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121-57-3

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121-57-3 Usage

Synthesize

Sulfanilic acid can be used for the determination of nitrite. Biochemical Research. Organic Synthesis. Sulfanilic acid is an important intermediate of sulfonamide drugs. This product has strong antibacterial effect on hemolytic streptococcus, meningitis and coccus, but due to poor efficacy and high toxicity, it is rarely used for oral administration. It is also rarely used. It is used as an intermediate for the synthesis of other sulfonamides, and is also used as a raw material for the synthesis of agricultural "Huangcaoling" abroad. Sulfanilic acid can also be used as an analytical reagent, such as a reagent for the photometric determination of nitrite and sodium nitroferricyanide. For biochemical research, organic synthesis and pharmaceutical industry. Sulfanilic acid is the main raw material for synthesizing sulfonamides. In addition to preparing crystalline sulfonamides for external anti-inflammatory, it can also synthesize other sulfonamides such as sulfamidine, sulfamethoxazine, and sulfamethazine.

Description

Sulfanilic acid (4-amino benzene sulfonic acid ) is an off-white crystalline solid which finds application in quantitative analysis of nitrate and nitrite ions. The solid acid exists as a zwitterion, and has an unusually high melting point.

Chemical Properties

greyish-white crystals or powder

Uses

Different sources of media describe the Uses of 121-57-3 differently. You can refer to the following data:
1. A toxic metabolite of Tartrazine (T007700). Used as Ehrlich’s reagent, for detecting of nitrites. Antibacterial.
2. Sulfanilic Acid (Sulfadimethoxine EP Impurity D) is a toxic metabolite of Tartrazine (T007700). Used as Ehrlich’s reagent, for detecting of nitrites. Antibacterial.
3. Sulfanilic acid may be used for the functionalization of single-walled carbon nanotubes (SWNTs) with aryl sulfonate groups.

Definition

ChEBI: An aminobenzenesulfonic acid that is aniline sulfonated at the para-position.

Application

As the compound readily form diazo compounds, it is used to make dyes and sulpha drugs . This property is also used for the quantitative analysis of nitrate and nitrite ions by diazonium coupling reaction with N-(1-Naphthyl) ethylene diamine , resulting in an azo dye, and the concentration of nitrate or nitrite ions were deduced from the color intensity of the resulting red solution by colorimetry. It is also used as a standard in combustion analysis.

General Description

White powder with faint purple tinge. Grayish-white flat crystals. Becomes anhydrous at around 212°F. Low toxicity (used medicinally).

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Sulfanilic acid is an amino acid. Reacts weakly with both acids and bases.

Fire Hazard

Flash point data for Sulfanilic acid are not available, however Sulfanilic acid is probably combustible.

Synthesis

Sulfanilic acid can be produced by sulfonation of aniline.

Purification Methods

Crystallise the acid (as dihydrate) from boiling water. Dry it at 105o for 2-3hours, then over 90% H2SO4 in a vacuum desiccator. The S-benzylisothiuronium salt has m 187o (from aqueous EtOH). [Beilstein 14 IV 2655.]

Check Digit Verification of cas no

The CAS Registry Mumber 121-57-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 121-57:
(5*1)+(4*2)+(3*1)+(2*5)+(1*7)=33
33 % 10 = 3
So 121-57-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)/p-1

121-57-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (41540)  Sulfanilic acid, ACS, 98.0-102.0%   

  • 121-57-3

  • 50g

  • 315.0CNY

  • Detail
  • Alfa Aesar

  • (41540)  Sulfanilic acid, ACS, 98.0-102.0%   

  • 121-57-3

  • 250g

  • 762.0CNY

  • Detail
  • Alfa Aesar

  • (A15825)  Sulfanilic acid, 98+%   

  • 121-57-3

  • 250g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A15825)  Sulfanilic acid, 98+%   

  • 121-57-3

  • 1000g

  • 568.0CNY

  • Detail
  • Alfa Aesar

  • (A15825)  Sulfanilic acid, 98+%   

  • 121-57-3

  • 5000g

  • 2433.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1419)  Sulfanilic Acid  pharmaceutical secondary standard; traceable to USP

  • 121-57-3

  • PHR1419-500MG

  • 718.73CNY

  • Detail
  • Sigma-Aldrich

  • (39441)  NitrateReagentB  for microbiology

  • 121-57-3

  • 39441-100ML-F

  • 356.85CNY

  • Detail
  • Fluka

  • (72326)  Sulfanilicacidsolution  volumetric, 0.1 M (0.1N)

  • 121-57-3

  • 72326-1L

  • 436.41CNY

  • Detail
  • Sigma-Aldrich

  • (86090)  Sulfanilicacid  puriss. p.a., ≥99.0% (T)

  • 121-57-3

  • 86090-5G

  • 522.99CNY

  • Detail
  • Sigma-Aldrich

  • (86090)  Sulfanilicacid  puriss. p.a., ≥99.0% (T)

  • 121-57-3

  • 86090-100G

  • 869.31CNY

  • Detail
  • Sigma-Aldrich

  • (86090)  Sulfanilicacid  puriss. p.a., ≥99.0% (T)

  • 121-57-3

  • 86090-500G

  • 2,666.43CNY

  • Detail
  • USP

  • (1633506)  Sulfanilicacid  United States Pharmacopeia (USP) Reference Standard

  • 121-57-3

  • 1633506-200MG

  • 14,578.20CNY

  • Detail

121-57-3SDS

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 4-aminobenzenesulfonic acid

1.2 Other means of identification

Product number -
Other names Sulfanilic Acid

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:121-57-3 SDS

121-57-3Synthetic route

p-nitrobenzenesulfonic acid
138-42-1

p-nitrobenzenesulfonic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With hydrazine In ethanol at 80℃; for 0.166667h; Catalytic behavior; chemoselective reaction;99.9%
With ammonium sulfide
With hydrogenchloride; tin(ll) chloride
aniline
62-53-3

aniline

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 180 - 190℃; for 1.5h; Time; Autoclave;98%
With sulfuric acid for 0.0666667h; microwave irradiation;93%
With sodium hydrogensulfite; pyridinium chlorochromate In neat (no solvent) at 100℃; under 1500.15 Torr; for 0.0416667h; Reagent/catalyst; Microwave irradiation;92%
aniline
62-53-3

aniline

A

2-amino-1-benzenesulfonic acid
88-21-1

2-amino-1-benzenesulfonic acid

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With chlorosulfonic acid In 1,2-dichloro-benzene at 135℃; for 1h; Product distribution; Kinetics; Mechanism; E(activ), oth. temperatures;A 3.2%
B 96.8%
With sulfur trioxide In 1,2-dichloro-ethane at 5℃; Rate constant; Thermodynamic data; Product distribution; oth. temperature, E(activ.), var. ratios of reactants;
With sulfuric acid In 1,2-dichloro-benzene at 180℃; Kinetics; Thermodynamic data; Equilibrium constant; variation of molar ratio and temperature, Ea, ΔGo, ΔHo, ΔSo;
With sulfuric acid In 1,2-dichloro-benzene at 24.9℃; Thermodynamic data; Mechanism; Activation Free Energy, Enthalpy, Entropy of sulfonation and desulfonation;
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene
57-67-0

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

A

bis(4-aminophenyl)disulfide
722-27-0

bis(4-aminophenyl)disulfide

B

sulfanilamide
63-74-1

sulfanilamide

C

aniline
62-53-3

aniline

D

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;A n/a
B 4.4%
C 95.1%
D 2.7%
4-amino-phenol
123-30-8

4-amino-phenol

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With aluminum (III) chloride; o-toluenesulfonic acid at 110℃; for 2h; Temperature;94%
4-amino-3-fluorobenzenesulfonic acid
2369-25-7

4-amino-3-fluorobenzenesulfonic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With hydrogen; sodium carbonate; palladium on activated charcoal In water for 16h;82.1%

A

aniline
62-53-3

aniline

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
at 200℃; under 40 Torr; for 1h;A n/a
B 61%
at 155℃; Kinetics; thermal decomposition, various temperature;
sodium 4-(4-diazenediyl-5-mercapto-3-methyl-1-phenyl-1,2-diazacyclopenta-2,4-diene)benzenesulfonate

sodium 4-(4-diazenediyl-5-mercapto-3-methyl-1-phenyl-1,2-diazacyclopenta-2,4-diene)benzenesulfonate

A

C20H20N6S2
77747-65-0

C20H20N6S2

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium dithionite In methanol; waterA 60%
B 28%
3-amino-benzenesulfonic acid, monosodium salt
1126-34-7

3-amino-benzenesulfonic acid, monosodium salt

A

2-amino-1-benzenesulfonic acid
88-21-1

2-amino-1-benzenesulfonic acid

B

aniline
62-53-3

aniline

C

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; sodium dihydrogenphosphate In methanol for 0.0166667h; Product distribution; Mechanism; Irradiation; effect of solvent and pH;A 15.6%
B 37.2%
C 39.3%
With perchloric acid; NaH2PO4-Na2HPO4 buffer; sodium chloride In water for 0.0166667h; Product distribution; Mechanism; Irradiation;A 2.80 % Turnov.
B 6.43 % Turnov.
C 7.02 % Turnov.
sulphapyridine
144-83-2

sulphapyridine

A

2-aminopyridine
504-29-0

2-aminopyridine

B

bis(4-aminophenyl)disulfide
722-27-0

bis(4-aminophenyl)disulfide

C

p-nitrobenzenesulfonamide
6325-93-5

p-nitrobenzenesulfonamide

D

sulfanilamide
63-74-1

sulfanilamide

E

aniline
62-53-3

aniline

F

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
In methanol for 48h; Product distribution; Mechanism; Irradiation; λ=254 nm;A 15.6%
B n/a
C n/a
D 6.1%
E 29.1%
F 20.1%
2-amino-1-benzenesulfonic acid
88-21-1

2-amino-1-benzenesulfonic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 180 - 190℃;
N,N'-Diphenyloxamid
620-81-5

N,N'-Diphenyloxamid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With sulfuric acid
succinic acid
110-15-6

succinic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

N-phenylbenzenesulfonamide
1678-25-7

N-phenylbenzenesulfonamide

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With sulfuric acid
4-diazobenzenesulfonic acid
305-80-6

4-diazobenzenesulfonic acid

p-toluidine hydrochloride
540-23-8

p-toluidine hydrochloride

A

p-methylbenzenediazonium chloride
2028-84-4

p-methylbenzenediazonium chloride

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-diazobenzenesulfonic acid
305-80-6

4-diazobenzenesulfonic acid

o-toluidine hydrochloride
636-21-5

o-toluidine hydrochloride

A

4-(4-amino-3-methyl-phenylazo)-benzenesulfonic acid
55994-15-5

4-(4-amino-3-methyl-phenylazo)-benzenesulfonic acid

B

o-toluene-diazonium chloride
2028-34-4

o-toluene-diazonium chloride

C

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-chloro-benzenesulfonic acid
98-66-8

4-chloro-benzenesulfonic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With ammonium hydroxide; copper chloride at 170℃; unter Druck;
2-amino-5-sulfo-benzoic acid
3577-63-7

2-amino-5-sulfo-benzoic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With water
4-(2-hydroxy-3,5-dimethyl-phenylazo)-benzenesulfonic acid
68941-04-8

4-(2-hydroxy-3,5-dimethyl-phenylazo)-benzenesulfonic acid

A

6-amino-2,4-xylenol
41458-65-5

6-amino-2,4-xylenol

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
durch Reduktion;
4-(3-nitro-phenylazo)-benzenesulfonic acid

4-(3-nitro-phenylazo)-benzenesulfonic acid

A

m-phenylenediamine
108-45-2

m-phenylenediamine

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
durch Reduktion;
N-(anilino-2-thio-oxalyl)-sulfanilic acid

N-(anilino-2-thio-oxalyl)-sulfanilic acid

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

2-nitro-4-(4'-sulfophenylazo)-phenol
67329-17-3

2-nitro-4-(4'-sulfophenylazo)-phenol

A

2,4-diaminophenol
95-86-3

2,4-diaminophenol

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
bei der Reduktion;
bei der Reduktion;
3,5-diamino-2-(4-sulfo-phenylazo)-benzoic acid

3,5-diamino-2-(4-sulfo-phenylazo)-benzoic acid

A

2,3,5-triamino-benzoic acid
609-87-0

2,3,5-triamino-benzoic acid

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; tin
2-amino-5-(4-sulfo-phenylazo)-benzene-1,3-disulfonic acid

2-amino-5-(4-sulfo-phenylazo)-benzene-1,3-disulfonic acid

A

1,4-phenylenediamine-2,6-disulphonic acid
6409-48-9

1,4-phenylenediamine-2,6-disulphonic acid

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; tin(ll) chloride
methyl orange
547-58-0

methyl orange

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With Pd-BaSO4; sodium acetate; acetic acid Hydrogenation;
With sodium dithionite; water
With sodium dithionite; ethanol
With hydrogen iodide
With sodium carbonate at 95℃; bei der elektrolytischen Reduktion;
N-methyl-N-phenyl-sulfanilic acid ; compound with aniline

N-methyl-N-phenyl-sulfanilic acid ; compound with aniline

A

benzhydrylidene(methyl)amine
552-82-9

benzhydrylidene(methyl)amine

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
at 210 - 215℃;
oxalic acid
144-62-7

oxalic acid

4-(4-hydroxy-[1]naphthylazo)-benzenesulfonic acid
574-69-6

4-(4-hydroxy-[1]naphthylazo)-benzenesulfonic acid

A

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

B

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With bacillus coli
meta-aminobenzoic acid
99-05-8

meta-aminobenzoic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With sulfuric acid
8-quinolinol
148-24-3

8-quinolinol

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid
574-70-9

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With hydrogenchloride; sodium nitrite In water at -5℃; for 0.25h;
Stage #2: 8-quinolinol With sodium hydroxide In water
100%
With hydrogenchloride; sodium nitrite
With hydrogenchloride; sodium hydroxide; ethylenediaminetetraacetic acid; sodium nitrite In ethanol for 0.0833333h;
4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-diazobenzenesulfonic acid
305-80-6

4-diazobenzenesulfonic acid

Conditions
ConditionsYield
With nitrosylchloride under 750.075 Torr; for 24h;100%
With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;67%
With sulfuric acid; sodium nitrite In water at 25℃; Rate constant; acid catalysis, further reactant 1M HClO4, var. acidities; add of Cl(1-), Br(1-), I(1-) and SCN(1-) as nucl. catalysts.;
4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

p-sulfobenzenediazonium chloride
6118-33-8

p-sulfobenzenediazonium chloride

Conditions
ConditionsYield
With hydrogenchloride; Nitrogen dioxide In water at 20℃; for 1h; Reagent/catalyst;100%
With hydrogenchloride; sodium nitrite In hydrogenchloride; water at 1.5℃; Rate constant;
With hydrogenchloride; sodium hydroxide; sodium nitrite In water for 0.25h; ice bath;
(R)-2-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyryl]-3,4-dihydro-2H-pyrazole-3-carboxylic acid
1078736-39-6

(R)-2-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyryl]-3,4-dihydro-2H-pyrazole-3-carboxylic acid

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

(R)-4-({2-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyryl]-3,4-dihydro-2H-pyrazole-3-carbonyl}amino)benzenesulfonic acid
1078736-57-8

(R)-4-({2-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluorophenyl)butyryl]-3,4-dihydro-2H-pyrazole-3-carbonyl}amino)benzenesulfonic acid

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h;100%
benzoyl chloride
98-88-4

benzoyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

potassium 4-benzamidobenzenesulfonate

potassium 4-benzamidobenzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃;100%
m-Chlorobenzoyl chloride
618-46-2

m-Chlorobenzoyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

potassium 4-(3-chlorobenzamido)benzenesulfonate

potassium 4-(3-chlorobenzamido)benzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃;100%
4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

potassium 4-(4-methylbenzamido)benzenesulfonate

potassium 4-(4-methylbenzamido)benzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃;100%
2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol

2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

C25H27N3O7S2
1122445-22-0

C25H27N3O7S2

Conditions
ConditionsYield
Stage #1: 2-tert-butylamino-1-(4-hydroxy-2-hydroxymethyl-phenyl)ethanol With RuCl2(PPh3)2(BAOBEA); dihydrogen peroxide In water at 60℃; for 0.5h;
Stage #2: 4-aminobenzene sulfonic acid In water for 0.0833333h; Reflux;
99.65%
2-Ethoxyphenol
94-71-3

2-Ethoxyphenol

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

sodium 4-((3-ethoxy-4-hydroxyphenyl)diazenyl)benzenesulfonate
1219948-46-5

sodium 4-((3-ethoxy-4-hydroxyphenyl)diazenyl)benzenesulfonate

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide; sodium nitrite In water at 0℃;
Stage #2: With hydrogenchloride In water at 0 - 5℃;
Stage #3: 2-Ethoxyphenol In ethanol; water at 5℃; for 4h;
99%
silver(l) oxide
20667-12-3

silver(l) oxide

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

(p-aminobenzenesulfonato)silver(I)

(p-aminobenzenesulfonato)silver(I)

Conditions
ConditionsYield
In water acid (2 mmol0 and Ag2O (1 mmol) stirred for 2 h; filtered, crystd. on slow evapn. overnight, elem. anal.;99%
pivaloyl chloride
3282-30-2

pivaloyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-[(2,2-dimethylpropanoyl)amino]benzenesulfonic acid

4-[(2,2-dimethylpropanoyl)amino]benzenesulfonic acid

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; Green chemistry;99%
methyl chloroformate
79-22-1

methyl chloroformate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-[(methoxycarbonyl)amino]benzenesulfonic acid
60007-73-0

4-[(methoxycarbonyl)amino]benzenesulfonic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry;99%
phenyl chloroformate
1885-14-9

phenyl chloroformate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-[(phenoxycarbonyl)amino]benzenesulfonic acid

4-[(phenoxycarbonyl)amino]benzenesulfonic acid

Conditions
ConditionsYield
In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry;99%
With sodium hydrogencarbonate In tetrahydrofuran at 20℃;89%
pyridoxal hydrochloride
58-56-0

pyridoxal hydrochloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

C14H14N2O5S
1122445-21-9

C14H14N2O5S

Conditions
ConditionsYield
Stage #1: pyridoxal hydrochloride With RuCl2(PPh3)2(BAOBEA); dihydrogen peroxide In water at 60℃; for 0.25h;
Stage #2: 4-aminobenzene sulfonic acid In water for 0.0833333h; Reflux;
98.25%
copper(I) oxide

copper(I) oxide

1,10-phenanthroline-2,9-dicarboxaldehyde
57709-62-3

1,10-phenanthroline-2,9-dicarboxaldehyde

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

2Na(1+)*[Cu2(C12H6N2(CHNC6H4SO3)2)2](2-)=Na2[Cu2(C12H6N2(CHNC6H4SO3)2)2]

2Na(1+)*[Cu2(C12H6N2(CHNC6H4SO3)2)2](2-)=Na2[Cu2(C12H6N2(CHNC6H4SO3)2)2]

Conditions
ConditionsYield
With NaHCO3 In water (Ar or N2); a flask charged with 1,10-phenanthroline-2,9-dicarboxaldehyde, sulfanilic acid, Cu2O, NaHCO3, sealed, purified of O2, H2O added, sealed, stirred overnight at room temp.; evapd. (vac.);98%
salicylaldehyde
90-02-8

salicylaldehyde

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

N‑(2‑hydroxybenzylidene)‑4‑aminobenzenesulfonic acid sodium salt
155140-18-4

N‑(2‑hydroxybenzylidene)‑4‑aminobenzenesulfonic acid sodium salt

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide In methanol for 1h; Reflux;
Stage #2: salicylaldehyde In methanol at 20℃; for 2h;
98%
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide In methanol for 1h; Reflux;
Stage #2: salicylaldehyde In methanol at 20℃; for 2h;
86%
Stage #1: 4-aminobenzene sulfonic acid With sodium hydroxide In methanol
Stage #2: salicylaldehyde In methanol at 80℃;
66%
2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride
199328-31-9

2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-{[(2-oxo-2,3-dihydro-1H-indol-5-yl)sulfonyl]amino}benzenesulfonic acid
1227783-62-1

4-{[(2-oxo-2,3-dihydro-1H-indol-5-yl)sulfonyl]amino}benzenesulfonic acid

Conditions
ConditionsYield
In toluene for 6h; Reflux;98%
chlorure d'acide ethyl-2 butyrique
2736-40-5

chlorure d'acide ethyl-2 butyrique

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-[(2-ethylbutanoyl)amino]benzenesulfonic acid

4-[(2-ethylbutanoyl)amino]benzenesulfonic acid

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; Green chemistry;98%
propoxycarbonyl chloride
109-61-5

propoxycarbonyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-[(propoxycarbonyl)amino]benzenesulfonic acid

4-[(propoxycarbonyl)amino]benzenesulfonic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry;98%
p-tolyl chloroformate
937-62-2

p-tolyl chloroformate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-{[(4-methylphenoxy)carbonyl]amino}benzenesulfonic acid

4-{[(4-methylphenoxy)carbonyl]amino}benzenesulfonic acid

Conditions
ConditionsYield
In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry;98%
1-naphthyl chloroformate
3759-61-3

1-naphthyl chloroformate

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-{[(naphthalen-1-yloxy)carbonyl]amino}benzenesulfonic acid

4-{[(naphthalen-1-yloxy)carbonyl]amino}benzenesulfonic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry;98%
3-fluorobenzoyl chloride
1711-07-5

3-fluorobenzoyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

potassium 4-(3-fluorobenzamido)benzenesulfonate

potassium 4-(3-fluorobenzamido)benzenesulfonate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran; water at 20℃;98%
bismuth(III) tert-butoxide

bismuth(III) tert-butoxide

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Bi(3+)*3C6H6NO3S(1-)

Bi(3+)*3C6H6NO3S(1-)

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;97%
4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-hydrazinylbenzenesulfonic acid hydrochloride

4-hydrazinylbenzenesulfonic acid hydrochloride

Conditions
ConditionsYield
Stage #1: 4-aminobenzene sulfonic acid With potassium nitrite In water at 25℃; Acidic conditions; Flow reactor;
Stage #2: With potassium pyrosulfite In water at 80 - 110℃;
Stage #3: With hydrogenchloride In water at 130℃;
96.7%
benzoyl chloride
98-88-4

benzoyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-(benzoylamino)benzenesulfonic acid
6052-43-3

4-(benzoylamino)benzenesulfonic acid

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 20℃; Green chemistry;96%
With sodium chloride In water; acetone for 0.25h;60%
With pyridine
2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

sodium 4-(2-nitrobenzamido)benzenesulfonate

sodium 4-(2-nitrobenzamido)benzenesulfonate

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;96%
salicylaldehyde
90-02-8

salicylaldehyde

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

4-((2-hydroxybenzylidene)amino)benzenesulfonic acid
32835-41-9

4-((2-hydroxybenzylidene)amino)benzenesulfonic acid

Conditions
ConditionsYield
In neat (no solvent, solid phase) at 20℃; for 0.25h;96%
In methanol; water for 1h; Reflux;76%

121-57-3Related news

Kinetic, mechanistic and spectral studies for the oxidation of Sulfanilic acid (cas 121-57-3) by alkaline hexacyanoferrate(III)09/25/2019

The kinetics of oxidation of sulfanilic acid (p-aminobenzenesulfonic acid) by hexacyanoferrate(III) in alkaline medium was studied spectrophotometrically. The reaction showed first order kinetics in hexacyanoferrate(III) and alkali concentrations and an order of less than unity in sulfanilic aci...detailed

A turn-on fluorescent probe for sensitive detection of sulfide anions and ascorbic acid by using Sulfanilic acid (cas 121-57-3) and glutathione functionalized graphene quantum dots09/24/2019

The rational surface functionalization of graphene quantum dots (GQDs) has attracted much attention to extend their application in fabricating bio/chemical sensing platform. In this paper, a GQDs-based copper ions (Cu2+) modulated dual-functional fluorescent probe was developed. The attachment o...detailed

Sulfanilic acid (cas 121-57-3) catalyzed solvent-free synthesis of 1,5-benzodiazepine derivatives09/10/2019

Sulfanilic acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones. This method is simple, effective and environmentally friendly and gives better yields.detailed

Enzymatic growth of single-layer MnO2 nanosheets in situ: Application to detect alkaline phosphatase and ascorbic acid in the presence of Sulfanilic acid (cas 121-57-3) functionalized graphene quantum dots09/08/2019

In this work, a rapid fluorescence “turn off-on” assay was developed to detect alkaline phosphatase (ALP) and ascorbic acid (AA) based on sulfanilic acid functionalized graphene quantum dots (SGQDs) and MnO2 nanosheets, which was fabricated through in situ formation of MnO2 nanosheets in the p...detailed

Electrochemical incineration of Sulfanilic acid (cas 121-57-3) at a boron-doped diamond anode09/06/2019

The anodic oxidation of sulfanilic acid solutions has been studied in acidic medium using a divided cell with a boron-doped diamond (BDD) anode and a stainless steel cathode. Overall mineralization was achieved under all experimental conditions tested due to the efficient destruction of sulfanil...detailed

Kinetic of the degradation of Sulfanilic acid (cas 121-57-3) azochromotrop (SPADNS) by Fenton process coupled with ultrasonic irradiation or L-cysteine acceleration09/05/2019

The degradation kinetics of sulfanilic acid azochromotrop (SPADNS) in aqueous phase by Fenton process has been examined. The effect of pH, hydrogen peroxide [H2O2], ferrous ion [Fe2+], molar ratio of [H2O2]/[Fe2+] and SPADNS concentration [SPADNS] have been estimated systematically. The optimu...detailed

Sulfanilic acid (cas 121-57-3) increases intracellular free-calcium concentration, induces reactive oxygen species production and impairs trypsin secretion in pancreatic AR42J cells09/04/2019

We studied the effects of the tartrazine-metabolite sulfanilic acid on the physiology of pancreatic AR42J cells. Sulfanilic acid (1 μM-1 mM) induced a slow and progressive increase in intracellular free-calcium concentration that reached a plateau. The effect of sulfanilic acid was not concentr...detailed

121-57-3Relevant articles and documents

The Photochemistry of Metanilic Acid: Photoisomerization and Photodegradation

Lally, John M.,Spillane, William J.

, p. 1571 - 1572 (1987)

In the photolysis of sodium metanilate (1,Na) a single triplet and a series of ?-complexes give rise to the isomeric aniline sulphonic acids (2) and (3) and aniline (4).

Conjugated Microspheres FeTCPP–TDI–TiO2 with Enhanced Photocatalytic Performance for Antibiotics Degradation Under Visible Light Irradiation

Yao, Binghua,Peng, Chao,He, Yangqing,Zhang, Wen,Zhang, Qinku,Zhang, Ting

, p. 2543 - 2554 (2016)

Abstract: Toluene disocyanate (TDI) was used as a bridging molecule, a bridge bonding conjugated microsphere (FeTCPP–TDI–TiO2) was successfully prepared by grafting tetra-(carboxyphenyl) porphyrin iron (FeTCPP) on the surface of TiO2 microspheres. The FT-IR spectra revealed that the hydroxyl group (–OH) of TiO2 microspheres surface and the carboxyl group (–COOH) of FeTCPP reacted respectively with the active isocyanato groups (–NCO) of TDI to form a surface conjugated microsphere FeTCPP–TDI–TiO2. The UV–vis DRS analysis demonstrated that the formation of FeTCPP–TDI–TiO2 extended remarkably the photoresponse of as-prepared samples to visible light region. The photocatalytic activity of FeTCPP–TDI–TiO2 was evaluated using the photocatalytic degradation of norfloxacin (NFC), tetracycline (TC) and sulfapyridine (SPY) antibiotics in aqueous solution under visible-light irradiation. The results showed that, TDI, as a bond unit, was used to form a steady chemical bridging bond linking between FeTCPP and the surface of TiO2 microspheres, and the prepared catalyst exhibited higher photocatalytic activity under visible-light irradiation for antibiotics degradation in comparison with P25. The degradation of antibiotics all followed the pseudo first-order reaction model under visible light irradiation, and the degradation mechanisms of NFC, TC and SPY were also proposed. Graphical Abstract: [Figure not available: see fulltext.]

Spillane,Scott

, p. 1251 (1967)

Novel Biomass-Derived Fe3O4@Pd NPs as Efficient and Sustainable Nanocatalyst for Nitroarene Reduction in Aqueous Media

Zhao, Linwei,Zheng, Kai,Tong, Jianying,Jin, Jianzhong,Shen, Chao

, p. 2607 - 2613 (2019)

Abstract: A novel magnetically recyclable nitrogen-doped Fe3O4@Pd NPs was prepared from the biomass-based materials which was employed as carbon and nitrogen source. The as-prepared catalysts were fully characterized by a variety of physicochemical techniques and were exploited for nitroaromatic hydrogenation with broad scope and excellent chemoselectivity using molecular hydrogen as a reductant. The heterogeneous catalysts can be recovered easily and reused for at least eight recycling reactions without obviously loss of catalytic properties. In addition, using this protocol, the key intermediate of marketed drug Osimertinib could be synthesized easily. Graphical Abstract: [Figure not available: see fulltext.].

Reduction of azo dyes with zero-valent iron

Nam, Sangkil,Tratnyek, Paul G.

, p. 1837 - 1845 (2000)

The reduction of azo dyes by zero-valent iron metal (Fe0) at pH 7.0 in 10 mM HEPES buffer was studied in aqueous, anaerobic batch systems. Orange II was reduced by cleavage of the azo linkage, as evidenced by the production of sulfanilic acid (a substituted aniline). Adsorption of the dyes on iron particles was less than 4% of the initial concentration, and >90% mass balance was achieved by summing aqueous concentrations of dye and product amine. All of the 9 azo dyes tested were reduced with first-order kinetics. The kinetics of decolorization at the λ(max) of each dye were rapid: a typical k(obs) was 0.35 ± 0.01 min-1 for Orange II at 130 rpm on an orbital shaker, corresponding to a surface area normalized rate constant (k(SA)) of 0.21 ± 0.01 L m-2 min-1. The rate of reduction of Crocein Orange G varied with initial dye concentration in a way that suggests saturation of surface sites on the Fe0, and varied with the square-root of mixing rate (rpm) in a manner indicative of mass transfer limited kinetics. Correlation analysis using k(obs) for all of the azo dyes, estimates of their diffusion coefficients, and calculated energies of their lowest unoccupied molecular orbitals (E(LUMO)), gave no strong trends that could be used to derive structure-activity relationships. Using an authentic sample of wastewater from a dye manufacturing operation and construction-grade granular Fe0, rapid decolorization was achieved that was consistent with reduction of azo dyes. (C) 2000 Elsevier Science Ltd. The reduction of azo dyes by zero-valent iron metal (Fe0) at pH 7.0 in 10 mM HEPES buffer was studied in aqueous, anaerobic batch systems. Orange II was reduced by cleavage of the azo linkage, as evidenced by the production of sulfanilic acid (a substituted aniline). Adsorption of the dyes on iron particles was less than 4% of the initial concentration, and >90% mass balance was achieved by summing aqueous concentrations of dye and product amine. All of the 9 azo dyes tested were reduced with first-order kinetics. The kinetics of decolorization at the λmax of each dye were rapid: a typical kobs was 0.35±0.01 min-1 for Orange II at 130 rpm on an orbital shaker, corresponding to a surface area normalized rate constant (kSA) of 0.21±0.01 L m-2 min-1. The rate of reduction of Crocein Orange G varied with initial dye concentration in a way that suggests saturation of surface sites on the Fe0, and varied with the square-root of mixing rate (rpm) in a manner indicative of mass transfer limited kinetics. Correlation analysis using kobs for all of the azo dyes, estimates of their diffusion coefficients, and calculated energies of their lowest unoccupied molecular orbitals (ELUMO), gave no strong trends that could be used to derive structure-activity relationships. Using an authentic sample of wastewater from a dye manufacturing operation and construction-grade granular Fe0, rapid decolorization was achieved that was consistent with reduction of azo dyes.

-

Scott,F.L. et al.

, p. 2666 - 2670 (1972)

-

Homogeneous palladium nanoparticles surface hosts catalyzed reduction of the chromophoric azo (-N=N-) group of dye, acid orange 7 by borohydride in alkaline media

Das, Ranendu Sekhar,Singh, Bula,Mandal, Arabinda,Banerjee, Rupendranath,Mukhopadhyay, Subrata

, p. 746 - 758 (2014)

In alkaline media, well-characterized gelatin-stabilized palladium (GPd) nanoparticles catalyze the reduction of the azo group containing pollutant dye, Acid Orange 7 (AO7) by sodium borohydride (NaBH4) to 1-amino-2-napthol and sulfanilic acid. Kinetic observations and detailed FTIR studies suggests that the reaction follows Langmuir-Hinshelwood kinetic model, where during the reaction both AO7 and borohydride are adsorbed on the GPd surface. Plots of lnko versus ln[AO7] or ln[NaBH4] show that the order of reaction with respect to AO7 and NaBH4 remains almost same over different molar ratios of [NaBH4]/[AO7]. The catalyzed reaction shows an initial induction period (t0) due to a surface-restructuring process of GPd nanoparticles, and (1/t0) can be defined as the rate of surface restructuring. The activation energy of the catalyzed reaction and energy of the surface-restructuring process of GPd are estimated as 22 ± 3 and 25 ± 7 kJ M-1, respectively.

Cyan color-emitting nitrogen-functionalized carbon nanodots (NFCNDs) from Indigofera tinctoria and their catalytic reduction of organic dyes and fluorescent ink applications

Abirami, Natarajan,Arul, Velusamy,Arulmozhi, Rajaram,Kavitha, Ganesan,Vinoth Kumar, Jothi

, p. 27745 - 27756 (2021)

The present study reports the synthesis of nitrogen-functionalized carbon nanodots (NFCNDs) by a low-cost hydrothermal method using the leaf extract of Indigofera tinctoria as a novel carbon precursor. The synthesized NFCNDs were characterized by diverse spectroscopic techniques. The optical properties of N-CNDs were analyzed by UV-visible and fluorescence spectroscopic studies. The quantum yield (QY) for the prepared NFCNDs was found to be 12.6%. The surface morphology, functional groups, and crystallinity of NFCNDs were evaluated by HR-TEM, FT-IR, XRD and Raman spectroscopic methods, respectively. The Raman results revealed the moderate graphite structure of NFCNDs, and the calculated ID/IG value was 0.49. The spherical appearance of the synthesized NFCNDs was confirmed by HR-TEM, and the calculated size of the NFCNDs was 4 nm. The XRD and SAED pattern results gives an evidence for the amorphous nature of the prepared NFCNDs. The thermal stability of NFCNDs was studied by TGA analysis. The resulting NFCNDs acted as a green nanocatalyst and thus efficiently improved the reducing capability of sodium borohydride (NaBH4) in the catalytic reduction of methylene blue (MB) and methyl orange (MO) dyes. Furthermore, the bright cyan emission characteristics of synthesized NFCNDs were utilized as a labeling agent in anti-counterfeiting applications.

-

Voronkov,M.G. et al.

, (1977)

-

Scale-up synthesis of zero-valent iron nanoparticles and their applications for synergistic degradation of pollutants with sodium borohydride

Ravikumar,Dubey, Swati,pulimi, Mrudula,Chandrasekaran, Natarajan,Mukherjee, Amitava

, p. 589 - 598 (2016)

The scale-up synthesis of nZVI (zero-valent iron nanoparticles) was optimized by response surface modeling (RSM). The synthesized nZVI was employed for synergistic degradation of metronidazole (MNZ) or methyl orange (MO) in the presence of sodium borohydr

Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions

Fatima, Touheeth,Duguta, Govardhan,Purugula, Venkanna,Yelike, Hemanth Sriram,Kamatala, Chinna Rajanna

, p. 1001 - 1006 (2020/07/27)

Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 in aqueous acetonitrile medium at room temperature within 1–4 h, while microwave assisted reactions took place within 1–4 min under solvent-free conditions. These observations indicate significant rate accelerations in microwave assisted reactions. which were explained due to the bulk activation of molecules induced by insitu generated high temperatures and pressures when microwaves are transmitted through reaction medium.

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