METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE

Base Information

• Chemical Name: METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE
• CAS No.: 35212-96-5
• Molecular Formula: C₁₀H₇ClO₂S
• Molecular Weight: 226.683
• Hs Code.: 2934999090
• Mol file: 35212-96-5.mol

Synonyms:5-Chloro-benzo[b]thiophene-2-carboxylicacid methyl ester;

Chemical Property of METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 9.66E-05mmHg at 25°C
• Melting Point: 113-115
• Refractive Index: 1.646
• Boiling Point: 338.7 °C at 760 mmHg
• Flash Point: 158.6 °C
• PSA: 54.54000
• Density: 1.391 g/cm³
• LogP: 3.34130

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 5-chlorobenzo[b]thiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5-chlorobenzo[b]thiophene-2-carboxylate acts as a reagent in the synthesis and biological evaluation of amide-, urea- and thiourea-functionalized dipeptides as selective linear tachykinin NK2 receptor antagonists, preparation and SAR of benzothiophene carboxamides as urotensin-II receptor antagonists.

Technology Process of METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE

There total 4 articles about METHYL 5-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLATE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

5-chlorobenzothiophene (20532-33-6) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → 5-chloro-2-benzo[b]thiophenecarboxylic acid methyl ester (35212-96-5)

Guidance literature:

5-chlorobenzothiophene; carbon dioxide; With 18-crown-6 ether; cesium fluoride; lithium tert-butoxide; at 160 ℃; for 3h; under 760.051 Torr; Inert atmosphere; Sealed tube;

methyl iodide; at 60 ℃; for 2h;

DOI:10.1002/chem.201805926

Reference yield: 91.0%

Methyl thioglycolate (2365-48-2) + 5-chloro-2-fluorobenzaldehyde (96515-79-6) → 5-chloro-2-benzo[b]thiophenecarboxylic acid methyl ester (35212-96-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 15h;

DOI:10.1016/j.ejmech.2019.04.024

Reference yield: 31.0%

5-chloro-2-nitrobenzaldehyde (6628-86-0) + Methyl thioglycolate (2365-48-2) → 5-chloro-2-benzo[b]thiophenecarboxylic acid methyl ester (35212-96-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 6h; Reflux;

upstream raw materials:

5-chloro-2-nitrobenzaldehyde

Methyl thioglycolate

5-chloro-2-fluorobenzaldehyde

5-chlorobenzothiophene

Downstream raw materials:

5-chloro-benzo(b)thiophene-2-carboxylic acid

2-Hydroxymethyl-5-chlor-benzothiophen

Refernces

• 1、 Li, Wen-Zhen,Xi, Hui-Zhi,Wang, Yi-Jie,Ma, Hong-Bo,Cheng, Zhi-Qiang,Yang, Yu,Wu, Meng-Ling,Liu, Ting-Mei,Yang, Wen,Wang, Qin,Liao, Meng-Ya,Xia, Yong,Zhang, Yi-Wen. "Design, synthesis, and biological evaluation of benzo[b]thiophene 1,1-dioxide derivatives as potent STAT3 inhibitors". . p. 835 - 849. Retrieved 2021/09/02.
• 2、 Shigeno, Masanori,Hanasaka, Kazuya,Sasaki, Keita,Nozawa-Kumada, Kanako,Kondo, Yoshinori. "Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6". supporting information. p. 3235 - 3239. Retrieved 2019/02/13.