2-Acetylthiophene CAS 88-15-3

Introduction：Basic information about 2-Acetylthiophene CAS 88-15-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-Acetylthiophene Basic information

• Product Name: 2-Acetylthiophene
• Synonyms: 1-(2-THIENYL)ETHAN-1-ONE;AKOS BBS-00000940;AKOS 91936;2-ACETYLTHIOLE;2-ACETYLTHIOPHENE;2-ACETOTHIOPHENE;LABOTEST-BB LT01593557;METHYL 2-THIENYL KETONE
• CAS: 88-15-3
• MF: C6H6OS
• MW: 126.18
• EINECS: 201-804-6
• Product Categories: Heterocycle-oher series;Sulphur Derivatives;Thiophene&Benzothiophene;thiophene Flavor;Thiophenes;1;bc0001
• Mol File: 88-15-3.mol

2-Acetylthiophene Chemical Properties

• Melting point: 10-11 °C (lit.)
• Boiling point: 214 °C (lit.)
• density: 1.168 g/mL at 25 °C (lit.)
• vapor pressure: 2.7 hPa (50 °C)
• refractive index: n20/D 1.565(lit.)
• Fp: 196 °F
• storage temp.: Store below +30°C.
• solubility: 14g/l
• form: Liquid
• color: Clear pale yellow to light brown
• Odor: at 100.00 %. sulfurous nutty hazelnut walnut
• Odor Type: sulfurous
• biological source: synthetic
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 107910
• Major Application: flavors and fragrances
• InChI: 1S/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
• InChIKey: WYJOVVXUZNRJQY-UHFFFAOYSA-N
• SMILES: CC(=O)c1cccs1
• LogP: 1.250
• CAS DataBase Reference: 88-15-3(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2-thienyl)-(88-15-3)
• EPA Substance Registry System: Ethanone, 1-(2-thienyl)- (88-15-3)

Safety Information

• Hazard Codes: T,Xi,Xn
• Risk Statements: 25-23/24/25-20/21/22
• Safety Statements: 45-38-36/37/39-28-36
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 3
• RTECS: OB6300000
• F: 13
• Autoignition Temperature: 265 °C DIN 51794
• Hazard Note: Irritant
• TSCA: TSCA listed
• HazardClass: 6.1
• PackingGroup: II
• HS Code: 29349990
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
• Hazard Classifications: Acute Tox. 2 Inhalation Acute Tox. 2 Oral Acute Tox. 3 Dermal
• Toxicity: LD50 orally in Rabbit: 25 - 200 mg/kg LD50 dermal Rat 370 mg/kg

2-Acetylthiophene Usage And Synthesis

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.

Chemical Properties

clear colorless to slightly yellow liquid

Uses

2-Acetylthiophene(2AT) is used as an intermediate in the manufacturing of drugs like Tiamonium Iodide, Suprofan, Stepronin, Tenonitrozole, Namirotene, etc. 2AT is used as an important precursor to thiophene-2-acetic acid (T2AA) or its acid chloride (Cl) and thiophene-2-carboxylic acid (T2CA) (Cl). It is important that the process used to synthesize 2AT yields the lowest amount of 3- acetylthiophene isomer.

Definition

ChEBI: 2-Acetylthiophene is an aromatic ketone.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 8, 1943
The Journal of Organic Chemistry, 36, p. 540, 1971 DOI: 10.1021/jo00803a011
Tetrahedron Letters, 40, p. 3109, 1999 DOI: 10.1016/S0040-4039(99)00476-1

Safety Profile

Poison by intraperitoneal route. A flammable liquid. When heated to decomposition emits toxic fumes of SOx,.

Solubility in organics

2-Acetylthiophene is miscible at 25°C with triethylene glycol, methanol, ethanol, n-butanol, diethyl ether, dioxane, cellulose butyl ester, ethyl acetate, acetone, acetonitrile, carbon disulphide, carbon tetrachloride, nitromethane, acetic acid, thiophene, tetranaphthalene, aminobenzene, and benzene . It is immiscible with water, glycerol, ethylene glycol, decahydronaphthalene, cyclohexane, diisobutylene, 1-hexadecene, and n-heptane. When equal volumes are mixed, 2-acetylthiophene is miscible with n-heptane above 60.8°C and with ethylene glycol above 31.1°C.
[1] JOHNSON G C. Physical Properties of 2-Acetylthiophene[J]. Journal of the American Chemical Society, 1947, 69 1: 150-152. DOI:10.1021/ja01193a040.

Purification Methods

Fractionally distil the thiophene through a 12-plate column, and fraction b 77o/4mm is collected. Also wet the acetylthiophene in order to remove and free thiophene which forms an azeotrope with H2O, b 68o. Store it in a brown bottle, and the clear colourless liquid remains thus for extended periods. [Kosak & Hartough Org Synth Coll Vol III 14 1955, Hartough & Kosak J Am Chem Soc 69 3093 1947.] The red 4-nitrophenylhydrazone crystallises from EtOH with m 181-182o. [Beilstein 17/9 V 387.]

2-Acetylthiophene Preparation Products And Raw materials

• Raw materials: Acetyl chloride
• Preparation Products: 4-Bromo-2-thiophenecarboxylic acid-->5-[2-(METHYLTHIO)PYRIMIDIN-4-YL]THIOPHENE-2-SULFONYL CHLORIDE-->5-ACETYL-2-THIOPHENECARBALDEHYDE-->3-OXO-3-THIOPHEN-2-YL-PROPIONIC ACID ETHYL ESTER-->5-THIEN-2-YL-4H-PYRAZOLE-3-CARBOXYLIC ACID-->Ethyl 5-thien-2-yl-1H-pyrazole-3-carboxylate-->2-Thiopheneacetic acid-->1-(4-BROMO-2-THIENYL)ETHAN-1-ONE-->2-(2-BROMOACETYL)THIOPHENE-->THIOPHENE-2-ACETAMIDE-->2,4-DIOXO-4-THIOPHEN-2-YL-BUTYRIC ACID METHYL ESTER-->2-Acetyl-5-bromothiophene-->2-(2-thienyl)propionic acid-->1-[2-Hydroxy-2(2-thienyl)ethyl]pyridinium bromide-->5-(2-sulfanylidene-3H-1,3-thiazol-4-yl)thiophene-2-carboxamide-->1,3,5-tri(thiophen-2-yl)benzene-->N-(2-THIOPHENECARBOMYL)PYRIDINIUM BROMIDE-->2-ACETYL-4-CHLOROTHIOPHENE-->2,5-Dihydrothiophene-->2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL