3-Chloro-4-(dichloromethyl)-2(5H)-furanone

Base Information

• Chemical Name: 3-Chloro-4-(dichloromethyl)-2(5H)-furanone
• CAS No.: 122551-89-7
• Molecular Formula: C5H3 Cl3 O2
• Molecular Weight: 201.437
• UNII: 427RD33L4C
• DSSTox Substance ID: DTXSID6021535
• Nikkaji Number: J313.412A
• Wikidata: Q27258504
• Mol file: 122551-89-7.mol

Synonyms:122551-89-7;3-Chloro-4-(dichloromethyl)-2(5H)-furanone;4-chloro-3-(dichloromethyl)-2H-furan-5-one;2(5H)-Furanone, 3-chloro-4-(dichloromethyl)-;CCRIS 4935;BRN 3604181;UNII-427RD33L4C;RMX;3-chloro-4-(dichloromethyl)furan-2(5H)-one;HSDB 7632;427RD33L4C;starbld0002769;C5H3Cl3O2;SCHEMBL4312225;C5-H3-Cl3-O2;DTXSID6021535;LS-70339;3-chloro-4(dichloromethyl)-2(5h)-furanone;3-chloro-4-(dichloromethyl)-2-(5h)-furanone;3-Chloro-4-(dichloromethyl)-2(5H)-furanone #;Q27258504;3-Chloro-4-(dichloromethyl)-2(5H)-furanone (red-mx);3-CHLORO-4-(DICHLOROMETHYL)-2(5H)-FURANONE [HSDB]

Chemical Property of 3-Chloro-4-(dichloromethyl)-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 0.000758mmHg at 25°C
• Boiling Point: 306.7°Cat760mmHg
• Flash Point: 146.3°C
• PSA: 26.30000
• Density: 1.61g/cm³
• LogP: 1.83980
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.919862
• Heavy Atom Count: 10
• Complexity: 197

Purity/Quality:

99%min ^*data from raw suppliers

3-Chloro-4-(dichloromethyl)-2(5H)-furanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(C(=O)O1)Cl)C(Cl)Cl
• Uses: 3-Chloro-4-(dichloromethyl)-2(5H)-furanone is mutagenic chlorine-substituted Furanone (F864050) compound. It is a byproduct of drinking water disinfection at some water purification facilities in the USA.

Technology Process of 3-Chloro-4-(dichloromethyl)-2(5H)-furanone

There total 3 articles about 3-Chloro-4-(dichloromethyl)-2(5H)-furanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

C5H5ClO3 (199536-77-1) → 3-Chloro-4-(dichloromethyl)-2(5H)-furanone (122551-89-7)

Guidance literature:

C₅H₅ClO₃; With pyridinium chlorochromate; sodium chloride; In dichloromethane; for 3h;

With phosphorus pentachloride; sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 4.33333h;

DOI:10.1016/j.tetlet.2012.04.044

Reference yield:

C11H15ClO6 (1380400-97-4) → 3-Chloro-4-(dichloromethyl)-2(5H)-furanone (122551-89-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / ethanol; water / 72 h / Inert atmosphere; Reflux

2.1: pyridinium chlorochromate; sodium chloride / dichloromethane / 3 h

2.2: 4.33 h / 20 °C

With toluene-4-sulfonic acid; pyridinium chlorochromate; sodium chloride; In ethanol; dichloromethane; water;

DOI:10.1016/j.tetlet.2012.04.044

Reference yield:

4-hydroxymethyl-5H-furan-2-one (80904-75-2) → 3-Chloro-4-(dichloromethyl)-2(5H)-furanone (122551-89-7) + 4-(Chloromethyl)-3,3,4-trichloro-2(5H)-furanone

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00296a053

upstream raw materials:

4-hydroxymethyl-5H-furan-2-one

C₁₁H₁₅ClO₆

C₅H₅ClO₃

Downstream raw materials:

5-Bromo-3-chloro-4-dichloromethyl-5H-furan-2-one

3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone

Refernces

• 1、 LaLonde, Robert T.,Perakyla, Hannu,Hayes, Michael P.. "Potentially Mutagenic, Chlorine-Substituted 2(5H)-Furanones: Studies of Their Synthesis and NMR Properties". . p. 2847 - 2855. Retrieved 2007/10/02.