131947-13-2

Basic information

• Product Name: 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID
• Synonyms: 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID;TIMTEC-BB SBB000369;4,5-dichloro-isothiazol-3-carboxylic acid
• CAS NO: 131947-13-2
• Molecular Formula: C₄HCl₂NO₂S
• Molecular Weight: 198.03
• Mol File: 131947-13-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 205.9°Cat760mmHg
• Flash Point: 78.4°C
• Appearance: /
• Density: 1.824g/cm³
• Vapor Pressure: 0.147mmHg at 25°C
• Refractive Index: 1.646
• Storage Temp.: 2-8°C
• PKA: 1.79±0.25(Predicted)
• CAS DataBase Reference: 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID(131947-13-2)
• EPA Substance Registry System: 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID(131947-13-2)

Safety Data

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• HazardClass: IRRITANT
• Hazardous Substances Data: 131947-13-2(Hazardous Substances Data)

Usage

General Description

4,5-Dichloroisothiazole-3-carboxylic acid is a chemical compound with the molecular formula C5H2Cl2NOS. It is a chlorinated isothiazole derivative that is primarily used as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and dyes. 4,5-DICHLOROISOTHIAZOLE-3-CARBOXYLIC ACID is known for its potent antimicrobial properties and is commonly used as a building block in the development of antimicrobial agents. Additionally, it is also utilized in the production of corrosion inhibitors for metal surfaces. 4,5-Dichloroisothiazole-3-carboxylic acid is notable for its versatile applications in the field of medicinal and agricultural chemistry, making it a valuable chemical compound in the industry.

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

Upstream product

• 118888-36-1 4,5-dichloro-3-trichloromethyl-1,2-thiazole 

Downstream Products

• 654056-79-8 C₁₈H₁₀Cl₂N₂O₂S 
• 654057-00-8 C₁₈H₁₁Cl₂N₃OS₂ 
• 166668-76-4 methyl 4,5-dichloro-isothiazole-3-carboxylate 

Relevant articles and documents

Polyhalonitrobutadienes as versatile building blocks for the biotargeted synthesis of substituted N-heterocyclic compounds

Substituted nitrogen heterocycles are structural key units in many important pharmaceuticals. A new synthetic approach towards heterocyclic compounds displaying antibacterial activity against Staphylococcus aureus or cytotoxic activity has been developed. The selective synthesis of a series of 64 new N-heterocycles from the three nitrobutadienes 2-nitroperchloro-1,3-butadiene, 4-bromotetrachloro-2-nitro-1,3-butadiene and (Z)-1,1,4-trichloro-2,4-dinitrobuta-1,3-diene proved feasible. Their reactions with N-, O- and S-nucleophiles provide rapid access to push-pull substituted benzoxazolines, benzimidazolines, imidazolidines, thiazolidinones, pyrazoles, pyrimidines, pyridopyrimidines, benzoquinolines, isothiazoles, dihydroisoxazoles, and thiophenes with unique substitution patterns. Antibacterial activities of 64 synthesized compounds were examined. Additionally, seven compounds (thiazolidinone, nitropyrimidine, indole, pyridopyrimidine, and thiophene derivatives) exhibited a significant cytotoxicity with IC50-values from 1.05 to 20.1 μM. In conclusion, it was demonstrated that polyhalonitrobutadienes have an interesting potential as structural backbones for a variety of highly functionalized, pharmaceutically active heterocycles.

THE SYNTHESIS AND SOME REACTIONS OF 3-TRICHLOROMETHYL-4,5-DICHLOROISOTHIAZOLE

The reaction of 2-nitropentachloro-1,3-butadiene with elemental sulfur proceeds with the participation of the nitro group and leads to 3-trichloromethyl-4,5-dichloroisothiazole.The action of piperidine and sodium alcoholates on the isothiazole obtained gives 5-amino and 5-alkoxy derivatives of the starting isothiazole.The action of nitric acid on the starting isothiazole leads to hydrolysis of the trichloromethyl group with the formation of 4,5-dichloroisothiazole-3-carboxylic acid.Zinc in ethanol reduced the trichloromethyl group of 3-trichloromethyl-4,5-dichloroisothiazole to a dichloromethyl group, while the use of PbCl2 as the reducing agent gives dechlorodimerization of the starting isothiazole with the formation of 1,2-bis(4,5-dichloroisothiazole)tetrachloroethane.