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ChemicalBook--->CAS DataBase List--->4576-90-3

4576-90-3

4576-90-3 Structure

4576-90-3 Structure
IdentificationBack Directory
[Name]

3-Isothiazolecarboxylic acid
[CAS]

4576-90-3
[Synonyms]

3-Carboxyisothiazole
3-Isothiazolecarboxylic 
isothiazole-3-carboxylic acid
3-ISOTHIAZOLE CARBOXYLIC ACID
1,2-thiazole-3-carboxylic acid
Isothiazole-3-carboxylicacid97%
Isothiazole-3-carboxylic acid 97%
3-Carboxyisothiazole, 1,2-Thiazole-3-carboxylic acid
[Molecular Formula]

C4H3NO2S
[MDL Number]

MFCD09834765
[MOL File]

4576-90-3.mol
[Molecular Weight]

129.14
Chemical PropertiesBack Directory
[Boiling point ]

178 °C
[density ]

1.525
[Fp ]

62 °C
[storage temp. ]

Sealed in dry,2-8°C
[form ]

solid
[pka]

1.08±0.10(Predicted)
[color ]

Beige
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319
[Precautionary statements ]

P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
[HS Code ]

2934100090
Hazard InformationBack Directory
[Uses]

3-Isothiazolecarboxylic acid
[Synthesis]

3-METHYLISOTHIAZOLE

693-92-5

3-Isothiazolecarboxylic acid

4576-90-3

The general procedure for the synthesis of isothiazole-3-carboxylic acid using 3-methylisothiazole as starting material was as follows: chromium(IV) oxide (9.00 mmol) was added batchwise to a solution of 3-methylisothiazole (3.03 mmol) dissolved in fuming sulphuric acid (10 mL) under the condition of ice bath at 0°C. The reaction mixture was gradually warmed to room temperature and the reaction was stirred at this temperature for 16 hours. Upon completion of the reaction, the mixture was diluted with ice water (100 mL) followed by multiple extractions with ether (6 x 200 mL). All organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by preparative high performance liquid chromatography (HPLC) to give isothiazole-3-carboxylic acid in 13% yield as a white solid. The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-d6) and LC/MS: 1H-NMR δ 3.43 (s, 1H), 9.17 (d, 1H), 7.80 (d, 1H), 3.43 (s, 1H); LC/MS (ESI) m/z [M + 1]+ 128.

[References]

[1] Patent: WO2018/160878, 2018, A1. Location in patent: Page/Page column 183
[2] Patent: WO2009/55437, 2009, A2. Location in patent: Page/Page column 66
[3] Journal of the Chemical Society, 1965, p. 7274 - 7276
[4] Journal of the Chemical Society, 1965, p. 7277 - 7282
Spectrum DetailBack Directory
[Spectrum Detail]

3-Isothiazolecarboxylic acid(4576-90-3)1HNMR
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