Benzo[b]thiophene,1,1-dioxide supplier

Name
THIANAPHTHENE-1,1-DIOXIDE
EINECS 212-544-8
CAS No. 825-44-5
Article Data39
CAS DataBase
Density 1.403 g/cm³
Solubility
Melting Point 138-142 °C
Formula C₈H₆O₂S
Boiling Point 371.1 °C at 760 mmHg
Molecular Weight 166.2
Flash Point 244 °C
Transport Information
Appearance White to cream colored powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzo[b]thiopheneS,S-dioxide;Benzothiophene 1,1-dioxide;Benzothiophene sulfone;NSC 82162;Thianaphthene 1,1-dioxide;Thionaphthene 1,1-dioxide;
PSA 42.52000
LogP 2.52540

Synthetic route

: 95-15-8
Benzo[b]thiophene

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
With methanesulfonyl chloride; triethylamine In dichloromethane at 10 - 20℃; for 5h;	85%

: 95-15-8
Benzo[b]thiophene

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

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

Conditions

Conditions	Yield
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.

: 95-15-8
Benzo[b]thiophene

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

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

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

: 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

Conditions

Conditions	Yield
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

...Expand

(+-)-(3ar,7ac)-3a,4,7,7a-tetrahydro-4c(?),7c(?)-episulfido-benzo<b>thiophene-1,1,8-trioxide: (+-)-(3ar,7ac)-3a,4,7,7a-tetrahydro-4c(?),7c(?)-episulfido-benzo<b>thiophene-1,1,8-trioxide

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

Conditions

Conditions	Yield
at 184℃;
With 1,2-dichloro-benzene

: 95-15-8
Benzo[b]thiophene

peroxybenzoic acid <1mol): peroxybenzoic acid <1mol)

monoperoxyphthalic acid (1mol): monoperoxyphthalic acid (1mol)

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

...Expand

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

: 7732-18-5
water

sodium-amalgam: sodium-amalgam

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

...Expand

thionaphthenequinone-S dioxide: thionaphthenequinone-S dioxide

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

Conditions

Conditions	Yield
With acetic acid; zinc

: 7722-84-1
dihydrogen peroxide

: 64-19-7
acetic acid

: 95-15-8
Benzo[b]thiophene

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

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

...Expand

: sodium thiosulfate

: 95-15-8
Benzo[b]thiophene

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

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran

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

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

Conditions

Conditions	Yield
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;

: 446-52-6
2-Fluorobenzaldehyde

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

Conditions

Conditions	Yield
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

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

: 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

Conditions

Conditions	Yield
at 150℃; for 11h; Diels-Alder reaction; neat (no solvent); stereoselective reaction;	100%
With xylene

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

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

Conditions

Conditions	Yield
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%

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

: 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

Conditions

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

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

: 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

Conditions

Conditions	Yield
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

: 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

Conditions

Conditions	Yield
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%

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

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

: C16H13NO4S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	98%

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

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

: C15H10BrNO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	98%

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

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

: C16H10F3NO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	98%

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

: 698-16-8
benzohydroximoyl chloride

: C15H11NO3S

Conditions

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

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

: 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

Conditions

Conditions	Yield
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%

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

: 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

Conditions

Conditions	Yield
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%

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

: 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

Conditions

Conditions	Yield
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%

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

: 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

Conditions

Conditions	Yield
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%

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

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

: C19H13NO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	97%

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

: 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

Conditions

Conditions	Yield
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%

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

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

: C19H19NO5S

Conditions

Conditions	Yield
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%

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

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

: C18H16ClNO4S

Conditions

Conditions	Yield
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%

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

: 105363-16-4
N-hydroxycinnamimidoyl chloride

: C17H13NO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	96%

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

: 1129-37-9
4-nitrobenzaldehyde oxime

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

Conditions

Conditions	Yield
With aluminum oxide; N-chloro-succinimide at 20 - 145℃; for 0.166667h; Irradiation;	95%

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

: 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

Conditions

Conditions	Yield
at 100℃; for 6h; Diels-Alder reaction; neat (no solvent); stereoselective reaction;	95%

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

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

: C18H16N2O3S

Conditions

Conditions	Yield
for 24h; Reflux;	95%

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

: 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

Conditions

Conditions	Yield
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%

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

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

: C17H17NO2S

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;	95%

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

: 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

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Solvent; Inert atmosphere; diastereoselective reaction;	95%

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

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

: C15H10FNO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	95%

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

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

: C15H10BrNO3S

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 20℃; for 1h;	95%

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

: 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

Conditions

Conditions	Yield
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%

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

: 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

Conditions

Conditions	Yield
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%

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

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

Conditions

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

Benzo[b]thiophene,1,1-dioxide Specification

The Benzo[b]thiophene,1,1-dioxide, with the CAS registry number 825-44-5, is also known as Thianaphthene 1,1-dioxide. Its EINECS registry number is 212-544-8. This chemical's molecular formula is C₈H₆O₂S and molecular weight is 166.19704. Its IUPAC name is called 1-benzothiophene 1,1-dioxide. The product should be sealed and stored in cool and dry place. When you are using this chemical, please be cautious about it. You must avoid contacting it with skin and eyes. This chemical is white to cream colored powder.

Physical properties of Benzo[b]thiophene,1,1-dioxide: (1)ACD/LogP: 1.54; (2)ACD/LogD (pH 5.5): 1.53; (3)ACD/LogD (pH 7.4): 1.53; (4)ACD/BCF (pH 5.5): 8.63; (5)ACD/BCF (pH 7.4): 8.63; (6)ACD/KOC (pH 5.5): 162.84; (7)ACD/KOC (pH 7.4): 162.84; (8)#H bond acceptors: 2; (9)Index of Refraction: 1.64; (10)Molar Refractivity: 42.69 cm³; (11)Molar Volume: 118.3 cm³; (12)Surface Tension: 51.6 dyne/cm; (13)Density: 1.403 g/cm³; (14)Flash Point: 244 °C; (15)Enthalpy of Vaporization: 59.38 kJ/mol; (16)Boiling Point: 371.1 °C at 760 mmHg; (17)Vapour Pressure: 2.25E-05 mmHg at 25°C.

Preparation: this chemical can be prepared by benzo[b]thiophene. This reaction will need reagent aq. H₂O₂, [(n-Bu₃Sn)₂MoO₄]*nH₂O and solvent 1,2-dichloro-ethane. The reaction time is 1 hour with reaction temperature of 35 °C. The yield is about 57%.

Uses of Benzo[b]thiophene,1,1-dioxide: it can be used to produce trans-3-azido-2-iodo-2,3-dihydrobenzo[b]thiophene 1,1-dioxide. This reaction will need reagent iodine azide and solvent acetonitrile.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C2C(=C1)C=CS2(=O)=O
(2)InChI: InChI=1S/C8H6O2S/c9-11(10)6-5-7-3-1-2-4-8(7)11/h1-6H
(3)InChIKey: FRJNKYGTHPUSJR-UHFFFAOYSA-N

Product Name

THIANAPHTHENE-1,1-DIOXIDE

Synthetic route

Benzo[b]thiophene,1,1-dioxide Specification

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