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78-40-0

Basic Information
CAS No.: 78-40-0
Name: Triethyl phosphate
Molecular Structure:
Molecular Structure of 78-40-0 (Triethyl phosphate)
Formula: C6H15O4P
Molecular Weight: 182.15 .
Synonyms: Triethylphosphate;Phosphoric acid, triethyl ester;Triethoxyphosphine oxide;1-diethoxyphosphoryloxyethane;Ethyl phosphate ((EtO)3PO);Triethylfosfat [Czech];Tris(ethyl) phosphate;Phosphoric acid,esters,triethyl ester;Levagard TEP;Ethyl phosphate (VAN);TEP Triethyl phosphate;Triethyl phosphate (TEP);Triethyl Phosp;TEP;Triethyl phosphate(TEP);
EINECS: 201-114-5
Density: 1.066 g/cm3
Melting Point: -56.4 ºC
Boiling Point: 219.3 ºC at 760 mmHg
Flash Point: 115.6 ºC
Solubility: SOLUBLE
Appearance: colourless liquid with a mild odour
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 25
Transport Information:
PSA: 54.57000
LogP: 2.20400
Synthetic route
126-68-1

O,O,O-triethyl phosphorothioate

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%
2651-89-0

O,O,O-triethylselenophosphate

78-40-0

triethyl phosphate

Conditions
ConditionsYield
With pyridine; trifluoroacetic anhydride for 2h;100%
With ozone In dichloromethane at -75℃;94%
With Oxone In tetrahydrofuran; methanol Ambient temperature;85%
64-17-5

ethanol

762-04-9

phosphonic acid diethyl ester

78-40-0

triethyl phosphate

Conditions
ConditionsYield
With iodosylbenzene In tetrahydrofuran for 24h; Heating;100%
With tetraethylammonium iodide In acetonitrile at 25℃; electrosynthesis;98.7%
With oxygen; copper dichloride at 50℃; for 5h; Product distribution; effect of the temp., the reagent ratio, the reaction time;97%
64-17-5

ethanol

78-40-0

triethyl phosphate

Conditions
ConditionsYield
With phosphorous; oxygen; copper dichloride In benzene at 50℃;98.2%
With phosphorous; oxygen; copper dichloride In benzene at 50℃; Product distribution; Mechanism; other alkylalcohols, var. concentrations of reagents;98.2%
With trichlorophosphate In acetone at 10 - 30℃; under 10 Torr; for 4h;97.7%
122-52-1

triethyl phosphite

A

64-67-5

diethyl sulfate

B

78-40-0

triethyl phosphate

C

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
With sulfur trioxide In dichloromethane at -78℃;A 97%
B 2%
C 1%
With sulfur trioxide In dichloromethane at -78℃;A 17%
B 55%
C 28%
111-25-1

1-bromo-hexane

122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

78-38-6

ethylphosphonic acid diethyl ester

C

16165-66-5

diethyl hexylphosphonate

Conditions
ConditionsYield
at 170℃; for 12h; Inert atmosphere; Dean-Stark;A n/a
B n/a
C 95%
64-17-5

ethanol

A

1623-14-9

ethyl phosphate

B

598-02-7

Diethyl phosphate

C

78-40-0

triethyl phosphate

Conditions
ConditionsYield
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis;A n/a
B n/a
C 84%
866-23-9

diethyl (trichloromethyl)phosphonate

64-17-5

ethanol

762-04-9

phosphonic acid diethyl ester

A

78-40-0

triethyl phosphate

B

3167-62-2

diethyl (dichloromethyl)phosphonate

Conditions
ConditionsYield
With triethylamine at 20℃;A n/a
B 84%
67751-11-5

N,N,N',N'-Tetramethylharnstoff-diethylacetal

762-04-9

phosphonic acid diethyl ester

A

78-40-0

triethyl phosphate

B

124-40-3

dimethyl amine

C

119949-72-3

diethyl phosphonate

Conditions
ConditionsYield
at 80℃; under 400 Torr; reduced pressure;A n/a
B n/a
C 83%

6-Hydroxy-5-(triaethoxyphosphoranylidenamino)-5,6-dihydro-β-ionon

A

78-40-0

triethyl phosphate

B

5,6-epimino-5,6-dihydro-β-ionone

Conditions
ConditionsYield
With ethanol In dichloromethane at 40℃; for 0.5h;A n/a
B 82%

(4R*,5S*)-2,2,2-Triaethoxy-4,5-diphenyl-1,3,2λ5-oxazaphospholidin

A

78-40-0

triethyl phosphate

trans-2,2-Diphenylaziridine
25125-72-8

trans-2,2-Diphenylaziridine

Conditions
ConditionsYield
With ethanol In dichloromethane at 40℃; for 0.5h;A n/a
B 82%
64-17-5

ethanol

(1,1,1-trichloromethyl)phosphonic acid diisopropyl ester

(1,1,1-trichloromethyl)phosphonic acid diisopropyl ester

762-04-9

phosphonic acid diethyl ester

A

78-40-0

triethyl phosphate

B

55696-11-2

dichloromethylphosphonic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine at 20℃;A n/a
B 82%
64-17-5

ethanol

53582-73-3

di-n-propyl trichloromethylphosphonate

762-04-9

phosphonic acid diethyl ester

A

78-40-0

triethyl phosphate

B

56973-22-9

O,O-di-n-propyl 1,1-dichloromethylphosphonate

Conditions
ConditionsYield
With triethylamine at 20℃;A n/a
B 81%
106-45-6

para-thiocresol

122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

4143-38-8

thiophosphoric acid O,O'-diethyl ester S-p-tolyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; Reagent/catalyst;A 12%
B 81%
615-41-8

2-iodochlorobenzene

122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

78-38-6

ethylphosphonic acid diethyl ester

C

28036-18-2

2-Chlorphenylphosphonsaeurediethylester

Conditions
ConditionsYield
With Pd/C (30%) at 175℃; for 12h; Inert atmosphere; Dean-Stark;A n/a
B n/a
C 80%
64-17-5

ethanol

A

78-40-0

triethyl phosphate

B

78-38-6

ethylphosphonic acid diethyl ester

C

762-04-9

phosphonic acid diethyl ester

Conditions
ConditionsYield
With phosphorous; CuCl2bpy3 In N,N-dimethyl-formamide at 50℃; Electrolysis;A 79.3%
B 5.4%
C 15.3%
With phosphorous; CuCl2bpy3 In acetonitrile at 50℃; Electrolysis;A 55%
B 15.5%
C 29.5%
With phosphorous; CuCl2bpy3 at 50℃; Electrolysis;A 28.5%
B 17.5%
C 16%
1474-78-8

triethyl phosphonoformate

A

78-40-0

triethyl phosphate

B

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
at 395℃; for 8h;A 79%
B 8%
64-17-5

ethanol

5887-93-4

trichloromethyl-phosphonic acid dibutyl ester

762-04-9

phosphonic acid diethyl ester

A

78-40-0

triethyl phosphate

B

66703-06-8

C9H19Cl2O3P

Conditions
ConditionsYield
With triethylamine at 20℃;A n/a
B 79%
122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

762-04-9, 123-22-8

Diethyl phosphonate

Conditions
ConditionsYield
With Oxone In tetrahydrofuran; methanol Ambient temperature;A 78%
B n/a

2-(bromo(phenyl)methyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

1080-32-6

O,O-diethyl benzylphosphonate

C

762-04-9

phosphonic acid diethyl ester

Conditions
ConditionsYield
at 130℃; for 0.5h; Inert atmosphere;A n/a
B 76%
C n/a
1379148-12-5

diethyl {2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)}benzoylphosphonate

122-52-1

triethyl phosphite

A

78-40-0

triethyl phosphate

B

1379148-13-6

diethyl (7,13-dioxo-13,13a-dihydro-7H-benzo[de]indolo[2,1-a]isoquinolin-13a-yl)phosphonate

C

1379148-15-8

diethyl 7-oxo-7H-benzo[de]indolo[2,1-a]isoquinolin-13-ylphosphate

D

1379148-14-7

C27H31NO9P2

Conditions
ConditionsYield
In toluene at 115℃; for 17h;A n/a
B 75%
C 5%
D 10 %Spectr.
78-40-0

triethyl phosphate

33821-94-2

3-bromopropyltetrahydropyranylether

117144-98-6

[3-(Tetrahydro-pyran-3-yloxy)-propyl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
at 175℃; for 5h;100%
78-40-0

triethyl phosphate

154057-56-4

3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline

154057-57-5

diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate

Conditions
ConditionsYield
In toluene for 12h; Heating;100%
78-40-0

triethyl phosphate

zirconium(IV)

zirconiumoxide ethylphosphate

Conditions
ConditionsYield
In sulfuric acid precipitation of zirconiumoxide ethylphosphate from 3.6n H2SO4 solution, heating 12-15 hours;;100%
In sulfuric acid precipitation of zirconiumoxide ethylphosphate from boiling heat;;
In sulfuric acid hydrolysis of a 0.1 mol Zr containing 6n H2SO4 solution with 375 ml (C2H5)3PO4 per mol ZrO2;; precipitation after heating for 5-6 hours;
78-40-0

triethyl phosphate

25542-62-5

6-bromo-hexanoic acid ethyl ester

54965-29-6

6-(diethoxyphosphoryl)hexanoic acid ethyl ester

Conditions
ConditionsYield
at 160℃; for 14h; Inert atmosphere;100%
78-40-0

triethyl phosphate

823-78-9

meta-bromobenzyl bromide

128833-03-4

P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester

Conditions
ConditionsYield
at 160℃; for 2h;100%
78-40-0

triethyl phosphate

1,5-diazabicyclo[4.3.0]-5-nonenium diethylphosphate

Conditions
ConditionsYield
Stage #1: triethyl phosphate With diethylamine at 125℃; for 30h;
Stage #2: DBN
99.7%
78-40-0

triethyl phosphate

109-89-7

diethylamine

5802-75-5

diethylammonium diethylphosphate

Conditions
ConditionsYield
at 125℃; for 30h;99.7%
848906-02-5

1,2,3,4-tetramethylimidazolium methyl carbonate

78-40-0

triethyl phosphate

1,2,3,4-tetramethylimidazolium diethylphosphate

Conditions
ConditionsYield
Stage #1: triethyl phosphate With diethylamine at 125℃; for 30h;
Stage #2: 1,2,3,4-tetramethylimidazolium methyl carbonate In methanol Reagent/catalyst;
99.5%
78-40-0

triethyl phosphate

109-89-7

diethylamine

5802-76-6

diethyl triethylammonium phosphate

Conditions
ConditionsYield
at 125℃; for 30h;99.5%
616-47-7

1-methyl-1H-imidazole

78-40-0

triethyl phosphate

3-ethyl-1-methylimidazol-3-ium diethyl phosphate

Conditions
ConditionsYield
In water at 130℃; for 14h;99%
at 100℃; for 36h;97.3%
at 140℃; Inert atmosphere;
78-40-0

triethyl phosphate

877-88-3

3,5-dimethoxybenzyl bromide

108957-75-1

diethyl 3,5-dimethoxybenzylphosphonate

Conditions
ConditionsYield
at 160℃; for 4h;99%
at 120℃; for 10h;95%
at 160℃; for 4h;95%
78-40-0

triethyl phosphate

17162-77-5

β-ethoxyvinyldichlorophosphine

((2-ethoxyvinyl)-bis(phosphonato)phosphine)

Conditions
ConditionsYield
In toluene Michaelis-Arbuzov Synthesis; Schlenk technique; Inert atmosphere;99%
78-40-0

triethyl phosphate

74-88-4

methyl iodide

683-08-9

Diethyl methylphosphonate

Conditions
ConditionsYield
at 60℃; for 4h;99%
78-40-0

triethyl phosphate

1,2,3,4-tetramethylimidazolinium methyl carbonate

1,2,3,4-tetramethylimidazolinium diethyl phosphate salt

Conditions
ConditionsYield
In methanol at 120℃; under 7500.75 Torr; for 36h;99%
78-40-0

triethyl phosphate

monomethyl carbonate N-picoline salt

diethyl phosphate N-picoline salt

Conditions
ConditionsYield
In methanol at 80℃; under 15001.5 Torr; for 48h;98.7%
78-40-0

triethyl phosphate

N-methylpyrrollium monomethyl carbonate salt

diethyl phosphate N-methylpyrrollium salt

Conditions
ConditionsYield
In methanol at 130℃; under 7500.75 Torr; for 36h;98.7%
67-56-1

methanol

78-40-0

triethyl phosphate

triethyl hydrazine monomethyl methyl carbonate

diethyl phosphate methyl triethyl hydrazine

Conditions
ConditionsYield
at 100℃; under 7500.75 Torr; for 36h;98.2%
78-40-0

triethyl phosphate

839-90-7

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione

C15H27N3O11P2

Conditions
ConditionsYield
With sodium carbonate at 78 - 200℃; Temperature;98.07%
78-40-0

triethyl phosphate

93345-12-1

4-(3,4-Dichloro-benzenesulfonylamino)-benzenesulfonyl azide

93345-13-2

C18H23Cl2N2O7PS2

Conditions
ConditionsYield
In toluene at 0℃;98%
78-40-0

triethyl phosphate

939-26-4

2-bromomethylnaphthyl bromide

57277-25-5

(naphthalen-2-ylmethyl)phosphonic acid diethyl ester

Conditions
ConditionsYield
at 140℃; for 12h;98%
78-40-0

triethyl phosphate

60792-57-6

3-methyl-1-oxo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile

121105-88-2

5-ethyl-3-methyl-1-oxo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile

Conditions
ConditionsYield
With potassium carbonate for 1h; Heating;98%

potassium [14C]formate

78-40-0

triethyl phosphate

41279-20-3

ethyl <1-14C>formate

Conditions
ConditionsYield
for 0.333333h; microwave irradiation;98%
78-40-0

triethyl phosphate

811-73-4

trimethylstannyl iodide

O,O'-diethyl-O''-trimethylstannyl phosphate

Conditions
ConditionsYield
In further solvent(s) byproducts: C2H5I; to (EtO)3PO Me3SnI added, stirred at 85°C; volatiles removed, residue crystalized; elem. anal.;98%
In 1,4-dioxane Kinetics; byproducts: C2H5I; (EtO)3PO and Me3SnI in dioxane mixad, 85°C, sealed tube; not isolated, detected by NMR;
78-40-0

triethyl phosphate

1493-13-6

trifluorormethanesulfonic acid

triethoxy(hydroxy)phosphonium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;98%
895550-03-5

2-(bromomethyl)-3-methylbenzo[b]thiophene

78-40-0

triethyl phosphate

957059-39-1

(3-methylbenzo[b]thiophen-2-ylmethyl)phosphonic acid diethyl ester

Conditions
ConditionsYield
In toluene for 18h; Arbuzov reaction; Reflux;98%
78-40-0

triethyl phosphate

62601-06-3

sodium 1-(13)C-propionate

78217-95-5

Propanoic-1-13C Acid Ethyl Ester

Conditions
ConditionsYield
1.) reflux, 3.5 h;97%
for 3.5h; Heating;97%
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History

 Triethyl phosphate was firstly studied by a French chemist named Jean Louis Lassaigne in the early 1800s.

Specification

1. Introduction of Triethyl Phosphate
Triethyl Phosphate, its synonyms are Phosphoric acid, triethyl ester; Tris(ethyl) phosphate; Triethylfosfat; TEP; Triethoxyphosphine oxide; Ethyl phosphate. Triethyl phosphate is a colorless liquid.

2. Properties of Triethyl Phosphate
Water Solubility: soluble
Density: 1.066 g/cm3
Flash Point: 115.6 °C
Enthalpy of Vaporization: 43.72 kJ/mol
Boiling Point: 219.3 °C at 760 mmHg
Vapor pressure: 1 mm Hg ( 40 °C)
Melting Point: -56 °C
Vapour Pressure of Triethyl Phosphate (CAS NO.78-40-0): 0.177 mmHg at 25 °C
Classification Code: Mutation data; Reproductive Effect; Skin / Eye Irritant
Product Categories: Organics;Functional Materials;Phosphates (Plasticizer);Plasticizer

3. Structure Descriptors of Triethyl Phosphate
Canonical SMILES: P(OCC)(OCC)(OCC)=O
InChI: InChI=1/C6H15O4P/c1-4-8-11(7,9-5-2)10-6-3/h4-6H2,1-3H3

4. Toxicity of Triethyl Phosphate

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 605, 1969.
guinea pig LD50 oral 1600mg/kg (1600mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 605, 1969.
guinea pig LD50 skin > 20mL/kg (20mL/kg)   National Technical Information Service. Vol. OTS0528351,
mouse LC inhalation > 44300ug/m3/4 (44.3mg/m3)   "Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 227, 1999.
mouse LD50 intraperitoneal 485mg/kg (485mg/kg)   Therapie. Vol. 15, Pg. 237, 1960.
mouse LD50 oral 1180mg/kg (1180mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 227, 1999.
rat LCLo inhalation 28000ppm/6H (28000ppm)   American Industrial Hygiene Association Journal. Vol. 34, Pg. 286, 1973.
rat LD50 intraperitoneal 800mg/kg (800mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 605, 1969.
rat LD50 oral 1165mg/kg (1165mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: ATAXIA
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 227, 1999.
rat LDLo intravenous 1gm/kg (1000mg/kg) BEHAVIORAL: GENERAL ANESTHETIC
BEHAVIORAL: MUSCLE WEAKNESS
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Nature. Vol. 179, Pg. 154, 1957.

5. Safety Information of Triethyl Phosphate
Hazard Codes: Xn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 25
S25: Avoid contact with eyes.
WGK Germany: 1
RTECS of Triethyl Phosphate: TC7900000

6. Use of Triethyl Phosphate
Triethyl Phosphate, its primary uses are as an industrial catalyst, a polymer resin modifier, and a plasticizer (eg. for unsaturated polyesters). In smaller scale it is used as a solvent for eg. cellulose acetate, flame retardant, an intermediate for pesticides and other chemicals, stabilizer for peroxides, a strength agent for rubber and plastic including vinyl polymers and unsaturated polyesters, etc. It is is also a common intermediate in the manufacture of pesticides. Triethyl phosphate is also a common intermediate in the manufacture of pesticides.

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