321-54-0

Basic information

• Product Name: COUMAPHOS-OXON
• Synonyms: phosphoricacid,diethylester,esterwith3-chloro-7-hydroxy-4-methylcoumari;3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl diethyl phosphate;COUMARIN,3-CHLORO-7-HYDROXY-4-METHYL-,DIETHYLPHOSPHATE;Coralox;Phosphoric acid (3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl)diethyl ester;Phosphoric acid 3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl diethyl;Phosphoric acid 3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yldiethyl ester;(3-chloro-4-methyl-2-oxo-chromen-7-yl) diethyl phosphate
• CAS NO: 321-54-0
• Molecular Formula: C₁₄H₁₆ClO₆P
• Molecular Weight: 346.7
• EINECS: 206-288-6
• Mol File: 321-54-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 226.5°C
• Flash Point: 347°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 1.01E-07mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: COUMAPHOS-OXON(CAS DataBase Reference)
• NIST Chemistry Reference: COUMAPHOS-OXON(321-54-0)
• EPA Substance Registry System: COUMAPHOS-OXON(321-54-0)

Safety Data

• RIDADR: 2783
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 321-54-0(Hazardous Substances Data)

Usage

Safety Profile

Deadly poison by ingestion. When heated to decomposition it emits very toxic fumes of POx and Cl-. See also ESTERS and PHOSPHATES.

InChI:InChI=1/C14H16ClO6P/c1-4-18-22(17,19-5-2)21-10-6-7-11-9(3)13(15)14(16)20-12(11)8-10/h6-8H,4-5H2,1-3H3

Upstream product

• 56-72-4 coumaphos 
• 6174-86-3 3-chloro-4-methylumbelliferone 
• 814-49-3 diethyl chlorophosphate 

Relevant articles and documents

Diethyl phosphite production from phosphorothioate degradation with molybdenum peroxides and hydrogen peroxide in ethanol

A polystyrene-supported molybdate-peroxide polymer (Mo-Y(s)) destroys phosphorothioate pesticides of the form (ArO)P(=S)(OEt)2 in EtOH under mild oxidative (H2O2) conditions and produces a commodity organophosphate. This is the first report of a metal-based system that successfully degrades the “live” pesticides parathion, diazinon and coumaphos. In addition to the operational advantages of heterogeneous reaction chemistry, the Mo-Y(s) support degrades multiple equivalents of the pesticide in H2O2(aq). Of particular importance is the predominant production of diethyl phosphite, a commodity chemical, from diazinon degradation over Mo-Y(s) in EtOH; no toxic oxon is found. Coumaphos and parathion produce the corresponding oxon which have ΔH? (kcal/mol) of 15.4 (0.5) and 21.7 (0.8), respectively; these activation parameters are consistent with key observations found in the relative amount of coumoxon and paraoxon produced. Finally, a discrete molybdate-peroxide complex is presented as a possible solution model for this heterogeneous reaction.

Analogues with fluorescent leaving groups for screening and selection of enzymes that efficiently hydrolyze organophosphorus nerve agents

Enzymes that efficiently hydrolyze highly toxic organophosphorus nerve agents could potentially be used as medical countermeasures. As sufficiently active enzymes are currently unknown, we synthesized twelve fluorogenic analogues of organophosphorus nerve agents with the 3-chloro-7-oxy-4- methylcoumarin leaving group as probes for high-throughput enzyme screening. This set included analogues of the pesticides paraoxon, parathion, and dimefox, and the nerve agents DFP, tabun, sarin, cyclosarin, soman, VX, and Russian-VX. Data from inhibition of acetylcholinesterase, in vivo toxicity tests of a representative analogue (cyclosarin), and kinetic studies with phosphotriesterase (PTE) from Pseudomonas diminuta, and a mammalian serum paraoxonase (PON1), confirmed that the analogues mimic the parent nerve agents effectively. They are suitable tools for high-throughput screens for the directed evolution of efficient nerve agent organophosphatases.