Structure via PubChem · Public domain (PubChem)
dichlorocarbene
Sign in to saveAlso known as dichloromethylene, dichloromethylidene, carbon dichloride, CCl2
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.
Chemical data
- Formula
- CCl2
- Molecular weight
- 82.91 g/mol
- SMILES
- [C](Cl)Cl
- InChIKey
- PFBUKDPBVNJDEW-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 81.937705
Show 3 more facts
- chemical formula
- CCl₂
- canonical SMILES
- [C](Cl)Cl
- Commons category
- Dichlorocarbene
via Wikidata · CC0
~4 min read
Article
13 sectionsContents
- Preparation
- Other reagents and routes
- Reactions
- With alkenes
- With phenols
- With amines
- History
- Related reactions
- Chlorocarbene
- See also
- Explanatory notes
- References
- External links
Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.
==Preparation== Dichlorocarbene is most commonly generated by reaction of chloroform and a base such as potassium tert-butoxide or aqueous sodium hydroxide. A phase transfer catalyst, for instance benzyltriethylammonium bromide, facilitates the migration of the hydroxide in the organic phase. HCCl3 + NaOH → CCl2 + NaCl + H2O