Ethenone, dichloro-
Basic information
- CAS
4591-28-0- Standard SMILES
O=C=C(Cl)Cl- InChIKey
TVWWMKZMZALOFP-UHFFFAOYSA-N- Molecular formula
- C2Cl2O
- Average molar mass
- 110.92 g/mol
- Monoisotopic mass
- 109.93261998
Overview
structure given in first source
Names & identifiers
- Preferred name
- Ethenone, dichloro-
- IUPAC
- 2,2-dichloroethenone
- English name
- dichloroketene
- Molecular formula
- C2Cl2O
- Molecular weight
- 110.93
Names & synonyms
Dichloroketene4591-28-0Ethenone, dichloro-DTXSID40196653RefChem:592670DTXCID80119144224-980-6dichloroethen-1-oneEINECS 224-980-62,2-dichloro-ethenoneCl2C=C=OSCHEMBL976513
Show more names
Ethenone, dichloro- (9CI)
DB-243393NS00031563
Database identifiers
- CAS
4591-28-0- PubChem CID
- 78338
- DTXSID
DTXSID40196653- EC Number
- 224-980-6
- Nikkaji
- J57.962I
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 67.7
Experimental & physicochemical properties
SpringerMaterials PropertiesSchoenflies notation
Physicochemical properties
- Boiling point
- 57.1 · 57.1±33.0 °C(Predicted)
- Density
- 1.385 · 1.385±0.06 g/cm3(Predicted)
- solubility
- sol ether, pentane, hexane.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: Ethenone, dichloro-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Chemistry & industry
Applications
UsesIchloroketene is a dichloroacetylating agent; it undergoes cyclization with a variety of substrates.
Preparation methods
PreparationDichloroketene is typically prepared in situ by dehalogenation of trichloroacetyl halides or dehydrohalogenation of dichloroacetyl halides. Elimination of dichloroacetyl chloride with Triethylamine affords the desired ketene, although material formed in this manner is of limited reactivity. Reduction of Trichloroacetyl Chloride with Zinc/Copper Couple activated with either Phosphorus Oxychloride or 1,1- Dimethoxyethane provides fully reactive dichloroketene. Recently, thermal activation of Zinc dust was used to generate dichloroketene.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
3 records
Compound notes
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