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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.

1468-84-4

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1468-84-4 Usage

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

Check Digit Verification of cas no

The CAS Registry Mumber 1468-84-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,6 and 8 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1468-84:
(6*1)+(5*4)+(4*6)+(3*8)+(2*8)+(1*4)=94
94 % 10 = 4
So 1468-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H8OS/c9-7-3-1-2-6-4-5-10-8(6)7/h4-5H,1-3H2

1468-84-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 5,6-dihydro-4H-1-benzothiophen-7-one

1.2 Other means of identification

Product number -
Other names 4,5,6,7-tetrahydro-7-ketothianaphthene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1468-84-4 SDS

1468-84-4Relevant academic research and scientific papers

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

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Paragraph 0054-0055, (2019/03/31)

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)

Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds

Lesieur, Mathieu,Genicot, Christophe,Pasau, Patrick

supporting information, p. 1987 - 1990 (2018/04/16)

A continuous mesofluidic process has been developed for benzylic C-H oxidation with moderate to good yields using a photocatalyst (riboflavin tetraacetate, RFT) activated by a UV lamp and an iron additive [Fe(ClO4)2] via incorporation of singlet oxygen (1O2) for the direct formation of oxidized C=O or CH-OH compounds.

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

Fang, Jingxian,Li, Lesong,Yang, Chu,Chen, Jinping,Deng, Guo-Jun,Gong, Hang

supporting information, (2018/11/23)

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.

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

Fang, Jingxian,Li, Lesong,Yang, Chu,Chen, Jinping,Deng, Guo-Jun,Gong, Hang

supporting information, p. 7308 - 7311 (2018/11/25)

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.

FUSED THIOPHENE AND THIAZOLE DERIVATIVES AS ROR GAMMA MODULATORS

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Page/Page column 117; 118; 119; 120, (2015/07/16)

The present invention provides fused thiophene and thiazole derivatives of formula (I), which may be therapeutically useful, more particularly as RORγ modulators; in which R1, R2, R3, R4, R5, R6, R7, X1, X2, L, m, n and ring A have the meanings given in the specification, and pharmaceutically acceptable salts thereof that are useful in the treatment and prevention of diseases or disorders, in particular their use in disease(s) or disorder(s) where there is an advantage in modulating RORγ receptor. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of the fused thiophene and thiazole derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent or excipient therefor.

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

Motiwala, Hashim F.,Vekariya, Rakesh H.,Aubé, Jeffrey

, p. 5484 - 5487 (2015/11/18)

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.

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

Yu, Jiajia,Zhao, Huijun,Liang, Shuguang,Bao, Xiaoguang,Zhu, Chen

supporting information, p. 7924 - 7927 (2015/07/27)

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C-C bond cleavage/C-C bond formation is involved.

MULTICYCLIC COMPOUNDS AND METHODS OF USE THEREOF

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Page/Page column 109, (2011/06/25)

Provided herein are multicyclic compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin

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Page/Page column 148, (2008/06/13)

The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R14; with R1, R2, R3, R4, R5, R6, R7, R8, and R14 defined herein.

New structures able to prevent the inhibition by hydroxyl radicals of glutamate transport in cultured astrocytes

Cauquil-Caubere, Isoline,Kamenka, Jean-Marc

, p. 867 - 877 (2007/10/03)

4,5,6,7-Tetrahydro-benzothiophen-7-ylamines, 4,5,6,7-tetrahydro- benzothiophen-4-ylamines, and 5,6-dihydro-4H-thieno[2,3-b] thiopyran-4- ylamines were designed, synthesized, and tested as OH radical scavengers. Most of them displayed chemical scavenging properties better than or in the same range as salicylic acid. Moreover, some compounds were able to protect in vitro the astroglial glutamate transporters against inhibitory action of radicals promoted by xanthine/xanthine oxidase. Thus, such compounds might be useful for lowering the large amounts of excitotoxic glutamate liberated during acute CNS diseases: they might protect the glutamate reuptake in astrocytes from the inhibitory action due to radicals co-liberated with glutamate.

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