5-ISOTHIAZOLECARBOXYLIC ACID

5-ISOTHIAZOLECARBOXYLIC ACID Property

Melting point:

196-200℃ (decomposition)

Boiling point:

178.4±23.0℃ (760 Torr)

Density 

1.525±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

61.7±22.6℃

storage temp. 

2-8°C

form 

Solid

pka

1.23±0.10(Predicted)

color 

Off-white to light brown

Safety

HS Code 

2934208090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

5-ISOTHIAZOLECARBOXYLIC ACID Chemical Properties,Usage,Production

Uses

Isothiazole-5-carboxylic acid (8-Isoquinoline-methaneaminedihydrochloride) is an organic compound with antibacterial, anticancer and anti-inflammatory properties. Isothiazole-5-carboxylic acid can be used to develop novel compounds to combat various diseases. Isothiazole-5-carboxylic acid exhibits a wide range of potential pharmacological activities and helps improve existing inhibitory schemes.

Synthesis

Methyl isothiazole-5-carboxylate (0.50 g, 3.49 mmol) was dissolved in a THF/MeOH solvent mixture (20 mL/5 mL) at room temperature, followed by slow addition of 1N NaOH solution (5.24 mL, 5.24 mmol). The reaction mixture was stirred continuously for 16 h at room temperature and the completion of the reaction was confirmed by thin layer chromatography (TLC) monitoring. Upon completion of the reaction, the reaction mixture was acidified to pH 2 with 1N HCl solution, at which point a precipitate was observed to be generated. The precipitate was separated by filtration and dried to afford the target product isothiazole-5-carboxylic acid (Compound 2) as a beige solid in a yield of 0.35 g (76% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-d6) with chemical shifts of δ 8.69 (d, 1H) and 7.85 (d, 1H), respectively.

References

[1] Patent: US2007/105864, 2007, A1. Location in patent: Page/Page column 151-152
[2] Patent: US2007/117804, 2007, A1. Location in patent: Page/Page column 78