21609-70-1

Basic information

• Product Name: 2,3,4,5-tetrahydro-1-benzothiepin-5-one
• Synonyms: 3,4-Dihydro-2H-benzo[b]thiepin-5-one;2,3-DIHYDRO-1-BENZOTHIEPIN-5(4H)-ONE;2,3,4,5-tetrahydro-1-benzothiepin-5-one
• CAS NO: 21609-70-1
• Molecular Formula: C₁₀H₁₀OS
• Molecular Weight: 178.2508
• Mol File: 21609-70-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 78-79 °C(Solv: methanol (67-56-1))
• Boiling Point: 308.9 °C at 760 mmHg
• Flash Point: 162.1 °C
• Appearance: /
• Density: 1.188 g/cm³
• Vapor Pressure: 0.000662mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 2,3,4,5-tetrahydro-1-benzothiepin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-tetrahydro-1-benzothiepin-5-one(21609-70-1)
• EPA Substance Registry System: 2,3,4,5-tetrahydro-1-benzothiepin-5-one(21609-70-1)

Safety Data

• Hazardous Substances Data: 21609-70-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 2728, 1961 DOI: 10.1021/jo01066a027

InChI:InChI=1/C10H10OS/c11-9-5-3-7-12-10-6-2-1-4-8(9)10/h1-2,4,6H,3,5,7H2

Upstream product

• 138738-23-5 4-phenylsulfanyl-butyryl chloride 
• 108-98-5 thiophenol 
• 627-00-9 γ-chlorobutyric acid 
• 7446-70-0 aluminum (III) chloride 
• 17742-51-7 4-phenylsulfanyl-butyric acid 

Downstream Products

• 93622-04-9 5-Oxo-2.3.4.5-tetrahydro-benzothiepin-semicarbazon 
• 4370-78-9 2,3,4,5-tetrahydro-1-benzothiepin 
• 20500-27-0 5-Hydroxy-2,3,4,5-tetrahydro-benzothiepin 
• 84571-92-6 C₂₃H₂₁ClN₂S 
• 81326-69-4 4-[1-p-Tolyl-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]thiepin-5-one 
• 81326-76-3 C₂₈H₂₆O₂S₂ 
• 53371-28-1 4-(p-chlorobenzylidene)-5-homothiochromanone 
• 81326-75-2 4-[(4-Chloro-phenyl)-hydroxy-methyl]-3,4-dihydro-2H-benzo[b]thiepin-5-one 
• 53371-29-2 4-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]thiepin-5-one 
• 40322-45-0 4-(hydroxy-phenyl-methyl)-3,4-dihydro-2H-benzo[b]thiepin-5-one 
• 40322-44-9 C₂₇H₂₄O₂S₂ 
• 40322-46-1 4-benzylidene-5-homothiochromanone 
• 81326-70-7 4-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]thiepin-5-one 
• 53371-30-5 4-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-3,4-dihydro-2H-benzo[b]thiepin-5-one 

Relevant articles and documents

Friedel–Crafts reactions of acyl trifluoromethanesulfonates and cyclic acylsulfonium cations generated from acyl fluorides

Reactive acyl trifluoromethanesulfonates are formed from the reaction of acyl fluorides with trimethylsilyl trifluoromethanesulfonate (TMSOTf). These electrophiles undergo Friedel–Crafts reactions with electron-rich aromatics at room temperature. When a sulfur atom is present at their γ position, their cyclization to acylsulfonium cations is observed and is followed by a rearrangement leading to benzothiepinones (or dibenzo[b,e]thiepinones) in 40–85% yield.

Analogues of N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamide and N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamide-6,6-dioxide: Syntheses, characterization, antimicrobial, antituberculosis, and antitumor activity

A series of N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c]pyrazole-3- carboxamides (11a-m) and N,1-diphenyl-4,5-dihydro-1H-[1]benzothiepino[5,4-c] pyrazole-3-carboxamide-6,6-dioxides (12a-m) were synthesized by varying the active part (carboxamide group) of the pyrazole and were characterized by IR, 1H-NMR, 13C-NMR, mass spectral data, and elemental analyses. All compounds were evaluated for their antibacterial and antifungal activity. Compounds 11k and 12k showed higher activity than chloroamphenicol against Klebsiella pneumonia and Escherichia coli. Compounds 11b, 11c, 11l, 12b, 12c, and 12l displayed higher activity towards amikacin in inhibiting the growth of Escherichia coli (MIC 3.125 mg mL-1). Compounds 11k and 12k were equipotent to clotrimazole in inhibiting the growth of Candida albicans (MIC 3.125 mg mL-1). All compounds were screened for their cytotoxic activity against two tumor cell lines, namely the human colon tumor cell line (HCT116) and human cervical cancer cell line (HeLa). Most of the test compounds exhibited potent antitumor activity, especially compounds 11k and 12k, which displayed the highest activity among the test compounds with an IC50 equal to 18 and 12 μM for HeLa cells, and 16 and 10 μM for HCT116 cells, respectively. All the synthesized compounds showed low to moderate inhibitory activities against M. tuberculosis (MTB) H37Rv, whereas 11k and 12k were found to be more active against M. tuberculosis, with MIC values of 8.2 and 7.8 μM, compared to other analogues.

Polycyclic thiazolidin-2-ylidene amines, process for their preparation, and their use as pharmaceuticals

Polycyclic thiazolidin-2-ylidene amines and their physiologically tolerable salts and physiologically functional derivatives of the formula I in which the radicals have the meanings indicated, and their physiologically tolerable salts and a process for their preparation are described. The compounds are suitable, for example, as anorectics.