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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:15 UTC
Update Date2017-10-23 19:06:13 UTC
HMDB IDHMDB0013860
Secondary Accession Numbers
  • HMDB13860
Metabolite Identification
Common NameChloroacetaldehyde
DescriptionBeing bifunctional, chloroacetaldehyde is a versatile precursor to many heterocyclic compounds. It condenses with thiourea derivatives to give aminothiazoles. This reaction was once important as a precursor to sulfathiazole, one of the first sulfa drugs. Chloroacetaldehyde is the organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hydrate (acetal), ClCH2CH(OH)2. Chloroacetaldehyde is a useful intermediate in the synthesis, e.g. of 2-aminothiazole or many pharmaceutical compounds. Another use is to facilitate bark removal from tree trunks.
Structure
Thumb
Synonyms
ValueSource
2-chloro-1-EthanalChEBI
2-ChloroethanalChEBI
ChloroaldehydeChEBI
MonochloroacetaldehydeChEBI
2-chloro-AcetaldehydeHMDB
2-ChloroacetaldehydeHMDB
CH2ClCHOHMDB
ChloroacetalaldehydeHMDB
Chloroacetaldehyde monomerHMDB
ChloroethanalHMDB
Rcra waste number P023HMDB
Chloroacetaldehyde hydrateMeSH
Chemical FormulaC2H3ClO
Average Molecular Weight78.498
Monoisotopic Molecular Weight77.987242425
IUPAC Name2-chloroacetaldehyde
Traditional Namechloroacetaldehyde
CAS Registry Number107-20-0
SMILES
[H]C(=O)CCl
InChI Identifier
InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
InChI KeyQSKPIOLLBIHNAC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as organochlorides. These are compounds containing a chemical bond between a carbon atom and a chlorine atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganohalogen compounds
Sub ClassOrganochlorides
Direct ParentOrganochlorides
Alternative Parents
Substituents
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Indirect biological role:

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-16.3 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility161 g/LALOGPS
logP0.18ALOGPS
logP0.16ChemAxon
logS0.31ALOGPS
pKa (Strongest Acidic)11.84ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.47 m³·mol⁻¹ChemAxon
Polarizability6.47 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-24afbbb98f664db69229View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-54aa5db6a89c270c5cb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-773bd9fcaa86caff6ffbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-e828fa0840b3f7c4a695View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-ceaa73e80f8d51802bafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9000000000-ffa9949420745b970ff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-1fa707d184f90bd8818bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-9000000000-37aafbd8f12ae548e09bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Cyclophosphamide Metabolism PathwayPw000580Pw000580 greyscalePw000580 simpleNot Available
Cyclophosphamide PathwayPw000248Pw000248 greyscalePw000248 simpleNot Available
Ifosfamide Metabolism PathwayPw000581Pw000581 greyscalePw000581 simpleNot Available
Ifosfamide PathwayPw000249Pw000249 greyscalePw000249 simpleNot Available
Displaying all 4 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00023
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCHLOROACETALDEHYDE
BiGG IDNot Available
Wikipedia LinkChloroacetaldehyde
METLIN IDNot Available
PubChem Compound0
PDB IDNot Available
ChEBI ID27871
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
Chloroacetaldehyde + NAD + Water → Chloroacetic acid + NADH + Hydrogen Iondetails