5-Chloro-1-benzothiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-Chloro-1-benzothiophene-2-carbaldehyde
• CAS No.: 28540-51-4
• Molecular Formula: C9H5ClOS
• Molecular Weight: 196.66
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10594127
• Nikkaji Number: J3.514.281I
• Wikidata: Q82488866
• Mol file: 28540-51-4.mol

Synonyms:28540-51-4;5-chloro-1-benzothiophene-2-carbaldehyde;5-chlorobenzo[b]thiophene-2-carbaldehyde;5-chlorobenzothiophene-2-carboxaldehyde;Benzo[b]thiophene-2-carboxaldehyde, 5-chloro-;5-Chlorobenzo[b]thiophene-2-carboxaldehyde;5-Chloro-1-benzothiophene-2-carboxaldehyde;5-chlorobenzo[b]thiophene-2-carboxaldehyde;SCHEMBL3618744;DTXSID10594127;ZKNZDTHWZYRQIH-UHFFFAOYSA-N;5-chlorobenzothiophene-2-carbaldehyde;MFCD16622780;AKOS006336790;DE-0702;DA-07346;CS-0021452;E84456;EN300-3044060;J-517382;Z1201628726

Chemical Property of 5-Chloro-1-benzothiophene-2-carbaldehyde

Chemical Property:

• Melting Point: 135 °C(Solv: ethanol (64-17-5))
• Boiling Point: 338.8±22.0 °C(Predicted)
• PSA: 45.31000
• Density: 1.439±0.06 g/cm3(Predicted)
• LogP: 3.36720
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.9749636
• Heavy Atom Count: 12
• Complexity: 185

Purity/Quality:

97% ^*data from raw suppliers

5-Chloro-1-benzothiophene-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C=C(S2)C=O
• Uses: 5-Chloro-1-benzothiophene-2-carboxaldehyde possesses anti-viral activity against the PR8 strain of influenza A virus and IHD strain of vaccinia virus; Potential inhibitory agents for the treatment of prostate cancer.

Technology Process of 5-Chloro-1-benzothiophene-2-carbaldehyde

There total 6 articles about 5-Chloro-1-benzothiophene-2-carbaldehyde 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: 86.0%

5-chlorobenzothiophene (20532-33-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-chlorobenzo[b]thiophene-2-carboxaldehyde (28540-51-4)

Guidance literature:

5-chlorobenzothiophene; N,N-dimethyl-formamide; With tris(trimethylsilyl)amine; tetramethylammonium fluoride; at 20 ℃; for 21h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In water; at 20 ℃; for 1.5h;

DOI:10.1021/acs.oprd.8b00247

Reference yield: 27.0%

4-chlorophenyl methyl sulfide (123-09-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-chlorobenzo[b]thiophene-2-carboxaldehyde (28540-51-4)

Guidance literature:

4-chlorophenyl methyl sulfide; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tert-butyl methyl ether; at 0 - 20 ℃; for 3.5h; Inert atmosphere; Schlenk technique;

N,N-dimethyl-formamide; In tert-butyl methyl ether; at 20 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.8b00850

Reference yield:

5-chlorobenzothiophene (20532-33-6) → 5-chlorobenzo[b]thiophene-2-carboxaldehyde (28540-51-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

upstream raw materials:

5-chlorobenzothiophene

N,N-dimethyl-formamide

(4-chlorophenyl)(2,2-diethoxyethyl)sulfane

p-Chlorothiophenol

Downstream raw materials:

2-Hydroxymethyl-5-chlor-benzothiophen

2-bromomethyl-5-chlorobenzo[b]thiophene