5381-20-4

Basic information

• Product Name: 1-Benzothiophene-3-carbaldehyde
• Synonyms: 1-BENZOTHIOPHENE-3-CARBALDEHYDE;1-BENZOTHIOPHENE-3-CARBOXALDEHYDE;BENZO[B]THIOPHENE-3-CARBOXALDEHYDE;BUTTPARK 154\50-70;RARECHEM AM LA 0006;THIANAPHTHENE-3-CARBOXALDEHYDE;BENZOTHIOPHENE-3-CARBOXALDEHYDE;Benzo[B]Thiophene-3-Carboxalde
• CAS NO: 5381-20-4
• Molecular Formula: C₉H₆OS
• Molecular Weight: 162.21
• EINECS: 1312995-182-4
• Product Categories: Pharmaceutical Intermediates;Heterocycles;Heterocyclic Compound;Heterocycle-oher series
• Mol File: 5381-20-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: 53-57 °C(lit.)
• Boiling Point: 166 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: yellow to brown crystalline powder
• Density: 1.2123 (rough estimate)
• Vapor Pressure: 0.000944mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1-Benzothiophene-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzothiophene-3-carbaldehyde(5381-20-4)
• EPA Substance Registry System: 1-Benzothiophene-3-carbaldehyde(5381-20-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 5381-20-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to brown crystalline powder

Uses

Thianaphthene-3-carboxaldehyde (Benzo[b]thiophene-3-carboxaldehyde) may be used as a starting material in the multi-step synthesis of anthra[2,3-b:7,6-b′]bis[1benzothiophenes (ABBTs). It may be used in the synthesis of :6-(N,N-dimethylamino)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one6-(pyrrolidin-1-yl)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one(Z)-2-(benzo-[b]-thio-phen-3-yl-methyl-ene)-1-aza-bi-cyclo-[2.2.2]-octan-3-one

General Description

Thianaphthene-3-carboxaldehyde, also known as benzo[b]thiophene-3-carboxaldehyde, can be synthesized from 3-methyl-benzo[b]thiophene. It undergoes phosphine-free palladium coupling with aryl halides to form 2-arylbenzo[b]thiophenes.

InChI:InChI=1/C9H6OS/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-6H

Upstream product

• 5312-73-2 dichloromethyl n-butyl ether 
• 95-15-8 Benzo[b]thiophene 
• 7342-82-7 3-Bromothianaphthene 
• 119072-55-8 tert-butylisonitrile 
• 1207738-76-8 N-methoxy-N-methylbenzo[b]thiophene-3-carboxamide 
• 5381-25-9 benzo[b]thiophene-3-carboxylic acid 
• 5381-24-8 benzo[b]thiophen-3-yl methanol 
• 24434-84-2 benzo[b]thiophene-3-carbonitrile 
• 1196-19-6 3-(bromomethyl)benzothiophene 
• 1455-18-1 3-methylbenzothiophene 
• 4885-02-3 Dichloromethyl methyl ether 
• 3216-47-5 3-chloromethylbenzothiophene 
• 201230-82-2 carbon monoxide 
• 50-00-0 formaldehyd 

Downstream Products

• 4565-13-3 3-styrylbenzothiophene 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 693228-22-7 2-(4-methoxyphenyl)-1-benzothiophene-3-carbaldehyde 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 693228-25-0 2-(4'-benzotrifluoride)-benzo[b]thiophene-3-carboxaldehyde 
• 1591-30-6 (1,1'-biphenyl)-4,4'-dicarbonitrile 
• 4341-02-0 biphenyl-2,2'-dicarbonitrile 
• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 39827-12-8 benzothiophene-3-carbonyl chloride 

Relevant articles and documents

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.

PPAR (peroxisome proliferator-activated receptor) agonist and application thereof to treatment of senile dementia and other diseases

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