Product Name

  • Name

    O,O,O-TRIETHYLPHOSPHOROTHIOATE

  • EINECS
  • CAS No. 126-68-1
  • Article Data93
  • CAS DataBase
  • Density 1.109g/cm3
  • Solubility
  • Melting Point >280 °C (decomp)
  • Formula C6H15 O3 P S
  • Boiling Point 200.4°Cat760mmHg
  • Molecular Weight 198.223
  • Flash Point 75°C
  • Transport Information
  • Appearance
  • Safety Poison by inhalation and intravenous routes. A cholinesterase inhibitor. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits very toxic fumes of POx and SOx. See also PARATHION.
  • Risk Codes
  • Molecular Structure Molecular Structure of 126-68-1 (O,O,O-TRIETHYLPHOSPHOROTHIOATE)
  • Hazard Symbols Toxic by ingestion, cholinesterase inhibitor.
  • Synonyms Ethylphosphorothioate, (EtO)3PS (6CI); Ethyl thiophosphate, (EtO)3PS (5CI); NSC2650; O,O,O-TEPT; O,O,O-Triethyl phosphorothioate; O,O,O-Triethylthiophosphate; O,O',O''-Triethyl phosphorothioate; Thiophosphoric acidtri-O-ethyl ester; Triethoxyphosphine sulfide; Triethyl phosphorothioate;Triethyl phosphorothionate; Triethyl thiophosphate
  • PSA 69.59000
  • LogP 2.97100

Synthetic route

triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With N,N'-dimethylthioperoxydicarbamic acid In acetonitrile at 20℃;99%
With N-Bromosuccinimide; triphenylsilanethiol In benzene for 1h;93%
With propylene sulphide; [ReOCl3(OPPh3)(SMe2)] In dichloromethane for 0.333333h; Ambient temperature;85%
diphenyl-4,5 dithiole-1,3 thiones-2
17534-37-1

diphenyl-4,5 dithiole-1,3 thiones-2

A

tetraphenyl-[2,2']bi[1,3]dithiolylidene
23780-79-2

tetraphenyl-[2,2']bi[1,3]dithiolylidene

B

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With triethyl phosphite In acetonitrile for 16h; Irradiation;A 91%
B n/a
N-(chlorosulfanyl)morpholine
2958-89-6

N-(chlorosulfanyl)morpholine

triethyl phosphite
122-52-1

triethyl phosphite

A

Diethyl 4-morpholidophosphate
37097-43-1

Diethyl 4-morpholidophosphate

B

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

C

O,O-diethyl S-morpholino phosphorothioate
56341-75-4

O,O-diethyl S-morpholino phosphorothioate

Conditions
ConditionsYield
6-13 deg C then rt., 4 h;A 81%
B 4%
C 15%
6-13 deg C then rt., 4 h;A 23%
B 7%
C 70%
at 6 - 13℃;A 9%
B 7%
C 10.7 g
sodium ethanolate
141-52-6

sodium ethanolate

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
In ethanol at 20℃; for 14h;78.2%
diisopropoxyphosphinothionyl tert-butylamino trisulfide
76289-06-0

diisopropoxyphosphinothionyl tert-butylamino trisulfide

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

diisopropoxyphosphinothionyl tert-butylamino disulfide
76276-34-1

diisopropoxyphosphinothionyl tert-butylamino disulfide

Conditions
ConditionsYield
In diethyl ether at 0℃; for 0.25h;A 78%
B 63.5%
dicyclohexyl-carbodiimide
538-75-0

dicyclohexyl-carbodiimide

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

O,O'-diethyl thiophosphoric acid

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

C

tetraethyl thiopyrophosphate
645-78-3

tetraethyl thiopyrophosphate

D

1,3-dicyclohexylthiourea
1212-29-9

1,3-dicyclohexylthiourea

Conditions
ConditionsYield
In diethyl ether for 240h; Mechanism; Product distribution; Ambient temperature; solvent: acetonitrile;A n/a
B n/a
C 45%
D 77%
O,O'-diethyl thiophosphoric acid
2465-65-8

O,O'-diethyl thiophosphoric acid

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

C

tetraethyl thiopyrophosphate
645-78-3

tetraethyl thiopyrophosphate

D

1,3-dicyclohexylthiourea
1212-29-9

1,3-dicyclohexylthiourea

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In diethyl ether for 240h; Ambient temperature;A n/a
B n/a
C 45%
D 77%
ethanol
64-17-5

ethanol

O-phenyl> O,O-diethyl phosphorothioate
106259-91-0

O-phenyl> O,O-diethyl phosphorothioate

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O-(o-aminophenyl) O,O-diethyl phosphorothioate
106259-89-6

O-(o-aminophenyl) O,O-diethyl phosphorothioate

Conditions
ConditionsYield
for 10h; Heating;A 69%
B 71%
3-phenylethanoic dithioperoxyanhydride
15088-78-5

3-phenylethanoic dithioperoxyanhydride

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

phenacetyl sulfide
97754-54-6

phenacetyl sulfide

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 0.0833333h;A 70%
B n/a
triethyl phosphite
122-52-1

triethyl phosphite

A

diethyl sulfate
64-67-5

diethyl sulfate

B

triethyl phosphate
78-40-0

triethyl phosphate

C

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

D

ethylphosphonic acid diethyl ester
78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -78℃;A 2%
B 70%
C 23%
D 5%
ethanol
64-17-5

ethanol

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

O,O'-diethyl thiophosphoric acid

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

Conditions
ConditionsYield
With thiamine diphosphate; diethylazodicarboxylate In benzene at 35 - 40℃; for 6h; Yield given;A n/a
B 66%
With thiamine diphosphate; diethylazodicarboxylate In benzene at 35 - 40℃; for 6h; Yields of byproduct given;A n/a
B 66%
Lawessons reagent
19172-47-5

Lawessons reagent

triethyl phosphate
78-40-0

triethyl phosphate

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane
137171-51-8, 67218-02-4

2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane

Conditions
ConditionsYield
In benzene for 12h; Heating;A 61%
B n/a
1,2-epithio-3-methoxypropane
19858-14-1

1,2-epithio-3-methoxypropane

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

methylallylether
627-40-7

methylallylether

cyclohexene sulfide
286-28-2

cyclohexene sulfide

diethyl ether
60-29-7

diethyl ether

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

cyclohexene
110-83-8

cyclohexene

carbon disulfide
75-15-0

carbon disulfide

methyl-imidophosphoric acid triethyl ester
71867-67-9

methyl-imidophosphoric acid triethyl ester

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

O-ethyl dichlorothiophosphate
1498-64-2

O-ethyl dichlorothiophosphate

sodium ethanolate
141-52-6

sodium ethanolate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

ethanol
64-17-5

ethanol

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With sulfur; toluene; phosphorus trichloride
With trichlorophosphate
With phosphorus(V) oxybromide
sodium ethanolate
141-52-6

sodium ethanolate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With trichlorophosphate
propylene sulphide
1072-43-1

propylene sulphide

triethyl phosphite
122-52-1

triethyl phosphite

A

propene
187737-37-7

propene

B

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

ethanol
64-17-5

ethanol

sodium acetate
127-09-3

sodium acetate

diethyl phosphorochloridothioate
2524-04-1

diethyl phosphorochloridothioate

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

phenylmethanethiol
100-53-8

phenylmethanethiol

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

toluene
108-88-3

toluene

Conditions
ConditionsYield
Gluehlampenlicht.Irradiation;
Diethyl disulfide
110-81-6

Diethyl disulfide

triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With di-tert-butyl peroxide at 140℃;
Diethyl disulfide
110-81-6

Diethyl disulfide

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

Conditions
ConditionsYield
at 160℃;
dibenzyl disulphide
150-60-7

dibenzyl disulphide

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

dibenzyl sulfide
538-74-9

dibenzyl sulfide

C

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

D

toluene
108-88-3

toluene

Conditions
ConditionsYield
at 60℃; Irradiation;
diethyl sulphide
352-93-2

diethyl sulphide

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
at 140℃;
Octanethiol
111-88-6

Octanethiol

triethyl phosphite
122-52-1

triethyl phosphite

A

octane
111-65-9

octane

B

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
unter der Einwirkung von Licht;
dibutyl disulfide
629-45-8

dibutyl disulfide

di-tert-butyl peroxide
110-05-4

di-tert-butyl peroxide

triethyl phosphite
122-52-1

triethyl phosphite

A

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

B

Isobutane
75-28-5

Isobutane

C

Dibutyl sulfide
544-40-1

Dibutyl sulfide

D

n-butane
106-97-8

n-butane

Conditions
ConditionsYield
at 140℃;
thiocyanogen
505-14-6

thiocyanogen

triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

diacetyl disulfide
592-22-3

diacetyl disulfide

triethyl phosphite
122-52-1

triethyl phosphite

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

ethanol
64-17-5

ethanol

diethyl thiophosphorocyanidate
87174-50-3

diethyl thiophosphorocyanidate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Conditions
ConditionsYield
With potassium hydroxide In water for 0.25h;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

triethyl phosphate
78-40-0

triethyl phosphate

Conditions
ConditionsYield
With pyridine; trifluoroacetic anhydride for 24h;100%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 20h;100%
With ozone In dichloromethane at -75℃;95%
aluminum(III) perchlorate hydrate

aluminum(III) perchlorate hydrate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Al(3+)*3(OC2H5)2POS(1-)=Al((OC2H5)2POS)3

Al(3+)*3(OC2H5)2POS(1-)=Al((OC2H5)2POS)3

Conditions
ConditionsYield
In neat (no solvent) Al(ClO4)3 dissolved in a large excess of organic compound at ambient temp., temp. increased by 1-2°C per min, precipitated at 85-90.dergree.C, mixture allowed to cool; supernatant removed, washed with anhydrous diethyl ether, stored in vac. over anhydrous CaSO4; elem. anal.;95%
In ethanol byproducts: ethyl perchlorate; dissolving metal perchlorate in ethanol/triethyl orthoformate; stirringat 50°C for 2 h; cooling to room temp.; addn. of ligand; stirring at 80-90°C; pptn. after 20-40 mins; elem. anal.;35-50
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

A

Diethyl phosphate
598-02-7

Diethyl phosphate

B

ethylphosphonic acid diethyl ester
78-38-6

ethylphosphonic acid diethyl ester

C

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

Conditions
ConditionsYield
With magnesium monoperoxyphthalate hexahydrate In water at 25℃; for 24h;A 10%
B 81%
C 9%
[Cp(CO)2Fe(THF)]PF6

[Cp(CO)2Fe(THF)]PF6

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

(η-cyclopentadienyl)dicarbonyl(triethylthiophosphato)iron hexafluorophosphate
115565-36-1

(η-cyclopentadienyl)dicarbonyl(triethylthiophosphato)iron hexafluorophosphate

Conditions
ConditionsYield
In dichloromethane stirring of a mixture of the THF-complex and the P-ligand in CH2Cl2 at room temp. for 36 h under N2; addn. of ether, filtn. of ppt., washing (ether), drying in vacuo, recrystn. (CH2Cl2/ether), elem. anal.;70%
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

acetonitrile
75-05-8

acetonitrile

A

triethyl phosphate
78-40-0

triethyl phosphate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

C

bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

D

N-(ethyl)acetonitrilium tetrafluoroborate
462-35-1

N-(ethyl)acetonitrilium tetrafluoroborate

E

NO

NO

Conditions
ConditionsYield
With nitrosonium tetrafluoroborate In water 15-30 min; Further byproducts given. Yields of byproduct given;A n/a
B n/a
C 42%
D n/a
E n/a
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

acetonitrile
75-05-8

acetonitrile

A

triethyl phosphate
78-40-0

triethyl phosphate

B

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

C

ethanol
64-17-5

ethanol

D

bis(diethylphosphoryl)disulfide
4403-51-4

bis(diethylphosphoryl)disulfide

E

N-(ethyl)acetonitrilium tetrafluoroborate
462-35-1

N-(ethyl)acetonitrilium tetrafluoroborate

F

NO

NO

Conditions
ConditionsYield
With nitrosonium tetrafluoroborate for 0.5h;A n/a
B n/a
C n/a
D 42%
E 65 % Spectr.
F n/a
copper(II) perchlorate hydrate

copper(II) perchlorate hydrate

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Cu(2+)*2(OC2H5)2POS(1-)=Cu((OC2H5)2POS)2

Cu(2+)*2(OC2H5)2POS(1-)=Cu((OC2H5)2POS)2

Conditions
ConditionsYield
In ethanol byproducts: ethyl perchlorate; dissolving metal perchlorate in ethanol/triethyl orthoformate; stirringat 50°C for 2 h; cooling to room temp.; addn. of ligand; stirring at 80-90°C for 2 h; elem. anal.;3%
ethyl bromide
74-96-4

ethyl bromide

O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

Conditions
ConditionsYield
at 160℃;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Isobutyl iodide
513-38-2

Isobutyl iodide

O,O-diethyl (S)-isobutylphosphorothioate
26629-01-6

O,O-diethyl (S)-isobutylphosphorothioate

Conditions
ConditionsYield
at 120℃; im Rohr;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

sodium isobutoxide
13259-29-5

sodium isobutoxide

thiophosphoric acid O-ethyl ester-O-isobutyl ester; silver salt

thiophosphoric acid O-ethyl ester-O-isobutyl ester; silver salt

Conditions
ConditionsYield
With 2-methyl-propan-1-ol bei nachfolgender Einw. von Silbernitrat;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

Diethyl phosphoramidate
1068-21-9

Diethyl phosphoramidate

Conditions
ConditionsYield
With diethyl ether; ammonia at 150℃;
With ethanol; ammonia at 120℃;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

O,O,S-triethyl phosphorothioate
1186-09-0

O,O,S-triethyl phosphorothioate

Conditions
ConditionsYield
at 200℃;
at 180℃;
With silver nitrate man setzt das erhaltene S-Silbersalz des Thiophosphorsaeure-O.O-diaethylesters mit Aethyljodid in Alkohol;
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

sulfotep
3689-24-5

sulfotep

Conditions
ConditionsYield
With sulfuric acid
O,O,O-triethyl phosphorothioate
126-68-1

O,O,O-triethyl phosphorothioate

diethoxyoxophosphoranesulfenyl chloride
1186-08-9

diethoxyoxophosphoranesulfenyl chloride

Conditions
ConditionsYield
With tetrachloromethane; chlorine at -5℃;
With sulfuryl dichloride
With sulfuryl dichloride In benzene

Triethyl phosphorothioate Chemical Properties

IUPAC Name: Triethoxy(sulfanylidene)-λ5-phosphane 
Molecular Formula: C6H15O3PS
Molecular Weight: 198.24g/mol
EINECS: 204-797-8
Density: 1.109g/cm3
Boiling Point: 231.6 °C at 760 mmHg
Flash Point: 93.9 °C
Freely Rotating Bonds: 6
Polar Surface Area: 70.64 Å2
Index of Refraction: 1.452
Molar Refractivity: 48.2 cm3
Molar Volume: 178.4 cm3
Polarizability: 19.11 ×10-24 cm3
Surface Tension: 34.6 dyne/cm
Enthalpy of Vaporization: 44.92 kJ/mol
Vapour Pressure: 0.0938 mmHg at 25°C
The Cas Register Number  of Triethyl phosphorothioate is 126-68-1.The chemical synonyms of Triethyl phosphorothioate (CAS NO.126-68-1) are (C2H5O)3PS ; Ethyl phosphorothioate ((EtO)3PS) ; O,O,O-Triethyl thiophosphate ; O,O,O-Triethylester kyseliny thiofosforecne ; O,O,O-triethylesterkyselinythiofosforecne ; O,O,O-Triethylthiofosfat ; O,O,O-triethylthiophosphate ; Phosphine sulfide, triethoxy- .The molecular structure of Triethyl phosphorothioate (CAS NO.126-68-1) is.

Triethyl phosphorothioate Uses

 Triethyl phosphorothioate (CAS NO.126-68-1) is used as pesticide.

Triethyl phosphorothioate Toxicity Data With Reference

1.    

ihl-rat LCLo:41 ppm/4H

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,207.
2.    

ivn-rat LDLo:250 mg/kg

    NATUAS    Nature. 179 (1957),154.

Triethyl phosphorothioate Safety Profile

Poison by inhalation and intravenous routes. A cholinesterase inhibitor. Combustible when exposed to heat or flame; can react with oxidizing materials. When heated to decomposition it emits very toxic fumes of POx and SOx. See also PARATHION.
Safety Statements: 22-24/25 
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3

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