free conditions to afford the title compounds in good yields.

Synthesis and herbicidal activity of O,O-dialkyl phenoxyacetoxyalkylphosphonates containing fluorine

A series of substituted phenoxyacetoxyalkylphosphonates bearing fluorine were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR and MS and were tested for herbicidal activity in greenhouse at a rate of 1.5 kg/ha. The results of preliminary bioassay showed that fluorine moiety introduced to the core structure could help to improve the herbicidal activity, and compounds with a 3-trifluoromethyl in benzene ring exhibited higher inhibitory activity.