6329-48-2

Basic information

• Product Name: dimethyl [(4-chlorophenyl)(hydroxy)methyl]phosphonate
• CAS NO: 6329-48-2
• Molecular Formula: C₉H₁₂ClO₄P
• Molecular Weight: 250.6159
• Mol File: 6329-48-2.mol

Chemical Properties

• Boiling Point: 370.4°C at 760 mmHg
• Flash Point: 177.8°C
• Density: 1.348g/cm³
• Vapor Pressure: 3.86E-06mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: dimethyl [(4-chlorophenyl)(hydroxy)methyl]phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl [(4-chlorophenyl)(hydroxy)methyl]phosphonate(6329-48-2)
• EPA Substance Registry System: dimethyl [(4-chlorophenyl)(hydroxy)methyl]phosphonate(6329-48-2)

Safety Data

• Hazardous Substances Data: 6329-48-2(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 868-85-9 Dimethyl phosphite 
• 121-45-9 phosphorous acid trimethyl ester 
• 623-12-1 4-chloromethoxybenzene 
• 33493-32-2 dimethyl p-chlorobenzoylphosphonate 
• 122-01-0 4-chloro-benzoyl chloride 
• 36198-87-5 dimethyl trimethylsilyl phosphite 
• 96-36-6 methyl phosphite 
• 2033-24-1 cycl-isopropylidene malonate 

Downstream Products

• 845899-03-8 (2,4-dichloro-phenoxy)-acetic acid (4-chloro-phenyl)-(dimethoxy-phosphoryl)-methyl ester 
• 667462-16-0 chloro-acetic acid (4-chloro-phenyl)-(dimethoxy-phosphoryl)-methyl ester 
• 1146599-29-2 O,O-dimethyl 1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H-1,2,3-triazol-4-ylcarbonyloxy-(4-chlorophenyl)methyl-phosphonate 
• 1208065-66-0 dimethyl [(4-chlorophenyl)(6-oxo-6λ5-dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)ethyl]phosphonate 
• 63694-16-6 1-(4-chlorophenyl)-1-hydroxymethylphosphonic acid 
• 1332458-74-8 (4-chlorophenyl)(dimethoxyphosphoryl)methyl 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate 
• 1352612-24-8 (4-chlorophenyl)(dimethoxyphosphoryl)methyl cinnamate 
• 1614827-39-2 O,O-dimethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(4-chlorophenyl)methylphosphonate 
• 123989-29-7 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one 

Relevant articles and documents

O-allylated pudovik and passerini adducts as versatile scaffolds for product diversification

The palladium-catalyzed O-allylation of α-hydroxyphosphonates and α-hydroxyamides obtained from Pudovik and Passerini multicomponent reactions has allowed interesting and highly straightforward access to a variety of building blocks for product diversific

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.

Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation

A promiscuous lipase-catalyzed carbon-phosphorus bond formation is presented. The developed enzymatic Pudovik-Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α-hyd

Phosphorylation of (1-aryl-1-hydroxymethyl)phosphonates

The reaction of dimethyl (1-aryl-1-hydroxymethyl)phosphonates with 1-chloro-3-phospholene 1-oxides, diphenylphosphinic chloride or diphenyl chloridophosphonate affords the corresponding (1-phosphoryloxymethyl)phosphonates. The products with two different

Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids

New, green methods have been elaborated for the syntheses of α-hydroxyphosphonates and α-hydroxymethylenebisphosphonic derivatives (HMBPs, dronates). α-Hydroxyphosphonates were prepared via the Pudovik reaction, while the synthesis of HMBPs has been performed in the three-component reaction of carboxylic acids, phosphorus trichloride and phosphorus acid.

Palladium-catalysed O-Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles

We report here an unprecedented palladium-catalysed O-allylation of α-hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji-Trost type O-allylation/Ring-Closing Metathesis to afford a variety of phosphorylated heterocycles

Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates

A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1–14 were designed and synthesized. The structures of all the title compounds were confirmed by 1H-NMR, 13C-NMR, 31P-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20–80% larvicidal activity against Mythimna separata at 1000?mg/L.

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.

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 biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates

(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.