T3DB: Tris(2-chloroethyl)phosphate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (1)XML

Targets (1)

Record Information

Version

2.0

Creation Date

2014-09-17 20:02:27 UTC

Update Date

2014-12-24 20:27:00 UTC

Accession Number

T3D4950

Identification

Common Name

Tris(2-chloroethyl)phosphate

Class

Small Molecule

Description

Tris(2-chloroethyl) phosphate (TCEP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates. It was included in January 2011 in the European Chemicals Agency (ECHA) list of Substances of Very High Concern (SVHC) due to its being toxic for reproduction. Substances in the list of SVHCs are those for which ECHA is considering imposing a requirement for authorization for some or all uses.

Compound Type

Ester
Industrial/Workplace Toxin
Organic Compound
Organochloride
Plasticizer
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Phosphoric acid, tris(2-chloroethyl)ester
Tri(2-chloroethyl) phosphate
Tris(2-chloroethyl) orthophosphate
Tris(2-chloroethyl)phosphic acid
Tris(beta-chloroethyl) phosphate
Tris(chloroethyl)phosphate

Chemical Formula

C₆H₁₂Cl₃O₄P

Average Molecular Mass

285.490 g/mol

Monoisotopic Mass

283.954 g/mol

CAS Registry Number

115-96-8

IUPAC Name

tris(2-chloroethyl) phosphate

Traditional Name

tris(2-chloroethyl)phosphate

SMILES

ClCCOP(=O)(OCCCl)OCCCl

InChI Identifier

InChI=1S/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2

InChI Key

InChIKey=HQUQLFOMPYWACS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Trialkyl phosphates

Alternative Parents

Substituents

Trialkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organochlorine compound (CHEBI:35037 )
trialkyl phosphate (CHEBI:35037 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoskeleton
Membrane
Microsome
Mitochondrial Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Mismatch repair	Not Available	map03430
Cell cycle	Not Available	map04110
Base excision repair	Not Available	map03410
Anticonvulsants	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	6.57 g/L	ALOGPS
logP	1.36	ALOGPS
logP	2.11	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	56.13 m³·mol⁻¹	ChemAxon
Polarizability	23.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0390000000-6775e4c721647a5a3e32	2021-09-24	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03ka-9450000000-0b72b9ee93abd407ef94	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03l1-9460000000-384cbe62f62e1efaaed1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-008i-0190000000-b23aa0983b0f66b053b4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-0960000000-5f457885a6c84a268fb5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-008i-0190000000-f26c6787ab96da8aab25	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03l0-6090000000-2ff653400988c9855017	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03l0-8290000000-817dc166ce8aa6781835	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-052e00872865bfaf0dfd	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-9c8aaade1730674178f0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00e9-0590000000-3f032bbcfc9677fd9a57	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-3910000000-0d7df033a49f8fb9a53e	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06r2-9580000000-6cc979ed4f6998e16219	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-10-27	View 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)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

Tris(2-chloroethyl) phosphate is used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

Not Available

ChEMBL ID

CHEMBL1413786

ChemSpider ID

7994

KEGG ID

8295

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

C031324

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D4950.pdf

General References

International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Androgen receptor

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Molecular Weight:: 98987.9 Da

References

Suzuki G, Tue NM, Malarvannan G, Sudaryanto A, Takahashi S, Tanabe S, Sakai S, Brouwer A, Uramaru N, Kitamura S, Takigami H: Similarities in the endocrine-disrupting potencies of indoor dust and flame retardants by using human osteosarcoma (U2OS) cell-based reporter gene assays. Environ Sci Technol. 2013 Mar 19;47(6):2898-908. doi: 10.1021/es304691a. Epub 2013 Mar 1. [23398518 ]

Tris(2-chloroethyl)phosphate (T3D4950)

Structure for T3D4950: Tris(2-chloroethyl)phosphate

Targets

References