Bis(chloromethyl) ketone (CHEM004251)

Record Information
Version1.0
Creation Date2016-05-19 01:38:53 UTC
Update Date2026-08-22 12:47:37 UTC
Accession NumberCHEM004251
Identification
Common NameBis(chloromethyl) ketone
ClassSmall Molecule
Description
A ketone that is propan-2-one in which a hydrogen at positions 1 and 3 have been replaced by chloro groups. It is used in the synthesis of citric acid. Also used as a solvent and as an intermediate in organic synthesis.
Contaminant Sources
  • Clean Air Act Chemicals
  • Disinfection Byproducts
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,3-Dichloro-2-propanoneChEBI
1,3-DichloropropanoneChEBI
alpha,Alpha'-dichloroacetoneChEBI
Bis(chloromethyl) ketoneChEBI
Bis(chloromethyl)ketoneChEBI
Sym-dichloroacetoneChEBI
a,Alpha'-dichloroacetoneGenerator
Α,alpha'-dichloroacetoneGenerator
Chemical FormulaC3H4Cl2O
Average Molecular Mass126.969 g/mol
Monoisotopic Mass125.964 g/mol
CAS Registry Number534-07-6
IUPAC Name1,3-dichloropropan-2-one
Traditional Name1,3-dichloroacetone
SMILESClCC(=O)CCl
InChI IdentifierInChI=1S/C3H4Cl2O/c4-1-3(6)2-5/h1-2H2
InChI KeySUNMBRGCANLOEG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-chloroketones
Alternative Parents
Substituents
  • Alpha-chloroketone
  • Organic oxide
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.52 g/LALOGPS
logP0.72ALOGPS
logP1.18ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.7 m³·mol⁻¹ChemAxon
Polarizability10.42 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)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0244164
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBis(chloromethyl) ketone
Chemspider ID21106513
ChEBI ID156485
PubChem Compound ID10793
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12470958
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18022565
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26051979
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=27477907
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3004254
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=30248496
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=32039320
8. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.