Product Name

  • Name

    Coumaphos

  • EINECS 200-285-3
  • CAS No. 56-72-4
  • Article Data11
  • CAS DataBase
  • Density 1.38 g/cm3
  • Solubility Insoluble in water < 1 mg/ml at 22 deg. C. Slightly soluble in DMSO, ethanol ?1 mg/l), acetone, chloro- -7 form. r.d. at 20 deg. C. 1.474. v.p. 1 x10 mm at 20 deg. C.
  • Melting Point 91ºC
  • Formula C14H16 Cl O5 P S
  • Boiling Point 449.9 °C at 760 mmHg
  • Molecular Weight 362.771
  • Flash Point 225.9 °C
  • Transport Information UN 2811
  • Appearance tan or beige solid
  • Safety 28-36/37-45-60-61-36-26-16
  • Risk Codes R21;R28;R50/53   
  • Molecular Structure Molecular Structure of 56-72-4 (Coumaphos)
  • Hazard Symbols
  • Synonyms Coumarin,3-chloro-7-hydroxy-4-methyl-, O-ester with O,O-diethyl phosphorothioate (8CI);Umbelliferone, 3-chloro-4-methyl-, O,O-diethyl phosphorothioate (6CI);3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate;3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester;3-Chloro-4-methylumbelliferone O-ester with O,O-diethyl phosphorothioate;3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate;3-Chloro-7-hydroxy-4-methyl-coumarin O-ester with O,O-diethyl phosphorothioate;Agridip; Asuntol; Bayer 21/199; Baymix; Baymix 50; Co-ral; Co-ral (phosphate);Coumafos; Coumaphos; ENT 17,957; Koral; Meldane; Meldone; Muscatox; Muscotox;NSC 8944; O,O-Diethyl 3-chloro-4-methyl-7-umbelliferone thiophosphate;O,O-Diethyl O-(3-chloro-4-methyl-2-oxo-2H-benzopyran-7-yl) phosphorothioate;O,O-Diethyl O-(3-chloro-4-methyl-7-coumarinyl) phosphorothioate; O,O-DiethylO-3-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl phosphorothioate;O-(3-Chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl) O,O-diethyl phosphorothioate;O-3-Chloro-4-methyl-7-coumarinyl O,O-diethyl phosphorothioate; Perizin; Prince;Resitox
  • PSA 99.80000
  • LogP 5.08170

Synthetic route

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

Sodium; 3-chloro-4-methyl-2-oxo-2H-chromen-7-olate

Sodium; 3-chloro-4-methyl-2-oxo-2H-chromen-7-olate

coumaphos
56-72-4

coumaphos

Conditions
ConditionsYield
In N,N-dimethyl-formamide64%
3-chloro-4-methylumbelliferone
6174-86-3

3-chloro-4-methylumbelliferone

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

coumaphos
56-72-4

coumaphos

Conditions
ConditionsYield
Stage #1: 3-chloro-4-methylumbelliferone With n-butyllithium In tetrahydrofuran; hexane for 1h;
Stage #2: diethyl phosphorochloridothioate In tetrahydrofuran; hexane at 20℃; for 12h;		58%
With copper; potassium carbonate; butanone
coumaphos
56-72-4

coumaphos

o,o-diethyl 6a,12a-dichloro-6a,6b,12a,12b-tetrahydro-6b,12b-dimethyl-6,12(6H,12H)-dioxocyclobuta<1,2-c:3,4-c'>bis<1>benzopyran-3,9-di-o-thiophosphate

o,o-diethyl 6a,12a-dichloro-6a,6b,12a,12b-tetrahydro-6b,12b-dimethyl-6,12(6H,12H)-dioxocyclobuta<1,2-c:3,4-c'>bis<1>benzopyran-3,9-di-o-thiophosphate

Conditions
ConditionsYield
In chloroform for 250h; Irradiation;20%
coumaphos
56-72-4

coumaphos

O,O,O,O-tetraethyl-O,O-4,4'-dimethyl-2,2'-dioxo-(3,3'-bi-2H-1-benzopyran-7,7'-diyl)-diphosphorothioate

O,O,O,O-tetraethyl-O,O-4,4'-dimethyl-2,2'-dioxo-(3,3'-bi-2H-1-benzopyran-7,7'-diyl)-diphosphorothioate

Conditions
ConditionsYield
With oxygen In chloroform Irradiation;
coumaphos
56-72-4

coumaphos

A

O-(4-Acetyl-3-hydroxyphenyl) O,O-diethyl thiophosphate

O-(4-Acetyl-3-hydroxyphenyl) O,O-diethyl thiophosphate

B

thiophosphoric acid O-[6a,12a-dichloro-9-(diethoxy-thiophosphoryloxy)-6b,12b-dimethyl-6,12-dioxo-6a,12,12a,12b-tetrahydro-6H,6bH-5,11-dioxa-dibenzo[a,b]biphenylen-3-yl] ester O',O''-diethyl ester

thiophosphoric acid O-[6a,12a-dichloro-9-(diethoxy-thiophosphoryloxy)-6b,12b-dimethyl-6,12-dioxo-6a,12,12a,12b-tetrahydro-6H,6bH-5,11-dioxa-dibenzo[a,b]biphenylen-3-yl] ester O',O''-diethyl ester

C

thiophosphoric acid O-[6a,12a-dichloro-9-(diethoxy-thiophosphoryloxy)-6b,12b-dimethyl-6,12-dioxo-6a,12,12a,12b-tetrahydro-6H,6bH-5,11-dioxa-dibenzo[a,b]biphenylen-3-yl] ester O',O''-diethyl ester

thiophosphoric acid O-[6a,12a-dichloro-9-(diethoxy-thiophosphoryloxy)-6b,12b-dimethyl-6,12-dioxo-6a,12,12a,12b-tetrahydro-6H,6bH-5,11-dioxa-dibenzo[a,b]biphenylen-3-yl] ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium dodecyl-sulfate In phosphate buffer at 30℃; pH=7.4; Dimerization; UV-irradiation;
...Expand
coumaphos
56-72-4

coumaphos

A

3-chloro-4-methylumbelliferone
6174-86-3

3-chloro-4-methylumbelliferone

B

O,O'-diethyl thiophosphoric acid
2465-65-8

O,O'-diethyl thiophosphoric acid

Conditions
ConditionsYield
With sodium perchlorate; cycloplatinated aryl ketoxime In acetonitrile at 25℃; pH=8.5; Kinetics;
methanol
67-56-1

methanol

coumaphos
56-72-4

coumaphos

Thiophosphorsaeure-O,O-diethyl-O-methylester
15959-01-0

Thiophosphorsaeure-O,O-diethyl-O-methylester

Conditions
ConditionsYield
With triethylamine; Pd(dmba)(py)(OTf) at 25℃; pH=10.80; Kinetics;
coumaphos
56-72-4

coumaphos

A

Coralox
321-54-0

Coralox

B

3-chloro-4-methylumbelliferone
6174-86-3

3-chloro-4-methylumbelliferone

C

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

Conditions
ConditionsYield
With water; dihydrogen peroxide In ethanol at 40℃; Kinetics; Temperature; Reagent/catalyst;
...Expand

Coumaphos Chemical Properties

IUPAC Name: 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one
CAS: 56-72-4
Formula : C14H16ClO5PS
Molecular Weight: 362.77

Density: 1.38 g/cm3 
Flash Point: 225.9 °C
Boiling Point: 449.9 °C at 760 mmHg
Appearance: tan or beige solid 
Index of Refraction: 1.577 
Molar Refractivity: 86.84 cm3 
Molar Volume: 261.8 cm3 
Polarizability: 34.42×10-24cm3 
Surface Tension: 53.9 dyne/cm 
Enthalpy of Vaporization: 70.87 kJ/mol 
Vapour Pressure: 2.76E-08 mmHg at 25°C
Water Solubility: 1.541(mg/L) at 25 °C
Product Categories: acaricidespesticides&metabolites;alpha sort;calphabetic;acaricidesalphabetic;C;CO - CZPesticides;insecticides;oeko-tex standard 100;organophorousmethod specific;pesticides;pesticides&metabolites.

Coumaphos Toxicity Data With Reference

1.    

otr-rat:emb 1400 ng/plate

     JJATDK    JAT, Journal of Applied Toxicology. 1 (1981),190.
2.    

orl-rat LD50:13 mg/kg

     DOEAAH    Down to Earth. A Review of Agricultural Chemical Progress. 35 (1979),25.
3.    

ihl-rat LC50:303 mg/m3

     VHTODE    Veterinary and Human Toxicology. 24 (1982),87.
4.    

skn-rat LD50:860 mg/kg

     WRPCA2    World Review of Pest Control. 9 (1970),119.
5.    

ipr-rat LD50:7500 µg/kg

     PSEBAA    Proceedings of the Society for Experimental Biology and Medicine. 129 (1968),699.
6.    

orl-mus LD50:28 mg/kg

     HYSAAV    Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 33 (12)(1968),334.
7.    

ipr-mus LD50:200 mg/kg

     PCOC**    Pesticide Chemicals Official Compendium ,Association of the American Pesticide Control Officials, Inc.(Topeka, KS.: ),1966,282.
8.    

orl-rbt LD50:80 mg/kg

     HYSAAV    Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 33 (12)(1968),334.
9.    

skn-rbt LD50:500 mg/kg

     VHTODE    Veterinary and Human Toxicology. 24 (1982),87.

Coumaphos Consensus Reports

NCI Carcinogenesis Bioassay (feed); No Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-96 ,1979. . EPA Extremely Hazardous Substances List.

Coumaphos Safety Profile

Poison by ingestion, skin contact, inhalation, and intraperitoneal routes. Mutation data reported. When heated to decomposition, it emits very toxic fumes of SOx, POx, and Cl−. See also COUMARIN.
Safety Information about 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one (56-72-4):
Hazard Codes:
T+:   N:   Xn:   F: 
Risk Statements about 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one (56-72-4): 
R21: Harmful in contact with skin.
R28:   Very Toxic if swallowed.
R50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R36: Irritating to the eyes.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R11: Highly Flammable.
Safety Statements about 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one (56-72-4):
S28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer).
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
S60: This material and/or its container must be disposed of as hazardous waste.
S61: Avoid release to the environment. Refer to special instructions safety data sheet.
S36: Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S16: Keep away from sources of ignition - No smoking.
RIDADR: 2783
RTECS: GN6300000
HazardClass: 6.1(a)
PackingGroup: II

Coumaphos Specification

  The chemical synonyms of 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylchromen-2-one (56-72-4) are 3-Chloro-4-methyl-7-coumarinyl diethyl phosphorothioate ; 3-chloro-4-methyl-7-coumarinyldiethylphosphorothioate ; 3-Chloro-4-methyl-7-hydroxycoumarin diethyl thiophosphoric acid ester ; 3-Chloro-4-methyl-7-hydroxycoumarindiethylthiophosphoricacidester ; 3-Chloro-4-methylumbelliferone o-ester with O,O-diethyl phosphorothioate ; 3-Chloro-4-methylumbelliferoneo-esterwitho,o-diethylphosphorothioate ; 3-Chloro-7-diethoxyphosphinothioyloxy-4-methylcoumarin ; 3-Chloro-7-hydroxy-4-methyl-coumarin O,O-diethyl phosphorothioate .Very toxic, probable oral lethal dose is 50-500 mg/kg, or between 1 teaspoonful and 1 oz. for a 70 kg (150 lb.) person. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes.When heated to decomposition, Coumaphos emits very toxic fumes of sulfur oxides, phosphorus oxides, and chlorides. Incompatible with piperonyl butoxide.

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