7506-98-1

Basic information

• Product Name: diethyl [(2-chlorophenyl)(hydroxy)methyl]phosphonate
• Synonyms: .alpha.-Toluenephosphonic acid, o-chloro-.alpha.-hydroxy-, diethyl ester; Phosphonic acid, (O-chloro-alpha-hydroxybenzyl)-, diethyl ester
• CAS NO: 7506-98-1
• Molecular Formula: C₁₁H₁₆ClO₄P
• Molecular Weight: 278.6691
• Mol File: 7506-98-1.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 387.6°C at 760 mmHg
• Flash Point: 188.2°C
• Density: 1.273g/cm³
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Refractive Index: 1.519
• CAS DataBase Reference: diethyl [(2-chlorophenyl)(hydroxy)methyl]phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl [(2-chlorophenyl)(hydroxy)methyl]phosphonate(7506-98-1)
• EPA Substance Registry System: diethyl [(2-chlorophenyl)(hydroxy)methyl]phosphonate(7506-98-1)

Safety Data

• Hazardous Substances Data: 7506-98-1(Hazardous Substances Data)

Upstream product

• 762-04-9 Diethyl phosphonate 
• 89-98-5 2-chloro-benzaldehyde 
• 122-52-1 triethyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 

Downstream Products

• 16656-42-1 diethyl ortho-chlorobenzoylphosphonate 
• 1614827-43-8 O,O-diethyl 1-((4,6-dichloropyrimidin-2-yl)carbamyloxy)-1-(2-chlorophenyl)methylphosphonate 
• 1024598-68-2 1-(2-chlorophenyl)-1-hydroxymethylphosphonic acid 
• 18442-44-9 diethyl α-trimethylsilyloxy-2-chlorobenzylphosphonate 
• 212071-38-0 C₁₉H₃₅ClN₂O₄P₂ 

Relevant articles and documents

Method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis

The invention relates to a method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis. The method comprises the following steps: dissolving diethyl phosphite and aromatic aldehyde in an organic solvent, adding a cop

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.

Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst

Choline hydroxide has been found to be an efficient basic ionic liquid catalyst for the synthesis of α-hydroxyphosphonates. Hydrophosphonylation of aldehydes was performed via the nucleophilic addition of diethylphosphite to aldehydic carbonyl compounds, in the presence of choline hydroxide under neat as well as solvent conditions. A wide array of substrates, including aromatic, fused aromatic, and heterocyclic aldehydes, were efficiently converted to their corresponding products in good yields. This protocol provides an alternative method for the straightforward synthesis of α-hydroxyphosphonates in high yields.