63675-73-0

Basic information

• Product Name: 4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE
• Synonyms: 4-METHOXY-ALPHA-[(3-METHOXYPHENYL)THIO]ACETOPHENONE;4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE;4-METHOXY-[(3-METHOXYPHENYL)THIO]ACETOPHENONE;4-Methoxy-A-[(3-Methoxyphenyl)Thiol]Acetophenone;1-(4-METHOXYPHENYL)-2-(3-MEETHOXYPHENYLTHIO)ETHANONE;2-(3,4-dimethoxyphenylthio)-1-phenylethanone;4-Methoxy-à-[(3-Methoxyphenyl)thio]Acetophenone;1-(4-Methoxyphenyl)-2-(3-methoxyphenylthio)ethanone
• CAS NO: 63675-73-0
• Molecular Formula: C₁₆H₁₆O₃S
• Molecular Weight: 288.36
• Mol File: 63675-73-0.mol

Chemical Properties

• Boiling Point: 407.464°C at 760 mmHg
• Flash Point: 198.084°C
• Appearance: /
• Density: 1.235g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE(63675-73-0)
• EPA Substance Registry System: 4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE(63675-73-0)

Safety Data

• Hazardous Substances Data: 63675-73-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE is used as a building block/intermediate for the synthesis of Raloxifene (R100000) and other benzothiophene-containing structures. It plays a crucial role in the development of these pharmaceutical compounds.
Used in Cancer Treatment:
4-METHOXY-A-((3-METHOXY PHENYL)THIO)ACETOPHENONE is used in the preparation of estrogen receptor targeting antagonists for the treatment of proliferative diseases, including cancer. It is particularly effective in treating breast cancer, as it helps in blocking the estrogen receptors and inhibiting the growth of cancer cells.

InChI:InChI=1/C15H14O3S/c1-17-12-8-6-11(7-9-12)15(16)19-14-5-3-4-13(10-14)18-2/h3-10H,1-2H3

Upstream product

• 15570-12-4 3-methoxybenzenethiol 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 2196-99-8 2-chloro-1-(4-methoxyphenyl)ethanone 
• 59014-89-0 bis(3-methoxyphenyl)disulfide 
• 21875-72-9 1-(4-methoxy-phenyl)-2-phenylsulfanyl-ethanone 
• 153163-79-2 chloromethoxyacetophenone 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 

Downstream Products

• 1649501-81-4 (6-methoxybenzo[b]thiophen-2-yl)(4-methoxyphenyl)methanone 
• 1649501-95-0 (Z)-1-(4-methoxyphenyl)-2-(3-methoxyphenylthio)-3-(dimethylamino)prop-2-en-1-one 

Relevant articles and documents

A new anti-tubulin agent containing the benzo[b]thiophene ring system

A new type of inhibitor of tubulin polymerization was discovered based on the 3-aroyl-2-arylbenzo[b]thiophene molecular skeleton. The lead compound in this series, 2-(4'-methoxyphenyl)-3-(3',4',5'-trimethoxybenzoyl)-6- methoxybenzo[b]thiophene 1, inhibited tubulin polymerization, caused an increase in the mitotic index of CA46 Burkitt lymphoma cells, and inhibited the growth of several human cancer cell lines.

ESTROGEN RECEPTOR TARGETING ANTAGONISTS

The present disclosure relates to compounds that act as antagonists via binding to the ER ligand binding domain non-covalently or covalently, or act as both antagonists and ER protein degraders, and the synthesis of the same. Further, the present disclosure teaches the utilization of such compounds in a treatment for proliferative diseases, including cancer, particularly breast cancer, and especially ER+ breast cancer.

Facile synthesis of 3-aryl benzofurans, 3-aryl benzothiophenes, 2-aryl indoles and their dimers

The preparation of 3-aryl benzofuran and benzothiophenes and their dimers at 2-position and, 2-aryl indoles and their 3-position dimers preparation is described.

Efficient synthetic approach to substituted benzo[b]furans and benzo[b]thiophenes by iodine-promoted cyclization of enaminones

An efficient synthetic approach to the substituted benzo[b]furan and benzo[b]thiophene scaffolds by iodine-mediated cyclization of the corresponding enaminones is described. This protocol was applied to a large series of these latter precursors to afford the respective benzoheterocycles substituted at the C-2 position by a carbonyl group functionality. A study of the factors that control this process reveals that the reactivity depends on the presence of electron-donor groups in the aryl ring of the aryloxycarbonylic and arylthiocarbonylic moieties.

PROCESS FOR THE PREPARATION OF RALOXIFENE HYDROCHLORIDE

The present invention provides an improved process for the preparation of α-(3- methoxyphenylthio)-4-methoxyacetophenone. The present invention also provides a process for the preparing free flowing solid of 6-methoxy-2-(4-methoxyphenyl)- benzo[b]-thiophene. The present invention further provides a process for the preparation of substantially pure 6-methoxy-2-(4-methoxyphenyl)-benzo[b]-thiophene. The present invention further provides a process for purification of raloxifene hydrochloride.

Rhodium-catalyzed organothio exchange reaction of α-organothioketones with disulfides

RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe) catalyzed the organothio exchange reaction of α-organothioketones and organic disulfides. The reaction was affected by the structure of the substrate: α-phenylthio and α-alkylthio aryl ketones reacted effectively with diaryl and dialkyl disulfides; α-phenylthio dialkyl ketones reacted with diaryl disulfides but not with dialkyl disulfides; diaryl disulfides with electron-donating p-substituents were more reactive than those with electron-withdrawing p-substituents.

Method for the production of alpha-(3-arylthio)-acetophenones

A process for preparing α-(3-arylthio)acetophenones of the general formula I in which the substituents R1 and R2 are each independently C1-C6-alkyl, SiR33 where the substituent R3 is a C1-C6-alkyl radical, or an optionally substituted phenyl or benzyl radical, which comprises reacting, in methanol acetophenones of the general formula II in which the substituent X is Cl or Br with a thiolate of the general formula III in which M is an alkali metal.

Process for preparing benzoic acids

An improved process for the preparation of 4[(2-piperidin-1-yl)ethoxy]benzoic acid derivatives, comprising reacting a haloalkyl amine of formula (III) with a compound of formula (IV) in the presence of a hydrated inorganic base in an appropriate solvent.

METHOD FOR THE PRODUCTION OF Γ(A)-(3-ARYLTHIO)-ACETOPHENONES

The invention relates to a method for the production of α-(3-arylthio)-acetophenones of general formula (I), wherein the substituents R1 and R2 independently represent C1-C6-alkyl, SiR33, and the substituent R3 represents a C1-C6-alkyl radical, or an optionally substituted phenyl or benzyl radical.The invention is characterised in that acetophenons of general formula (II), wherein the substitutent X represents Cl or Br, is reacted in methanol with a thiolate of general formula (III) wherein M represents an alkali metal.

METHOD FOR PRODUCING α-(3-ARYLTHIO)-ACETOPHENONES

The invention relates to a method for producing α-(3-arylthio)-acetophenones of general formula (I), in which substituents R1 and R2, independent of one another, represent C1-C6 alkyl or an optionally substituted phenyl radical or benzyl radical. The inventive method is characterized in that: A) acetophenones of general formula (II), in which substituent R1 has the aforementioned meaning, are reacted with sulfuryl chloride and are subsequently hydrolyzed, and; B) the reaction mixture obtained in this manner is reacted with a thiophenol of general formula (III), in which substituent R2 has the aforementioned meaning.