Dichloro-1,2-dithiacyclopentenone Chemical Properties

Melting point:

52-56 °C

Flash point:

200 °C

storage temp. 

2-8°C

form 

Solid

BRN 

1342220

InChI

InChI=1S/C3Cl2OS2/c4-1-2(5)7-8-3(1)6

InChIKey

QGSRKGWCQSATCL-UHFFFAOYSA-N

SMILES

S1C(Cl)=C(Cl)C(=O)S1

EPA Substance Registry System

4,5-Dichloro-1,2-dithiacyclopentenone (1192-52-5)

Safety Information

Hazard Codes 

T

Risk Statements 

25-37/38

Safety Statements 

36/37/39-45

RIDADR 

2811

WGK Germany 

3

RTECS 

JP1290000

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

mouse,LD50,intravenous,13mg/kg (13mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07423,

Dichloro-1,2-dithiacyclopentenone Usage And Synthesis

Uses

4,5-Dichloro-3H-1,2-dithiol-3-one (Dichloro-1,2-dithiacyclopentenone) is an E. coli FabH inhibitor (IC50: 2.9 μM). 4,5-Dichloro-3H-1,2-dithiol-3-one can be used as a slimicide in the manufacture of food-contact paper and paperboard [1][2].

Synthesis

Using tetrachloroethylene and trichloromethane as the starting materials, 4,5-dichloro-1,2-dithiolenone was obtained by Foucault reaction, alkaline dechlorination to alkene, and catalytic and sulfur cyclization.

Purification Methods

Dissolve it in CH2Cl2 (1g in 250ml), filter, wash it twice with H2O, evaporate and distil the residue in vacuo and then recrystallise it from pet ether. IR: max 1650 cm-1. [Boberg Justus Liebigs Ann Chem 679 109 1964, Boberg Justus Liebigs Ann Chem 693 212 1966, Beilstein 19/4 V 72.]

References

[1] Song X, et al. Synthesis and antibacterial activity of cinnamaldehyde acylhydrazone with a 1,4-benzodioxan fragment as a novel class of potent β-ketoacyl-acyl carrier protein synthase III (FabH) inhibitor. Chem Pharm Bull (Tokyo). 2014;62(11):1110-8. DOI:10.1248/cpb.c14-00485
[2] Mary S. Wolfe, et al. Chapter. National Toxicology Program. Book. Toxicology and Regulatory Process. 2006. Pages. 32

Dichloro-1,2-dithiacyclopentenone(1192-52-5)Related Product Information

• DL-Limonene
• 1,3-Cyclopentadiene
• Dichloroacetonitrile
• TRANS-1,3-PENTADIENE
• Dicyclopentadiene
• 1,2-PENTADIENE
• 2',4'-Dichloroacetophenone
• Selenium sulfide
• Cyclopentene
• 1,2-Dichloroethane
• METHYLCYCLOPENTADIENE DIMER
• Dichloroacetic acid
• Disulfur dichloride
• CIS-1,2-DICHLOROETHYLENE
• Dichloro-1,2-dithiacyclopentenone