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88-15-3

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88-15-3 Usage

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 is used as an intermediate in the manufacturing of drugs like Tiamonium Iodide, Suprofan, Stepronin, Tenonitrozole, Namirotene, etc.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 8, 1943The Journal of Organic Chemistry, 36, p. 540, 1971 DOI: 10.1021/jo00803a011Tetrahedron 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,.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 88-15-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 88-15:
(4*8)+(3*8)+(2*1)+(1*5)=63
63 % 10 = 3
So 88-15-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3

88-15-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A13062)  2-Acetylthiophene, 99%   

  • 88-15-3

  • 100g

  • 374.0CNY

  • Detail
  • Alfa Aesar

  • (A13062)  2-Acetylthiophene, 99%   

  • 88-15-3

  • 500g

  • 1629.0CNY

  • Detail
  • Alfa Aesar

  • (A13062)  2-Acetylthiophene, 99%   

  • 88-15-3

  • 2500g

  • 6557.0CNY

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  • Aldrich

  • (A22602)  2-Acetylthiophene  98%

  • 88-15-3

  • A22602-25G

  • 293.67CNY

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  • Aldrich

  • (A22602)  2-Acetylthiophene  98%

  • 88-15-3

  • A22602-100G

  • 519.48CNY

  • Detail

88-15-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Acetylthiophene

1.2 Other means of identification

Product number -
Other names 2-ACETOTHIOPHENE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:88-15-3 SDS

88-15-3Synthetic 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%
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%
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%
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%
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%
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%

88-15-3Relevant articles and documents

Effects of oligothiophene π-bridge length on physical and photovoltaic properties of star-shaped molecules for bulk heterojunction solar cells

Min, Jie,Luponosov, Yuriy N.,Baran, Derya,Chvalun, Sergei N.,Shcherbina, Maxim A.,Bakirov, Artem V.,Dmitryakov, Petr V.,Peregudova, Svetlana M.,Kausch-Busies, Nina,Ponomarenko, Sergei A.,Ameri, Tayebeh,Brabec, Christoph J.

, p. 16135 - 16147 (2014)

The preparation of four different star-shaped donor (D)-π-acceptor (A) small molecules (N(Ph-1T-DCN-Me)3, N(Ph-2T-DCN-Me)3, N(Ph-2T-DCN-Hex)3and N(Ph-3T-DCN-Hex)3) possessing various oligothiophene π-bridge lengths and their use in solution-processed bulk heterojunction small molecule solar cells is reported. Optical and electrochemical data show that increasing oligothiophene π-bridge length leads to a decrease of the optical band gap due to a parallel increase of the highest occupied molecular orbital (HOMO) level. Furthermore, subtle modifications of a molecular π-bridge length strongly affect the thermal behavior, solubility, crystallization, film morphology and charge carrier mobility, which in turn significantly change the device performance. Although the moderately increasing oligothiophene π-bridge length uplifts the HOMO level, it nevertheless induces an increase of the efficiency of the resulting solar cells due to a simultaneous improvement of the short circuit current (Jsc) and fill factor (FF). The study demonstrates that such an approach can represent an interesting tool for the effective modulation of the photovoltaic properties of the organic solar cells (OSCs) at a moderate cost.

High luminescence quantum yields and long luminescence lifetime from Eu(III) complex containing two crystal water based on a new β-diketonate ligand

Sun, Youyi,Gao, Jiangang,Zheng, Zhi,Su, Wei,Zhang, Qijin

, p. 977 - 980 (2006)

New members of family of Eu(III) complex based on the thenoylacetophenone have been synthesized and characterized. The compounds were found for high metal luminescence quantum yields and long luminescence lifetime, especially for compound with two crystal water, corresponding with other compounds containing two crystal water. The result is attributed to high molar absorption coefficients of the Eu(III) complex according to UV-vis and emission spectra. The high molar absorption coefficients balance quenching effect from O{single bond}H oscillators of water contained in compound.

Method for oxidative cracking of compound containing unsaturated double bonds

-

Paragraph 0108-0114; 0173-0175, (2021/07/09)

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei

supporting information, p. 5905 - 5908 (2021/06/18)

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

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