77439-76-0

Basic information

• Product Name: 3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE
• Synonyms: 3-Chloro-4-(dichloromethyl)-5-hydroxy-2,5-dihydrofuran-2-one;3-Chloro-4-(dichloromethyl)-5-hydroxyfuran 2(5H)-one;3-Chloro-4-(dichloromethyl)-5;Mutagen X;3-chloro-4-dichloromethyl-5-hydroxy-2(5h)-furanon;chloro(dichloromethyl)-5-hydroxy-2(5h)-furanone;3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE;MX
• CAS NO: 77439-76-0
• Molecular Formula: C₅H₃Cl₃O₃
• Molecular Weight: 217.43
• Product Categories: Heterocycles;Mutagenesis Research Chemicals
• Mol File: 77439-76-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 311.99°C (rough estimate)
• Flash Point: 188.9 ºC
• Appearance: /
• Density: 1.7771 (rough estimate)
• Refractive Index: 1.4775 (estimate)
• Storage Temp.: −20°C
• PKA: 8?+-.0.60(Predicted)
• CAS DataBase Reference: 3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE(77439-76-0)
• EPA Substance Registry System: 3-CHLORO-4-(DICHLOROMETHYL)-5-HYDROXY-2(5H)-FURANONE(77439-76-0)

Safety Data

• Hazard Codes: T
• Statements: 46-23/24/25-43
• Safety Statements: 53-36/37/39-45
• RIDADR: 2810
• RTECS: LU3482000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 77439-76-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange Oil

Uses

3-Chloro-4-(dichloroMethyl)-5-hydroxy-2(5H)-furanone is a chlorinated furanone that accounts for more of the mutagenic activity of drinking water than any other disinfection byproduct. de, MX, 4-nitroquinoline N-oxide, sodium azide, 1-nitropyrene, and captan) used in the present study have been known to subject to the nucleotide excision repair system.

InChI:InChI=1/C5H3Cl3O3/c6-2-1(3(7)8)4(9)11-5(2)10/h3-4,9H

Upstream product

• 121-33-5 vanillin 
• 54-12-6 Trp 
• 122551-89-7 3-Chloro-4-(dichloromethyl)-2(5H)-furanone 
• 1380400-97-4 C₁₁H₁₅ClO₆ 
• 97055-35-1 2,3,4,4-Tetrachloro-3-dichloromethyl-butyric acid methyl ester 
• 97055-33-9 methyl 3-(dichloromethyl)-4,4-dichlorocrotonate 
• 134-96-3 syringic aldehyde 
• 556-02-5 ?Tyr 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 136269-33-5 1-dichloromethyl-3,4,5-trimethoxybenzene 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 

Downstream Products

• 220437-29-6 3-(β-D-ribofuranosyl)-7-formylimidazo[1,2-a]purin-9(4H)-one 
• 1380400-98-5 C₁₄H₁₄Cl₃NO 
• 97055-38-4 3-chloro-4-(dichloromethyl)-5-methoxy-2,5-dihydrofuran-2-one 
• 132059-52-0 3-chloro-4-(dibromomethyl)-5-hydroxy-2,5-dihydrofuran-2-one 
• 132059-53-1 3-bromo-4-(dibromomethyl)-5-hydroxy-2(5H)-furanone 
• 132059-51-9 4-(bromochloromethyl)-3-chloro-5-hydroxy-2,5-dihydrofuran-2-one 

Relevant articles and documents

Factors on the formation of strong mutagen [3-chloro-4-(dichloromethyl)- 5-hydroxy-2(5H)-furanone] MX by chlorination of syringaldehyde

Syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) was chlorinated in the laboratory at different reaction time, temperature, pH and chlorine dose, and MX was determined and quantified by GC/MS. The finding suggests that the optimal chlorination conditions are as follows: temperature = 298 K, pH = 5, Cl:syrin. (mol:mol) = 9:1. We also found that the formation of MX increased with the syringaldehyde concentration in a linear relationship. In addition, when syringaldehyde was chlorinated with a different chlorine dose in an alkaline condition, no MX was detected. This study will conduce to elucidating the kinetic process for the formation of MX from syringaldehyde and will be of great help for better control of MX in drinking water. Syringaldehyde (4-hydroxy-3,5-dimethoxybenzaldehyde) was chlorinated in the laboratory at different reaction time, temperature, pH and chlorine dose, and MX was determined and quantified by GC/MS. The finding suggests that the optimal chlorination conditions are as follows: temperature = 298 K, pH = 5, Cl:syrin. (mol:mol) = 9:1. We also found that the formation of MX increased with the syringaldehyde concentration in a linear relationship. In addition, when syringaldehyde was chlorinated with a different chlorine dose in an alkaline condition, no MX was detected. This study will conduce to elucidating the kinetic process for the formation of MX from syringaldehyde and will be of great help for better control of MX in drinking water. (C) 2000 Elsevier Science Ltd.

Facile synthesis of mutagen X (MX): 3-chloro-4-(dichloromethyl)-5-hydroxy- 5H-furan-2-one

3-Chloro-4-(dichloromethyl)-5-hydroxy-5H-furan-2-one (mutagen X, MX) was synthesized in six steps from commercially-available and inexpensive starting materials (27% overall yield). This synthesis enables the preparation of MX analogs and does not require the use of chlorine gas, as do previously reported methods.

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.