39244-06-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorothieno[2,3-b]thiophene-2-carbonyl chloride is used as an intermediate in the production of pharmaceuticals. Its unique structure and reactivity allow for the synthesis of various drug molecules, contributing to the development of new medications.
Used in Agrochemical Industry:
In the agrochemical industry, 3-chlorothieno[2,3-b]thiophene-2-carbonyl chloride serves as an intermediate for the synthesis of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in agricultural applications.
Used in Research and Development:
3-Chlorothieno[2,3-b]thiophene-2-carbonyl chloride is utilized in research and development as a building block for the synthesis of various organic compounds. Its reactivity and unique structure make it a valuable tool for creating new molecules with potential applications in various fields.
It is important to handle 3-chlorothieno[2,3-b]thiophene-2-carbonyl chloride with caution due to its potential health hazards and reactivity. Proper safety measures should be taken during its use to minimize risks.

InChI:InChI=1/C7H2Cl2OS2/c8-4-3-1-2-11-7(3)12-5(4)6(9)10/h1-2H

Upstream product

• 1195-52-4 trans-3-(3-thienyl)acrylic acid 

Downstream Products

• 119647-14-2 3-chloro-N-phenylthieno<2,3-b>thiophene-2-carboxamide 
• 886180-47-8 N-(4'-cyanophenyl)-3-chlorothieno[3,2-b]thiophene carboxanilide 

Relevant academic research and scientific papers

Synthesis, photochemical synthesis and antitumor evaluation of novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones.

The novel derivatives of thieno[3',2':4,5]thieno[2,3-c]quinolones 6a, 6b, 7, 10a and 10b were synthesized in multistep synthesis starting from thiophene-3-carboxaldehyde and malonic acid reacting in aldol condensation or from 3-bromothiophenes or methyl 4-bromothiophene-2-carboxylate reacting in Heck reaction. They resulted in corresponding substituted thienylacrylic acids 3a-c, which were cyclized into thieno[2,3-c]thiophene-2-carbonyl chlorides 4a-c and converted into thieno[2,3-c]thiophene-2-carboxamides 5a-d. Prepared carboxamides were photochemically dehydrohalogenated into corresponding substituted thieno[3',2':4,5]thieno[2,3-c]quinolones 6a-d. Compound 7 was prepared from 6d by alkylation with N-[3-(dimethylamino)propyl]chloride hydrochloride in the presence of NaH. Compounds 10a and 10b were prepared from 6c in the multistep synthesis over acid 8 and acid chloride 9. Compounds 6a, 6b, 7, 10a and 10b were found to exert cytostatic activities against malignant cell lines: pancreatic carcinoma (MiaPaCa2), breast carcinoma (MCF7), cervical carcinoma (HeLa), laryngeal carcinoma (Hep2), colon carcinoma (CaCo-2), melanoma (HBL), and human fibroblast cell lines (WI-38). The compound 6b, which bears the 3-dimethylaminopropyl substituent on quinolone nitrogen and methoxycarbonyl substituent on position 9, exhibited marked antitumor activity. On the contrary, compound 7, which also bears the 3-dimethylaminopropyl substituent on the quinolone nitrogen but anilido substituent on position 9, exhibited less antitumor activity than the others.