Chloroacetaldehyde (CHEM003854)

Record Information
Version1.0
Creation Date2014-09-11 05:21:22 UTC
Update Date2026-08-22 09:35:47 UTC
Accession NumberCHEM003854
Identification
Common NameChloroacetaldehyde
ClassSmall Molecule
Description
Being 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.
Contaminant Sources
  • Clean Air Act Chemicals
  • Disinfection Byproducts
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Aldehyde
  • Indicator and Reagent
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
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 hydrateHMDB
Chemical FormulaC2H3ClO
Average Molecular Mass78.498 g/mol
Monoisotopic Mass77.987 g/mol
CAS Registry Number107-20-0
IUPAC Name2-chloroacetaldehyde
Traditional Namechloroacetaldehyde
SMILES[H]C(=O)CCl
InChI IdentifierInChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2
InChI KeyQSKPIOLLBIHNAC-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganochlorides
Sub ClassNot Available
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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-16.3 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility161 g/LALOGPS
logP0.18ALOGPS
logP0.16ChemAxon
logS0.31ALOGPS
pKa (Strongest Acidic)14.07ChemAxon
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0013860
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChloroacetaldehyde
Chemspider IDNot Available
ChEBI ID27871
PubChem Compound ID33
Kegg Compound IDC06754
YMDB IDNot Available
ECMDB IDM2MDB004232
References
Synthesis ReferenceNot Available
MSDSNot Available
General References