3,4-DICHLOROISOTHIAZOLE-5-CARBOXYLIC ACID Chemical Properties

Melting point:

175-177°C

Boiling point:

205.9±40.0 °C(Predicted)

Density 

1.824

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder

pka

0.74±0.28(Predicted)

color 

Off white

InChI

InChI=1S/C4HCl2NO2S/c5-1-2(4(8)9)10-7-3(1)6/h(H,8,9)

InChIKey

HQZKNCJWLIWCSV-UHFFFAOYSA-N

SMILES

S1C(C(O)=O)=C(Cl)C(Cl)=N1

EPA Substance Registry System

3,4-Dichloro-5-isothiazolecarboxylic acid (18480-53-0)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2934100080

3,4-DICHLOROISOTHIAZOLE-5-CARBOXYLIC ACID Usage And Synthesis

Application

3,4-Dichloroisothiazol-5-carboxylic acid can be used as an organic synthesis intermediate and a pharmaceutical intermediate in laboratory research and development processes and in the synthesis of pharmaceutical chemicals.

Synthesis

The general procedure for the synthesis of 3,4-dichloroisothiazole-5-carboxylic acid from 3,4-dichloro-5-cyanoisothiazole was as follows: 42.4 g of crude 3,4-dichloro-5-cyanoisothiazole was placed in three 500 mL round-bottomed flasks, and diluted by adding 100 mL of methanol and 30 g of 45% sodium hydroxide solution. The reaction was stirred at 40°C for 2 h. The progress of the reaction was monitored by thin layer chromatography (TLC) until 3,4-dichloro-5-cyanoisothiazole was completely disappeared. After completion of the reaction, the residual methanol was removed by concentration under reduced pressure. Subsequently, the pH of the reaction solution was adjusted to 3 with concentrated hydrochloric acid, the precipitate was collected by filtration and washed with cold water to afford 17.6 g of white solid 3,4-dichloroisothiazole-5-carboxylic acid (II). The product can be used directly in the subsequent reaction without further purification. Depending on the experimental requirements, the reaction can be scaled up or down to prepare different amounts of 3,4-dichloroisothiazole-5-carboxylic acid (II). This synthesis method has the same effect as the commercially available compounds.

References

[1] Patent: US5240951, 1993, A
[2] Patent: CN102942565, 2016, B. Location in patent: Paragraph 0015; 0022-0023; 0083-0084

3,4-DICHLOROISOTHIAZOLE-5-CARBOXYLIC ACID(18480-53-0)Related Product Information

• 4-(CHLOROMETHYL)THIAZOLE HYDROCHLORIDE
• 2-Methyl-4-isothiazolin-3-one
• Isothiazole
• 5-ISOTHIAZOLECARBOXYLIC ACID
• 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID
• 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID METHYL ESTER