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Diethyl ethylphosphonate

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Name

Diethyl ethylphosphonate

EINECS 201-111-9
CAS No. 78-38-6 Density 1.01 g/cm3
PSA 45.34000 LogP 2.27240
Solubility Miscible with water or organic solvents Melting Point N/A
Formula C6H15O3P Boiling Point 198 °C at 760 mmHg
Molecular Weight 166.157 Flash Point 92.7 °C
Transport Information UN 3082 9/PG 3 Appearance Colorless liquid with a mild odor
Safety 37/39-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 78-38-6 (DIETHYL ETHYLPHOSPHONATE) Hazard Symbols IrritantXi
Synonyms

Ethanephosphonic acid, diethyl ester;Phosphonic acid, ethyl-, diethyl ester;CCRIS 6230;AI3-18558;HSDB 2560;NSC 2671;1-[Ethoxy(ethyl)phosphoryl]oxyethane;

Article Data 141

Diethyl ethylphosphonate Synthetic route

74-96-4

ethyl bromide

122-52-1

triethyl phosphite

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
at 180 - 200℃; for 0.416667h; Michaelis-Arbuzov reaction; microwave irradiation;100%
at 100℃; for 12h; reaction de Michaelis Arbuzov'a;95%
for 24h; Michaelis-Arbuzov Synthesis; Reflux;80%
In neat (no solvent) at 150℃; for 0.833333h; Temperature; Arbuzov Reaction; Flow reactor;5%
at 150℃; for 4h; Arbuzov Reaction;
75-03-6

ethyl iodide

122-52-1

triethyl phosphite

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
In neat (no solvent) at 150℃; for 0.833333h; Temperature; Arbuzov Reaction; Flow reactor;99%
for 3h; Heating;98%
for 3h; Reflux;98%
1765-40-8

(bromomethyl)pentafluorobenzene

122-52-1

triethyl phosphite

A

78-38-6

ethylphosphonic acid diethyl ester

B

2,3,4,5,6-pentafluorobenzylphosphonic acid ethyl ester

Conditions
ConditionsYield
at 160℃; for 12h;A n/a
B 99%
100-39-0

benzyl bromide

122-52-1

triethyl phosphite

A

74-96-4

ethyl bromide

B

78-38-6

ethylphosphonic acid diethyl ester

C

1080-32-6

O,O-diethyl benzylphosphonate

Conditions
ConditionsYield
at 140℃; for 0.25h; Michaelis-Arbuzov reaction; microwave irradiation;A n/a
B n/a
C 98%

ethyl 4-(diethoxyphosphorylmethyl)-5-(iodomethyl)furan-3-carboxylate

122-52-1

triethyl phosphite

A

78-38-6

ethylphosphonic acid diethyl ester

B

ethyl 4,5-bis-(diethoxyphosphorylmethyl)furan-3-carboxylate

C

75-03-6

ethyl iodide

Conditions
ConditionsYield
at 90 - 170℃; for 0.166667h; Arbuzov Reaction;A n/a
B 98%
C n/a
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%
64-17-5

ethanol

1066-50-8

Ethylphosphonic dichloride

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
With aluminum oxide at 20℃;96%
78-40-0

triethyl phosphate

811-49-4

ethyllithium

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 0℃;95%
122-52-1

triethyl phosphite

78-38-6

ethylphosphonic acid diethyl ester

Conditions
ConditionsYield
With iodine for 24h; Heating;95%
With trifluorormethanesulfonic acid at 60℃; for 16h; Reagent/catalyst; Schlenk technique; Inert atmosphere;95%
With diiodomethane at 100℃; for 120h;67%
With trimethylsilyl iodide at 80℃; Inert atmosphere;25%
With trifluorormethanesulfonic acid at 60℃; for 16h; Reagent/catalyst; Temperature; Time; Inert atmosphere;
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%

Diethyl ethylphosphonate Specification

The Diethyl ethylphosphonate with CAS registry number of 78-38-6 is also known as Phosphonic acid,P-ethyl-, diethyl ester. The IUPAC name is 1-[Ethoxy(ethyl)phosphoryl]oxyethane. Its EINECS registry number is 201-111-9. In addition, the formula is C6H15O3P and the molecular weight is 166.16. This chemcial is a colorless liquid with a mild odor and it is used as efficient organic phosphorus flame retardant which can be added extensively in a variety of rigid foam.

Physical properties about Diethyl ethylphosphonate are: (1)ACD/LogP: 0.82; (2)ACD/LogD (pH 5.5): 0.82; (3)ACD/LogD (pH 7.4): 0.82; (4)ACD/BCF (pH 5.5): 2.46; (5)ACD/BCF (pH 7.4): 2.46; (6)ACD/KOC (pH 5.5): 66.29; (7)ACD/KOC (pH 7.4): 66.29; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.403; (11)Molar Refractivity: 40.21 cm3; (12)Molar Volume: 164.4 cm3; (13)Surface Tension: 29.2 dyne/cm; (14)Density: 1.01 g/cm3; (15)Flash Point: 92.7 °C; (16)Enthalpy of Vaporization: 41.64 kJ/mol; (17)Boiling Point: 198 °C at 760 mmHg; (18)Vapour Pressure: 0.518 mmHg at 25 °C.

Preparation of Diethyl ethylphosphonate. Firstly, ethanol, methyl red are mixed with solvent and the mixture is added to the reactor. Then ammonia is passed into the reaction solution under stirring at the temperature of 0 °C. Dropping phosphorus trichloride slowly at the same time. The reaction needs 2-3 hours with the reaction temperature of 0-10 °C. Secondly, the reaction mixture is dissolved in water. After solvent recovery by vacuum distillation, the reservoir is vacuum distillated to collect triethyl phosphite at 52-53 °C with the yield of 70-75%. At last, product is obtained by isomerization reaction with catalyst.

Diethyl ethylphosphonate isprepared by reaction of ethanol, methyl red, solvent and ammonia.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOP(=O)(CC)OCC
2. InChI: InChI=1S/C6H15O3P/c1-4-8-10(7,6-3)9-5-2/h4-6H2,1-3H3
3. InChIKey: AATNZNJRDOVKDD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2500mg/kg (2500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 120, 1999.
rat LD50 oral 2330mg/kg (2330mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
"Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 120, 1999.

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