125974-08-5

Basic information

• Product Name: 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone
• Synonyms: 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone;3-CHLORO-4-(CHLOROMETHYL)-5-HYDROXY-2-FURANONE
• CAS NO: 125974-08-5
• Molecular Formula: C5H4 Cl2 O3
• Molecular Weight: 182.9895
• Mol File: 125974-08-5.mol

Chemical Properties

• Boiling Point: 399.5°Cat760mmHg
• Flash Point: 195.4°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 4.83E-08mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone(125974-08-5)
• EPA Substance Registry System: 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone(125974-08-5)

Safety Data

• Hazardous Substances Data: 125974-08-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H4Cl2O3/c6-1-2-3(7)5(9)10-4(2)8/h4,8H,1H2

Upstream product

• 125974-04-1 5-Bromo-3-chloro-4-chloromethyl-5H-furan-2-one 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 
• 125973-99-1 4-(Chloromethyl)-2(5H)-furanone 
• 125974-01-8 3-Chloro-4-(chloromethyl)-2(5H)-furanone 

Relevant articles and documents

Synthesis of chlorinated 5-hydroxy 4-methyl-2(5H)-furanones and mucochloric acid

An improved procedure for the synthesis of chlorinated 5-hydroxy-4-methyl-2(5H)-furanones is described. By this method also carbon-labelled (13C and 14C at C-3) hydroxyfuranones, including mucochloric acid, can be prepared. Each step of the method was examined in an effort to optimize both the yield and the purity of the compounds.

Potentially Mutagenic, Chlorine-Substituted 2(5H)-Furanones: Studies of Their Synthesis and NMR Properties

The mutagen 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX), 1, and seven analogues of it were synthesized from 4-(hydroxymethyl)-2(5H)-furanone, 2.This investigation was untertaken to learn if 2 would serve as a versatile starting point for the preparation of MX analogues required for structure/activity studies of genotoxicity.Compound 2 was treated with thionyl chloride-pyridine to develop the C-4 chloromethyl group.Oxidation of 2 with pyridinium chlorochromate to the aldehyde, followed by treatment of the latter with phosphorus pentachloride, developed the C-4 dichloromethyl group.Thereafter, when attachment of chlorine at C-3 was desired, the aluminum chloride promoted chlorine addition to the C-3-C-4 double bond followed by the triethylamine-promoted elimination of hydrogen chloride resulted in the required 3-chloro-4-(chloromethyl) or 4-(dichloromethyl)-5-desoxy analogues of MX.Hydroxylation at C-5 was achieved in two steps, involving first bromine substitution employing NBS under free radical conditions followed by metal ion assisted hydrolysis of the bromide in aqueous acetone.Special regard was paid to the characterization of MX and its analogues by assessing the values of 13C NMR chemical shift, the consistency of substitution effects, and the occurrence and magnitude of direct and long-range couplings in the spectra of these compounds.