Showing Compound Card for alpha-Chloroacetophenone (CDB000502)

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Record Information
Version1.0
Created at2020-03-19 00:40:30 UTC
Updated at2020-12-07 19:07:28 UTC
CannabisDB IDCDB000502
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namealpha-Chloroacetophenone
Descriptionalpha-Chloroacetophenone or 2-Chloroacetophenone, also known as mace, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. alpha-Chloroacetophenone is a useful building block in organic chemistry. Although it is potentially a toxic compound, alpha-chloroacetophenone is commonly used as a tear gas. Due to its peripheral sensory irritant effect, it has been historically used as a riot control agent. alpha-Chloroacetophenone is synthesized by the Friedel-Crafts acylation of benzene using chloroacetyl chloride, with an aluminium chloride catalyst.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-ChloroacetophenoneChEMBL
2 ChloroacetophenoneMeSH
MaceMeSH
2 chloro 1 PhenylethanoneMeSH
2-chloro-1-PhenylethanoneMeSH
ChloracetophenoneMeSH
ChloroacetophenoneMeSH
Omega chloroacetophenoneMeSH
Omega-chloroacetophenoneMeSH
3'-ChloroacetophenoneMeSH
alpha ChloroacetophenoneMeSH
alpha-ChloroacetophenoneMeSH
3' ChloroacetophenoneMeSH
Chemical FormulaC8H7ClO
Average Molecular Weight154.59
Monoisotopic Molecular Weight154.0185
IUPAC Name2-chloro-1-phenylethan-1-one
Traditional Namephenacyl chloride
CAS Registry Number532-27-4
SMILES
ClCC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2
InChI KeyIMACFCSSMIZSPP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Aryl alkyl ketone
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-haloketone
  • Alpha-chloroketone
  • Organic oxide
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Organoleptic effect:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.9ALOGPS
logP2.07ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)15.37ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.21 m³·mol⁻¹ChemAxon
Polarizability15.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a6r-8900000000-c32565b7ca6b1213ffa02014-09-20View Spectrum
Predicted GC-MSalpha-Chloroacetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSalpha-Chloroacetophenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-34ef2ec4e3393faeffd52016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-663386a4ad502d3905712016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-b6a72863a6ee429ecb872016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-b96bc74585ae77f666852016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4900000000-87cfd39438a866f31ca22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-0ee68b64ac45876209c42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1900000000-9735c2f52a472954a3852021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-3900000000-9c3cc20d13a5d47dbd452021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h00-9400000000-a8280c955165ca82a2e72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-ccd414570820207d17f22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-4900000000-9f40f047950e796918d42021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-00dcf30564fdf514b7ca2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0245061
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10303
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenacyl chloride
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available