A simple synthesis of brominated analogues of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX)

Synthetic Communications

Volumn 33, Issue 19, 2003, Pages 3411-3417

  Lumbard, Keith W ^a   Nixon, Neil S ^a   Scheinmann, Feodor ^a  

^a Ultrafine UFC Ltd   (United Kingdom)

Author keywords

Brominated hydroxyfuranones; Disinfection by products; Mutagenicity

Indexed keywords

3 CHLORO 4 DICHLOROMETHYL 5 HYDROXY 2(5H) FURANONE; DRINKING WATER; FURANONE DERIVATIVE; HALOGEN; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; CHLORINATION; DISINFECTION; MUTAGENICITY; POLLUTANT; SYNTHESIS;

EID: 0041832070     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120024000     Document Type: Article

References (27)

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16. MX is available from several companies including Ultrafine (UFC Ltd.) and Sigma (Sigma-Aldrich Co.).
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18. max 224 nm (ε 8100) for MX.
19. Purity determined by analytical HPLC.
20. 4 in MeOH (1 mL) and the solution was heated at 70° (bath temp.) for 1 h. The methyl acetal was extracted into hexane (2 x 2 mL) and the solvent was evaporated.
21. LaLonde, R.T.; Bu, L.; Henwood, A.; Fiumano, J.; Zhang, L. Bromine-, chlorine-, and mixed halogen-substituted 4-methyl-2(5H)-furanones: synthesis and mutagenic effects of halogen and hydroxyl group replacements. Chem. Res. Toxicol. 1997, 10 (12), 1427-1436.
22. Lloveras, M.; Ramos, I.; Molins, E.; Messeguer, A. Improved synthesis of three brominated analogs of the potent environmental mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX). Tetrahedron 2000, 56 (21), 3391-3397.
23. Prior to January 1999 UFC Ltd was called Salford Ultrafine Chemicals and Research Ltd.
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25. Horth, H.; Fielding, M.; James, C.P.; James, H.A.; Gwilliam, R.D. Identification of Mutagens in Drinking Water: Final Report to the Department of the Environment (UK), Report No. DoE 2489-M(P); WRc, Medmenham, Marlow: UK, 1991.
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