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825-44-5

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825-44-5 Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1702, 1949 DOI: 10.1021/ja01173a043

Check Digit Verification of cas no

The CAS Registry Mumber 825-44-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 5 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 825-44:
(5*8)+(4*2)+(3*5)+(2*4)+(1*4)=75
75 % 10 = 5
So 825-44-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H6O2S/c9-11(10)6-5-7-3-1-2-4-8(7)11/h1-6H

825-44-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A14063)  Benzo[b]thiophene 1,1-dioxide, 98%   

  • 825-44-5

  • 5g

  • 1402.0CNY

  • Detail
  • Alfa Aesar

  • (A14063)  Benzo[b]thiophene 1,1-dioxide, 98%   

  • 825-44-5

  • 25g

  • 5570.0CNY

  • Detail

825-44-5Synthetic route

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
With dibenzo-18-crown-6; dihydrogen peroxide In ethanol at 45℃; for 18h;100%
With tert.-butylhydroperoxide; [Mo2(O)4{[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 1h; Reflux;100%
With [(C18H37)2(CH3)2N]3[SiO4H(WO5)3]; dihydrogen peroxide In ethyl acetate at 69.84℃; for 2h;100%
C8H8O3S

C8H8O3S

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In dichloromethane at 10 - 20℃; for 5h;85%
Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

B

(+/-)-benzo[b]thiophene 1-oxide
51500-42-6

(+/-)-benzo[b]thiophene 1-oxide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; [Mo2(O)4{[2,2'-(1,3-phenylene)bis(4,5-dihydrooxazole-4,2-diyl)]dimethanol}(acac)2] In 1,2-dichloro-ethane for 0.5h; Reflux;A 20%
B 75%
With α-manganese oxide In octane at 25℃; Catalytic behavior; Reagent/catalyst; Green chemistry;
With [V2(O)4(H2O)4BOX]; dihydrogen peroxide In ethanol for 1h; Catalytic behavior; Reflux; chemoselective reaction;A 80%Chromat.
B 20%Chromat.
Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

B

benzo[b]naphtho[2,1-d]thiophene 11-oxide
121823-04-9

benzo[b]naphtho[2,1-d]thiophene 11-oxide

C

11-thiabenzo[a]fluorene
239-35-0

11-thiabenzo[a]fluorene

rac-(6aS,11S,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11S,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11R,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

rac-(6aS,11R,11aR)-6a,11a-dihydrobenzo[b]naphtho[2,1-d]thiophene 11-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;A 60%
B 0.026 g
C 0.018 g
D 0.045 g
E 0.015 g
(+-)-(3ar,7ac)-3a,4,7,7a-tetrahydro-4c(?),7c(?)-episulfido-benzothiophene-1,1,8-trioxide

(+-)-(3ar,7ac)-3a,4,7,7a-tetrahydro-4c(?),7c(?)-episulfido-benzothiophene-1,1,8-trioxide

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
at 184℃;
With 1,2-dichloro-benzene
Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

peroxybenzoic acid <1mol)

peroxybenzoic acid <1mol)

monoperoxyphthalic acid (1mol)

monoperoxyphthalic acid (1mol)

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

3-iodo-2,3-dihydro-benzo[b]thiophene-1,1-dioxide

3-iodo-2,3-dihydro-benzo[b]thiophene-1,1-dioxide

water
7732-18-5

water

sodium-amalgam

sodium-amalgam

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

thionaphthenequinone-S dioxide

thionaphthenequinone-S dioxide

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
With acetic acid; zinc
dihydrogen peroxide
7722-84-1

dihydrogen peroxide

acetic acid
64-19-7

acetic acid

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

A

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

B

Benzonaphthto<1,2-d>thiophene 7,7-dioxide
20841-53-6

Benzonaphthto<1,2-d>thiophene 7,7-dioxide

sodium thiosulfate

sodium thiosulfate

Benzo[b]thiophene
95-15-8

Benzo[b]thiophene

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran
(+/-)-benzo[b]thiophene 1-oxide
51500-42-6

(+/-)-benzo[b]thiophene 1-oxide

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
With TBA4H2[BW11Mn(H2O)O39]*H2O; dihydrogen peroxide In water; acetonitrile at 22 - 24℃; Darkness; Green chemistry;
With dihydrogen peroxide In 2,2,4-trimethylpentane at 80℃; for 1.66667h; Temperature;
2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 100 °C / Inert atmosphere
2: triethylamine; methanesulfonyl chloride / dichloromethane / 5 h / 10 - 20 °C
View Scheme
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

hexachlorocyclopentadiene
77-47-4

hexachlorocyclopentadiene

endo-1,11,12,13,14,14-hexachloro-tetracyclo[9.2.11,11.02,10.04,9]tetradeca-4,6,8,12-tetraene S,S-dioxide

endo-1,11,12,13,14,14-hexachloro-tetracyclo[9.2.11,11.02,10.04,9]tetradeca-4,6,8,12-tetraene S,S-dioxide

Conditions
ConditionsYield
at 150℃; for 11h; Diels-Alder reaction; neat (no solvent); stereoselective reaction;100%
With xylene
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

2,3-dihydrobenzo[b]thiophene 1,1-dioxide
14315-13-0

2,3-dihydrobenzo[b]thiophene 1,1-dioxide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 24h;100%
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran; ethanol at 20℃; under 1034.32 Torr; for 0.25h;98%
With palladium 10% on activated carbon; hydrogen In ethanol under 760.051 Torr; for 24h;97%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

1,2-di(prop-2-yn-1-yl)benzene
50423-48-8

1,2-di(prop-2-yn-1-yl)benzene

7,12,5a,13a-tetrahydroanthra[2,3-b]benzo[d]thiophene-S,S-dioxide

7,12,5a,13a-tetrahydroanthra[2,3-b]benzo[d]thiophene-S,S-dioxide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)biphenyl In 1,2-dichloro-ethane at 80℃; for 1.5h;99%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

2,3-diprop-2-ynyl-naphthalene
50423-55-7

2,3-diprop-2-ynyl-naphthalene

6,14,4a,14a-tetrahydrotetraceno[2,3-b]benzo[2,3-d]thiophene-S,S-dioxide

6,14,4a,14a-tetrahydrotetraceno[2,3-b]benzo[2,3-d]thiophene-S,S-dioxide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)biphenyl In 1,2-dichloro-ethane at 80℃; for 1.5h;99%
N-tert-butoxycarbonyl-2-mercapto-1H-indole-3-carbaldehyde

N-tert-butoxycarbonyl-2-mercapto-1H-indole-3-carbaldehyde

benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

tert-butyl(6aR,11aR,12S)-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; Reagent/catalyst; Solvent; enantioselective reaction;99%
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-2-phenylacetamide In toluene at 0℃; Reagent/catalyst;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride
38435-51-7

N-hydroxy-4-methoxy-benzenecarboximidoyl chloride

C16H13NO4S

C16H13NO4S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

2-bromo N-hydroxybenzimidoyl chloride
38435-47-1

2-bromo N-hydroxybenzimidoyl chloride

C15H10BrNO3S

C15H10BrNO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-hydroxy-4-(trifluoromethyl)benzenecarboximidoyl chloride
74467-05-3

N-hydroxy-4-(trifluoromethyl)benzenecarboximidoyl chloride

C16H10F3NO3S

C16H10F3NO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

benzohydroximoyl chloride
698-16-8

benzohydroximoyl chloride

C15H11NO3S

C15H11NO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h; Reagent/catalyst; Solvent; Time;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-tert-butoxycarbonyl-6-chloro-2-mercapto-1H-indole-3-carbaldehyde

N-tert-butoxycarbonyl-6-chloro-2-mercapto-1H-indole-3-carbaldehyde

tert-butyl(6aR,11aR,12S)-3-chloro-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-3-chloro-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃;98%
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;96%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

C15H17NO4S

C15H17NO4S

tert-butyl(6aR,11aR,12S)-12-hydroxy-3-methoxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-12-hydroxy-3-methoxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
In toluene at 0℃;98%
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

2-formylthiophenol
29199-11-9

2-formylthiophenol

(5aR,10aR,11S)-11-hydroxy-5a,10a-dihydro-11H-benzo[4,5]thieno[3,2-b]thiochromene 10,10-dioxide

(5aR,10aR,11S)-11-hydroxy-5a,10a-dihydro-11H-benzo[4,5]thieno[3,2-b]thiochromene 10,10-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

C15H17NO3S

C15H17NO3S

tert-butyl(6aR,11aR,12S)-12-hydroxy-2-methyl-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-12-hydroxy-2-methyl-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;98%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-hydroxy-2-naphthalenecarboximidoyl chloride
65788-68-3

N-hydroxy-2-naphthalenecarboximidoyl chloride

C19H13NO3S

C19H13NO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;97%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

C15H17NO4S

C15H17NO4S

tert-butyl(6aR,11aR,12S)-12-hydroxy-2-methoxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-12-hydroxy-2-methoxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
In toluene at 0℃;97%
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;96%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

methyl N-(4-methoxybenzylidene)glycinate
126079-16-1

methyl N-(4-methoxybenzylidene)glycinate

C19H19NO5S

C19H19NO5S

Conditions
ConditionsYield
With (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); tetrakis(actonitrile)copper(I) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 20℃; for 48h; Inert atmosphere; Schlenk technique; stereoselective reaction;96%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

methyl N-(4-chlorobenzylidene)glycinate
76862-09-4

methyl N-(4-chlorobenzylidene)glycinate

C18H16ClNO4S

C18H16ClNO4S

Conditions
ConditionsYield
With (S)-(+)-4,4'-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-3,3'-bi(1,2-methylenedioxybenzene); tetrakis(actonitrile)copper(I) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; stereoselective reaction;96%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-hydroxycinnamimidoyl chloride
105363-16-4

N-hydroxycinnamimidoyl chloride

C17H13NO3S

C17H13NO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;96%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

(3aR,8bR)-3-(4-Nitro-phenyl)-3a,8b-dihydro-benzo[4,5]thieno[2,3-d]isoxazole 4,4-dioxide
135921-75-4

(3aR,8bR)-3-(4-Nitro-phenyl)-3a,8b-dihydro-benzo[4,5]thieno[2,3-d]isoxazole 4,4-dioxide

Conditions
ConditionsYield
With aluminum oxide; N-chloro-succinimide at 20 - 145℃; for 0.166667h; Irradiation;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

1,2,3,4-tetramethylcyclopenta-1,3-diene
4249-10-9

1,2,3,4-tetramethylcyclopenta-1,3-diene

endo-1,11,12,13-tetramethyl-3-thiatetracyclo[9.2.11,11.02,10.04,9]tetradeca-4,6,8,12-tetraene S,S-dioxide

endo-1,11,12,13-tetramethyl-3-thiatetracyclo[9.2.11,11.02,10.04,9]tetradeca-4,6,8,12-tetraene S,S-dioxide

Conditions
ConditionsYield
at 100℃; for 6h; Diels-Alder reaction; neat (no solvent); stereoselective reaction;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

1-benzylidene-3-oxo-1-pyrazolidinium-2-ide
17822-51-4

1-benzylidene-3-oxo-1-pyrazolidinium-2-ide

C18H16N2O3S

C18H16N2O3S

Conditions
ConditionsYield
for 24h; Reflux;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide
170751-34-5

N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide

2-tosyl-4,10-dimethyl-2,3,4a,9b-tetrahydro-1H-benzo[4,5]-thieno[2,3-f]isoindole-S,S-dioxide

2-tosyl-4,10-dimethyl-2,3,4a,9b-tetrahydro-1H-benzo[4,5]-thieno[2,3-f]isoindole-S,S-dioxide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis(diphenylphosphino)biphenyl In 1,2-dichloro-ethane at 80℃; for 1.5h; Reagent/catalyst;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

C17H17NO2S

C17H17NO2S

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
93102-05-7

N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

2-benzyl-2,3,3a,8b-tetrahydro-1H-benzo[4,5]thieno[2,3-c]pyrrole 4,4-dioxide

2-benzyl-2,3,3a,8b-tetrahydro-1H-benzo[4,5]thieno[2,3-c]pyrrole 4,4-dioxide

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Solvent; Inert atmosphere; diastereoselective reaction;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

4-fluoro-N-hydroxybenzimidoyl chloride
42202-95-9

4-fluoro-N-hydroxybenzimidoyl chloride

C15H10FNO3S

C15H10FNO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

3-bromo-N-hydroxybenzimidoyl chloride
86405-09-6

3-bromo-N-hydroxybenzimidoyl chloride

C15H10BrNO3S

C15H10BrNO3S

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

C14H14BrNO3S

C14H14BrNO3S

tert-butyl(6aR,11aR,12S)-3-bromo-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-3-bromo-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-2-phenylacetamide In toluene at 0℃;95%
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

N-tert-butoxycarbonyl-5-bromo-2-mercapto-1H-indole-3-carbaldehyde

N-tert-butoxycarbonyl-5-bromo-2-mercapto-1H-indole-3-carbaldehyde

tert-butyl(6aR,11aR,12S)-2-bromo-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

tert-butyl(6aR,11aR,12S)-2-bromo-12-hydroxy-11a,12-dihydrobenzo[4',5']thieno[2',3':5,6]thiopyrano[2,3-b]indole-5(6aH)-carboxylate 11,11-dioxide

Conditions
ConditionsYield
With (S)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)-N-((1S,2S)-2-(dimethylamino)cyclohexyl)-3,3-dimethylbutanamide In toluene at 0℃; for 48h; enantioselective reaction;95%
benzothiophene-1,1-dioxide
825-44-5

benzothiophene-1,1-dioxide

trans-2-azido-3-bromo-2,3-dihydrobenzothiophene 1,1-dioxide

trans-2-azido-3-bromo-2,3-dihydrobenzothiophene 1,1-dioxide

Conditions
ConditionsYield
With bromine azide In dichloromethane Ambient temperature;94%

825-44-5Relevant articles and documents

Surfactant-encapsulated high-nuclear polyoxometalate complexes for catalytic oxidative desulfurization of model oil

Wang, Tingting,Lu, Ying,Wu, Hongli,Wang, Enbo

, p. 13 - 18 (2016)

Two novel surfactant-encapsulated high-nuclear polyoxometalates catalysts (DODA)20[(HPMo6O21)4(O2CCH2CO2)6]·27H2O and (DODA)10[(HPMo6O21)2(C2O4)3]·11H2O have been prepared and characterized by TG, FT-IR,1H NMR and UV-Vis. They were used for the oxidative desulfurization of model oil containing sulfur compounds such as dibenzothiophene (DBT), 4,6-dimethyldibenzothiophene (4,6-DMDBT), benzothiophene (BT) with H2O2as an oxidant under mild conditions. The removal of DBT, 4,6-DMDBT and BT could reach above 98% under the optimal conditions of n(S)/n(catalyst)/n(H2O2) = 220:1:880 at 60 °C for 2.5 h, 4.5 h and 5 h respectively, which improved to be a promising catalyst in the ODS process. The oxidative reactivity of the sulfur-containing compounds decreased according to DBT > 4,6-DMDBT > BT. We investigated the main factors affecting the process including temperature, the polymeric structures of catalysts, and O/S (H2O2/DBT) molar ratio in detail. Moreover, the catalyst can be reused 5 times with high recycling efficiency.

Hexagonal nanoplates of high-quality γ-gallium oxide: Controlled synthesis and good heterogeneous catalytic performance for thiophenes

Yang, Zun,Song, Le Xin,Wang, Ya Qian,Ruan, Mao Mao,Teng, Yue,Xia, Juan,Yang, Jun,Chen, Shan Shan,Wang, Fang

, p. 2914 - 2921 (2018)

Hexagonal nanoplates of high-quality γ-gallium oxide (γ-Ga2O3) were successfully synthesized by using a competitive and cooperative interaction model based on multiple equilibria, including a precipitation interaction, a coordination interaction and two binding interactions. The synthetic method is straightforward and affords the desired product in very high yield. It is important to note that only a combination of the coordination interaction and binding interactions can contribute to the formation of hexagonal nanoplates by effectively suppressing the generation of gallium oxide hydroxide and directly limiting the assembly of the nanoplates into microflowers. This model is significant because it allows us to understand how the disassembly process of nanostructures is related to the synergistic mechanism of multiple interactions. Furthermore, the γ-Ga2O3 hexagonal nanoplates exhibit good heterogeneous catalytic performance for the oxidation reaction of thiophenes. A possible mechanism was proposed for the catalytic process, and this may open up a new perspective in the study of oxidative desulfurization.

Boosting Oxidative Desulfurization of Model and Real Gasoline over Phosphotungstic Acid Encapsulated in Metal–Organic Frameworks: The Window Size Matters

Wang, Xu-Sheng,Li, Lan,Liang, Jun,Huang, Yuan-Biao,Cao, Rong

, p. 971 - 979 (2017)

It is desirable to develop new materials that can efficiently lower sulfur content in fossil fuels, such as gasoline and diesel oil. Polyoxometallic acids supported on metal–organic frameworks (MOFs) are an important class of heterogeneous catalysts for oxidative desulfurization. However, there has been no comprehensive study on the correlation between desulfurization activity and the window size of MOFs. A series of robust MOFs, which include MIL-100(Fe), UiO-66, and ZIF-8, with different window sizes were exploited as hosts to encapsulate phosphotungstic acid by the “bottle around the ship” method and utilized for the ultra-deep oxidative desulfurization (ODS) of model and real gasoline. Compared with UiO-66 and ZIF-8, which have very small window sizes, mesoporous MIL-100(Fe), which has a large window size, exhibited the best catalytic performance in the ODS of refractory sulfur compounds (benzothiophene, dibenzothiophene, and 4,6-dimethyl-dibenzothiophene) and in recycling experiments. The correlations between the desulfurization activity and the window size of the corresponding MOFs could provide insights for the design of new porous catalysts for ODS and other size-selective catalysis reactions in the future.

A new organic-inorganic hybrid based on dimeric [Mn2V22O64]10 - Polyoxoanion as catalyst for oxidation of sulfides

Wang, Ting-Ting,Lu, Ying,Liu, Ding,Wang, En-Bo

, p. 47 - 51 (2016)

A new organic-inorganic hybrid compound constructed from [Mn2V22O64]10 - units, H6[(C6H4NO2Cu(H2O)4)]2[Mn2V22O64]·28H2O 1, has been synthesized and characterized by single-crystal X-ray diffraction, IR, powder X-ray diffraction (XPRD) and TG. Compound 1 is composed of dimeric [Mn2V22O64]10 - polyoxoanions, metal-organo fragments [(C6H4NO2Cu(H2O)4)]2 + and lattice water molecules. Moreover, a three-dimensional supramolecular structure is formed in 1 by the extensive hydrogen bond interaction among the terminal oxygen atoms of [Mn2V22O64]10 - anions, the coordinated waters of Cu2 + ions and crystal water molecules. Compound 1 exhibits remarkable catalytic activity for the heterogeneous oxidation of sulfides under mild condition.

Oxidative desulfurization (ODS) of organosulfur compounds catalyzed by peroxo-metallate complexes of WOx-ZrO2: Thermochemical, structural, and reactivity indexes analyses

Torres-Garcia,Galano,Rodriguez-Gattorno

, p. 201 - 208 (2011)

An experimental and theoretical study on the relationships between oxidative reactivity, thermochemical viability, and structural requirement of the activity sites in oxidative desulfurization (ODS) process has been performed. A series of aromatic sulfur compounds and peroxo-metallate complexes of WOx-ZrO2 with different structures have been studied. The models chosen for mimicking the catalyst correspond to surface densities of ~7 W nm-2. The results indicate that the ODS takes place in two consecutive stages: (i) the formation of sulfoxide and (ii) the formation of sulfone. However, a detailed analysis suggests that these stages occur in two separated steps, (a) addition and (b) elimination, involving the formation of intermediate adducts and that the elimination of sulfoxide from the site surface is the rate-determining step. The results also reveal that the thermochemical feasibility of the studied reactions depends on both: the local structure of the WOx-ZrO2 surface and on the nature of the aromatic sulfur compound. It was found that the reactions involving dibenzothiophene (DBT) and 4,6-dimethyldibenzothiophene (46DMDBT) are the most favored reactions, while the reaction of thiophene (Th) is the least favored. Therefore, highly substituted dibenzothiophenes are the most readily oxidized species, which is in agreement with experimental evidence. An explanation to the different reactivity shown by sulfur compounds, during ODS processes, is provided.

New enantiopure bis(thioether) and bis(sulfoxide) ligands from benzothiophene

Madec, David,Mingoia, Francesco,Macovei, Cristian,Maitro, Guillaume,Giambastiani, Giuliano,Poli, Giovanni

, p. 552 - 557 (2005)

The C2-symmetric compound 2,3,2′,3′-tetrahydro-2, 2′-bi(benzo[b]thiophenyl) and three diastereomeric bis(oxide) derivatives can be synthesized in a few steps from benzo[b]-thiophene by oxidative homocoupling of (R)-2,3-dihydro-benzo[b]thiophene 1-oxide. This new family of enantiopure bis(thioether) and bis(sulfoxide) ligands forms stable chelating PdII complexes. The fused pentacyclic structure of the complexes imparts a rigid chiral environment around the metal centre. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

A Novel Oxidation of Thiophenes using HOF*MeCN

Rozen, Shlomo,Bareket, Yifat

, p. 1959 - 1960 (1994)

The complex, HOF*MeCN made directly by bubbling fluorine through aqueous MeCN, oxidizes various types of thiophenes to the corresponding S,S-dioxides, including ones which could not be oxidized by any other method.

Catalytic [2 + 2 + 2] cycloaddition of benzothiophene dioxides with α,ω-diynes for the synthesis of condensed polycyclic compounds

Tahara, Yu-Ki,Gake, Manami,Matsubara, Riku,Shibata, Takanori

, p. 5980 - 5983 (2014)

A Rh-catalyzed intermolecular [2 + 2 + 2] cycloaddition of the 2,3-double bond of benzothiophene dioxides with α,ω-diynes gave sulfone-containing cycloadducts in high yields. This is the first example of a catalytic [2 + 2 + 2] cycloaddition that uses the

Sulfur elimination by oxidative desulfurization with titanium-modified SBA-16

Rivoira, Lorena P.,Vallés, Verónica A.,Ledesma, Brenda C.,Ponte, María V.,Martínez, María L.,Anunziata, Oscar A.,Beltramone, Andrea R.

, p. 102 - 113 (2016)

TiO2-modified mesoporous SBA-16 and titanium-substituted mesoporous SBA-16 were developed and tested in the oxidative desulfurization (ODS) of dibenzothiophene prevailing in liquid fuel. Pure TiO2 was used as reference. The titania-based catalysts were characterized by chemical analysis, XRD, EDX and TEM. The titanium state as tetrahedral (in Ti-SBA-16 sample) or octahedral (in TiO2/SBA-16 sample) coordination surrounding in the silicate matrix was determined by XPS, UV-vis DRS, FTIR, Raman and XANES. We assessed the impact exerted on performance of different reaction variables, including (nature and amount of the active catalytic species, phase system, molar ratio of oxidant H2O2 and DBT, reaction temperature, nature of the substrate and reuse of catalysts). In addition, we carried out a kinetic study and the activation energy was determined. We achieved 90% of S removal from a 0.2 wt.% dibenzothiophene solution at 60 °C in less than 1 h of reaction. The best catalytic results are obtained with high exposed surface of nanometric TiO2 species of TiO2/SBA-16 sample. The activated catalyst is very active in ODS reaction and can be reused four times with no loss in activity.

12-tungstophosphoric acid/silica catalyst for oxidation of benzothiophene

Lesbani, Aldes,Marpaung, Arianti,Fithri, Najma Annuria,Mohadi, Risfidian

, p. 617 - 621 (2016)

12-Tungstophosphoric acid H3[α-PW12O40] was impregnated with silica to form 12-tungstophosphoric acid/silica catalyst. Structural properties of catalyst were characterized using Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, and nitrogen adsorption desorption. The results showed that silica was impregnated into H3[α-PW12O40] with increasing surface area properties. The catalytic activity under mild condition from H3[α-PW12O40] after impregnation with silica slightly increased compared to original catalyst. The structure of catalyst after reaction was stable, which indicate the possibility of reusing the catalyst.

Preparation of CoWO4/g-C3N4 and its Ultra-Deep Desulfurization Property

Xing, Pengfei,Zhao, Rongxiang,Li, Xiuping,Gao, Xiaohan

, p. 271 - 279 (2017)

The ultra-deep desulfurization of fuel oil has become inevitable for environmental protection. Here, CoWO4/g-C3N4 was used as a catalyst, H2O2 as an oxidant, and 1-ethyl-3-methylimidazolium ethylsulfate ([EMIM][EtSO4], IL) as an extractant for the oxidative desulfurization of model oil. Scanning electron microscopy, FT-IR spectroscopy, N2 adsorption isotherms, and X-ray diffraction were used to confirm the morphology, structure, and properties of the catalysts. The influence of calcination temperature, loading dose of cobalt, amount of H2O2, reaction temperature, and other parameters were investigated. The removal rate of sulfide in model oil could reach 92.9% at 80°C in 180min under the optimal operation conditions (V(oil)≤5mL, T≤80°C, m(catalyst)≤0.03g, V(H2O2)≤0.4mL, t≤180min, V(IL)≤1.0mL). In addition, the catalyst was reused five times with no significant reduction in the catalytic activity.

Oxidative desulfurization of thiophene derivatives with H2O2 in the presence of catalysts based on MoO3/Al2O3 under mild conditions

Shen,Lu,Ma,He,Zhang,Zhan,Xia

, p. 28 - 33 (2017)

The catalysts based on MoO3/Al2O3 were synthesized and tested using aqueous hydrogen peroxide as the oxidant in the oxidative desulfurization of thiophene, benzothiophene (BT) and dibenzothiophene (DBT) into the corresponding sulfones. Among catalysts tested, 15%(MoO3–WO3)/Al2O3 prepared by a conventional impregnation method was considerably active for the oxidation of thiophene, BT and DBT, which could achieve higher than 99.2% conversions at lower reaction temperature (≤338 K). The use of hexadecyltrimethyl ammonium bromide as the phase-transfer reagent in small amounts could promote the reaction efficiently.

-

Davies,James

, p. 15,17,18 (1954)

-

Preparation and characterization of organotin-oxomolybdate coordination polymers and their use in sulfoxidation catalysis

Abrantes, Marta,Valente, Anabela A.,Pillinger, Martyn,Goncalves, Isabel S.,Rocha, Joao,Romao, Carlos C.

, p. 2685 - 2695 (2003)

The organotin-oxomolybdates [(R3Sn)2MoO4]·n H2O (R = methyl, n-butyl, cyclohexyl, phenyl, benzyl) have been prepared and tested as catalysts for the oxidation of benzothiophene with aqueous hydrogen peroxide, at 35°C and atmospheric pressure. In all cases, the 1,1-dioxide was the only observed product. The kinetic profiles depend on the nature of the tin-bound R group and also on the addition of a cosolvent. For the tribenzyltin derivative, the apparent activation energies for sulfoxidation as a function of the cosolvent are in the order 1,2-dichloroethane (5 kcalmol-1) -1). The solid could be recovered by centrifugation from the three-phase (solid-liquid-liquid) system containing 1,2-dichloroethane. The catalyst was reused in a second reaction cycle with no significant loss of activity. Increasing the oxidant/substrate ratio from 2:1 to 6:1 allows the corresponding sulfone to be obtained in quantitative yield within 24 h. Changing the nature of the tin-bound R group in the catalyst precursors modifies their physical properties and hence their catalytic performance. The variation in hydrophobic/hydrophilic character is important, since the Me, nBu and Cy derivatives crystallize as anhydrous compounds, whereas the other two derivatives are hydrates. The polymers also have different structures, as evidenced by X-ray powder diffraction. Mo K-edge and Sn K-edge EXAFS spectroscopy confirmed that the structures arise from the self-assembly of tetrahedral [MoO4]2- subunits and [R3Sn]+ spacers. The Mo ... Sn separation in the trimethyltin derivative is a uniform 3.84 A. By contrast, the EXAFS results revealed the coexistence of short (3.67 - 3.79 A) and long (3.93 - 4.07 A) Mo ... Sn separations in the other coordination polymers. The catalyst precursors were also characterized in the solid state by thermogravimetric analysis, FTIR, and Raman spectroscopy, and MAS NMR (13C, 119Sn) spectroscopy.

Oxidative Removal of Organo-sulfur Species via H2O2 Oxidation Catalyzed by Lacunary Keggin 11-tungstophosphates

Wang, Han,Wang, Rui,Zhang, Yongqiang,Dou, Shuaiyong,Olga, Silchenkova,Vladimir, Korchak

, p. 2501 - 2509 (2018)

Abstract: The lacunary Keggin 11-tungstophosphates were evaluated as catalysts for the oxidation of dibenzothiophene with hydrogen peroxide as oxidant in normal octane/acetonitrile biphasic system. The Na5[PW11O39Ni] exhibited good catalytic activity with the desulfurization efficiency above 99.5%. The key factors affecting the reaction, including amount of catalyst, O/S molar ratio, catalyst dosage and initial sulfur content, were investigated, whereby the favorable conditions were determined. The presence and the oxidative effect of the peroxo-heteropoly species in the oxidative reaction were determined in the contrast experiments. Moreover, the Na5[PW11O39Ni] catalyst was confirmed to have a high potential for deep desulfurization of diesel oil.

Ultra-deep oxidative desulfurization of fuel with H2O2 catalyzed by molybdenum oxide supported on alumina modified by Ca2+

Jin, Wei,Tian, Yongsheng,Wang, Guanghui,Zeng, Danlin,Xu, Qian,Cui, Jiawei

, p. 48208 - 48213 (2017)

A highly active catalyst of molybdenum oxide supported on mesoporous alumina modified by Ca2+ was synthesized by an in situ method and applied in the catalytic oxidative desulfurization (CODS) system. This catalyst was characterized by FT-IR, XRD, BET and XPS. The influences of m(catalyst)/m(model oil), V(H2O2)/V(model oil), reaction temperature and reaction time on oxidative desulfurization of 4,6-dimethyldibenzothiophene (4,6-DMDBT), dibenzothiophene (DBT) and benzothiophene (BT) were investigated. This catalyst has high desulfurization activity in the removal of organic sulfides under mild conditions. The catalytic oxidation reactivity of sulfur-containing compounds is in the order of DBT > 4,6-DMDBT > BT. The kinetic studies reveal that the oxidative desulfurization of the organic sulfides can present a pseudo first-order kinetic process, and the apparent activation energies of 4,6-DMDBT, DBT and BT are 34.67 kJ mol-1, 33.01 kJ mol-1 and 40.16 kJ mol-1, respectively. The recycling experiments indicate that 4,6-DMDBT, DBT and BT removal can still reach 90.0%, 89.9% and 87.3% after eight cycles.

Polyoxometalate-Based Organic-Inorganic Hybrids as Heterogeneous Catalysts for Cycloaddition of CO2with Epoxides and Oxidative Desulfurization Reactions

Zhao, Yu-Qing,Liu, Ying-Ying,Ma, Jian-Fang

, p. 1019 - 1027 (2021/01/13)

Self-assembly of polyoxometalates, transition metal salts, and 2,6-bis(2′-pyridyl)-4-hydroxypyridine (LOH) obtained four organic-inorganic hybrids [Co2.5(LOH)(LO)2(H2O)2(PW12O39)]·3CH3CN·2OH (1), [Zn1.5(LOH)3]·(PMo12O40)·CH3OH·2H2O (2), [Cd1.5(LOH)3]·(PW12O40)·2CH3OH·1.5H2O (3), and [Mn(LOH)2]·(PW12O40)·2CH3CN·H3O (4). Hybrid 1 exhibits an extended chain, which could be further connected into a 3D supramolecular architecture by H-bonds. Hybrids 2-4 feature monomolecular structures, which are further bridged via H-bonds to yield charming 3D supramolecular structures. Noteworthy, 1 and 2 can be employed as recyclable and highly efficient heterogeneous catalysts. The activated 1 displays a high catalytic activity for the cycloaddition reaction of CO2 and epoxides. Hybrid 2 exhibits an excellent catalytic performance for the oxidative desulfurization reaction.

Assembly of polyoxometalate-thiacalix[4]arene-based inorganic-organic hybrids as efficient catalytic oxidation desulfurization catalysts

Li, Jie,Du, Peng,Liu, Ying-Ying,Ma, Jian-Fang

supporting information, p. 1349 - 1356 (2021/02/09)

Self-assembly of polyoxometalates, Ni(ii)/Ag(i) cations and tetra-[5-(mercapto)-1-methyltetrazole]-thiacalix[4]arene (L) yielded three inorganic-organic hybrids, namely, [Ni3L2(CH3OH)6(H2O)4][PMo12O40]2·3CH3OH·2H2O (1), [Ni3L2(CH3OH)6(H2O)4][PW12O40]2·3CH3OH·2H2O (2) and [Ag3L(PMo12O40)] (3). In hybrids (1) and (2), Ni(ii) cations are linked by L ligands to produce layered frameworks, and H bonds among the [PMo12O40]3?/[PW12O40]3?anions and L ligands lengthen the structures to form 3D supramolecular architectures. Hybrid (3) exhibits a 3D architecture, of which Ag(i) cations not only coordinated with the N and O atoms of L ligands and [PMo12O40]3?anions simultaneously, but also connected each other by Ag-Ag interactions. It is worth mentioning that1and3as recyclable catalysts show excellent heterogeneous catalytic activity in oxidation desulfurization reactions.

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