3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime

Base Information

• Chemical Name: 3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime
• CAS No.: 14006-55-4
• Molecular Formula: C₉H₆ClNOS
• Molecular Weight: 211.672
• DSSTox Substance ID: DTXSID901237051
• Mol file: 14006-55-4.mol

Synonyms:DTXSID901237051;3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime

Chemical Property of 3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 210.9858627
• Heavy Atom Count: 13
• Complexity: 212

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(S2)C=NO)Cl

Technology Process of 3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime

There total 4 articles about 3-Chlorobenzo[b]thiophene-2-carboxaldehyde oxime 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: 67.0%

3-chloro-1-benzothiophen-2-carbaldehyde (14006-54-3) → 3-chlorobenzo[b]thiophene-2-carbaldehyde oxime (14006-55-4)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In methanol; at 20 ℃;

Reference yield:

C11H11ClNS(1+)*Cl(1-) → 3-chlorobenzo[b]thiophene-2-carbaldehyde oxime (14006-55-4)

Guidance literature:

With hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 5h;

DOI:10.1055/a-1398-7237

Reference yield:

methyl 3-(hydroxy)thieno[3,2-b][1]benzothiophene-2-carboxylic acid methyl ester (881033-97-2) → 3-chlorobenzo[b]thiophene-2-carbaldehyde oxime (14006-55-4)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / dimethyl sulfoxide; water / 2 h / 120 °C / Inert atmosphere

2: trichlorophosphate / 3 h / 15 - 60 °C

3: hydroxylamine hydrochloride / N,N-dimethyl-formamide / 5 h / 20 - 60 °C

With hydroxylamine hydrochloride; sodium hydroxide; trichlorophosphate; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: |Vilsmeier-Haack Formylation;

DOI:10.1055/a-1398-7237

upstream raw materials:

3-chloro-1-benzothiophen-2-carbaldehyde

methyl 3-(hydroxy)thieno[3,2-b][1]benzothiophene-2-carboxylic acid methyl ester

Refernces

• 1、 -. "SPIRO-OXADIAZOLINE COMPOUNDS AS AGONISTS OF α-7-NICOTINIC ACETYLCHOLINE RECEPTORS". Paragraph 00408-00409. . Retrieved 2015/05/19.