59743-88-3

Basic information

• Product Name: 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol
• Synonyms: 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol;4-HYDROXY-10-METHOXY-4-(1-METHYL-4-PIPERIDINYL)-4H-BENZO(4,5)CYCLOHEPTA(1,2-B)THIOPHENE;Einecs 261-907-7;4-Hydroxy-9,10-dehydro-10-Methoxy Ketotifen;10-Methoxy-4-(1-Methyl-4-piperidinyl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophene-4-ol;Ketotifen FuMarate EP IMpurity B;10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5] cyclopheta[1.2-b]thiophene-4-ol;10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ol
• CAS NO: 59743-88-3
• Molecular Formula: C₂₀H₂₃NO₂S
• Molecular Weight: 341.46712
• EINECS: 261-907-7
• Product Categories: Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 59743-88-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 194-196℃ (ethanol )
• Boiling Point: 524°C at 760 mmHg
• Flash Point: 270.7°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 8.27E-12mmHg at 25°C
• Refractive Index: 1.652
• PKA: 12.91±0.40(Predicted)
• CAS DataBase Reference: 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol(59743-88-3)
• EPA Substance Registry System: 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol(59743-88-3)

Safety Data

• Hazardous Substances Data: 59743-88-3(Hazardous Substances Data)

Usage

Description

10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol is a complex organic compound with a unique molecular structure. It is characterized by its benzo[4.5]cyclohepta[1,2-b]thiophene core, which is fused with a 4H-benzo ring and a 4-ol hydroxyl group. Additionally, it features a 10-methoxy substituent and a 1-methylpiperidin-4-yl group, which contribute to its distinct chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique molecular structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol serves as a starting material for the exploration of novel chemical reactions and the synthesis of new compounds with diverse properties. Its reactivity and structural features can be exploited to design and synthesize a wide range of organic molecules with potential applications in various industries.
Used in Separation of Enantiomers:
10-methoxy-4-(1-methylpiperidin-4-yl)-4H-benzo[4.5]cyclohepta[1,2-b]thiophene-4-ol is used as an impurity in the separation of enantiomers of Ketotifen and its polar intermediate by isotachophoresis. This application highlights its utility in the field of chiral separation and analysis, which is crucial for the development of enantiomerically pure drugs and the study of their pharmacological properties.

InChI:InChI=1/C20H23NO2S/c1-21-10-7-15(8-11-21)20(22)16-6-4-3-5-14(16)13-18(23-2)19-17(20)9-12-24-19/h3-6,9,12-13,15,22H,7-8,10-11H2,1-2H3

Upstream product

• 59743-84-9 10-methoxy-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-4-one 
• 63463-36-5 (1-methyl-4-piperidyl)magnesium chloride 
• 5570-77-4 4-chloro-1-methylpiperidine 
• 1622-55-5 9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-4-one 
• 34580-10-4 9,10-dibromo-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiophene-4-one 

Downstream Products

• 126939-27-3 4-hydroxy-4-(1-methyl-4-piperidyl)-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-10-one 
• 34580-13-7 ketotifen 
• 34580-13-7 (+)-(R)-4-(1-methyl-4-piperidylidene)-9,10-dihydro-4H-benzo<4,5>cyclohepta<1,2-b>thiopene-10-one 
• 34580-13-7 Ketotifen 
• 43076-16-0 4-(1-Methyl-4-piperidyliden)-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-9,10-dion 
• 43076-17-1 4-(1-benzyl-piperidin-4-ylidene)-4,9-dihydro-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one 
• 43076-12-6 9,10-Dihydro-4-(1-methyl-4-piperidyliden)-4H-benzo<4,5>cyclohepta<1,2-b>thiophen-10-ol 
• 88456-70-6 4-(1-methyl-1-oxy-piperidin-4-ylidene)-4,9-dihydro-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one 

Relevant articles and documents

4H-BENZOCYLOHEPTATHIOPHENES AND 9,10-DIHYDRO DERIVATIVES-SULFONIUM ANALOGUES OF PIZOTIFEN AND KETOTIFEN; CHIRALITY OF KETOTIFEN: SYNTHESIS OF THE 2-BROMO DERIVATIVE OF KETOTIFEN

Reaction of ketone IX with 4-tetrahydrothiopyranylmagnesium bromide and the following dehydration with thionyl chloride afforded the sulfide III which was transformed to the methiodide II (sulfonium analogue of pizotifen).Similar sequence starting from ketone XXIV and concluded by dehydration of the alcohol XX, cleavage of the enol ether, and by treatment with methyl iodide resulted in the formation of the sulfonium analogue of ketotifen (V).Three modified routes leading to ketotifen (IV) are being described.The chirality of ketotifen was proven by (1)H NMR spectrscopy with the help of,optically active NMR shift reagent.The resolution of racemic ketotifen (IV) was achieved by crystallization of salts with optically active O,O'-diacyltartaric acids and homogenous anantiomers were obtained.The X-ray crystallographic analysis of (+)-IV-O,O'-di(p-toluoyl)-(R)-tartrate led to the three- dimensional structure of the molecule of (+)-ketotifen which enabled to determine its absolute configuration to be (R).One of the products of bromination of the ketone IX, the following methanolysis and dehydrobromonation, identified as XXVII, was transformed by reaction with 1-methyl-4-piperidylmagnesium chloride, by the following acid-catalyzed dehydration, and cleavage of the enol ether to the 2-bromo derivative of ketotifen XXXIV. (R)(+)-Ketotifen (IV) was found to be the more active ketotifen enantiomer but the stereoselectivity of its action is only a partial one.The 2-bromo derivative of ketotifen (XXXIV) is much less active than ketotifen in the line antihistamine activity.

Synthetical pharmaceutics. 9 and 10 oxo derivatives of 9,10 dihydro 4H benzo [4,5] cyclohepta[1,2 b] thiophenes

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