Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI)

Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI) - Names and Identifiers

Name	Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI)
Synonyms	2-chloro-7-nitrolbenzothiazole 2-Chloro-7-nitro-benzothiazole Benzothiazole, 2-chloro-7-nitro- 2-Chloro-7-nitrobenzo[d]thiazole 2-Chloro-7-nitro-1,3-benzothiazole Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI)
CAS	2942-22-5

Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI) - Physico-chemical Properties

Molecular Formula	C7H3ClN2O2S
Molar Mass	214.63
Storage Condition	under inert gas (nitrogen or Argon) at 2-8°C

Benzothiazole, 2-chloro-7-nitro- (7CI,8CI,9CI) - Reference Information

Application

2-chloro-7-nitrobenzothiazole is an organic intermediate, 7-nitro-1, 3-benzothiazol-2-amine can be prepared from 3-nitrophenyl isothiocyanate, 2-chloro-7-nitrobenzothiazole is then prepared by diazotization reaction and can be used as an intermediate in organic synthesis and pharmaceutical intermediates, used in laboratory research and development process and chemical production process.

preparation

(3-nitrophenyl) thiourea: to 7.20g(40 mmol) in 25 mL methanol to phenyl 3-nitroisothiocyanate was added 28.5 mL(200 mmol) of 7 N ammonia in methanol. After 30 minutes, the slurry was concentrated to give 7.9g(100%) of the title compound as a yellow-orange powder which did not require further purification. MS Calcd.: 197; Found: 198 (M H). 7-nitro-1, 3-benzothiazol-2-amine: in 1 hour, to 0.60G (3.0 mmol) (3-nitrophenyl) to a solution of thiourea in 25 ml of carbon tetrachloride, a solution of 0.17 ML (3.4 mmol) of bromine in 10 ml of carbon tetrachloride was added dropwise. The mixture was heated to reflux for 18 h, cooled to room temperature, and the precipitate formed was collected by filtration. The precipitate was slurried in glacial acetic acid and the solid was collected by filtration. The solid thus obtained was slurried in water and saturated potassium carbonate was added until the pH was about 9. The free base was collected by filtration to give 0.30g(51%) of the title compound as a light orange solid. MS Calcd.: 195; Found: 196 (M H). 2-chloro-7-nitrobenzothiazole: to dissolve 0.195g(1.0 mmol) of 7-nitro-1, 3-benzothiazol-2-amine and 0.336g(2.5 mmol) to 2mL of N,N-dimethylformamide (DMF) was added 0.15mL(1.25mmol) of tert-butyl nitrite. The reaction was stirred at room temperature for 24 hours, poured into water and the resulting precipitate was collected and dried to give 0.163g(76%) of the title compound as a tan.

Last Update：2024-04-09 02:00:14