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88-19-7 Usage

Chemical Properties

2-Methylbenzene-1-sulfonamide is Colorless crystals. Soluble in alcohol; slightly soluble in water and ether. Combustible.

Uses

Different sources of media describe the Uses of 88-19-7 differently. You can refer to the following data:
1. 2-Methylbenzene-1-sulfonamide is a methylated sulfonamide and a major Impurity if Saccharin (S080800). Studies suggest that o-Toluenesulfonamide has potential mutagenic activity.
2. Plasticizer of thermosetting resin, as a raw material used in organic synthesis, preparation of nail polish, dyes, fluorescent pigments and coatings.
3. o-Toluenesulfonamide is a methylated sulfonamide and a major impurity if Saccharin (S080800). Studies suggest that o-Toluenesulfonamide has potential mutagenic activity.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. o-Toluenesulfonamide is a major impurity in artificial sweetening substances containing saccharin.

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Mildly toxic by ingestion. Experimental reproductive effects. Mutation data reported. An eye irritant. When heated to decomposition it emits very toxic fumes of NOx and SOx. Used as a chemical intermediate in the production of saccharin.

Purification Methods

Crystallise the amide from hot H2O (m 153o), then from EtOH or Et2O/pet ether. The N-o-toluenesulfonylphthalimide has m 182o (from EtOH). [Evans & Dehn J Am Chem Soc 51 3652 1929, Beilstein 11 H 86, 11 I 23, 11 II 39, 11 III 167, 11 IV 229.]

Check Digit Verification of cas no

The CAS Registry Mumber 88-19-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 88-19:
(4*8)+(3*8)+(2*1)+(1*9)=67
67 % 10 = 7
So 88-19-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2S/c1-6-4-2-3-5-7(6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

88-19-7 Well-known Company Product Price

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  • Alfa Aesar

  • (B20544)  o-Toluenesulfonamide, 99%   

  • 88-19-7

  • 10g

  • 345.0CNY

  • Detail
  • Alfa Aesar

  • (B20544)  o-Toluenesulfonamide, 99%   

  • 88-19-7

  • 50g

  • 825.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1473)  o-Toluenesulfonamide  pharmaceutical secondary standard; traceable to USP

  • 88-19-7

  • PHR1473-500MG

  • 1,109.39CNY

  • Detail
  • USP

  • (1672010)  o-Toluenesulfonamide  United States Pharmacopeia (USP) Reference Standard

  • 88-19-7

  • 1672010-200MG

  • 7,294.95CNY

  • Detail
  • Aldrich

  • (257990)  o-Toluenesulfonamide  99%

  • 88-19-7

  • 257990-25G

  • 483.21CNY

  • Detail
  • Aldrich

  • (257990)  o-Toluenesulfonamide  99%

  • 88-19-7

  • 257990-100G

  • 1,577.16CNY

  • Detail

88-19-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name o-Toluenesulfonamide

1.2 Other means of identification

Product number -
Other names 2-Methylbenzene-1-sulfonamide

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:88-19-7 SDS

88-19-7Synthetic route

2-methyl-2-(toluene-2-ylsulfonylamino)propionic acid

2-methyl-2-(toluene-2-ylsulfonylamino)propionic acid

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With oxygen; copper(II) oxide In dimethyl sulfoxide at 100℃; for 8h;93%
2-thiocresol
137-06-4

2-thiocresol

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium hydroxide; iodine In water; acetonitrile at 100℃; for 16h;87%
With ammonium hydroxide; manganese(IV) oxide; oxygen In water; N,N-dimethyl-formamide at 90℃; under 7500.75 Torr; for 40h; Autoclave;83%
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 24h; Inert atmosphere; chemoselective reaction;78%
hexylidenetriphenylphosphoran
16666-79-8, 19493-12-0

hexylidenetriphenylphosphoran

N-benzylidene-2-methylbenzenesulfonamide
14674-28-3

N-benzylidene-2-methylbenzenesulfonamide

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

(18)O-triphenylphosphine oxide
98511-61-6

(18)O-triphenylphosphine oxide

Conditions
ConditionsYield
Stage #1: hexylidenetriphenylphosphoran; N-benzylidene-2-methylbenzenesulfonamide In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere;
Stage #2: With 18O-labeled water In tetrahydrofuran; hexane at 20℃; for 4h; stereoselective reaction;
A 72%
B 82%
2-methylphenyl diazonium tetrafluoroborate
2093-46-1

2-methylphenyl diazonium tetrafluoroborate

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine In water; acetonitrile at 80℃; for 12h; Inert atmosphere;70%
With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine In water; acetonitrile at 80℃; for 12h; Inert atmosphere; Schlenk technique;70%
N-Ethyl(o-methyl)benzenesulfonamide

N-Ethyl(o-methyl)benzenesulfonamide

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 3h; Dealkylation; Irradiation;69%
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 3h; ultrasonic irradiation;69%
triisopropyl(o-tolylthio)silane

triisopropyl(o-tolylthio)silane

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
Stage #1: triisopropyl(o-tolylthio)silane With sulfuryl dichloride; potassium nitrate In acetonitrile at 0℃;
Stage #2: With ammonium hydroxide In acetonitrile
67%
ortho-tolylmagnesium bromide
932-31-0

ortho-tolylmagnesium bromide

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With N-sulfinyl-O-(tert-butyl)hydroxylamine In tetrahydrofuran at -78 - 20℃; for 18h; Inert atmosphere;64%
(i) SO2Cl2, (ii) aq. NH3; Multistep reaction;
sodium (o-tolylsulfonyl)amide
27444-83-3

sodium (o-tolylsulfonyl)amide

methyl iodide
74-88-4

methyl iodide

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

N-methyl(o-methyl)benzenesulfonamide
13440-22-7

N-methyl(o-methyl)benzenesulfonamide

C

N,N,2-trimethylbenzenesulfonamide
67448-06-0

N,N,2-trimethylbenzenesulfonamide

Conditions
ConditionsYield
In methanol for 16h; Inert atmosphere; Schlenk technique;A 15%
B n/a
C 27%
toluenesulfinic acid
13165-77-0

toluenesulfinic acid

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With ethanol; ammonia; chlorine at 35 - 40℃;
toluene
108-88-3

toluene

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With aluminium trichloride; sulphamoyl chloride
Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With ammonia; water
With ammonia aus p-Toluolsulfochlorid enthaltendem Edukt1 mit gasfoermigem oder fluessigem Edukt2 und Entfernen aus dem Rohamid des Chlorammoniums durch wenig kaltes Wasser;
With ammonium hydroxide; sodium hydroxide In water
2-methylbenzenesulfonyl isocyanate
32324-19-9

2-methylbenzenesulfonyl isocyanate

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With Methamphetamin In dichloromethane for 0.5h; Yield given;
With water Yield given;
C13H7F5INO2S

C13H7F5INO2S

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
In toluene for 1h; Heating;
N-(1,1-dioxo-1λ6-benz[d]isothiazol-3-yl)-toluene-2-sulfonamide
14121-26-7

N-(1,1-dioxo-1λ6-benz[d]isothiazol-3-yl)-toluene-2-sulfonamide

alkaline solution

alkaline solution

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

saccharin
81-07-2

saccharin

ammonium hydroxide

ammonium hydroxide

Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

ammonium carbonate

ammonium carbonate

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Toluene-2-sulfonyl chloride
133-59-5

Toluene-2-sulfonyl chloride

ammonium dicarbonate

ammonium dicarbonate

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

o-toluenesulfo bromide

o-toluenesulfo bromide

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
With ethanol; ammonia
ethanol
64-17-5

ethanol

toluenesulfinic acid
13165-77-0

toluenesulfinic acid

ammonia
7664-41-7

ammonia

chlorine
7782-50-5

chlorine

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
at 40℃;
N-phenyl-S-(2-methylphenyl) sulfonamide
56776-55-7

N-phenyl-S-(2-methylphenyl) sulfonamide

KMnO4

KMnO4

acid

acid

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

ethanol
64-17-5

ethanol

5-amino-2-methylbenzenesulfonamide
6973-09-7

5-amino-2-methylbenzenesulfonamide

mixture of gaseous nitrogen oxides

mixture of gaseous nitrogen oxides

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
Erhitzen des Reaktionsproduktes mit absol. Alkohol unter Druck;
(2-tolyl)tributyltin
68971-87-9

(2-tolyl)tributyltin

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

potassium ferricyanide

potassium ferricyanide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 15 h / Ambient temperature
2: H2O
View Scheme
Dibutylbis(2-methylphenyl)stannane

Dibutylbis(2-methylphenyl)stannane

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

B

potassium ferricyanide

potassium ferricyanide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 10 h / 40 °C
2: H2O
View Scheme
1-methyl-2-(trimethylstannyl)benzene
17113-82-5

1-methyl-2-(trimethylstannyl)benzene

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CH2Cl2 / 15 h / 20 °C
2: ice / CH2Cl2 / 0.5 h
View Scheme
C35H49N3O3PRhS

C35H49N3O3PRhS

A

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

C28H40N2OPRh

C28H40N2OPRh

Conditions
ConditionsYield
In tetrahydrofuran-d8 Solvent; Inert atmosphere; Schlenk technique; Heating;
o-toluenesulfonic acid
88-20-0

o-toluenesulfonic acid

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Reaktion der Alkalisalzen
View Scheme
Multi-step reaction with 2 steps
1: Reaktion der Alkalisalzen
View Scheme
Multi-step reaction with 2 steps
1: Reaktion der Alkalisalzen
2: ammonia
View Scheme
toluene
108-88-3

toluene

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / <100 / Sulfurieren
2: Reaktion der Alkalisalzen
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / <100 / Sulfurieren
2: Reaktion der Alkalisalzen
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / <100 / Sulfurieren
2: Reaktion der Alkalisalzen
3: ammonia
View Scheme
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

4-((1H-indol-3-yl)methyl)benzoic acid
949928-48-7

4-((1H-indol-3-yl)methyl)benzoic acid

C23H20N2O3S

C23H20N2O3S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

benzoic acid
65-85-0

benzoic acid

N-(o-tolylsulfonyl)benzamide
146448-52-4

N-(o-tolylsulfonyl)benzamide

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 1h;99%
With dmap; amberlyst-15; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide on Merrifield's resin 1.) ClCH2CH2Cl, t-BuOH, rt., 24 h; 2.) EtOAc, 2 h; Yield given. Multistep reaction;
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-diphenyl-2-methylbenzenesulfonamide

N,N-diphenyl-2-methylbenzenesulfonamide

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃; for 24h;99%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

2-chloro-6-[3-(1-trifluoromethylcyclobutylmethoxy)pyrazole-1-yl]nicotinic acid

2-chloro-6-[3-(1-trifluoromethylcyclobutylmethoxy)pyrazole-1-yl]nicotinic acid

2-chloro-N-(o-tolylsulfonyl)-6-[3-[[1-(trifluoromethyl)cyclobutyl]methoxy]pyrazol-1-yl]pyridine-3-carboxamide

2-chloro-N-(o-tolylsulfonyl)-6-[3-[[1-(trifluoromethyl)cyclobutyl]methoxy]pyrazol-1-yl]pyridine-3-carboxamide

Conditions
ConditionsYield
Stage #1: 2-chloro-6-[3-(1-trifluoromethylcyclobutylmethoxy)pyrazole-1-yl]nicotinic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h;
Stage #2: methyl 2-(aminosulfonyl)benzoate With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 2h;
99%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

benzaldehyde N-boc imine
150884-50-7

benzaldehyde N-boc imine

(S)-tert-butyl N-[(2-methylphenylsulfonamido)(phenyl)methyl]carbamate

(S)-tert-butyl N-[(2-methylphenylsulfonamido)(phenyl)methyl]carbamate

Conditions
ConditionsYield
With (R)-VAPOL calcium phosphate In diethyl ether at 20℃; for 15h; Inert atmosphere; enantioselective reaction;99%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

4-ethoxyphenylacetylene
79887-14-2

4-ethoxyphenylacetylene

N-[1-(4-ethoxyphenyl)-ethylidene]-2-methyl-benzenesulfonamide
1228275-18-0

N-[1-(4-ethoxyphenyl)-ethylidene]-2-methyl-benzenesulfonamide

Conditions
ConditionsYield
With triphenylphosphine gold(I)chloride; silver trifluoromethanesulfonate In toluene at 100℃; for 9h;98%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

benzalacetophenone
94-41-7

benzalacetophenone

N-((1R,2R)-2-bromo-3-oxo-1,3-diphenylpropyl)-2-methylbenzenesulfonamide
1246850-32-7

N-((1R,2R)-2-bromo-3-oxo-1,3-diphenylpropyl)-2-methylbenzenesulfonamide

Conditions
ConditionsYield
With N-Bromosuccinimide; C31H44N4O4; scandium tris(trifluoromethanesulfonate) In dichloromethane at 0℃; for 24h; Molecular sieve; optical yield given as %ee; enantioselective reaction;98%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

N-benzhydryl-2-methylbenzenesulfonamide
904-02-9

N-benzhydryl-2-methylbenzenesulfonamide

Conditions
ConditionsYield
With Bromodiphenylmethane In neat (no solvent) at 130℃; for 24h; Sealed tube; Green chemistry;98%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 80℃; for 2h;90 %Chromat.
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

1-phenylpyrrolidin-2-one
4641-57-0

1-phenylpyrrolidin-2-one

(E)-2-methyl-N-(1-phenylpyrrolidin-2-ylidene)benzenesulfonamide

(E)-2-methyl-N-(1-phenylpyrrolidin-2-ylidene)benzenesulfonamide

Conditions
ConditionsYield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;98%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

2-chloro-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxylic acid

2-chloro-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxylic acid

2-chloro-N-(o-tolylsulfonyl)-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxamide

2-chloro-N-(o-tolylsulfonyl)-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxamide

Conditions
ConditionsYield
Stage #1: 2-chloro-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h;
Stage #2: methyl 2-(aminosulfonyl)benzoate With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 16h;
98%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

2,5-dimethoxyphenyl vinyl ketone
79238-14-5

2,5-dimethoxyphenyl vinyl ketone

(2,5-dimethoxyphenyl)(4-(2,5-dimethoxyphenyl)-4-hydroxy-1-(o-tolylsulfonyl)piperidin-3-yl)methanone

(2,5-dimethoxyphenyl)(4-(2,5-dimethoxyphenyl)-4-hydroxy-1-(o-tolylsulfonyl)piperidin-3-yl)methanone

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; Michael-Michael-Aldol cascade reaction; diastereoselective reaction;97%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

N-(4-(tert-butyl)phenyl)-2-methylbenzenesulfonamide

N-(4-(tert-butyl)phenyl)-2-methylbenzenesulfonamide

Conditions
ConditionsYield
With (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine In acetonitrile at 55℃; for 48h; Temperature; Inert atmosphere; Irradiation; Sealed tube;97%
ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

benzoisothiazolo[1,2-b][1,2]isoquinolin-11-one-1,1-dioxide

benzoisothiazolo[1,2-b][1,2]isoquinolin-11-one-1,1-dioxide

Conditions
ConditionsYield
Stage #1: ortho-methylbenzoic acid With lithium diisopropyl amide In tetrahydrofuran at 0℃;
Stage #2: methyl 2-(aminosulfonyl)benzoate In tetrahydrofuran at 20℃;
96%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-2-methylbenzenesulfonamide
27200-69-7

N-acetyl-2-methylbenzenesulfonamide

Conditions
ConditionsYield
With zinc(II) chloride at 23℃;96%
With zinc(II) chloride at 20℃;94%
With zinc(II) chloride at 50℃;82%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

2-methyl-N-(2,2,2-trichloroethylidene)benzenesulfonamide
1608121-38-5

2-methyl-N-(2,2,2-trichloroethylidene)benzenesulfonamide

N,N′-(2,2,2-trichloroethane-1,1-diyl)bis-(2-methylbenzenesulfonamide)
1608121-39-6

N,N′-(2,2,2-trichloroethane-1,1-diyl)bis-(2-methylbenzenesulfonamide)

Conditions
ConditionsYield
In Trichloroethylene at 90℃; for 3h;96%
methanol
67-56-1

methanol

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

N-methyl(o-methyl)benzenesulfonamide
13440-22-7

N-methyl(o-methyl)benzenesulfonamide

Conditions
ConditionsYield
With [(Cp*IrCl)2(4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine)][Cl]2; potassium hydroxide In water at 130℃; for 12h;96%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;92%
With [(Cp*IrCl)2(4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine)][Cl]2; potassium hydroxide In water at 130℃; for 12h; Schlenk technique;91%
With [Cp*Ir(2-(1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazole)Cl][Cl]; caesium carbonate at 120℃; for 12h; Schlenk technique;90%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

chloral
75-87-6

chloral

2-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)benzenesulfonamide
121583-22-0

2-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)benzenesulfonamide

Conditions
ConditionsYield
With sulfuric acid at 20 - 65℃; for 0.5h;95%
With hydrogenchloride for 16h; Heating;79%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(E)-2-methyl-N-(4-methylbenzylidene)benzenesulfonamide
951762-79-1

(E)-2-methyl-N-(4-methylbenzylidene)benzenesulfonamide

Conditions
ConditionsYield
With pyrrolidine In chloroform at 60℃; for 24h; Molecular sieve;95%
boron trifluoride diethyl etherate Heating;83%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

methyl o-tolylsulfonylcarbamate

methyl o-tolylsulfonylcarbamate

Conditions
ConditionsYield
In toluene Reflux;95%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

acetonitrile
75-05-8

acetonitrile

diethyl 2,2'-((1-((o-tolylsulfonyl)imino)ethyl)azanediyl)(E)-diacetate

diethyl 2,2'-((1-((o-tolylsulfonyl)imino)ethyl)azanediyl)(E)-diacetate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) at 80℃; for 2h;95%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

acetonitrile
75-05-8

acetonitrile

C17H24N2O6S

C17H24N2O6S

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) at 80℃; for 2h;95%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

C17H15NO3

C17H15NO3

C24H22N2O4S

C24H22N2O4S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;95%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;95%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

3-methoxy-p-toluic acid
7151-68-0

3-methoxy-p-toluic acid

3-methoxy-4-methyl-N-(o-tolylsulfonyl) Benzamide
1414930-94-1

3-methoxy-4-methyl-N-(o-tolylsulfonyl) Benzamide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25 - 35℃;94.7%
Estragole
140-67-0

Estragole

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

N-[2-(4-methoxyphenyl)-1-methylethyl]-2-methyl-benzenesulfonamide
1344994-15-5

N-[2-(4-methoxyphenyl)-1-methylethyl]-2-methyl-benzenesulfonamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silica gel In water; toluene at 85℃; for 20h;94%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

methyl o-tolylsulfonylcarbamate
310897-86-0

methyl o-tolylsulfonylcarbamate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 4h; Acylation;93%
With dmap; triethylamine In dichloromethane at 20℃;75%
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
With dmap; sodium monohydrogen sulfate; triethylamine In dichloromethane7.0 g (88%)
norborn-2-ene
498-66-8

norborn-2-ene

methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

exo-N-bicyclo[2.2.1]hept-2-yl-2-methyl-benzenesulfonamide

exo-N-bicyclo[2.2.1]hept-2-yl-2-methyl-benzenesulfonamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silica gel In water; toluene at 85℃; for 20h;93%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

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

N,N-dimethyl-formamide

N,N-dimethyl-N′-(o-tolylsulfonyl)formimidamide
1344029-80-6

N,N-dimethyl-N′-(o-tolylsulfonyl)formimidamide

Conditions
ConditionsYield
With tert.-butylhydroperoxide; sodium iodide In water at 90℃; for 3h;93%
With N-Bromosuccinimide; water at 80℃;87%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

C8H7F3N2O2S
84796-65-6

C8H7F3N2O2S

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran for 2.5h; Ambient temperature;92%
methyl 2-(aminosulfonyl)benzoate
88-19-7

methyl 2-(aminosulfonyl)benzoate

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(E)-2-methyl-N-(4-methoxybenzylidene)benzenesulfonamide
951762-78-0

(E)-2-methyl-N-(4-methoxybenzylidene)benzenesulfonamide

Conditions
ConditionsYield
With pyrrolidine In chloroform at 60℃; for 24h; Molecular sieve;92%
boron trifluoride diethyl etherate Heating;61%

88-19-7Relevant articles and documents

Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl- O-(tert-butyl)hydroxylamine, t-BuONSO

Davies, Thomas Q.,Hall, Adrian,Skolc, David,Tilby, Michael J.,Willis, Michael C.

supporting information, p. 9495 - 9499 (2020/12/21)

Sulfonamides have played a defining role in the history of drug development and continue to be prevalent today. In particular, primary sulfonamides are common in marketed drugs. Here we describe the direct synthesis of these valuable compounds from organometallic reagents and a novel sulfinylamine reagent, t-BuONSO. A variety of (hetero)aryl and alkyl Grignard and organolithium reagents perform well in the reaction, providing primary sulfonamides in good to excellent yields in a convenient one-step process.

Sulfonamide compound and synthesis method and application thereof

-

Paragraph 0094-0097, (2019/04/02)

The invention discloses a synthesis method of a sulfonamide compound represented in a formula (2). According to the method, diazonium salt is used as a reaction raw material, and under the action of an inorganic nitrogen reagent, an inorganic sulfur dioxide reagent, an additive and a phosphine reagent, the diazonium salt is reacted in a solvent at 60-100 DEG C to obtain various sulfonamide compounds. According to the method inorganic salt is used as a nitrogen atom source and a sulfur dioxide source under a metal-free catalytic condition to construct the sulfonamide compound through one step,thereby avoiding the conventional multi-step synthesis of sulfonamide by condensing unstable acid chloride and amine; and the developed sulfonamide synthesis method can be further applied to the synthesis of the arthritis drug celecoxib and the psychotropic drug sulpiride.

Metal-free construction of primary sulfonamides through three diverse salts

Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng

supporting information, p. 5469 - 5473 (2019/01/03)

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with -SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.

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