13679-73-7

Basic information

• Product Name: 2-ACETYL-4-METHYLTHIOPHENE
• Synonyms: 1-(4-METHYL-2-THIENYL)ETHANONE;2-ACETYL-4-METHYLTHIOPHENE;1-(4-methyl-2-thienyl)ethan-1-one;1-(4-Methyl-thiophen-2-yl)-ethanone;1-(4-methyl-2-thienyl)ethanone(SALTDATA: FREE);2-Acetyl-4-methylthiophene 97%;Ethanone, 1-(4-methyl-2-thienyl)-;CHEMBRDG-BB 4004647
• CAS NO: 13679-73-7
• Molecular Formula: C₇H₈OS
• Molecular Weight: 140.2
• EINECS: 237-180-7
• Product Categories: Thiophene&Benzothiophene;Heterocyclic Compounds;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 13679-73-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 108-109 °C(lit.)
• Flash Point: 221 °F
• Appearance: /
• Density: 1.224 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0461mmHg at 25°C
• Refractive Index: n20/D 1.5600(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 111378
• CAS DataBase Reference: 2-ACETYL-4-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYL-4-METHYLTHIOPHENE(13679-73-7)
• EPA Substance Registry System: 2-ACETYL-4-METHYLTHIOPHENE(13679-73-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36-43
• Safety Statements: 26-37/39
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 13679-73-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 23, p. 2443, 1967 DOI: 10.1016/0040-4020(67)80080-2

InChI:InChI=1/C7H8OS/c1-5-3-7(6(2)8)9-4-5/h3-4H,1-2H3

Upstream product

• 616-44-4 3-Methylthiophene 
• 108-24-7 acetic anhydride 
• 31805-48-8 2-ethyl-3-methyl-thiophene 
• 151051-11-5 6,6-dimethyl-2H,6H-thiin-3-one 1-oxide 
• 145931-44-8 6,6-dimethyl-2H,6H-thiin-3-one 
• 78191-00-1 N-Methoxy-N-methylacetamide 

Downstream Products

• 14282-78-1 4-methylthiophene-2-carboxylic acid 
• 33148-86-6 5-acetylthiophene-3-carboxylic acid 
• 91306-74-0 1-(4-Methyl-thiophen-2-yl)-4-phenyl-butane-1,4-dione 
• 91307-10-7 2-(4-Methyl-thiophen-2-yl)-1,5-diphenyl-1H-pyrrole 
• 91307-11-8 1-(4-Chloro-phenyl)-2-(4-methyl-thiophen-2-yl)-5-phenyl-1H-pyrrole 
• 1222103-50-5 (2E,4E)-1-(4-methylthiophen-2-yl)-5-phenylpenta-2,4-dien-1-one 
• 1313405-62-7 (2E)-3-(2-chloro-8-methylquinolin-3-yl)-1-(4-methylthien-2-yl)prop-2-en-1-one 
• 1397709-39-5 1-[5-(3-aminophenyl)-4-methylthiophen-2-yl]ethanone 
• 1353877-64-1 (2E)-1-(4-methylthiophen-2-yl)-3-(4-piperidin-1-ylphenyl)prop-2-en-1-one 
• 1449075-16-4 C₂₀H₁₄F₈O₂S₂ 
• 1544431-38-0 ((2R,3S)-3-phenylaziridin-2-yl)(4-methylthiophen-2-yl) methanone 

Relevant articles and documents

Kinetics of the Detritiation of a Series of 4- and 5-Substituted 2-(acetyl)thiophenes

A series of 4- and 5-substituted 2-(acetyl)thiophenes have been prepared and the kinetics of the hydroxide-catalysed detritiation studied at 25.0 deg C.The second-order detritiation rate constants parallel those observed for the corresponding meta- and para-substituted acetophenones but as the reaction constant ρ is higher (1.61) the range of reactivity is much wider than that witnessed for the acetophenones.

Practical access to metallo thiophenes: Regioselective synthesis of 2,4-disubstituted thiophenes

This report describes a protocol for functionalization of thiophenes, utilizing a regioselective magnesiation mediated by commercial Grignard reagents and catalytic 2,2,6,6-tetramethylpiperidine. This metalation provides practical access to metallo thiophenes, avoiding cryogenic conditions, prolonged reaction times, and prohibitively expensive reagents. Application to a target thiophene-phthalazinone 6 was accomplished by addition of 2-magnesio-4- methylthiophene to phthalic anhydride, providing the product with >40:1 regioselectivity. This also solved a chemoselectivity issue encountered with analogous lithio-thiophene reagents and cyclic anhydrides, or with magnesio-thiophene generated by simultaneous lithium-to-magnesium transmetalation/anhydride acylation. These alternative in situ transmetalation sequences were plagued by an age effect dictated by the kinetic solubility of MgCl2/THF complexes.

CATALYZED LIQUID-PHASE OXIDATION OF DIALKYLTHIOPHENES

The oxidation of 3-methyl-2-ethylthiophene with molecular oxygen in glacial acetic acid in the presence of cobalt-bromide catalyst was investigated.It was established that there is a dependence of the rate of oxidation of this compound on its concentration, on the catalyst (cobalt acetate) concentration, and on the initiator (NaBr) concentration.The principal oxidation products are 3-methyl-2-acetothienone (III) and 1-(3-methyl-2-thienyl)ethyl acetate, which were isolated and characterized.The reactivity of 3-methyl-2-ethylthiophene in the oxidation reaction is higher than that of 4-methyl-2-ethylthiophene.