3-Hydroxybenzothiophene

Base Information

• Chemical Name: 3-Hydroxybenzothiophene
• CAS No.: 520-72-9
• Molecular Formula: C8H6OS
• Molecular Weight: 150.201
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70199970
• Nikkaji Number: J25.399E
• Wikidata: Q72483277
• ChEMBL ID: CHEMBL3311419
• Mol file: 520-72-9.mol

Synonyms:3-Hydroxybenzothiophene;520-72-9;benzo[b]thiophen-3-ol;1-Benzothiophen-3-ol;Benzothiophen-3-ol;BENZO(b)THIOPHENE-3-OL;3-Hydroxythianaphthene;BRN 0114954;Benzo[b]thiophene-3-ol;5-17-04-00188 (Beilstein Handbook Reference);Thioindoxyl;1-Benzothiophen-3-ol #;3-hydroxybenzo[b]thiophene;SCHEMBL276823;CHEMBL3311419;DTXSID70199970;AKOS003611445;benzothiophen-3-ol;Benzo[b]thiophen-3-ol;LS-41270;CS-0453212;FT-0632278;A828913

Chemical Property of 3-Hydroxybenzothiophene

Chemical Property:

• Vapor Pressure: 0.000585mmHg at 25°C
• Refractive Index: 1.727
• Boiling Point: 301.6 °C at 760 mmHg
• PKA: 9.15±0.40(Predicted)
• Flash Point: 136.2 °C
• PSA: 48.47000
• Density: 1.347 g/cm³
• LogP: 2.60690
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 150.01393598
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

Benzo[b]thiophen-3-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)O

Technology Process of 3-Hydroxybenzothiophene

There total 35 articles about 3-Hydroxybenzothiophene 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: 53.0%

methyl 2-(methylthio)benzoate (3704-28-7) → 3-hydroxybenzothiophene (520-72-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

Reference yield:

Benzo[b]thiophene (95-15-8,11095-43-5) → 1-benzothiophen-6-ol (19301-39-4) + benzo[b]thiophen-5-ol (19301-35-0) + benzo[b]-2,3-dihydrothiophen-2-one (496-31-1) + 4-hydroxybenzothiophene (3610-02-4) + 3-hydroxybenzothiophene (520-72-9) + thioindoxyl (130-03-0)

Guidance literature:

With dinitrogen monoxide; In water; at 30 ℃; Product distribution; Rate constant; Mechanism; Irradiation; K₃Fe(CN)6, or NaOH were added;

DOI:10.1021/j150614a029

Reference yield:

2-acetyl-3-oxo-2,3-dihydro-benzo[b]thiophene-2-carboxylic acid → 3-hydroxybenzothiophene (520-72-9) + trans-thioindigo (3844-31-3)

Guidance literature:

beim Umkrystallisieren;

upstream raw materials:

(o-carboxyphenyl)thioacetic acid

3-hydroxy-benzo[b]thiophene-2-carboxylic acid

aniline

tetrachloromethane

Downstream raw materials:

ethylbenzene

2-((Ξ)-7tphenyl-hepta-2t,4t,6-trienylidene)-benzo[b]thiophen-3-one

2-[5-(2,4-dinitro-phenylimino)-penta-1,3-dienyl]-benzo[b]thiophen-3-ol

acetophenone

Refernces

Anellated quinolones

10.1002/ardp.19763090105

This study discusses the synthesis and investigation of 1,3-dicarbonyl compounds with a particular focus on cyclized quinolones. The aim of this study was to obtain quinolone lb via thermal condensation of 3-benzofuranone and anthranilic acid and to report the synthesis of substituted 2-benzoyl-3-hydroxy-benzo[b]thiophenes that can cyclize to form cyclized quinolones 7. This study aimed to explore the potential of heterocyclic ketones in the formation of cyclized quinolones, with oxygen, nitrogen, or sulfur as heteroatoms instead of methylene groups. The key chemicals used in the process included 3-benzofuranone, anthranilic acid, N-methylanthranilic acid, 3-acetoxyindole, thioindoxyl, and various heterocyclic compounds. The conclusions drawn from the study indicated that the cyclization was mainly carried out via Schiff bases and that the synthesis of indoles and benzothieno[3,2-b]-quinolones could be similar to the synthesis of cyclized chromones from heterocyclic β-dicarbonyl compounds. The study also highlights the potential pharmaceutical value of benzothieno[3,2-b][1]-chromones and benzothieno[3,2-b][1]-chromone-derived substances due to their antiallergic and antiallergic effects, as well as the discovery of O-ketoimidates and O-ketoamidines as new anti-inflammatory agents with no ulcerogenic effects on the gastrointestinal mucosa.