Acetyl hypochlorite
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Systematic IUPAC name
Chloro acetate | |
Other names
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Properties | |
C2ClH3O2 | |
Molar mass | 94.50 g/mol |
Appearance | Colorless liquid |
Melting point | 100 °C (212 °F; 373 K) (decomposes) |
Reacts | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acetyl hypochlorite, also known as chlorine acetate, is a chemical compound with the formula CH3COOCl. It is a photosensitive colorless liquid that is a short lived intermediate in the Hunsdiecker reaction.[1]
Preparation, properties, and structure
Acetyl hypochlorite is reported to be produced by the reaction of acetic anhydride and dichlorine monoxide at very low temperatures:[2]
- Cl2O + (CH3CO)2O → 2CH3COOCl
The liquid can be distilled at reduced pressure, however it cannot be heated, as it violently decomposes at 100 °C to acetic anhydride,
This compound reacts with various metals such as
In modern uses, the compound is usually prepared
The
Uses
This compound is used for the chlorination of various compounds, especially aromatic compounds, such as the chlorination of methyl acetamide, and has been proven to be a better chlorinating agent than molecular chlorine and hypochlorous acid.[4] However, this reaction is an unwanted side reaction in the Hunsdiecker reaction involving aromatic carboxylates.[1]
The Hunsdieker reaction is a mechanism to convert salts of carboxylic acids(usually salts of silver) into organic halides which uses aryl hypohalites, such as acetyl hypochlorite(produced in situ by the reaction of silver acetate and chlorine). In the mechanism of this reaction, 2 is the aryl hypohalite intermediate. However, the chlorine analog of the Hunsdiecker reaction is not efficient compared to the bromine and iodine and is not used very much compared to them due to the inconvenience of using a gaseous reagent.[5][1]
An important use of this compound is the conversion of alkenes into
References
- ^ ISBN 9780470771273. Retrieved 24 October 2022.
- ^ a b c P. Schutzenberger (1861). "Substitution des corps electronegatifs (chlore, brome, iode, cyanogene, soufre, etc.) aux metaux dans les sels oxygenes: production d'une nouvelle classe de sels dans lesquels les corps electro-negatifs replacent l'hydrogene basique". Comptes Rendus (in French). 52: 135.
- ^ .
- ^ doi:10.1139/v69-423.
- .