ContaminantDB: Triethyl phosphonoacetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:34:37 UTC

Update Date

2016-11-09 01:15:39 UTC

Accession Number

CHEM017723

Identification

Common Name

Triethyl phosphonoacetate

Class

Small Molecule

Description

Triethyl phosphonoacetate is a reagent for organic synthesis used in the Horner-Wadsworth-Emmons reaction (HWE) or the Horny-Emmons modification. Triethyl phosphonoacetate can be added dropwise to sodium methoxide solution to prepare a phosphonate ylide. It has an acidic proton that can easily be abstracted by a weak base. When used in an HWE reaction with a carbonyl the resulting alkene formed is usually the E alkene, and is generated with excellent regioselectivity.

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Triethyl phosphonoacetic acid	Generator
Ethyl 2-(diethoxyphosphoryl)acetic acid	Generator

Chemical Formula

C₈H₁₇O₅P

Average Molecular Mass

224.193 g/mol

Monoisotopic Mass

224.081 g/mol

CAS Registry Number

867-13-0

IUPAC Name

ethyl 2-(diethoxyphosphoryl)acetate

Traditional Name

triethyl phosphonoacetate

SMILES

CCOC(=O)CP(=O)(OCC)OCC

InChI Identifier

InChI=1S/C8H17O5P/c1-4-11-8(9)7-14(10,12-5-2)13-6-3/h4-7H2,1-3H3

InChI Key

GGUBFICZYGKNTD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dialkyl alkylphosphonates. Dialkyl alkylphosphonates are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphonic acids and derivatives

Sub Class

Phosphonic acid diesters

Direct Parent

Dialkyl alkylphosphonates

Alternative Parents

Substituents

Dialkyl alkylphosphonate
Phosphonic acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organophosphorus compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	20.4 g/L	ALOGPS
logP	1.1	ALOGPS
logP	0.63	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	17.78	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	51.61 m³·mol⁻¹	ChemAxon
Polarizability	21.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00mk-0910000000-a8d98da54db300a4a6f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tj-2900000000-c7c58eeb509c2e89e466	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-4900000000-182327f4af4580a3c16e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-1920000000-dfe99376ace3c47ec597	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1900000000-0a714b45a38987afac51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-3900000000-c2e205f665647a14ad29	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Triethyl phosphonoacetate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

13345

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Triethyl phosphonoacetate (CHEM017723)

Structure for CHEM017723: Triethyl phosphonoacetate