1468-84-4

Basic information

• Product Name: 5,6-DIHYDRO-1-BENZOTHIOPHENE-7(4H)-ONE
• Synonyms: RARECHEM AK MA K002;5,6-DIHYDRO-1-BENZOTHIOPHENE-7(4H)-ONE;5,6-dihydro-1-benzothiophen-7(4H)-one;5,6-DIHYDROBENZO[B]THIOPHEN-7(4H)-ONE
• CAS NO: 1468-84-4
• Molecular Formula: C₈H₈OS
• Molecular Weight: 152.21
• Mol File: 1468-84-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 267.006 °C at 760 mmHg
• Flash Point: 115.281 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5,6-DIHYDRO-1-BENZOTHIOPHENE-7(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDRO-1-BENZOTHIOPHENE-7(4H)-ONE(1468-84-4)
• EPA Substance Registry System: 5,6-DIHYDRO-1-BENZOTHIOPHENE-7(4H)-ONE(1468-84-4)

Safety Data

• Hazardous Substances Data: 1468-84-4(Hazardous Substances Data)

Usage

Description

5,6-Dihydro-1-benzothiophene-7(4H)-one is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a benzene ring fused with a thiophene ring and a ketone group at the 7-position. This structure endows it with versatile reactivity and potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
5,6-Dihydro-1-benzothiophene-7(4H)-one is used as an intermediate for the preparation of thiadiaminooxopyrimidine derivatives, which exhibit antitumor activities. These derivatives have the potential to be developed into novel anticancer drugs, offering new treatment options for patients with various types of cancer.
Additionally, 5,6-dihydro-1-benzothiophene-7(4H)-one is used in the synthesis of (aminoalkyl)benzoand -thienocycloalkanones, which are atypical antipsychotic agents. These compounds have shown promise in the treatment of psychiatric disorders, such as schizophrenia and bipolar disorder, by targeting specific neurotransmitter systems in the brain.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 2, p. 44, 1965 DOI: 10.1002/jhet.5570020109Tetrahedron Letters, 16, p. 2885, 1975

InChI:InChI=1/C8H8OS/c9-7-3-1-2-6-4-5-10-8(6)7/h4-5H,1-3H2

Upstream product

• 188290-36-0 thiophene 
• 4635-59-0 4-Chlorobutanoyl chloride 
• 13129-17-4 4,5,6,7-tetrahydrobenzo[b]thiophene 
• 1505-47-1 4-(thien-3-yl)butyric acid 
• 498-62-4 3-thiophene carboxaldehyde 
• 57070-76-5 2-(3'-thiophenyl)-1-bromoethane 
• 19995-15-4 diethyl 2-(2-(thiophen-3-yl)ethyl)malonate 
• 19995-16-5 2-(2-(thiophen-3-yl)ethyl)malonic acid 
• 114896-65-0 3-(2'-iodoethyl) thiophene 
• 13781-67-4 3-(2-hydroxyethyl)thiophene 
• 4653-08-1 4-oxo-4-thiophen-2-yl-butyric acid 
• 4653-11-6 2-thiophenebutyric acid 
• 13414-95-4 4-keto-4,5,6,7-tetrahydrothianaphthene 

Downstream Products

• 240403-80-9 N-<(7-oxo-4,5,6,7-tetrahydrobenzothiophene-6-yl)acetyl>-4-(p-fluorobenzoyl)piperidine 
• 274925-56-3 3-bromo-4,5,6,7-tetrahydro-benzo[b]thiophene-7-one 
• 263250-49-3 7-(1-trityl-1H-imidazol-4-yl)-4,5,6,7-tetrahydro-benzo[b]thiophen-7-ol 

Relevant articles and documents

A rapid method for open-loop/oxidation based on substituted cyclobutanol cyclization reaction preparation Tetralone derivatives (by machine translation)

The invention discloses a method for quickly based on substituted cyclobutanol oxidation open-loop/cyclization reaction preparation Tetralone derivatives of the method, the method is that the aryl substituted cyclobutanol cerium amine in the nitric acid oxidation of a pot of reaction under the action of the generating Tetralone derivatives; this method has the advantages of fast response (30 seconds in the completion of the reaction), the operation is simple (the open reaction), mild reaction conditions, one-step reaction, does not need to use noble metal catalytic, the yield is high, can be expands the quantity reaction and the like, overcome in the prior art long reaction time, requires the use of a noble metal catalyst, more reaction steps, more byproducts and the like. (by machine translation)

Tandem Oxidative Ring-Opening/Cyclization Reaction in Seconds in Open Atmosphere for the Synthesis of 1-Tetralones in Water-Acetonitrile

A mild and practical tandem oxidative ring-opening/cyclization reaction mediated by Ce4+ for the synthesis of 1-tetralones is presented. This rapid transformation was completed within 30 s and conducted in an open reactor at 0 °C in a water-acetonitrile mixture. Various cyclobutanol derivatives are transformed into desired products in good to high yields, and this reaction can be easily scaled up to the gram scale.

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel-Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential reaction mechanisms are reported.