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1-Benzo[b]thiophen-2-yl-ethanone
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22720-75-8 Usage

Uses

A novel anti-osteoporosis agent, by enhansing expression of the BMP-2 gene.

Chemical Properties

white to light yellow crystal powder
InChI:InChI=1/C10H8OS/c1-7(11)10-6-8-4-2-3-5-9(8)12-10/h2-6H,1H3

22720-75-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1724689)  ZileutonRelatedCompoundC  United States Pharmacopeia (USP) Reference Standard 22720-75-8 1724689-50MG 14,500.98CNY Detail
Aldrich (683477)  2-Acetylbenzothiophene  97% 22720-75-8 683477-5G 1,406.34CNY Detail
Aldrich (683477)  2-Acetylbenzothiophene  97% 22720-75-8 683477-1G 446.94CNY Detail
Alfa Aesar (B21173)  2-Acetylbenzo[b]thiophene, 98%    22720-75-8 5g 4661.0CNY Detail
Alfa Aesar (B21173)  2-Acetylbenzo[b]thiophene, 98%    22720-75-8 1g 1241.0CNY Detail

22720-75-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Acetylbenzo[b]thiophene

1.2 Other means of identification

Product number -
Other names 1-(Benzo[b]thiophen-2-yl)ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:22720-75-8 SDS

22720-75-8Synthetic route

2-(ethylsulfanyl)benzenecarbaldehyde
53606-33-0

2-(ethylsulfanyl)benzenecarbaldehyde

chloroacetone
78-95-5

chloroacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With calcium oxide In acetone at 59℃;100%
With calcium oxide for 3h; Reflux;
1-(benzo[b]thiophen-2-yl)ethanol
51868-95-2

1-(benzo[b]thiophen-2-yl)ethanol

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); potassium tert-butylate; acetone In n-heptane at 50℃; for 24h; Schlenk technique; Inert atmosphere;98%
With chromium(VI) oxide; sulfuric acid; water In acetone at 20℃; for 24h; Inert atmosphere;94%
With pyridinium chlorochromate In dichloromethane at 20℃; for 10h;78%
diethylacetamide
685-91-6

diethylacetamide

sodium trisulfide

sodium trisulfide

chloroacetone
78-95-5

chloroacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
In diethyl ether; water95%
2-(methylsulfanyl)benzaldehyde
7022-45-9

2-(methylsulfanyl)benzaldehyde

chloroacetone
78-95-5

chloroacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With magnesium oxide In toluene at 120℃; for 4h; Reagent/catalyst;95%
2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

chloroacetone
78-95-5

chloroacetone

acetylacetone
123-54-6

acetylacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Stage #1: 2,2'-dithiodibenzaldehyde; acetylacetone With potassium carbonate; dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere;
Stage #2: chloroacetone at 50℃; for 1.5h; Inert atmosphere;
94%
IMB-05
148520-10-9

IMB-05

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With ammonium chloride; zinc In ethanol at 0℃; for 1h;93%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

1-mercaptopropan-2-one
24653-75-6

1-mercaptopropan-2-one

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;84%
trans-4-(2-iodophenyl)-3-buten-2-one

trans-4-(2-iodophenyl)-3-buten-2-one

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With copper diacetate; potassium ethyl xanthogenate In dimethyl sulfoxide at 100℃; for 3h;84%
2-(prop-1-en-2-yl)benzo[b]thiophene
135555-29-2

2-(prop-1-en-2-yl)benzo[b]thiophene

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; oxygen; 2,5-Dimercapto-1,3,4-thiadiazole In acetonitrile at 20 - 80℃; under 760.051 Torr; for 15h; Schlenk technique;82%
2-(hydroxymethyl)thiophenoxyacetone
130966-65-3

2-(hydroxymethyl)thiophenoxyacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With pyridine-SO3 complex; triethylamine In dichloromethane; dimethyl sulfoxide79%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Stage #1: Benzo[b]thiophene With n-butyllithium In diethyl ether; hexane at -78℃; for 1.5h; Reflux;
Stage #2: N,N-dimethyl acetamide In diethyl ether; hexane for 2h; Reflux;
78%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 22℃;35%
2-(methylsulfanyl)benzaldehyde
7022-45-9

2-(methylsulfanyl)benzaldehyde

chloroacetone
78-95-5

chloroacetone

A

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

B

1-(benzo[b]thiophen-2-yl)-1,4-pentanedione

1-(benzo[b]thiophen-2-yl)-1,4-pentanedione

Conditions
ConditionsYield
With magnesium hydroxide In neat (no solvent) at 120℃; for 3h;A 71%
B 22.5 %Chromat.
(E)-4-(2-iodophenyl)but-3-en-2-one
122752-74-3

(E)-4-(2-iodophenyl)but-3-en-2-one

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With copper(l) iodide; potassium sulfide In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; Sealed tube;65%
N-Methoxy-N-methylacetamide
78191-00-1

N-Methoxy-N-methylacetamide

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 22℃;62%
With n-butyllithium In tetrahydrofuran; ethanol; pentane
2-ethylbenzo[b]thiophene
1196-81-2

2-ethylbenzo[b]thiophene

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With tert.-butylnitrite; N-hydroxyphthalimide; oxygen In benzonitrile at 80℃; under 760.051 Torr; for 24h; Schlenk technique;60%
2,2'-dithiodibenzaldehyde
55164-16-4

2,2'-dithiodibenzaldehyde

acetylacetone
123-54-6

acetylacetone

A

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

B

2-mercaptobenzaldehyde potassium salt
1005199-10-9

2-mercaptobenzaldehyde potassium salt

Conditions
ConditionsYield
With potassium carbonate; dimethyl sulfoxideA 45%
B n/a
benzaldehyde
100-52-7

benzaldehyde

chloroacetone
78-95-5

chloroacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Stage #1: benzaldehyde With sulfur; n-butyllithium; N,N',N'-trimethylenediamine In tetrahydrofuran; hexane at -20℃; for 3h; Dehydrogenation; substitution;
Stage #2: chloroacetone With potassium carbonate In tetrahydrofuran for 24h; Alkylation; cyclization;
38%
1-[2-(methylsulfanyl)phenyl]diazonium tetrafluoroborate

1-[2-(methylsulfanyl)phenyl]diazonium tetrafluoroborate

methyl ethynyl ketone
1423-60-5

methyl ethynyl ketone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With copper In acetone Ambient temperature;37%
benzothiophen-2-yllithium
50779-55-0

benzothiophen-2-yllithium

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
With lithium acetate
acetic anhydride
108-24-7

acetic anhydride

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

B

3-acetylbenzothiophene
1128-05-8

3-acetylbenzothiophene

Conditions
ConditionsYield
With boron fluoride ether
With trifluoroacetic acid at 20℃; for 1.5h; Friedel-Crafts Acylation; Overall yield = 92 %; Overall yield = 121 mg;
thiophenol
108-98-5

thiophenol

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

chloroacetone
78-95-5

chloroacetone

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Yield given. Multistep reaction;
acetyl chloride
75-36-5

acetyl chloride

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

B

3-acetylbenzothiophene
1128-05-8

3-acetylbenzothiophene

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: acetyl chloride With aluminium trichloride In nitrobenzene at 10℃; for 1h;
Stage #2: Benzo[b]thiophene In nitrobenzene for 1h; Friedel-Crafts reaction; Title compound not separated from byproducts;
ethyl benzo[b]thiophene-2-carboxylate
17890-55-0

ethyl benzo[b]thiophene-2-carboxylate

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / t-BuOK / 2 h / Ambient temperature
2: 93 percent / 10percent aq. NH4Cl, Zn / ethanol / 1 h / 0 °C
View Scheme
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 94 percent / K2CO3 / dimethylformamide / 1.) 0 deg C, 30 min, 2.) RT, 24 h
2: 90 percent / t-BuOK / 2 h / Ambient temperature
3: 93 percent / 10percent aq. NH4Cl, Zn / ethanol / 1 h / 0 °C
View Scheme
2-(hydroxymethyl)thiophenoxide

2-(hydroxymethyl)thiophenoxide

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 0.33 h / 0 - 5 °C
2: 79 percent / Et3N, SO3*Py / CH2Cl2; dimethylsulfoxide
View Scheme
Thiosalicylic acid
147-93-3

Thiosalicylic acid

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) LiAlH4, 2.) EtOAc, H2O / 1a.) THF, 0-5 deg C, 1b.) RT, 1h, 2.) 0-5 deg C, 30 min
2: tetrahydrofuran / 0.33 h / 0 - 5 °C
3: 79 percent / Et3N, SO3*Py / CH2Cl2; dimethylsulfoxide
View Scheme
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

N-Methoxy-N-methylacetamide
78191-00-1

N-Methoxy-N-methylacetamide

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

diethylacetamide
685-91-6

diethylacetamide

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
In toluene
ISOPROPYLAMIDE
563-83-7

ISOPROPYLAMIDE

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

petrol

petrol

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

Conditions
ConditionsYield
In dichloromethane; toluene
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-(benzo[b]thiophen-2-yl)-2-bromoethanone
97511-06-3

1-(benzo[b]thiophen-2-yl)-2-bromoethanone

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 15h; Product distribution / selectivity;100%
With tetrabuthylammonium tribromide In methanol; dichloromethane at 22℃; for 6h;95%
With copper(ll) bromide In methanol; chloroform at 60℃; for 15h;89%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

(R)-(+)-1-(benzo[b]thiophen-2-yl)ethanol
560108-31-8

(R)-(+)-1-(benzo[b]thiophen-2-yl)ethanol

Conditions
ConditionsYield
With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 20℃; for 0.666667h;100%
With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 20℃; for 29.5h; Inert atmosphere; optical yield given as %ee;97%
With C38H38IrN4S2(1+)*F6P(1-); ammonium formate; 3-methyl-5-p-methoxyphenyl-1-hydropyrazole In tetrahydrofuran; water at 40℃; for 9h; enantioselective reaction;93%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

2,5-dimethoxybenzaldehyde
93-02-7

2,5-dimethoxybenzaldehyde

(E)-1-(1-benzothiophen-2-yl)-3-(2,5-dimethoxyphenyl)-2-propen-1-one

(E)-1-(1-benzothiophen-2-yl)-3-(2,5-dimethoxyphenyl)-2-propen-1-one

Conditions
ConditionsYield
With pyrrolidine; acetic acid In tetrahydrofuran for 13h; Aldol Condensation; Reflux; Inert atmosphere;100%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-(benzo[b]thiophen-2-yl)ethanol
51868-95-2

1-(benzo[b]thiophen-2-yl)ethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; water for 1.5h; Heating;99%
With methanol; sodium tetrahydroborate In water at 5 - 10℃; for 2h;90%
With sodium tetrahydroborate In methanol at 0℃; for 0.333333h; Reduction;87%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

C13H27BO2Si

C13H27BO2Si

2-(benzo[b]thiophen-2-yl)-4-((trimethylsilyl)methyl)pent-4-en-2-ol

2-(benzo[b]thiophen-2-yl)-4-((trimethylsilyl)methyl)pent-4-en-2-ol

Conditions
ConditionsYield
In toluene at 20℃;98%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl 1-hydroxy-1-(benzothiophen-2-yl)ethylphosphonate
1370037-12-9

diethyl 1-hydroxy-1-(benzothiophen-2-yl)ethylphosphonate

Conditions
ConditionsYield
With {(μ-η5:η1):η1-2-[(2,6-Me2C6H3)NCH2](C4H3N)YN(SiMe3)2}2 In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;97%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-(1,1-Dioxo-1H-1λ6-benzo[b]thiophen-2-yl)-ethanone
64845-11-0

1-(1,1-Dioxo-1H-1λ6-benzo[b]thiophen-2-yl)-ethanone

Conditions
ConditionsYield
With Oxone In neat (no solvent) for 1.5h; Milling; Green chemistry; chemoselective reaction;97%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

(S)-(+)-1-(benzo[b]thiophen-2-yl)ethanol
597553-10-1

(S)-(+)-1-(benzo[b]thiophen-2-yl)ethanol

Conditions
ConditionsYield
With formic acid; C28H36N3O2RuS; triethylamine at 60℃; for 3h; Inert atmosphere; enantioselective reaction;96%
With baker's yeast; water In methanol at 20℃;92%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

ethyl acetate
141-78-6

ethyl acetate

(1R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane
1059697-84-5

(1R)-1-acetoxy-1-(benzo[b]thiophen-2-yl)ethane

Conditions
ConditionsYield
With novozyme 435; dicarbonylhydro[2,5-di(trimethylsilyl)-3,4-butylene-1-hydroxy(η5-cyclopentadienyl)]iron; hydrogen In toluene at 90℃; under 750.075 Torr; Schlenk technique; Enzymatic reaction; enantioselective reaction;96%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

2-acetylbenzothiophene oxime
147396-07-4

2-acetylbenzothiophene oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol; water for 4h; Heating;95%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water Reflux;94.2%
With hydroxylamine
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-((methylthio)methyl)-1H-benzo[d][1,2,3]triazole
183164-38-7

1-((methylthio)methyl)-1H-benzo[d][1,2,3]triazole

2-(1-benzothiphen-2-yl)-1-(1H-1,2,3-benzotriazol-1-yl)-1-(methylthio)-2-propanol

2-(1-benzothiphen-2-yl)-1-(1H-1,2,3-benzotriazol-1-yl)-1-(methylthio)-2-propanol

Conditions
ConditionsYield
Stage #1: 1-((methylthio)methyl)-1H-benzo[d][1,2,3]triazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: 2-acetyl benzo[b]thiophene In tetrahydrofuran; hexane at -78℃; for 1h;
94%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(S)-2-(benzo[b]thiophen-2-yl)pent-4-en-2-ol

(S)-2-(benzo[b]thiophen-2-yl)pent-4-en-2-ol

Conditions
ConditionsYield
Stage #1: 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With (S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-3-methyl-1-(pyrrolidin-1-yl)butan-1-one; sodium t-butanolate In tetrahydrofuran; methanol; toluene at -30℃; for 0.5h; Inert atmosphere;
Stage #2: 2-acetyl benzo[b]thiophene In tetrahydrofuran; methanol; toluene at -30℃; for 8h; Inert atmosphere; enantioselective reaction;
94%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

saccharin
81-07-2

saccharin

2-(3-(benzo[b]thiophen-2-yl)-3-oxopropyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

2-(3-(benzo[b]thiophen-2-yl)-3-oxopropyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide

Conditions
ConditionsYield
With ruthenium trichloride; sodium carbonate; Selectfluor at 120℃; for 6h; Mannich Aminomethylation;93%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-iodocyclohexane
626-62-0

1-iodocyclohexane

2-acetyl-3-cyclohexylbenzothiophene

2-acetyl-3-cyclohexylbenzothiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; caesium carbonate at 110℃; for 36h; Inert atmosphere; Schlenk technique; regioselective reaction;92%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

ethyl 2-diazo-3-oxo-4,4,4-trifluorobutyrate
18955-75-4

ethyl 2-diazo-3-oxo-4,4,4-trifluorobutyrate

3-(benzo[b]thiophene-2-carbonyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

3-(benzo[b]thiophene-2-carbonyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate

Conditions
ConditionsYield
With copper hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 4h; Glovebox; Inert atmosphere; Sealed tube; regioselective reaction;92%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

methyl 2-(benzo[b]thiophen-2-yl)-N-hydroxy-2-oxoethanimidothioate

methyl 2-(benzo[b]thiophen-2-yl)-N-hydroxy-2-oxoethanimidothioate

Conditions
ConditionsYield
With iodine; sodium nitrite at 90℃; for 12h;91%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

2-(1-ethenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
102820-40-6

2-(1-ethenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

rac-(E)-2-(benzo[b]thiophen-2-yl)hepta-4,6-dien-2-ol

rac-(E)-2-(benzo[b]thiophen-2-yl)hepta-4,6-dien-2-ol

B

rac-2-(benzo[b]thiophen-2-yl)hepta-4,6-dien-2-ol

rac-2-(benzo[b]thiophen-2-yl)hepta-4,6-dien-2-ol

Conditions
ConditionsYield
Stage #1: 2-(1-ethenyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With copper (I) acetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In tetrahydrofuran for 0.166667h; Inert atmosphere; Glovebox;
Stage #2: 2-acetyl benzo[b]thiophene In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;
Stage #3: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; stereoselective reaction;
A 90%
B n/a
2-bromo-pyridine
109-04-6

2-bromo-pyridine

2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

1-(2-bromopyridin-3-yl)-1-(benzo[b]thiophen-2-yl)-ethan-1-ol

1-(2-bromopyridin-3-yl)-1-(benzo[b]thiophen-2-yl)-ethan-1-ol

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 2-acetyl benzo[b]thiophene In tetrahydrofuran at -78 - 25℃; for 18h; Inert atmosphere;
89%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

hydroxylamine
7803-49-8

hydroxylamine

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
Stage #1: hydroxylamine; methyl carbamate With sodium hydroxide In water at 5 - 30℃;
Stage #2: 2-acetyl benzo[b]thiophene With methanol; sodium tetrahydroborate In tetrahydrofuran; water at 10 - 40℃;
Stage #3: With hydrogenchloride; acetic acid at 40 - 45℃; for 3h;
88%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

((1-(benzo[b]thiophen-2-yl)vinyl)oxy)(tert-butyl)dimethylsilane

((1-(benzo[b]thiophen-2-yl)vinyl)oxy)(tert-butyl)dimethylsilane

Conditions
ConditionsYield
Stage #1: 2-acetyl benzo[b]thiophene With triethylamine In dichloromethane at 20 - 25℃; for 1h; Inert atmosphere;
Stage #2: t-butyldimethylsiyl triflate In dichloromethane at 20 - 25℃; Inert atmosphere;
88%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

2-(benzo[b]thiophen-2-yl)but-3-en-2-ol

2-(benzo[b]thiophen-2-yl)but-3-en-2-ol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Sonication;85%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

ethanol
64-17-5

ethanol

1-(1-benzo[b]thiophen-2-yl)-2,2-diethoxyethan-1-one

1-(1-benzo[b]thiophen-2-yl)-2,2-diethoxyethan-1-one

Conditions
ConditionsYield
With diphenyl diselenide; oxygen; toluene-4-sulfonic acid; copper(I) bromide at 130℃; for 9h; Sealed tube;85%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

toluene
108-88-3

toluene

1-(1-benzothiophen-2-yl)-2-(4-methylphenyl)ethanone

1-(1-benzothiophen-2-yl)-2-(4-methylphenyl)ethanone

Conditions
ConditionsYield
Stage #1: toluene With thianthrene-5-oxide; trifluoromethylsulfonic anhydride In acetonitrile at -20 - 20℃; for 0.666667h; Inert atmosphere; Schlenk technique;
Stage #2: 2-acetyl benzo[b]thiophene With palladium diacetate; cesium fluoride; XPhos In N,N-dimethyl-formamide; acetonitrile at 80℃; for 11h; Inert atmosphere; Schlenk technique;
85%

22720-75-8Downstream Products

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