Isothiazole Chemical Properties

Melting point:

176 °C (decomp)(Solv: water (7732-18-5))

Boiling point:

114°C(lit.)

Density 

1.1566 (rough estimate)

refractive index 

1.5280 to 1.5320

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform, Ethyl Acetate

form 

Oil

pka

4.00±0.12(Predicted)

color 

Clear Colourless

λmax

242nm(lit.)

Safety Information

RIDADR 

UN 1993 3/PG II

HS Code 

2934.10.2000

HazardClass 

3

PackingGroup 

II

Isothiazole Usage And Synthesis

Chemical Properties

Isothiazole is a colorless liquid with a pyridine-like odor. It is only slightly soluble in water but readily dissolves in organic solvents such as ethanol and benzene. When treated with butyl lithium at -70°C, it undergoes lithiation at the 5-position. Isothiazole serves as a versatile intermediate for the synthesis of various 5-substituted derivatives, including alkyl groups (R-), formyl (-CHO), carboxyl (-COOH), and acyl groups (RCO-), among others. Electrophilic substitution reactions, such as nitration, sulfonation, and halogenation, predominantly occur at the 4-position.

Uses

Isothiazole, is a versatile building block that can be used in the synthesis of more complex compounds with biological activity such as the pharmaceutical drugs ziprasidone (Z485000), and perospirone (P288900).

Definition

ChEBI: Isothiazole is a mancude organic heteromonocyclic parent, a monocyclic heteroarene and a member of 1,2-thiazoles.

Preparation

Isothiazole can be prepared by the reaction of propiolic aldehyde with sodium thiocyanate to first produce 3-thiocyanatoacrolein (NCSCH=CHCHO), which is then reacted with ammonia to obtain isothiazole.

References

[1] LAI CHEN. Discovery of Novel Isothiazole, 1,2,3-Thiadiazole, and Thiazole-Based Cinnamamides as Fungicidal Candidates[J]. Journal of Agricultural and Food Chemistry, 2019, 67 45: 12357-12365. DOI:10.1021/acs.jafc.9b03891.
[2] A. KLETSKOV. Isothiazoles in the Design and Synthesis of Biologically Active Substances and Ligands for Metal Complexes[J]. Synthesis-Stuttgart, 2019, 113 1: 159-188. DOI:10.1055/s-0039-1690688.
[3] BERA A, PATRA P, AZAD A, et al. Neat synthesis of isothiazole compounds, and studies on their synthetic applications and photophysical properties?[J]. New Journal of Chemistry, 2022, 24: 11685-11694. DOI:10.1039/D2NJ01962K.
[4] ZHU-ZHU ZHANG. Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers[J]. The Journal of Organic Chemistry, 2020, 86 1: 632-642. DOI:10.1021/acs.joc.0c02286.

Isothiazole(288-16-4)Related Product Information

• 2-Methyl-4-isothiazolin-3-one
• Methylchloroisothiazolinone/methylisothiazolinone mixture (MCIT/MIT)
• Isothiazolo[5,4-b]pyridin-3-amine
• thiazol-3-one
• Isothiazolo[5,4-b]pyridin-3(2H)-one, 1,1-dioxide
• ISOTHIAZOLE-5-BORONIC ACID
• 1,1-DIOXO-ISOTHIAZOLIDINE-3-CARBOXYLIC ACID
• Isothiazolo[5,4-b]pyridin-3-ol
• 4-Isothiazolecarbonitrile
• 3-Aminoisothiazolo[4,3-b]pyridine
• ISOTHIAZOLINE 1,1-DIOXIDE
• 4-Carboxyisothiazole
• Isothiazol-4-ylMethanaMine
• 3-Isothiazolecarboxamide
• isothiazol-3-ylMethanol
• 5-ISOTHIAZOLECARBOXYLIC ACID
• ISOTHIAZOLE-5-CARBALDEHYDE
• Isothiazole-5-methanol