Conditions | Yield |
---|---|
With hydrazine In ethanol at 80℃; for 0.166667h; Catalytic behavior; chemoselective reaction; | 99.9% |
With ammonium sulfide | |
With hydrogenchloride; tin(ll) chloride |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
A
bis(4-aminophenyl)disulfide
B
sulfanilamide
C
aniline
D
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm; | A n/a B 4.4% C 95.1% D 2.7% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; o-toluenesulfonic acid at 110℃; for 2h; Temperature; | 94% |
Conditions | Yield |
---|---|
With hydrogen; sodium carbonate; palladium on activated charcoal In water for 16h; | 82.1% |
dianilunium sulphate
A
aniline
B
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
at 200℃; under 40 Torr; for 1h; | A n/a B 61% |
at 155℃; Kinetics; thermal decomposition, various temperature; |
A
C20H20N6S2
B
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With hydrogenchloride; sodium dithionite In methanol; water | A 60% B 28% |
3-amino-benzenesulfonic acid, monosodium salt
A
2-amino-1-benzenesulfonic acid
B
aniline
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
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
A
2-aminopyridine
B
bis(4-aminophenyl)disulfide
C
p-nitrobenzenesulfonamide
D
sulfanilamide
E
aniline
F
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sulfuric acid at 180 - 190℃; |
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With sulfuric acid |
4-diazobenzenesulfonic acid
p-toluidine hydrochloride
A
p-methylbenzenediazonium chloride
B
4-aminobenzene sulfonic acid
4-diazobenzenesulfonic acid
o-toluidine hydrochloride
A
4-(4-amino-3-methyl-phenylazo)-benzenesulfonic acid
B
o-toluene-diazonium chloride
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With ammonium hydroxide; copper chloride at 170℃; unter Druck; |
Conditions | Yield |
---|---|
With water |
4-(2-hydroxy-3,5-dimethyl-phenylazo)-benzenesulfonic acid
A
6-amino-2,4-xylenol
B
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
durch Reduktion; |
Conditions | Yield |
---|---|
durch Reduktion; |
4-aminobenzene sulfonic acid
2-nitro-4-(4'-sulfophenylazo)-phenol
A
2,4-diaminophenol
B
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
bei der Reduktion; | |
bei der Reduktion; |
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
at 210 - 215℃; |
oxalic acid
4-(4-hydroxy-[1]naphthylazo)-benzenesulfonic acid
A
[1,4]naphthoquinone
B
4-aminobenzene sulfonic acid
tartrazine
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With bacillus coli |
Conditions | Yield |
---|---|
With sulfuric acid |
8-quinolinol
4-aminobenzene sulfonic acid
(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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.; |
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; | 100% |
4-aminobenzene sulfonic acid
C25H27N3O7S2
Conditions | Yield |
---|---|
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
4-aminobenzene sulfonic acid
sodium 4-((3-ethoxy-4-hydroxyphenyl)diazenyl)benzenesulfonate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In water acid (2 mmol0 and Ag2O (1 mmol) stirred for 2 h; filtered, crystd. on slow evapn. overnight, elem. anal.; | 99% |
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 20℃; Green chemistry; | 99% |
methyl chloroformate
4-aminobenzene sulfonic acid
4-[(methoxycarbonyl)amino]benzenesulfonic acid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry; | 99% |
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; | 89% |
Conditions | Yield |
---|---|
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% |
1,10-phenanthroline-2,9-dicarboxaldehyde
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
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
4-aminobenzene sulfonic acid
N‑(2‑hydroxybenzylidene)‑4‑aminobenzenesulfonic acid sodium salt
Conditions | Yield |
---|---|
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
4-aminobenzene sulfonic acid
4-{[(2-oxo-2,3-dihydro-1H-indol-5-yl)sulfonyl]amino}benzenesulfonic acid
Conditions | Yield |
---|---|
In toluene for 6h; Reflux; | 98% |
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 20℃; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 48h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran; water at 20℃; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 97% |
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
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
4-aminobenzene sulfonic acid
4-(benzoylamino)benzenesulfonic acid
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 20℃; Green chemistry; | 96% |
With sodium chloride In water; acetone for 0.25h; | 60% |
With pyridine |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; | 96% |
salicylaldehyde
4-aminobenzene sulfonic acid
4-((2-hydroxybenzylidene)amino)benzenesulfonic acid
Conditions | Yield |
---|---|
In neat (no solvent, solid phase) at 20℃; for 0.25h; | 96% |
In methanol; water for 1h; Reflux; | 76% |
The IUPAC name of Sulfanilic acid is 4-aminobenzenesulfonic acid. With the CAS registry number 121-57-3, it is also named as Aniline-4-sulfonic acid; Benzenesulfonic acid, 4-amino-. The product's categories are intermediates of dyes and pigments, inorganic & organic chemicals and organics. It is greyish-white crystals or powder which is stable and incompatible with strong oxidizing agents. It will produce toxic nitrogen oxide and sulfur oxide gases when buring. So the storage environment should be ventilate, low-temperature and dry. Keep Sulfanilic acid separate from raw materials of food.
The other characteristics of Sulfanilic acid can be summarized as:
(1)ACD/LogP: -1.568; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -5.05; (4)ACD/LogD (pH 7.4): -5.07; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.63; (13)Molar Refractivity: 40.72 cm3; (14)Molar Volume: 114.49 cm3; (15)Surface Tension: 67.5469970703125 dyne/cm; (16)Density: 1.513 g/cm3.
Preparation of Sulfanilic acid:
It can be obtained by aniline. This reaction needs reagent sulfuric acid monohydrate and solvent 1,2-dichloro-benzene at temperature of 175-180 °C. The reaction time is 3-5 hours. The yield is 87.2%.
Uses of Sulfanilic acid:
It is used to make dyes and sulpha drugs. It is also used in the manufacture pesticides which can cure wheat rust disease. In addition, it can be used in many organic synthesis. For example: It reacts with 6-chloro-pyrimidine-2,4-diamine to get 2,4-diamino-6-p-sulphoanilinopyrimidine. This reaction needs reagent cc HCl and solvent ethanol by heating. The reaction time is 4.0 hours. The yield is 85%.
When you are using Sulfanilic acid, please be cautious about it as the following:
It may cause burns and is irritating to eyes and skin. So people should avoid contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
People can use the following data to convert to the molecule structure.
(1)SMILES:O=S(=O)(O)c1ccc(N)cc1;
(2)Std. InChI:InChI=1S/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10);
(3)Std. InChIKey:HVBSAKJJOYLTQU-UHFFFAOYSA-N.
The following is the toxicity data of Sulfanilic acid:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intravenous | 6gm/kg (6000mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 211, Pg. 367, 1950. | |
rat | LD50 | oral | 12300mg/kg (12300mg/kg) | "Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku," Marhold, J.V., Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha, Czechoslovakia, 1972Vol. -, Pg. 180, 1972. |
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