Chemistry:Mucochloric acid
Mucochloric acid is an organic compound with the formula C
4H
2Cl
2O
3. It consists of a dichlorinated alkene bearing aldehyde and carboxylic acid functional groups. It is the chlorinated analog of mucobromic acid and one of the known mucohalic acids. Mucochloric acid exists in equilibrium between open-chain and cyclic (furanone hemiacetal) forms, analogous to mucobromic acid. Mucochloric acid occurs as a chlorine disinfection byproduct in drinking water.[1]
Synthesis
Mucochloric acid can be prepared by chlorination of furfural or related compounds such as furoic acid.[2]
Applications
Due to its reactive chlorine atoms, double bond, and carbonyl groups, mucochloric acid serves as a versatile intermediate in organic synthesis, including for substituted furanones and other heterocycles.[3][4]
Safety
Mucochloric acid is corrosive and toxic. It exhibits mutagenic and genotoxic activity.[1][5]
References
- ↑ 1.0 1.1 Jansson, Kristian; Hyttinen, Juha M. T.; Niittykoski, Minna; Mäki-Paakkanen, Jorma (1995). "Mutagenicity in vitro of 3,4-dichloro-5-hydroxy-2( 5H )-furanone (Mucochloric acid), a chlorine disinfection by-product in drinking water". Environmental and Molecular Mutagenesis 25 (4): 284–287. doi:10.1002/em.2850250404. PMID 7607182. Bibcode: 1995EnvMM..25..284J.
- ↑ Andrew P. Dunlop, Edward Sherman, "Preparation of mucochloric acid", US patent 2821553A, published 1958-01-28
- ↑ Bellina, Fabio; Anselmi, Chiara; Martina, Francesca; Rossi, Renzo (2003). "Mucochloric Acid: A Useful Synthon for the Selective Synthesis of 4-Aryl-3-chloro-2(5 H )-furanones, ( Z )-4-Aryl-5-[1-(aryl)methylidene]-3-chloro-2(5 H )-furanones and 3,4-Diaryl-2(5 H )-furanones". European Journal of Organic Chemistry (12): 2290–2302. doi:10.1002/ejoc.200300097.
- ↑ Kurbangalieva, A. R.; Devyatova, N. F.; Bogdanov, A. V.; Berdnikov, E. A.; Mannafov, T. G.; Krivolapov, D. B.; Litvinov, I. A.; Chmutova, G. A. (2007). "Synthesis of Novel Arylthio Derivatives of Mucochloric Acid". Phosphorus, Sulfur, and Silicon and the Related Elements 182 (3): 607–630. doi:10.1080/10426500601015989.
- ↑ Lalonde, Robert T.; Perakyla, Hannu; Cook, Gary P.; Dence, Carlton W. (1990). "Short Communication: Contribution of the 5-hydroxyl group to the mutagenicity of mucochloric acid". Environmental Toxicology and Chemistry 9 (6): 687–691. doi:10.1002/etc.5620090601. Bibcode: 1990EnvTC...9..687L.
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