Conditions | Yield |
---|---|
With pyridine; trifluoroacetic anhydride for 24h; | 100% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 20h; | 100% |
With ozone In dichloromethane at -75℃; | 95% |
Conditions | Yield |
---|---|
With pyridine; trifluoroacetic anhydride for 2h; | 100% |
With ozone In dichloromethane at -75℃; | 94% |
With Oxone In tetrahydrofuran; methanol Ambient temperature; | 85% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
triethyl phosphite
A
diethyl sulfate
B
triethyl phosphate
C
ethylphosphonic acid diethyl ester
Conditions | Yield |
---|---|
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% |
1-bromo-hexane
triethyl phosphite
A
triethyl phosphate
B
ethylphosphonic acid diethyl ester
C
diethyl hexylphosphonate
Conditions | Yield |
---|---|
at 170℃; for 12h; Inert atmosphere; Dean-Stark; | A n/a B n/a C 95% |
ethanol
A
ethyl phosphate
B
Diethyl phosphate
C
triethyl phosphate
Conditions | Yield |
---|---|
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis; | A n/a B n/a C 84% |
diethyl (trichloromethyl)phosphonate
ethanol
phosphonic acid diethyl ester
A
triethyl phosphate
B
diethyl (dichloromethyl)phosphonate
Conditions | Yield |
---|---|
With triethylamine at 20℃; | A n/a B 84% |
N,N,N',N'-Tetramethylharnstoff-diethylacetal
phosphonic acid diethyl ester
A
triethyl phosphate
B
dimethyl amine
C
diethyl phosphonate
Conditions | Yield |
---|---|
at 80℃; under 400 Torr; reduced pressure; | A n/a B n/a C 83% |
A
triethyl phosphate
Conditions | Yield |
---|---|
With ethanol In dichloromethane at 40℃; for 0.5h; | A n/a B 82% |
A
triethyl phosphate
trans-2,2-Diphenylaziridine
Conditions | Yield |
---|---|
With ethanol In dichloromethane at 40℃; for 0.5h; | A n/a B 82% |
ethanol
phosphonic acid diethyl ester
A
triethyl phosphate
B
dichloromethylphosphonic acid diisopropyl ester
Conditions | Yield |
---|---|
With triethylamine at 20℃; | A n/a B 82% |
ethanol
di-n-propyl trichloromethylphosphonate
phosphonic acid diethyl ester
A
triethyl phosphate
B
O,O-di-n-propyl 1,1-dichloromethylphosphonate
Conditions | Yield |
---|---|
With triethylamine at 20℃; | A n/a B 81% |
para-thiocresol
triethyl phosphite
A
triethyl phosphate
B
thiophosphoric acid O,O'-diethyl ester S-p-tolyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; Reagent/catalyst; | A 12% B 81% |
2-iodochlorobenzene
triethyl phosphite
A
triethyl phosphate
B
ethylphosphonic acid diethyl ester
C
2-Chlorphenylphosphonsaeurediethylester
Conditions | Yield |
---|---|
With Pd/C (30%) at 175℃; for 12h; Inert atmosphere; Dean-Stark; | A n/a B n/a C 80% |
ethanol
A
triethyl phosphate
B
ethylphosphonic acid diethyl ester
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
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% |
triethyl phosphonoformate
A
triethyl phosphate
B
ethylphosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 395℃; for 8h; | A 79% B 8% |
ethanol
trichloromethyl-phosphonic acid dibutyl ester
phosphonic acid diethyl ester
A
triethyl phosphate
B
C9H19Cl2O3P
Conditions | Yield |
---|---|
With triethylamine at 20℃; | A n/a B 79% |
Conditions | Yield |
---|---|
With Oxone In tetrahydrofuran; methanol Ambient temperature; | A 78% B n/a |
triethyl phosphite
A
triethyl phosphate
B
O,O-diethyl benzylphosphonate
C
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 130℃; for 0.5h; Inert atmosphere; | A n/a B 76% C n/a |
diethyl {2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)}benzoylphosphonate
triethyl phosphite
A
triethyl phosphate
B
diethyl (7,13-dioxo-13,13a-dihydro-7H-benzo[de]indolo[2,1-a]isoquinolin-13a-yl)phosphonate
C
diethyl 7-oxo-7H-benzo[de]indolo[2,1-a]isoquinolin-13-ylphosphate
D
C27H31NO9P2
Conditions | Yield |
---|---|
In toluene at 115℃; for 17h; | A n/a B 75% C 5% D 10 %Spectr. |
triethyl phosphate
3-bromopropyltetrahydropyranylether
[3-(Tetrahydro-pyran-3-yloxy)-propyl]-phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 175℃; for 5h; | 100% |
triethyl phosphate
3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline
diethyl <2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methylphosphonate
Conditions | Yield |
---|---|
In toluene for 12h; Heating; | 100% |
Conditions | Yield |
---|---|
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; |
triethyl phosphate
6-bromo-hexanoic acid ethyl ester
6-(diethoxyphosphoryl)hexanoic acid ethyl ester
Conditions | Yield |
---|---|
at 160℃; for 14h; Inert atmosphere; | 100% |
triethyl phosphate
meta-bromobenzyl bromide
P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 160℃; for 2h; | 100% |
Conditions | Yield |
---|---|
Stage #1: triethyl phosphate With diethylamine at 125℃; for 30h; Stage #2: DBN | 99.7% |
Conditions | Yield |
---|---|
at 125℃; for 30h; | 99.7% |
1,2,3,4-tetramethylimidazolium methyl carbonate
triethyl phosphate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
at 125℃; for 30h; | 99.5% |
Conditions | Yield |
---|---|
In water at 130℃; for 14h; | 99% |
at 100℃; for 36h; | 97.3% |
at 140℃; Inert atmosphere; |
triethyl phosphate
3,5-dimethoxybenzyl bromide
diethyl 3,5-dimethoxybenzylphosphonate
Conditions | Yield |
---|---|
at 160℃; for 4h; | 99% |
at 120℃; for 10h; | 95% |
at 160℃; for 4h; | 95% |
triethyl phosphate
β-ethoxyvinyldichlorophosphine
Conditions | Yield |
---|---|
In toluene Michaelis-Arbuzov Synthesis; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
at 60℃; for 4h; | 99% |
triethyl phosphate
Conditions | Yield |
---|---|
In methanol at 120℃; under 7500.75 Torr; for 36h; | 99% |
Conditions | Yield |
---|---|
In methanol at 80℃; under 15001.5 Torr; for 48h; | 98.7% |
triethyl phosphate
Conditions | Yield |
---|---|
In methanol at 130℃; under 7500.75 Torr; for 36h; | 98.7% |
Conditions | Yield |
---|---|
at 100℃; under 7500.75 Torr; for 36h; | 98.2% |
Conditions | Yield |
---|---|
With sodium carbonate at 78 - 200℃; Temperature; | 98.07% |
triethyl phosphate
4-(3,4-Dichloro-benzenesulfonylamino)-benzenesulfonyl azide
C18H23Cl2N2O7PS2
Conditions | Yield |
---|---|
In toluene at 0℃; | 98% |
triethyl phosphate
2-bromomethylnaphthyl bromide
(naphthalen-2-ylmethyl)phosphonic acid diethyl ester
Conditions | Yield |
---|---|
at 140℃; for 12h; | 98% |
triethyl phosphate
3-methyl-1-oxo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile
5-ethyl-3-methyl-1-oxo-1H,5H-pyrido<1,2-a>benzimidazole-4-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate for 1h; Heating; | 98% |
Conditions | Yield |
---|---|
for 0.333333h; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 98% |
2-(bromomethyl)-3-methylbenzo[b]thiophene
triethyl phosphate
(3-methylbenzo[b]thiophen-2-ylmethyl)phosphonic acid diethyl ester
Conditions | Yield |
---|---|
In toluene for 18h; Arbuzov reaction; Reflux; | 98% |
triethyl phosphate
sodium 1-(13)C-propionate
Propanoic-1-13C Acid Ethyl Ester
Conditions | Yield |
---|---|
1.) reflux, 3.5 h; | 97% |
for 3.5h; Heating; | 97% |
Triethyl phosphate was firstly studied by a French chemist named Jean Louis Lassaigne in the early 1800s.
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. |
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