Conditions | Yield |
---|---|
With sodium hydrogen sulfate; sulfuric acid at 200℃; for 19h; Reagent/catalyst; Temperature; | 99% |
With chlorosulfonic acid; 1,1,2,2-tetrachloroethane |
Conditions | Yield |
---|---|
With hydrogen at 120℃; under 30003 - 37503.8 Torr; for 0.75h; Reflux; | 97% |
With Raney nickel at 90 - 120℃; under 6000.6 - 9750.98 Torr; | 4200 kg |
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; |
Conditions | Yield |
---|---|
With (2,2':6',2''-terpyridine)(pyridine-2-carboxylate)iron(II)chloride; sodium hydroxide In water; acetonitrile | 95% |
2-nitrothiophenol
A
bis(2-nitrophenyl)disulfide
B
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 87℃; for 8h; | A 7% B 87% |
In 1,4-dioxane; water at 87℃; for 6.25h; | A 20.4% B 16.7% |
With water In 1,4-dioxane at 81 - 87℃; Rate constant; Mechanism; Product distribution; various water conc; different reaction times; |
Conditions | Yield |
---|---|
With chloramine-B; sodium hydroxide; palladium dichloride In water; acetonitrile at 80℃; pH=12; | 85% |
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; sodium hydroxide In water; acetonitrile at 39.84℃; Kinetics; Concentration; Solvent; Temperature; |
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. |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid |
Conditions | Yield |
---|---|
With phosphorus; hydrogen iodide at 110℃; im Druckrohr; | |
With sodium hydroxide; zinc |
4-bromo-3-sulfo-benzoic acid
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
With ammonia at 180℃; im Rohr; |
Conditions | Yield |
---|---|
With methanol | |
Multi-step reaction with 2 steps 1: water; chlorine 2: natrium carbonate / Ansaeuern mit Essigsaeure und Kochen mit Eisenpulver View Scheme |
Conditions | Yield |
---|---|
With ethanol; sulfur dioxide | |
With sulfur dioxide; water |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite |
Conditions | Yield |
---|---|
With sodium carbonate Ansaeuern mit Essigsaeure und Kochen mit Eisenpulver; | |
With potassium hydroxide anschliessend Erwaermen mit N2H4+H2O und Palladium/Kohle oder Raney-Nickel; |
Conditions | Yield |
---|---|
man reduziert das bei der Nitrierung entstandene Isomerengemisch nach Zugabe von Magnesiumoxyd mit Eisen und Schwefelsaeure; |
N-trimethylsilylaniline
chlorine ethoxysulfonate
A
2-amino-1-benzenesulfonic acid
B
ethyl phenylamidosulfate
C
N-ethyl-N-phenylamidosulfate
Conditions | Yield |
---|---|
With acetic acid 1) CH2Cl2, (-10)-(-15) deg C, 2 h; reflux, 3 h; 2) (-10)-(-15) deg C, 3 h; Multistep reaction. Further byproducts given; |
aniline sulfate
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid at 40℃; Product distribution; Rate constant; Thermodynamic data; var. temperature, var. reaction time, var. ratio of reagents, presence of tetrabisulfatoboric acid, ΔE(activ.); | |
With sulfuric acid at 180℃; for 7h; Thermodynamic data; Kinetics; Product distribution; ΔE(act.), various time, various temperature, various excess of H2SO4; | |
With sulfur trioxide; mercury(II) sulfate at 7.6℃; for 0.5h; Thermodynamic data; Mechanism; Product distribution; E(activ.), various temperature, SO3 and HgSO4 concentration; |
aniline sulfate
A
2-amino-1-benzenesulfonic acid
B
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene at 180℃; for 0.5h; Rate constant; Thermodynamic data; Kinetics; other temperature (165 and 195 deg C), reaction time 7 h, activation energy; | A 3.9 % Spectr. B 96.1 % Spectr. |
In 1,2-dichloro-benzene at 180℃; for 0.5h; Equilibrium constant; Mechanism; other temperature (165 and 195 deg C), reaction time 7 h; | A 3.9 % Spectr. B 96.1 % Spectr. |
In 1,2-dichloro-benzene at 183℃; for 0.5h; Rate constant; Thermodynamic data; Kinetics; water removal, other solvent and temperature (p-chlorotoluene: 162 deg C, p-bromochlorobenzene: 196 deg C), reaction time 7 h; | A 3.8 % Spectr. B 96.2 % Spectr. |
sodium phenylsulfamate
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
C
aniline
D
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In methanol for 0.0166667h; Product distribution; Irradiation; | A 22.2 % Chromat. B 5.1 % Chromat. C 27.0 % Chromat. D 39.4 % Chromat. |
In methanol Product distribution; Mechanism; Irradiation; varying solvents; | A 22.0 % Chromat. B 5.1 % Chromat. C 27.0 % Chromat. D 39.4 % Chromat. |
dianilunium sulphate
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid; mercury(II) sulfate at 60℃; for 1h; Title compound not separated from byproducts; | A 2.8 % Spectr. B 43.8 % Spectr. C 53.4 % Spectr. |
With sulfuric acid; sulfur trioxide at 90℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sulfuric acid at 90℃; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sulfuric acid; mercury(II) sulfate at 60℃; for 1h; Product distribution; variation of reagent conc., time, temperature, and catalyst rate; | A 2.8 % Spectr. B 43.8 % Spectr. C 53.4 % Spectr. |
3-aminobenzenesulfonic acid
A
2-amino-1-benzenesulfonic acid
B
aniline
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
In methanol for 0.0166667h; Irradiation; | A 15.6 % Turnov. B 37.2 % Turnov. C 39.3 % Turnov. |
aniline
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid at 180℃; for 7h; Yield given. Yields of byproduct given; | |
With sulfuric acid; mercury(II) sulfate at 100℃; for 1h; Title compound not separated from byproducts; | A 2.4 % Spectr. B 32.0 % Spectr. C 65.6 % Spectr. |
With sulfuric acid at 90℃; Kinetics; Rate constant; Thermodynamic data; other temp.(90 - 210 deg C); other conc.H2SO4 (80.06 - 99.71percent); E-activation; |
A
2-amino-1-benzenesulfonic acid
B
4-aminobenzene-1,3-disulfonic acid
D
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
at 160℃; for 8h; Yield given. Yields of byproduct given; | |
at 160℃; for 8h; Product distribution; Mechanism; other di- and trimethylanilinium butylamidosulfates, var. temperatures; |
4-aminobenzene sulfonic acid
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
Conditions | Yield |
---|---|
With sulfuric acid at 180℃; Title compound not separated from byproducts; | |
With sulfuric acid at 180℃; Rate constant; Kinetics; other temperatures; other conc. of H2SO4; E(activ.); | |
With sulfuric acid at 190℃; Product distribution; Rate constant; var. ratio of reactants, object of study - isomerization; | |
With sulfuric acid at 180℃; Thermodynamic data; Rate constant; E(excit.); |
<(2-Nitro-phenyl)sulfonyl>essigsaeure
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
water
aniline
A
2-amino-1-benzenesulfonic acid
B
N-phenylsulfamic acid
diethyl ether
N-Phenylhydroxylamine
A
2-amino-1-benzenesulfonic acid
B
N-phenylsulfamic acid
C
dianilunium sulphate
D
azoxybenzene
aniline
A
2-amino-1-benzenesulfonic acid
B
3-aminobenzenesulfonic acid
C
4-aminobenzene sulfonic acid
Conditions | Yield |
---|---|
at 0 - 95℃; beim Behandeln von Anilin-sulfat; |
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sodium nitrite In water at 30℃; Stage #2: With sodium sulfite In water at 100 - 120℃; Stage #3: With sulfuric acid In water at 130℃; | 99.2% |
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sodium nitrite In water at 30℃; Acidic conditions; Flow reactor; Stage #2: With sodium sulfite In water at 95 - 110℃; Stage #3: With hydrogenchloride In water at 130℃; | 99.1% |
Conditions | Yield |
---|---|
In water acid (2 mmol0 and Ag2O (1 mmol) stirred for 2 h; filtered, crystd. on slow evapn. overnight, elem. anal.; | 96% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 0.0833333h; Stage #2: With hydrogenchloride In water at 0 - 5℃; for 0.5h; Stage #3: acetoacetamido With sodium acetate; sodium hydroxide In ethanol; water for 1h; | 92% |
Conditions | Yield |
---|---|
With sulfuric acid; sodium carbonate; sodium nitrite In water at -10℃; for 0.5h; | 91% |
With sodium hydroxide; sulfuric acid; sodium nitrite | |
With ethanol; mixture of gaseous nitrogen oxides |
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With toluene-4-sulfonic acid In acetonitrile for 0.166667h; Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 10 - 20℃; for 1.16667h; | 91% |
Stage #1: 2-amino-1-benzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With sodium iodide In water at 0 - 50℃; for 14h; | 65% |
Stage #1: 2-amino-1-benzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sodium iodide In water at 0 - 50℃; for 14h; | 60% |
2-amino-1-benzenesulfonic acid
N-ethyl-N,N-diisopropylamine
1-isocyanato-4-trifluoromethoxy-benzene
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 91% |
2-amino-1-benzenesulfonic acid
malononitrile
2-(2-(dicyanomethylene)hydrazinyl)benzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sodium hydroxide In water at 20℃; Stage #2: With hydrogenchloride; sodium nitrite In water at -0.16℃; for 1h; Stage #3: malononitrile With sodium acetate In ethanol; water at -0.16℃; for 1h; Japp-Klingemann reaction; | 90% |
2-amino-1-benzenesulfonic acid
p-chlorphenylisocyanate
N-ethyl-N,N-diisopropylamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 89% |
Conditions | Yield |
---|---|
With sodium carbonate In water at 90℃; for 5h; pH=5 - 7; | 88% |
2-amino-1-benzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 20℃; for 15h; | 88% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: Cyanoaceton With sodium acetate; sodium hydroxide In ethanol; water at 0℃; Japp-Klingemann Hydrazone Synthesis; | 86% |
2-naphthylacetyl chloride
2-amino-1-benzenesulfonic acid
N-ethyl-N,N-diisopropylamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 4h; | 85% |
2-amino-1-benzenesulfonic acid
N-ethyl-N,N-diisopropylamine
p-trifluoromethyl-phenylisocyanate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 85% |
2-amino-1-benzenesulfonic acid
3,4-dichlorophenyl isocyanate
N-ethyl-N,N-diisopropylamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 85% |
1,3,5-trichloro-2,4,6-triazine
2-amino-1-benzenesulfonic acid
4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid
Conditions | Yield |
---|---|
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 1-amino-2-sulfonic acid-4-(3-amino-2,4,6-trimethyl-5-sulfoamidophenyl)anthraquinone monosodium salt In water at 0 - 5℃; for 4h; pH=4- 6.5; Stage #2: 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid In water at 28 - 35℃; pH=3.5 - 4; Stage #3: 2-amino-1-benzenesulfonic acid Further stages; | 84.23% |
2-amino-1-benzenesulfonic acid
4-morpholino-2-naphthol
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With potassium carbonate In water Stage #2: With hydrogenchloride; sodium nitrite In water at 5 - 10℃; Stage #3: 4-morpholino-2-naphthol With sodium hydroxide In water for 0.5h; Cooling; | 84% |
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With potassium carbonate In water Stage #2: With hydrogenchloride; sodium nitrite In water at 5℃; Stage #3: β-naphthol With sodium hydroxide In water for 0.5h; Cooling; | 84% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; | 84% |
2-amino-1-benzenesulfonic acid
4-Methoxyphenyl isocyanate
N-ethyl-N,N-diisopropylamine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 84% |
2-amino-1-benzenesulfonic acid
2,3-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With water In methanol at 20℃; for 24h; | 83% |
2-amino-1-benzenesulfonic acid
2-iodobenzenesulfonic acid
Conditions | Yield |
---|---|
Stage #1: 2-amino-1-benzenesulfonic acid With sodium carbonate In water Stage #2: With sodium nitrite In water at 0℃; for 0.75h; Further stages; | 82% |
durch Diazotierung und Zersetzung der Diazoverbindung mit rauch.Jodwasserstoffsaeure; | |
With sulfuric acid Diazotization.Erwaermen des Reaktionsprodukts mit Kaliumjodid; |
Conditions | Yield |
---|---|
In ethanol; water at 20℃; for 24h; | 82% |
The molecular structure of Aniline-2-sulfonic acid (CAS NO.88-21-1):
IUPAC Name: 2-Aminobenzenesulfonic acid
Molecular Weight: 173.18968 g/mol
Molecular Formula: C6H7NO3S
Density: 1.512 g/cm3
Melting Point: 300 °C
Index of Refraction: 1.629
Molar Refractivity: 40.71 cm3
Molar Volume: 114.4 cm3
Surface Tension: 67.5 dyne/cm
Water Solubility: sparingly soluble
XLogP3: 0.4
H-Bond Donor: 2
H-Bond Acceptor: 4
Rotatable Bond Count: 1
Exact Mass: 173.014664
MonoIsotopic Mass: 173.014664
Topological Polar Surface Area: 80.4
Heavy Atom Count: 11
Canonical SMILES: C1=CC=C(C(=C1)N)S(=O)(=O)O
InChI: InChI=1S/C6H7NO3S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
InChIKey: ZMCHBSMFKQYNKA-UHFFFAOYSA-N
EINECS: 201-810-9
Product Categories: Intermediates of Dyes and Pigments
Aniline-2-sulfonic acid (CAS NO.88-21-1) is used as dyes intermediates.
1. | mma-sat 6667 µg/plate | EMMUEG Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1. |
Reported in EPA TSCA Inventory.
Hazard Codes: C
Risk Statements: 34
R34:Causes burns.
Safety Statements: 26-36/37/39-45-28A
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 2585 8/PG 3
WGK Germany: 3
RTECS: DB4727700
HazardClass: 8
PackingGroup: III
Aniline-2-sulfonic acid (CAS NO.88-21-1) is also named as 1-Aminobenzene-2-sulfonic acid ; 2-Aminobenzenesulfonic acid ; AI3-52212 ; Aniline-2-sulfonic acid ; Aniline-o-sulfonic acid ; Aniline-o-sulphonic acid ; Anilino-o-sulfonic acid ; Anilino-o-sulphonic acid ; CCRIS 4575 ; NSC 147 ; Orthanilic acid ; o-Aminobenzenesulfonic acid ; o-Aminophenylsulfonic acid ; o-Sulfanilic acid . Aniline-2-sulfonic acid (CAS NO.88-21-1) is light brown powder. It is soluble in water. Aniline-2-sulfonic acid is an amino acid. It reacts weakly with both acids and bases. Flash point data for Aniline-2-sulfonic acid are not available, however it is probably combustible.
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