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Record Information

Version

2.0

Creation Date

2012-05-31 14:25:00 -0600

Update Date

2015-06-04 15:11:33 -0600

Secondary Accession Numbers

ECMDB20053

Identification

Name:

2,2-Dichloroacetaldehyde

Description

2,2-dichloroacetaldehyde is a member of the chemical class known as Organochlorides. These are organic compounds containing a chlorine atom. N2,3-Ethenoguanine (epsilon G) is a product of vinyl chloride reaction with DNA in vivo and of its ultimate metabolite, chloroacetaldehyde, in vitro. (PMID 2013138). It is a bifunctional compound, making it a useful building block chemical.

Structure

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

Synonyms:

2, 2-Dichloroacetaldehyde
2,2-Dichloro-Acetaldehyde
2-Chloroacetaldehyde
2-Chloroethanal
a,a-Dichloroacetaldehyde
a-Chloroacetyl chloride
Alpha,alpha-Dichloroacetaldehyde
Alpha-Chloroacetyl chloride
CH2ClCOCl
CHCl2CHO
Chloracetyl chloride
Chloraldehyde
Chlorid kyseliny chloroctove
Chlorid kyseliny chloroctove [czech]
Chloro-Acetyl chloride
Chloroacetate chloride
Chloroacetic acid chloride
Chloroacetic chloride
Chloroacetyl chloride [UN1752] [Poison]
Chloroaldehyde
Chloroethanal
Chloroethanoyl chloride
Chlorure de chloracetyle
Chlorure de chloracetyle [french]
Dichloro-Acetaldehyde
Dichloroacetaldehyde
InChI=1/C2H2Cl2O/c3-1-2(4)5/h1H
Monochloroacetaldehyde
Monochloroacetyl chloride
α,α-Dichloroacetaldehyde
α-Chloroacetyl chloride

Chemical Formula:

C₂H₃Cl₃

Weight:

Average: 133.404
Monoisotopic: 131.930033217

InChI Key:

UBOXGVDOUJQMTN-UHFFFAOYSA-N

InChI:

InChI=1S/C2H3Cl3/c3-1-2(4)5/h2H,1H2

CAS number:

79-02-7

IUPAC Name:

1,1,2-trichloroethane

Traditional IUPAC Name:

1,1, 2-trichloroethane

SMILES:

ClCC(Cl)Cl

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organochlorides

Sub Class

Not Available

Direct Parent

Organochlorides

Alternative Parents

Substituents

Hydrocarbon derivative
Organochloride
Alkyl halide
Alkyl chloride
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

chloroethanes (CHEBI:36018 )
a small molecule (112-TRICHLOROETHANE )

Physical Properties

State:

Liquid

Charge:

Melting point:

-37.5 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.93 g/L	ALOGPS
logP	2.02	ALOGPS
logP	2.17	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	25.71 m³·mol⁻¹	ChemAxon
Polarizability	10.43 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

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

2,2-Dichloroacetaldehyde + Glutathione <> S-(2,2-Dichloro-1-hydroxy)ethyl glutathione
2,2-Dichloroacetaldehyde + Glutathione <> S-(2-Chloroacetyl)glutathione + Hydrochloric acid
Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathione

SMPDB Pathways:

glutathione metabolism II

PW001927

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-bf79232c76a22826ba5c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-3f6b6c4778619860fc19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1900000000-de14959b0cb16e8cd707	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9000000000-eece4c8a26c8a21d5fb7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-cc11fb3585800aaf8723	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-bcf58e3a5f886b9be8cf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-9058e4afd6f1129806b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-6838b4c597e6d80ac4e2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-c2fa753da65a4bac80a1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-7900000000-ff817bfd636e4a77346c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-c8f6da92e011fc99d023	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-c8f6da92e011fc99d023	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-9000000000-97d9dd18a5aad6cec972	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-316c9aca46098f901713	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Singer, B., Kusmierek, J. T., Folkman, W., Chavez, F., Dosanjh, M. K. (1991). "Evidence for the mutagenic potential of the vinyl chloride induced adduct, N2, 3-etheno-deoxyguanosine, using a site-directed kinetic assay." Carcinogenesis 12:745-747. Pubmed: 2013138

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	36018
HMDB ID	HMDB0244041
Pubchem Compound ID	6576
Kegg ID	C14858
ChemSpider ID	6326
Wikipedia ID	1,1,2-Trichloroethane
BioCyc ID	CHLOROACETALDEHYDE
EcoCyc ID	CHLOROACETALDEHYDE

Enzymes

Protein Details

1. Glutathione S-transferase

General function:: Involved in protein binding
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles
Gene Name:: gst
Uniprot ID:: P0A9D2
Molecular weight:: 22868

Reactions

RX + glutathione = HX + R-S-glutathione.

Protein Details

2. GSH-dependent disulfide bond oxidoreductase

General function:: Not Available
Specific function:: Not Available
Gene Name:: yfcG
Uniprot ID:: P77526
Molecular weight:: Not Available

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2,2-Dichloroacetaldehyde (M2MDB000902)

Structure for #<Compound:0xa060c8cc>

Enzymes

Reactions