1468-83-3

Basic information

• Product Name: 3-Acetylthiophene
• Synonyms: 1-(Thien-3-yl)ethan-1-one, 1-Oxo-1-(thien-3-yl)ethane;3-Acetylthioph;Methyl 3-thienyl ketone for synthesis;METHYL 3-THIENYL KETONE;3-ACETYLTHIOPHENE;1-(3-THIENYL)ETHANONE;1-(3-Thienyl)-1-ethanone;1-Thiophen-3-yl-ethanone
• CAS NO: 1468-83-3
• Molecular Formula: C₆H₆OS
• Molecular Weight: 126.18
• EINECS: 215-996-4
• Product Categories: Thiophenes;Sulphur Derivatives;Thiophene&Benzothiophene;Heterocyclic Compounds;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1468-83-3.mol
• Article Data: 30

Chemical Properties

• Melting Point: 57-62 °C(lit.)
• Boiling Point: 208-210 °C748 mm Hg(lit.)
• Flash Point: 208-210°C
• Appearance: Beige to light brown/Adhering Crystals
• Density: 1.176 (estimate)
• Vapor Pressure: 0.541mmHg at 25°C
• Refractive Index: 1.5667 (estimate)
• Storage Temp.: Room temperature.
• Solubility: Chloroform, Hexane (Slightly)
• Sensitive: Light Sensitive
• BRN: 107241
• CAS DataBase Reference: 3-Acetylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetylthiophene(1468-83-3)
• EPA Substance Registry System: 3-Acetylthiophene(1468-83-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36/37-36-26
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1468-83-3(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

3-Acetylthiophene was used in the preparation of 1-(methylthiophenylidine)-8-naphthylamine(Schiff′s base) and 1-(thiophen-3-yl)ethanone.

General Description

3-Acetylthiophene modified glassy carbon electrode has been used in voltammetric determination of uric acid in urine samples.

Purification Methods

Recrystallise the thiophene from pet ether (b 30-60o) or EtOH. The 2,4-dinitrophenylhydrazone crystallises from CHCl3, m 265o, and the semicarbazone crystallises from EtOH, m 174-175o. [Campaigne & Le Suer J Am Chem Soc 70 1555 1948, Beilstein 17/9 V 399.]

InChI:InChI=1/C6H6OS/c1-5(7)6-2-3-8-4-6/h2-4H,1H3

Synthetic route

3-ethynylthiophene (67237-53-0) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;	93%
With water; silver trifluoromethanesulfonate for 7h; Heating;	90%
With water for 8h; Reflux;	87%

3-thienyl iodide (10486-61-0) + trimethylsiloxyethene (6213-94-1) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 100℃; for 2h; Heck Reaction; Microwave irradiation; regioselective reaction;	86%

1-(thiophen-3-yl)ethan-1-ol (14861-60-0) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With trimethylaluminum In toluene at 20℃; for 0.5h; Oppenauer oxidation;	84%
With tert.-butylnitrite; oxygen; 3,6-di(2'-pyridyl)-1,2,4,5-tetrazine; acetic acid In acetonitrile at 20℃; for 4.5h; Irradiation;	71%
With dipropylene glycol dimethyl ether; oxygen at 120℃;

3-Bromothiophene (872-31-1) + -butyl vinyl ether (111-34-2) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
Stage #1: 3-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;	82%

Thien-3-ylboronic acid (6165-69-1) + ethyl 2-cyanoacetate (105-56-6) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 60℃; for 5h;	80%

1,4-dithiane-2,5-diol (40018-26-6) + 4-methoxy-3-buten-2-one (4652-27-1) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
Stage #1: 1,4-dithiane-2,5-diol; 4-methoxy-3-buten-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50 - 67℃; for 3 - 10h; Stage #2: hydrogenchloride In water; acetonitrile at 60℃; for 2.5 - 3.5h; Product distribution / selectivity;	79%
at 110℃; for 30h; Product distribution / selectivity;	21%
hydrogenchloride In water; toluene at 65℃; for 3h; Product distribution / selectivity;	20 %Chromat.

2-Iodothiophene (3437-95-4) + carbon monoxide (201230-82-2) + tetramethylstannane (594-27-4) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With MCM-41-supported bidentate phosphine palladium(0) complex In N,N-dimethyl-formamide at 70℃; under 760.051 Torr; for 10h; Stille carbonylative cross-coupling;	75%

3-ethylthiophene (1795-01-3) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With tert.-butylhydroperoxide In water; acetonitrile at 50℃; for 15h; Electrolysis;	74%
With sodium anthraquinonesulfonate; air In water; acetonitrile at 20℃; for 18h; Irradiation;	91 %Chromat.

1,4-dithiane-2,5-diol (40018-26-6) + (E)-4-(dimethylamino)but-3-en-2-one (2802-08-6) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran at 65℃; for 16h;	58%

1,4-dithiane-2,5-diol (40018-26-6) + 4-dimethylamino-3-buten-2-one (1190-91-6) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
at 110℃; for 30h; Product distribution / selectivity;	9%
hydrogenchloride In water; toluene at 90℃; for 10h; Product distribution / selectivity;	32 %Chromat.
potassium carbonate In N,N-dimethyl-formamide at 80℃; for 8h; Product distribution / selectivity;	17 %Chromat.

3-thiophene carboxylic acid chloride (41507-35-1) + dimethylcadmium (506-82-1) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With diethyl ether

3-acetyl-2,5-dichlorothiophene (36157-40-1) → 1-(thiophen-3-yl)-ethanone (1468-83-3) + 1-(5-Chlor-3-thienyl)-ethanon (58119-67-8) + 3-acetyl-2-chlorothiophene (81557-66-6)

Conditions	Yield
With sodium tetrahydroborate; hydrogen; calcium oxide; palladium In ethanol at 20℃; under 760 Torr; Rate constant; other temperature, other solvent, other acceptor;

methyllithium (917-54-4) + 3-thiophenecarboxylic acid,N,N-diethylamide (73540-75-7) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With lanthanum(lll) triflate 1.) THF, -78 deg C then up to 0 deg C, 2.) -78 up to 0 deg C, 30 min; Yield given. Multistep reaction;

(+-)-1-<3>thienyl-ethanol → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With chromium(VI) oxide; acetic acid

(+-)-1-<3>thienyl-ethanol → 3-vinylthiophene (13679-64-6) + 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With potassium hydrogensulfate at 250℃;

1-butoxy-1-(3-thienyl)ethene (132387-75-8) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 0.5h;
With hydrogenchloride In water for 0.5h;

C8H10O2S → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 20℃;

2-(3-thienyl)propanal → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With sodium hydroxide; silver(l) oxide In ethanol at 40℃;

1-(thiophen-3-yl)ethan-1-ol (14861-60-0) + 1-(thien-2-yl)ethanol (115510-91-3) → 1-(thiophen-3-yl)-ethanone (1468-83-3) + 2-Acetylthiophene (88-15-3)

Conditions	Yield
With manganese(IV) oxide In toluene Heating / reflux;

L-Cysteine (52-90-4) + ascorbic acid (50-81-7) → [1,2,5,6]tetrathiocane (1940-01-8) + 1-(thiophen-3-yl)-ethanone (1468-83-3) + 2-Acetylthiazole (24295-03-2) + thieno[3,2-b]thiophene (251-41-2) + 3,5-dimethyl-1,2,4-trithiolane (23654-92-4) + 3-(vinylthio)thiophene (867253-51-8) + 4,6-dimethyl-1,2,3-trithiane + 4,6-dimethyl-1,2,3-trithiane + cis-3,5-diethyl-1,2,4-trithiolane + trans-3,5-diethyl-1,2,4-trithiolane

Conditions	Yield
at 141℃; for 2h; pH=9; aq. phosphate buffer;

...Expand

thiophene (188290-36-0) + acetic anhydride (108-24-7) → 1-(thiophen-3-yl)-ethanone (1468-83-3) + 2-Acetylthiophene (88-15-3)

Conditions	Yield
With Hierarchical-ZSM-5 zeolite In neat (no solvent) at 59.84℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Friedel-Crafts Acylation; Green chemistry;

3-(trimethylsilylethynyl)thiophene (130995-13-0) → 1-(thiophen-3-yl)-ethanone (1468-83-3)

Conditions	Yield
With iron(III) sulphate monohydrate; acetic acid at 70℃; for 16h; regioselective reaction;	98 %Chromat.

1-(thiophen-3-yl)-ethanone (1468-83-3) → 1-(thiophen-3-yl)ethan-1-ol (14861-60-0)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;	100%
With sodium tetrahydroborate In ethanol at 20℃; for 4h; Inert atmosphere;	99.5%
With isopropyl alcohol; sodium hydroxide at 80℃; for 21h; Reagent/catalyst;	97%

1-(thiophen-3-yl)-ethanone (1468-83-3) → (+)-(R)-1-(thiophen-3-yl)ethanol (153035-65-5)

Conditions	Yield
With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at -23℃;	100%
With C38H38IrN4S2(1+)*F6P(1-); ammonium formate; 3-methyl-5-p-methoxyphenyl-1-hydropyrazole In tetrahydrofuran; water at 40℃; for 8h; enantioselective reaction;	93%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; N-(tert-butoxycarbonyl)-L-valine-(6-amido-1-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranose); potassium tert-butylate; lithium chloride In tetrahydrofuran; isopropyl alcohol at 20℃; for 3h; enantioselective reaction;	92%

1-(thiophen-3-yl)-ethanone (1468-83-3) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → 2-(thiophen-3-yl)pent-4-en-2-ol

Conditions	Yield
With indium iodide In tetrahydrofuran at 40℃; for 24h;	100%
With methanol; indium (III) tris(hexamethyldisilyl) amide In toluene at 20℃; for 6h; Inert atmosphere;	81%

1-(thiophen-3-yl)-ethanone (1468-83-3) → 1-(thiophen-3-yl)ethanone oxime (59445-83-9)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃;	100%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;	92%
With sodium hydroxide; hydroxylamine hydrochloride In water at 0 - 100℃;	83%

1-(thiophen-3-yl)-ethanone (1468-83-3) + water (7732-18-5) → 1-(thiophen-3-yl)ethan-1-ol (14861-60-0)

Conditions	Yield
With sodium hydroxide In diethyl ether	100%

pyridine (110-86-1) + 1-(thiophen-3-yl)-ethanone (1468-83-3) → 1-[2-oxo-2-(thiophen-3-yl)ethyl]pyridinium iodide (1030917-93-1)

Conditions	Yield
With iodine	100%
With iodine at 140℃; for 3h;	100%
With iodine at 140℃; for 3h;	100%

1-(thiophen-3-yl)-ethanone (1468-83-3) + 1-phenyl-4-penten-1-yne (4289-20-7) → (R,Z)-7-phenyl-2-(thiophen-3-yl)hept-4-en-6-yn-2-ol

Conditions	Yield
With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; mesitylcopper(I) In tetrahydrofuran at -30℃; Inert atmosphere; stereoselective reaction;	100%

1-(thiophen-3-yl)-ethanone (1468-83-3) + ethylmagnesium bromide (925-90-6) → 2-(thiophen-3-yl)butan-2-ol

Conditions	Yield
Stage #1: ethylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.75h; Inert atmosphere; Stage #2: 1-(thiophen-3-yl)-ethanone In tetrahydrofuran; diethyl ether at 0℃; for 3h; Inert atmosphere;	99%
In diethyl ether at -20 - 20℃; for 1h;

1-(thiophen-3-yl)-ethanone (1468-83-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 3-dimethylamino-1-(thien-3-yl)-2-propen-1-one (79571-33-8)

Conditions	Yield
Heating / reflux;	99%
In N,N-dimethyl-formamide Heating;	93%
at 160℃; for 0.25h; Microwave irradiation;	86%

1-(thiophen-3-yl)-ethanone (1468-83-3) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,5,5-trimethyl-2-(thiophen-3-yl)-1,3-dioxane (138890-86-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 24h; Heating / reflux;	99%
With toluene-4-sulfonic acid In toluene for 24h; Reflux; Dean Stark;	99%
With toluene-4-sulfonic acid In toluene for 36h; Reflux;	93%
With sulfuric acid In toluene for 2h; Heating;	65%

1-(thiophen-3-yl)-ethanone (1468-83-3) + dimethyl trimethylsilyl phosphite (36198-87-5) → (1-thiophen-3-yl-1-trimethylsilanyloxy-ethyl)-phosphonic acid dimethyl ester (1172141-67-1)

Conditions	Yield
With C4H9O(1-)*C13H27KO6(1+) In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	99%

1-(thiophen-3-yl)-ethanone (1468-83-3) + octylmagnesium bromide (17049-49-9) → 2-(thiophen-3-yl)decan-2-ol (1227495-94-4)

Conditions	Yield
Stage #1: octylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; Grignard addition; Stage #2: 1-(thiophen-3-yl)-ethanone In tetrahydrofuran; diethyl ether at 0℃; for 3h; Grignard addition;	99%
Stage #1: octylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.75h; Inert atmosphere; Stage #2: 1-(thiophen-3-yl)-ethanone In tetrahydrofuran; diethyl ether at 0℃; for 3h; Inert atmosphere;	99%

1-(thiophen-3-yl)-ethanone (1468-83-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 3-(dimethylamino)-1-(thiophen-3-yl)prop-2-en-1-one (79571-33-8)

Conditions	Yield
In N,N-dimethyl acetamide for 18h; Reflux;	99%
In N,N-dimethyl acetamide at 120 - 125℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-methyl-benzaldehyde (104-87-0) → 3-(4-methylphenyl)-1-(3-thienyl)-2-propen-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	99%
With preheated fly-ash Aldol Condensation; Microwave irradiation; Sealed tube;	65%
With sodium hydroxide In ethanol at 20℃;
With sodium hydroxide In ethanol at 20℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + m-tolyl aldehyde (620-23-5) → 1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one (1245505-00-3)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	99%
With sodium hydroxide In ethanol at 20℃;
With sodium hydroxide In ethanol at 20℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-methyl-benzaldehyde (104-87-0) → (E)-1-(thiophen-3-yl)-3-p-tolylprop-2-en-1-one (148877-98-9)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	99%

1-(thiophen-3-yl)-ethanone (1468-83-3) + m-tolyl aldehyde (620-23-5) → (E)-1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one (1205545-63-6)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	99%

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-chlorobenzaldehyde (104-88-1) → (E)-3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With sodium hydroxide In ethanol Ambient temperature;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-Methylphenylazo tert-butyl sulfide (146767-34-2) → 3-Thienyl <(4-methylphenyl)hydrazono>methyl ketone (146767-44-4)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 25℃; Condensation;	98%
With potassium tert-butylate 2) room temp., 60 min; Yield given. Multistep reaction;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-bromo-benzaldehyde (1122-91-4) → (E)-3-(4-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With sodium hydroxide In ethanol Ambient temperature;

1-(thiophen-3-yl)-ethanone (1468-83-3) → (S)-1-(thiophen-3-yl)ethan-1-ol (222609-67-8)

Conditions	Yield
With potassium tert-butylate; hydrogen; trans-RuCl2[(R)-xylbinap][(R)-daipen] In isopropyl alcohol; tert-butyl alcohol at 25℃; under 6080.41 Torr; for 5h; Catalytic hydrogenation;	98%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; N-(tert-butoxycarbonyl)-L-valine-(6-thioamido-5-O-benzoyl-1-O-benzyl-6-deoxy-2,3-O-isopropylidene-α-D-mannofuranose); potassium tert-butylate; lithium chloride In tetrahydrofuran; isopropyl alcohol at 20℃; for 3h; enantioselective reaction;	91%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; C31H40N2O8S; sodium isopropylate; lithium chloride In tetrahydrofuran; isopropyl alcohol at 20℃; for 3h; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;	42%

1-(thiophen-3-yl)-ethanone (1468-83-3) + benzaldehyde (100-52-7) → (E)-3-phenyl-1-(3-thienyl)phenylprop-2-en-1-one (82833-71-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
Stage #1: 1-(thiophen-3-yl)-ethanone With sodium hydroxide In methanol at 20℃; for 0.0833333h; Stage #2: benzaldehyde In methanol at 20℃; for 16h;	61%
With potassium hydroxide In methanol at 0℃; for 3h;
With sodium hydroxide In ethanol; water at 0℃; for 0.5h;

1-(thiophen-3-yl)-ethanone (1468-83-3) → (E)-1-(thiophen-3-yl)ethanone oxime (110853-80-0)

Conditions	Yield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 60 - 65℃;	98%
With pyridine; hydroxylamine hydrochloride In ethanol at 20℃;	72%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 20h; Reflux;
With pyridine; hydroxylamine hydrochloride In ethanol at 60℃; for 1h;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-chlorobenzaldehyde (104-88-1) → 3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one (144080-41-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With preheated fly-ash Aldol Condensation; Microwave irradiation; Sealed tube;	66%
With sodium hydroxide In ethanol at 20℃;
With sodium hydroxide In ethanol at 20℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + benzaldehyde (100-52-7) → 3-phenyl-1-(thiophen-3-yl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With preheated fly-ash Aldol Condensation; Microwave irradiation; Sealed tube;	67%
With potassium hydroxide In methanol; water at 0℃; Claisen-Schmidt Condensation;	58.4%

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-methoxy-benzaldehyde (123-11-5) → 3-(4-methoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one (1245504-96-4)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With sodium hydroxide In ethanol at 20℃;
With sodium hydroxide In ethanol at 20℃;
With ethanol; sodium hydroxide

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-bromo-benzaldehyde (1122-91-4) → 3-(4-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one (144080-42-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With preheated fly-ash Aldol Condensation; Microwave irradiation; Sealed tube;	66%
With sodium hydroxide In ethanol at 20℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + 4-methoxy-benzaldehyde (123-11-5) → (2E)-3-(4-methoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one (947701-69-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	98%
With sodium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation;	92%

1-(thiophen-3-yl)-ethanone (1468-83-3) + m-bromobenzoic aldehyde (3132-99-8) → 3-(3-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one (1245504-98-6)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	97%
With preheated fly-ash Aldol Condensation; Microwave irradiation; Sealed tube;	65%
With sodium hydroxide In ethanol at 20℃;
With sodium hydroxide In ethanol at 20℃;

1-(thiophen-3-yl)-ethanone (1468-83-3) + m-bromobenzoic aldehyde (3132-99-8) → (E)-3-(3-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one (1205545-62-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 25℃;	97%

Upstream product

• 872-31-1 3-Bromothiophene 
• 111-34-2 -butyl vinyl ether 
• 14861-60-0 1-(thiophen-3-yl)ethan-1-ol 
• 115510-91-3 1-(thien-2-yl)ethanol 
• 42908-63-4 3-(prop-1-en-2-yl)thiophene 
• 130995-13-0 3-(trimethylsilylethynyl)thiophene 
• 1795-01-3 3-ethylthiophene 
• 6165-69-1 Thien-3-ylboronic acid 
• 105-56-6 ethyl 2-cyanoacetate 
• 188290-36-0 thiophene 
• 108-24-7 acetic anhydride 
• 67237-53-0 3-ethynylthiophene 
• 10486-61-0 3-thienyl iodide 
• 6213-94-1 trimethylsiloxyethene 

Downstream Products

• 100860-96-6 3-(dimethylamino)-1-(thiophen-3-yl)propan-1-one 
• 556110-53-3 1-(4-Acetyl-thiophen-2-yl)-2-chloro-ethanone 
• 77611-51-9 1-(3-thienyl)-4,4,4-trifluorobutane-1,3-dione 
• 22098-20-0 hydroxythiophen-3-ylacetic acid 
• 82833-71-4 (E)-3-phenyl-1-(3-thienyl)phenylprop-2-en-1-one 
• 138890-86-5 3-(2,5,5-Trimethyl-l,3-dioxane-2-yl)thiophene 
• 14861-60-0 1-(thiophen-3-yl)ethan-1-ol 
• 1245504-98-6 3-(3-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one 
• 144080-41-1 3-(4-chlorophenyl)-1-(thiophen-3-yl)prop-2-en-1-one 
• 1245504-96-4 3-(4-methoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one 
• 144080-42-2 3-(4-bromophenyl)-1-(thiophen-3-yl)prop-2-en-1-one 
• 331445-88-6 3-(2-methoxyphenyl)-1-(thiophen-3-yl)prop-2-en-1-one 
• 1245505-00-3 1-(thiophen-3-yl)-3-m-tolylprop-2-en-1-one 
• 1375113-22-6 3-(2-(3-chlorophenyl)-6-(thiophen-3-yl)pyridin-4-yl)phenol 

Relevant articles and documents

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Method for preparing carbonyl compound through oxidative cleavage of visible light excitation aqueous solution quantum dot catalytic olefin compound

The invention provides a method for preparing carbonyl compounds through oxidative cleavage of a visible light excitation aqueous solution quantum dot catalytic olefin compound. Belong to photocatalysis synthesis technical field. To the method, an aqueous solution quantum dot is used as a photocatalyst, and an aqueous solution quantum dot activated molecular oxygen catalytic oxidation aromatic alkene compound is excited by visible light to be cracked to prepare a carbonyl compound. Low-loading capacity is used, a simple aqueous solution quantum dot is used as a catalyst, the yield of the carbonyl compound is high, TON more than ten millions are obtained. The reaction conditions are mild, water serves as a main solvent for the reaction, and the carbonyl compound can be obtained by catalytic olefin compound oxidation cracking without addition of a cocatalyst or the like. The method is simple to operate, wide in substrate range and low in cost.

Enantiocomplementary C–H Bond Hydroxylation Combining Photo-Catalysis and Whole-Cell Biocatalysis in a One-Pot Cascade Process

Enantiocomplementary hydroxylation of alkyl aromatics through a one-pot photo-biocatalytic cascade reaction is described. The photoredox process is implemented in aqueous phase with O2 as oxidant and the subsequent (R)- or (S)-selective bioreduction is performed by whole cell system without the addition of the expensive cofactor (NADPH). This mild, operationally simple protocol transforms a wide variety of readily available aromatic compounds into valuable chiral alcohols with high yield (up to 90 %) and stereoselectivity (up to 99 %), thereby displaying important potentials in organic synthesis.