Product Name

  • Name

    2-Acetylthiophene

  • EINECS 201-804-6
  • CAS No. 88-15-3
  • Article Data247
  • CAS DataBase
  • Density 1.142 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 10-11 °C(lit.)
  • Formula C6H6OS
  • Boiling Point 212.6 °C at 760 mmHg
  • Molecular Weight 126.179
  • Flash Point 82.4 °C
  • Transport Information UN 2810 6.1/PG 2
  • Appearance clear colorless to slightly yellow liquid
  • Safety 45-38-36/37/39-28-36
  • Risk Codes 25-23/24/25-20/21/22
  • Molecular Structure Molecular Structure of 88-15-3 (2-Acetylthiophene)
  • Hazard Symbols ToxicT, IrritantXi, HarmfulXn
  • Synonyms Ethanone, 1- (2-thienyl)-;2-Acetothienone;ethanone, 1-(2-thienyl)-;1-thiophen-2-ylethanone;1-(2-thienyl)ethanone;alpha-Acetylthiophene;5-17-09-00387 (Beilstein Handbook Reference);2-Acetothiophene;Ketone, methyl 2-thienyl;2-Thienyl methyl ketone;Methyl 2-thienyl ketone;
  • PSA 45.31000
  • LogP 1.95070

Synthetic route

thiophene
188290-36-0

thiophene

acetic acid
64-19-7

acetic acid

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
Stage #1: thiophene; acetic acid With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h;
Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 1h;		100%
With pyridin-2-yl trifluoromethanesulfonate; trifluoroacetic acid for 4h; Heating;99%
With trifluoromethylsulfonic anhydride at 20℃; for 0.0333333h; Friedel-Crafts acylation;98%
1-(thien-2-yl)ethanol
115510-91-3

1-(thien-2-yl)ethanol

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With methanol; tetrachloromethane; bis(acetylacetonate)oxovanadium at 175℃; for 6h; Inert atmosphere; Autoclave;100%
With basolite C300; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen In 1,2-dichloro-ethane at 20℃; for 15h; Green chemistry;98%
With sulfuric acid; dihydrogen peroxide; sodium bromide In 1,4-dioxane; water at 70℃; Flow reactor; Green chemistry;96%
thiophene
188290-36-0

thiophene

acetic anhydride
108-24-7

acetic anhydride

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile for 0.25h; Friedel-Crafts Acylation; Inert atmosphere; Microwave irradiation; Heating; Green chemistry;99%
With phosphorus pentoxide; acetic acid In 1,2-dichloro-ethane at 85℃; for 8.5h; Reagent/catalyst; Solvent; Temperature;99.4%
With nano-sulfated titania at 50℃; for 30h; Friedel Crafts acylation; neat (no solvent);95%
thiophene
188290-36-0

thiophene

acetyl chloride
75-36-5

acetyl chloride

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With aluminum (III) chloride In ethyl acetate at 20℃; for 2.66667h; Cooling with ice;98%
With ytterbium(III) triflate In nitromethane at 20℃; for 4h; Friedel-Crafts acylation;92%
With benzyltributylammonium tetrachloroferrate at 50℃; for 0.0333333h; Friedel-Crafts reaction;90%
thiophene
188290-36-0

thiophene

2',3',4',5',6'-pentamethylacetophenone
2040-01-9

2',3',4',5',6'-pentamethylacetophenone

A

2-Acetylthiophene
88-15-3

2-Acetylthiophene

B

pentamethylbenzene,
700-12-9

pentamethylbenzene,

Conditions
ConditionsYield
trifluoroacetic acid for 10h; Heating;A 29%
B 98%
...Expand
4-methyl-N'-(1-(thiophen-2-yl)ethylidene)benzenesulfonohydrazide

4-methyl-N'-(1-(thiophen-2-yl)ethylidene)benzenesulfonohydrazide

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With silica-supported selenamide; dihydrogen peroxide In tert-butyl alcohol at 55℃; for 20h;98%
2-methyl-2-(thiophen-2-yl)-1,3-dithiane

2-methyl-2-(thiophen-2-yl)-1,3-dithiane

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 1h;98%
With eosin y In water; acetonitrile at 20℃; for 4h; Irradiation;95%
With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 0.5h; micellar medium;
2-acetylthiophene semicarbazone
3771-70-8

2-acetylthiophene semicarbazone

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With tribromo-isocyanuric acid In acetonitrile at 20℃; for 4.5h;98%
2-phenoxy-1-(thiophen-2-yl)ethan-1-one
188549-18-0

2-phenoxy-1-(thiophen-2-yl)ethan-1-one

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 3h; Schlenk technique; Inert atmosphere;98%
2-ethylthiophene
872-55-9

2-ethylthiophene

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With pyridine; tert.-butylhydroperoxide In decane; acetonitrile at 80℃; for 24h;96%
With tert.-butylhydroperoxide; 1-n-butyl-3-methylimidazolim bromide In water at 20℃; for 12h;95%
With potassium permanganate; copper(II) sulfate at 20℃; for 6h;90%
(5-acetylthiophen-2-yl)boronic acid

(5-acetylthiophen-2-yl)boronic acid

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With acetic acid at 130℃; for 2h; Green chemistry;96%
With palladium diacetate at 20℃; for 0.166667h;95%
Stage #1: (5-acetylthiophen-2-yl)boronic acid With nickel(II) iodide; trans-2-aminocyclohexanol hydrochloride; sodium hexamethyldisilazane In isopropyl alcohol Inert atmosphere;
Stage #2: With 3-iodooxetane In isopropyl alcohol at 80℃; for 0.333333h; Microwave irradiation;		60%
2-ethynyl-thiophene
4298-52-6

2-ethynyl-thiophene

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With indium(III) triflate; water; toluene-4-sulfonic acid In 1,2-dichloro-ethane for 0.3h; Sealed tube; Reflux; regioselective reaction;95%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) In methanol; water at 110℃; for 6h; Schlenk technique; regioselective reaction;93%
With chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I); water In methanol at 110℃; for 6h;93%
2-bromothiophene
1003-09-4

2-bromothiophene

carbon monoxide
201230-82-2

carbon monoxide

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
Stage #1: 2-bromothiophene; carbon monoxide; acetoacetic acid methyl ester With dichloro(1,5-cyclooctadiene)palladium(II); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride In 1,4-dioxane at 80℃; for 18h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water at 80℃; for 6h;		94%
With dichloro(1,5-cyclooctadiene)palladium(II); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride In 1,4-dioxane at 80℃; for 18h; Sealed tube;94%
...Expand
1-thiophen-2-yl-ethylamine
6309-16-6

1-thiophen-2-yl-ethylamine

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With 4-phenylnaphthalene-1,2-dione In acetonitrile at 80℃; for 36h;94%
2-Thiophenecarbonyl chloride
5271-67-0

2-Thiophenecarbonyl chloride

trimethyl indium
3385-78-2

trimethyl indium

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With mesoporous MCM-41-immobilized phosphine-free heterogeneous palladium(0)-schiff base complex In tetrahydrofuran at 68℃; for 2h; Inert atmosphere; Green chemistry;92%
2-acetylthiophene oxime
1956-45-2, 92313-45-6, 92313-54-7

2-acetylthiophene oxime

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With phosphoric acid In water at 95℃; for 2h;89%
With ferrous(II) sulfate heptahydrate; benzyl seleninic acid In ethyl acetate at 60℃; for 24h; Green chemistry;83%
With manganese(IV) oxide; silica gel for 0.1h; microwave irradiation;75%
With chromium(VI) oxide; silica gel In toluene at 72 - 75℃; for 4h; Oxidation; Deoximation;64%
With chromium(VI) oxide; silica gel In dichloromethane for 0.0222222h; Irradiation;61%
2-bromothiophene
1003-09-4

2-bromothiophene

-butyl vinyl ether
111-34-2

-butyl vinyl ether

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
Stage #1: 2-bromothiophene; -butyl vinyl ether With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In various solvent(s) at 125℃; for 30h; Regioselective Heck arylation;
Stage #2: With hydrogenchloride In various solvent(s) for 1h;		89%
2-chloro-2-(2-thienyl)ethane
28612-98-8

2-chloro-2-(2-thienyl)ethane

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation;89%
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;82%
2-Bromoacetylthiophene
10531-41-6

2-Bromoacetylthiophene

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With water; triphenylantimony at 120℃; for 0.166667h; Microwave irradiation;88%
Multi-step reaction with 2 steps
1: 75 percent / ethanol / 1 h / Heating
2: 8 percent / diethyl ether; tetrahydrofuran / 6 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: tetra-(n-butyl)ammonium iodide; potassium carbonate / dichloromethane; water / 20 °C
2: palladium(II) trifluoroacetate; 5,5′-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole; hydrogen / acetone / 24 h / 20 °C / 22502.3 Torr / Glovebox; Autoclave
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / Reflux
2: bis(pinacol)diborane; sodium t-butanolate; 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride / tetrahydrofuran; methanol / 3 h / 65 °C / Schlenk technique; Inert atmosphere
View Scheme
N,N-dimethyl-N'-(1-thiophen-2-yl-ethylidene)-hydrazine

N,N-dimethyl-N'-(1-thiophen-2-yl-ethylidene)-hydrazine

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With cerium(III) chloride; silica gel for 0.05h; Microwave irradiation;87%
thiophene
188290-36-0

thiophene

malonic acid
141-82-2

malonic acid

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With PPA at 60 - 80℃; for 2h; Acylation; Friedel-Crafts acylation;86%
2-thiophen-2-yl-oxirane
66256-03-9

2-thiophen-2-yl-oxirane

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In 1,3,5-trimethyl-benzene at 130℃; for 24h; Meinwald Rearrangement; Inert atmosphere;84%
2-acetyl-5-chlorothiophene
6310-09-4

2-acetyl-5-chlorothiophene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

A

2-Acetylthiophene
88-15-3

2-Acetylthiophene

B

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethan-1-one
942070-32-8

1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethan-1-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 23℃; under 760.051 Torr; for 0.5h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere; Irradiation;A n/a
B 84%
...Expand
2-bromothiophene
1003-09-4

2-bromothiophene

acetyl chloride
75-36-5

acetyl chloride

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
Stage #1: 2-bromothiophene With magnesium In tetrahydrofuran for 2h; Reflux; Inert atmosphere;
Stage #2: acetyl chloride With lithium manganese chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;		82%
2-Acetyl-5-bromothiophene
5370-25-2

2-Acetyl-5-bromothiophene

A

2-Acetylthiophene
88-15-3

2-Acetylthiophene

B

5,5'-di(1-oxoethyl)-2,2'-bithiophene
18494-73-0

5,5'-di(1-oxoethyl)-2,2'-bithiophene

Conditions
ConditionsYield
With tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; palladium diacetate In toluene at 105℃; for 4h;A 7%
B 80%
2-Iodothiophene
3437-95-4

2-Iodothiophene

carbon monoxide
201230-82-2

carbon monoxide

trimethyl indium
3385-78-2

trimethyl indium

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With mesoporous material MCM-41-immobilized palladium(II)-schiff base complex In tetrahydrofuran at 68℃; under 760.051 Torr; for 2.5h; Inert atmosphere;80%
...Expand
2-Iodothiophene
3437-95-4

2-Iodothiophene

carbon monoxide
201230-82-2

carbon monoxide

methylmercury(II) iodide
143-36-2

methylmercury(II) iodide

2-Acetylthiophene
88-15-3

2-Acetylthiophene

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); tetra-(n-butyl)ammonium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide under 760 Torr; for 7h; Ambient temperature;79%
...Expand
1-(2-bromophenyl)-1-thiophen-2-yl-ethanol
1176196-21-6

1-(2-bromophenyl)-1-thiophen-2-yl-ethanol

A

2-Acetylthiophene
88-15-3

2-Acetylthiophene

B

6-methyl-6-thien-2-yl-6H-benzo[c]chromene
1569315-63-4

6-methyl-6-thien-2-yl-6H-benzo[c]chromene

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; Inert atmosphere; Schlenk technique;A 55%
B 77%

2-Acetylthiophene Consensus Reports

Reported in EPA TSCA Inventory.

2-Acetylthiophene Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

2-Acetylthiophene Specification

The 2-Acetothienone is an organic compound with the formula C6H6OS. The IUPAC name of this chemical is 1-thiophen-2-ylethanone. With the CAS registry number 88-15-3, it is also named as 1-(2-thienyl)ethan-1-one. The product's categories are Thiophenes; Sulphur Derivatives; Thiophene & Benzothiophene; Thiophene Flavor. Besides, it is a clear colorless to slightly yellow liquid, which should be stored in a closed cool and dark place. It is used as solvent, extracting agent and pharmaceutical intermediates.

Physical properties about 2-Acetothienone are: (1)ACD/LogP: 1.25; (2)ACD/LogD (pH 5.5): 1.25; (3)ACD/LogD (pH 7.4): 1.25; (4)ACD/BCF (pH 5.5): 5.28; (5)ACD/BCF (pH 7.4): 5.28; (6)ACD/KOC (pH 5.5): 114.45; (7)ACD/KOC (pH 7.4): 114.45; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 45.31 Å2; (11)Index of Refraction: 1.54; (12)Molar Refractivity: 34.66 cm3; (13)Molar Volume: 110.4 cm3; (14)Polarizability: 13.74×10-24cm3; (15)Surface Tension: 38.7 dyne/cm; (16)Density: 1.142 g/cm3; (17)Flash Point: 82.4 °C; (18)Enthalpy of Vaporization: 44.89 kJ/mol; (19)Boiling Point: 212.6 °C at 760 mmHg; (20)Vapour Pressure: 0.172 mmHg at 25°C.

Preparation: this chemical can be prepared by acetic acid anhydride. The reaction temperature is 140 °C.



Uses of 2-Acetothienone: it can be used to produce 6-methyl-2-thiophen-2-yl-quinoline-4-carboxylic acid. It will need reagent aq.-ethanolic KOH.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer). Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(c1sccc1)C
(2)InChI: InChI=1/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
(3)InChIKey: WYJOVVXUZNRJQY-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
(5)Std. InChIKey: WYJOVVXUZNRJQY-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 40mg/kg (40mg/kg)   National Technical Information Service. Vol. AD691-490,

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