4927-10-0

Basic information

• Product Name: 2,5-diacetylthiophene
• Synonyms: 1,1'-(thiophene-2,5-diyl)bisethan-1-one;2,5-Diacetylthiophene;1-(5-acetyl-2-thienyl)ethanone;1-(5-acetylthiophen-2-yl)ethanone;1-(5-ethanoylthiophen-2-yl)ethanone
• CAS NO: 4927-10-0
• Molecular Formula: C₈H₈O₂S
• Molecular Weight: 168.21292
• EINECS: 225-556-3
• Mol File: 4927-10-0.mol

Chemical Properties

• Melting Point: 171-173℃
• Boiling Point: 306.2°Cat760mmHg
• Flash Point: 139°C
• Appearance: /
• Density: 1.184
• CAS DataBase Reference: 2,5-diacetylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-diacetylthiophene(4927-10-0)
• EPA Substance Registry System: 2,5-diacetylthiophene(4927-10-0)

Safety Data

• Hazardous Substances Data: 4927-10-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,1'-(thiophene-2,5-diyl)bisethan-1-one is used as a precursor for the synthesis of thiophene-containing organic materials, which are essential in the development of new pharmaceuticals. Its ability to form strong covalent bonds with other organic molecules makes it a valuable component in creating novel drug candidates.
Used in Dye Industry:
In the dye industry, 1,1'-(thiophene-2,5-diyl)bisethan-1-one is utilized as a starting material for the production of dyes. Its unique molecular structure contributes to the development of dyes with specific color properties and stability.
Used in Materials Science and Organic Electronics:
1,1'-(thiophene-2,5-diyl)bisethan-1-one is used as a building block in the field of materials science and organic electronics. Its electron-rich nature and unique molecular structure make it suitable for the development of materials with specific electronic properties, such as semiconductors and conductive polymers.
Used in Agrochemicals:
1,1'-(thiophene-2,5-diyl)bisethan-1-one is also employed in the development of new agrochemicals. Its strong covalent bonding capabilities allow for the creation of compounds with targeted biological activities, potentially leading to more effective and environmentally friendly pesticides and other agricultural products.
Organic Optoelectronics:
Due to its electron-rich nature and unique molecular structure, 1,1'-(thiophene-2,5-diyl)bisethan-1-one has potential applications in the field of organic optoelectronics. It can be used in the development of materials for organic light-emitting diodes (OLEDs), photovoltaic cells, and other optoelectronic devices, where its properties can contribute to improved performance and efficiency.

Upstream product

• 88-15-3 2-Acetylthiophene 
• 108-24-7 acetic anhydride 
• 1423-60-5 methyl ethynyl ketone 
• 1956-45-2 2-acetylthiophene oxime 
• 114774-08-2 5-acetyl-2-(α-methoxyimino)ethylthiophene 
• 188290-36-0 thiophene 
• 127-19-5 N,N-dimethyl acetamide 
• 186581-53-3 diazomethane 
• 60-29-7 diethyl ether 
• 18614-21-6 cis-tetrahydro-thiophene-2,5-dicarboxylic acid-dichloride 
• 114773-97-6 2-(α-methoxyimino)ethylthiophene 
• 3141-27-3 2,5-dibromothiophen 

Downstream Products

• 200337-67-3 (S)-(-)-2-acetyl-5-(1-hydroxyethyl)thiophene 

Relevant articles and documents

Synthesis of thiophene-pyrrole mixed oligomers end-capped with hexyl group for field-effect transistors

Mixed thiophene-N-methylpyrrole oligomers composed of the five and six heterocycles and hexyl substituents at both ends were synthesized, and their structural, electronic, and field-effect properties were investigated. These oligomers behaved as good p-ty

Insight into the roles of structures and energy levels of mono- and bis-β-diketones on sensitizing Nd(III) NIR-luminescence

Three neodymium complexes Nd(TTA)3(DMSO)2 (1, TTA = 2-thenoyltrifluoroacetone), Nd2(BDT)3(DMSO)6 (2, BDT = bis(4,4,4-trifluoro-1,3-dioxobutyl)thiophene) and Nd2(BTT)3(DMSO)4 (3, BTT = bis(4,4,4-trifluoro-1,3-dioxobutyl)(2,2′-bithiophene)) constructed from three thiophene-based β-diketonate ligands, were prepared for the purpose of building the relationships between the structures, energy levels of the complexes and NIR luminescence properties of Nd(iii) ions. X-ray crystallographical analysis reveals that complex 1 is a mononuclear structure, the central Nd(iii) ion is coordinated by eight oxygen atoms from three mono-β-diketones (TTA) and two DMSO, whereas, complexes 2 and 3 adopt triple-stranded dinuclear structures, in which the two Nd(iii) ions are wrapped by three bis-β-diketones, the central Nd(iii) ions are nine and eight coordinated by oxygen atoms from ligands and the coordinated DMSO molecules. The photophysical properties related to the electronic transition are characterized by the absorbance spectra, the excitation spectra, the phosphorescence spectra, the emission spectra, the emission quantum yields, and the emission lifetimes. The luminescence quantum yields experiment reveals that the dinuclear complexes (0.49% and 0.33% for 2 and 3) show higher luminescence efficiencies compared to the mononuclear complex 1 (0.22%). This enhancement is mainly attributed to their binuclear structures, which effectively represses the nonradiative transition caused by high-energy oscillators in ligands and/or solvents. On the other hand, the energy level matching also plays an important role in this enhancement.

Hydrogen-bond-directed catalysis: Faster, regioselective and cleaner heck arylation of electron-rich olefins in alcohols

A general method for the regioselective Heck reaction of electronrich olefins is presented. Fast, highly regioselective Pd-catalysed α-arylation of electron-rich olefins, vinyl ethers (1a-d), hydroxyl vinyl ethers (1e,f), enamides (1g,h) and a substituted vinyl ether (1i) has been accomplished with a diverse range of aryl bromides (2a-r), for the first time, in cheap, green and easily available alcohols with no need for any halide scavengers or salt additives. The reaction proceeds with high efficiency, leading exclusively to the a-products, in 2-propanol and particularly in ethylene glycol. In the latter, the arylation can be catalysed at a palladium loading of 0.1 mol% and finish in as short a time as 0.5 h. The remarkable performance of the alcohol solvents in promoting a regiocontrol is attributed to their hydrogen-bond- donating capability, which is believed to facilitate the dissociation of halide anions from PdII, and hence, the generation of a key ionic Pd II-olefin intermediate responsible for the a product. This belief is further strengthened by the study of a benchmark arylation reaction in 21 different solvents. The study revealed that exclusive α-regioselective arylation takes place in almost all of the protic solvents, and there is a rough correlation between the α-arylation rates and the solvent parameter ETN. The method is simpler, cleaner and more general than those established thus far.

Facile synthesis of 5-substituted 2-acetylthiophenes

5-Substituted 2-(α-alkoxyimino)ethylthiophenes 4-8 are obtained by the reaction of 2-(α-alkoxyimino)ethylthiophenes 3 and electrophilic reagents. Hydrolysis of thiophenes 4-8 produces 5-substituted 2-acetylthiophenes 9-13, respectively. Compounds 3 are easily obtained either by the reaction of 2-acetylthiophene (1) and an O-alkylhydroxylamine or by oxidation of 1 followed by O-alkylation.

Thiophene derivatives and methods for producing the same

Novel compounds, 2-(α-alkoxyimino)ethylthiophenes are susceptible to electrophilic substitution reactions, and the acetylation, nitration, sulfonation and halogenation of the compounds provide 5-acetyl-2-(α-alkoxyimino)ethylthiophenes, 5-nitro-2-(α-alkoxyimino)ethylthiophenes, 5-(α-alkoxyimino)ethyl-2-thiophenesulfonic acid and 5-halo-2-(α-alkoxyimino)ethylthiophenes, respectively. The hydrolysis of 5-acetyl-2-(α-alkoxyimino)ethylthiophenes readily provides a known compound, 2,5-diacetylthiophene which is an important intermediate for the production of medicines, whereas the haloform reaction provides novel compounds, 5-(α-alkoxyimino)ethyl-2-thiophenecarboxylic acids, the hydrolysis of which compounds readily provides a known compound, 5-acetyl-2-thiophenecarboxylic acids, an important intermediate for the production of medicines. The hydrolysis of 5-(α-alkoxyimino)ethyl-2-thiophenesulfonic acids and their salts provide novel 5-acetyl-2-thiophenesulfonic acid and its salts, respectively. Novel compounds, 2-(α-alkoxyimino)ethylthiophenes are obtained either by 0-alkylation of 2-acetylthiophene oxime or by directly reacting 2-acetylthiophene with an 0-alkylhydroxylamine.

REACTIONS OF ELEMENTAL SULFUR AND SELENIUM WITH SOME ACETYLENIC COMPOUNDS. FORMATION OF THIOPHENES AND SELENOPHENES

The reaction of 3-butyn-2-one with elemental sulfur at 205-215 deg C in benzene in a stainless autoclave afforded 2,4- and 2,5-diacetylthiophenes in 43percent and 22percent yields, respectively. Under similar conditions, the reaction with elemental selenium gave 2,4- and 2,5-diacetylselenophenes in 32percent and 29percent yields, respectively. Diphenylacetylene reacted with sulfur and selenium to produce tetraphenylthiophene (78percent) and tetraphenylselenophene (38percent), respectively. The reaction of di(2-thienyl)acetylene with sulfur provided tetra(2-thienyl)thiophene in 57percent yield. The reactionof dimethyl acetylenedicarboxylate with sulfur in the presence of diphenylacetylene afforded 2,3-bis(methoxycarbonyl)-4,5-diphenylthiophene (29percent) and tetrakis(methoxycarbonyl)thiophene (15percent). On the basis of these results, the mechanism for the formation of thiophenes and selenophenes is discussed.

Synthesis of 2,6-Disubstituted Pyridines, Polypyridinyls, and Annulated Pyridines

1,5-Enediones containing a variety of substituents in the 1,5-positions are formed in good yields by the reaction of methyl ketone enolates, generated with potassium tert-butoxide, with α-oxoketene dithioacetals, the latter being prepared from alkyl, cycloalkyl, aryl, or heteryl methyl ketones, NaH, CS2, and CH3I.Ring closure of the 1,5-enediones with NH4OAc gave 2,6-disubstituted 4-(methylthio)pyridines in good to excellent yields.This procedure is particularly suited for the synthesis of 2,6-diheterylpyridines and provides a simple synthesis of terpyridinyl and other oligopyridines.The methylthio groups in the α-oxoketene dithioacetals may be oxidized to the mono- and disulfoxides with m-chloroperbenzoic acid, but with excess peracid, in addition to oxidation to the disulfone, epoxidation of the double bond also occurs.The pyridine 4-methylthio substituent may also be oxidized to the sulfoxide and to the sulfone, and the latter may be displaced with cyanide ion to form the corresponding 4-carbonitrile.