Diethyl phosphate (HCID 654)

Overview

Diethyl hydrogen phosphate is a dialkyl phosphate having ethyl as the alkyl group. It has a role as a mouse metabolite and a human xenobiotic metabolite. It is a conjugate acid of a diethylphosphate(1-).

Names & identifiers

Preferred name: Diethyl phosphate
IUPAC: diethyl hydrogen phosphate
English name: Diethyl phosphate
Molecular formula: C4H11O4P
Molecular weight: 154.1

Names & synonyms

diethyl hydrogen phosphateDiethyl phosphate598-02-7Diethyl acid phosphatediethylphosphatephosphoric acid, diethyl esterdiethoxyphosphinic acidO,O-Diethyl hydrogen phosphateEthyl phosphate, di-Ethyl phosphate, (ETO)2(HO)PODTXSID1044699W0QQU4CAB7

Show more names

IETHYLPHOSPHATEdi-ethylphosphatETHYLACIDPHOSPHATEO,O-DIETHYLPHOSPHATEdiethylacidphosphatediethylphosphoricacidDiethyl phosphate,98%

CHEBI:27708NSC-97178RefChem:587273DTXCID9024699DTXCID20820146209-912-5DTXSID10872492Phosphoric acid diethyl ester

Database identifiers

CAS: 51501-07-6、52932-96-4、53397-17-4、598-02-7
PubChem CID: 654
DTXSID: DTXSID1044699
ChEMBL: CHEMBL1232324
ChEBI: CHEBI:27708
UNII: W0QQU4CAB7
EC Number: 209-912-5
Nikkaji: J1.649G

Properties

Computed structural properties

XLogP: -0.3
Topological polar surface area: 55.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 9
Formal charge: 0
Complexity: 103

Experimental & physicochemical properties

Chemical Classes · 3 items

Other Classes -> Organophosphates, Other

Organophosphate

Organophosphate diesters (OPDE)

SpringerMaterials PropertiesOptical coefficient

Physical Description · 3 items

Liquid

Colorless clear liquid; [MSDSonline]

Solid

Collision Cross Section129.2 Å² [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1044699]

Physicochemical properties

Melting point: 6 °C · 6 °C
Boiling point: 203 °C · 203 °C
Density: 1.29 · 1.29
refractive index: 1.417 · 1.4170
Flash point: 91 °C · 91 °C
storage temp.: 2 · Sealed in dry,2-8°C
solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka: 1.42 · 1.42±0.50(Predicted)
form: Liquid
color: Clear colorless to light yellow-orange
Stability: Moisture Sensitive
InChI: InChI=1S/C4H11O4P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3,(H,5,6)
InChIKey: UCQFCFPECQILOL-UHFFFAOYSA-N
SMILES: P(O)(OCC)(OCC)=O
FDA UNII: 0 QQU4CAB7 · W0QQU4CAB7
EPA Substance Registry System: Phosphoric acid, diethyl ester (598-02-7)
Symbol(GHS): 7 · GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 315 · H315-H317-H319-H335-H411-H372
Precautionary statements: 261 · P261-P273-P280-P305+P351+P338
Hazard Codes: Xi,T,F
Risk Statements: 36 · 36/37/38-39/23/24/25-23/24/25-11
Safety Statements: 37 · 37/39-26-36-45-36/37-16-7
RTECS: 665000 · TC0665000
TSCA: TSCA listed
HS Code: 29199000 · 29199000

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 44% (37 of 84) of reports.

Warning

H315 (56%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 84 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Hazard Traits - Developmental Toxicity; Neurotoxicity

Phosphoric acid, diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphoric acid, diethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Hazards SummaryAn irritant; [MSDSonline]

Hazard Classes and CategoriesSkin Irrit. 2 (56%)

Toxicology

Toxicity Summary · 1 item

S-Ethylisothiouronium diethylphosphate is a specific inhibitor of inducible NO synthase on hepatic NO production level. S-Ethylisothiouronium diethylphosphate affects systemic hemodynamic indices in the following way: the peripheral vascular resistance increases, the stroke volume and central blood volume increase, and the work of the left ventricle improves. (Wikipedia)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

tsca: TSCA listed
rtecs: TC0665000
hs_code: 29199000
risk_code: 36/37/38-39/23/24/25-23/24/25-11
Signal word: Danger
Symbol(GHS): GHS07,GHS08,GHS09
hazard_code: Xi,T,F
safety_code: 37/39-26-36-45-36/37-16-7
Hazard statements: H315-H317-H319-H335-H411-H372
Precautionary statements: P261-P273-P280-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Diethyl phosphorothioate is a known human metabolite of Diazoxon, Chlorpyrifos-oxon, and Chlorpyrifos.

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Uses & manufacturing

UsesThis is a man-made compound that is used as a pesticide.

U.S. Production2023: 41,165 lb

Consumer UsesSurfactant (surface active agent)

Industry UsesSurfactant (surface active agent)

General Manufacturing Information · 2 items

Paint and Coating Manufacturing

Phosphoric acid, diethyl ester: ACTIVE

Applications · 1 item

UsesPhosphoric acid diethyl ester is an organophosphate that is usually found in pesticides and is known to induce changes in male hormone profile by decreasing serum testosterone and inhibin B levels. Phosphoric acid diethyl ester is also known to negatively affect the health of women and newborns living in agricultural communities.