2-Acetylthiophene

Base Information

• Chemical Name: 2-Acetylthiophene
• CAS No.: 88-15-3
• Molecular Formula: C6H6OS
• Molecular Weight: 126.179
• Hs Code.: 29349990
• European Community (EC) Number: 201-804-6
• NSC Number: 2345
• UNII: 5ASO208T20
• DSSTox Substance ID: DTXSID2058960
• Nikkaji Number: J2.842.079J,J4.289G
• Wikipedia: 2-Acetylthiophene
• Wikidata: Q27261757
• Metabolomics Workbench ID: 45903
• ChEMBL ID: CHEMBL401911
• Mol file: 88-15-3.mol

Synonyms:2-acetylthiophene

Chemical Property of 2-Acetylthiophene

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 0.172mmHg at 25°C
• Melting Point: 10-11 °C(lit.)
• Refractive Index: n20/D 1.565(lit.)
• Boiling Point: 212.6 °C at 760 mmHg
• Flash Point: 82.4 °C
• PSA: 45.31000
• Density: 1.142 g/cm³
• LogP: 1.95070
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 14g/l
• Water Solubility.: Insoluble in water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.01393598
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

2-Acetylthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, Xi, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 25-23/24/25-20/21/22
• Safety Statements: 45-38-36/37/39-28-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: CC(=O)C1=CC=CS1
• Description: 2-Acetylthiophene occurs naturally in kohlrabi. It has a sulfurous nutty hazelnut odor. It can be used as a food additive. It is also used as an intermediate to produce drugs, such as Tiamonium Iodide, Suprofan, Stepronin, Tenonitrozole, Namirotene, etc.
• Uses: 2-Acetylthiophene is used as an intermediate in the manufacturing of drugs like Tiamonium Iodide, Suprofan, Stepronin, Tenonitrozole, Namirotene, etc.

Technology Process of 2-Acetylthiophene

There total 110 articles about 2-Acetylthiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(thien-2-yl)ethanol (115510-91-3) → 2-Acetylthiophene (88-15-3,97511-16-5)

Guidance literature:

With methanol; tetrachloromethane; bis(acetylacetonate)oxovanadium; at 175 ℃; for 6h; Inert atmosphere; Autoclave;

DOI:10.1134/S0965544108060121

Reference yield: 99.4%

thiophene (188290-36-0,8014-23-1,25233-34-5) + acetic anhydride (108-24-7) → 2-Acetylthiophene (88-15-3,97511-16-5)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In acetonitrile; for 0.25h; Inert atmosphere; Microwave irradiation; Heating; Green chemistry;

DOI:10.1039/c3gc40720a

Reference yield: 98.0%

2-methyl-2-(thiophen-2-yl)-1,3-dithiane → 2-Acetylthiophene (88-15-3,97511-16-5)

Guidance literature:

With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 1h;

upstream raw materials:

thiophene

acetyl iodide

acetoxytrichlorosilane

trifluoroacetic anhydride

Downstream raw materials:

1-[2-oxo-2-(thiophen-2-yl)ethyl]pyridinium iodide

(2E,4E)-5-phenyl-1-(thiophen-2-yl)penta-2,4-dien-1-one

3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride

3-(morpholin-4-yl)-1-(thiophen-2-yl)propan-1-one

Refernces

Synthesis and characterization of a new series of hydroxy pyrazolines

10.1080/00397910802241407

The research presents the synthesis and characterization of a new series of hydroxy pyrazolines, which are nitrogen-containing heterocyclic compounds known for their broad spectrum of biological activities such as antitumor, immunosuppressive, antibacterial, anti-inflammatory, anticancer, antidiabetic, and antidepressant properties. The study begins with the preparation of 3-phenyl-1-(thiophen-2-yl)prop-2-en-1-one (chalcone 1) through the Claisen-Schmidt condensation of 2-acetyl thiophene with benzaldehyde. This chalcone 1 is then converted into 2,3-dibromo-3-phenyl-1-(thiophen-2-yl)propan-1-one (chalcone dibromide 2) by reacting with bromine in chloroform. Further reaction of chalcone dibromide 2 with various thiosemicarbazides in the presence of triethylamine in absolute ethanol yields hydroxy pyrazolines 3a–h. The synthesized compounds are characterized using IR, 1H NMR, and 13C NMR spectroscopy, with their purity confirmed by elemental analysis. The research also includes the preparation of substituted thiosemicarbazides used in the reaction, and the detailed experimental procedures for the synthesis of each compound are provided in the article.