13244-33-2

Basic information

• Product Name: p-Anisidine-3-sulfonic acid
• Synonyms: 4-Aminoanisole-3-sulfonic Acid 2-Amino-5-methoxybenzenesulfonic Acid 4-Methoxyaniline-2-sulfonic Acid;p-Anisidine-3-Sulfonic;p-Anisidine-2-sulfonic Acid;2-amino-5-methoxy-benzenesulfonicaci;4-methoxy-2-sulfoaniline;kyselina4-aminoanisol-3-sulfonova;4-AMINOANISOLE-3-SULFONIC ACID;4-METHOXYANILINE-2-SULFONIC ACID
• CAS NO: 13244-33-2
• Molecular Formula: C₇H₉NO₄S
• Molecular Weight: 203.22
• EINECS: 236-224-2
• Mol File: 13244-33-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 314-318 C
• Appearance: beige powder
• Density: 1.4540 (rough estimate)
• Refractive Index: 1.6370 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.37±0.42(Predicted)
• CAS DataBase Reference: p-Anisidine-3-sulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: p-Anisidine-3-sulfonic acid(13244-33-2)
• EPA Substance Registry System: p-Anisidine-3-sulfonic acid(13244-33-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-43
• Safety Statements: 37/39-26-36-36/37
• RTECS: DB4950000
• Hazardous Substances Data: 13244-33-2(Hazardous Substances Data)

Usage

Chemical Properties

light beige powder

InChI:InChI=1/C7H9NO4S/c1-12-5-2-3-6(8)7(4-5)13(9,10)11/h2-4H,8H2,1H3,(H,9,10,11)/p-1

Synthetic route

6-methoxy-1,3-benzothiazole (2942-13-4) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 4.5h;	96%

2-(2,2-dimethylpropionylamino)-5-methoxy-benzenesulfonic acid (1190954-82-5) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
With hydrogenchloride; water at 85℃; for 21h;	95%

C6H5NO4S(2-)*2Na(1+) + methyl iodide (74-88-4) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Stage #1: C6H5NO4S(2-)*2Na(1+); methyl iodide at 20℃; under 760.051 Torr; for 0.666667h; Stage #2: With sulfuric acid at 115℃; for 1.16667h; Temperature;	86%

di(p-methoxy)anilinium sulfate → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
for 0.0666667h; microwave irradiation;	58%

sodium 5-methoxy-2-(phenylazo)benzenesulfonate → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
With sodium dithionite In water at 80 - 95℃;	51%

trisodium 7-({4-chloro-6-[(3-sulphonatophenyl)amino]-1,3,5-triazin-2-yl}methylamino)-4-hydroxy-3-[(4-methoxy-2-sulphonatophenyl)azo]naphthalene-2-sulphonate (70865-26-8) + isopropyl alcohol (67-63-0) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) + 3-Amino-7-{[4-chloro-6-(3-sulfo-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino}-4-hydroxy-naphthalene-2-sulfonic acid + acetone (67-64-1)

Conditions	Yield
In water Irradiation;

acidic sulfate p-anisidine → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

para-methoxynitrobenzene (100-17-4) + disulfite → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

sodium 5-hydroxy-2-(phenylazo)benzenesulfonate → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / NaOH / H2O / 5 h / 60 °C / pH 9.0 2: 51 percent / Na2S2O4 / H2O / 80 - 95 °C View Scheme

4-methoxy-N-pivaloylaniline (56619-94-4) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; pentane / 3.33 h / -78 - -15 °C / Inert atmosphere 1.2: 18 h / -10 - 20 °C / Inert atmosphere 2.1: hydrogenchloride; water / 21 h / 85 °C View Scheme

4-methoxy-aniline (104-94-9) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / water; acetic acid 2.1: n-butyllithium / tetrahydrofuran; pentane / 3.33 h / -78 - -15 °C / Inert atmosphere 2.2: 18 h / -10 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; water / 21 h / 85 °C View Scheme

4-amino-phenol (123-30-8) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid / 1.75 h / 40 °C / 11251.1 Torr 2.1: sodium hydroxide / 0.83 h / 55 °C 3.1: 0.67 h / 20 °C / 760.05 Torr 3.2: 1.17 h / 115 °C View Scheme

phenol (108-95-2) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sulfuric acid; sodium nitrate / water / 0.67 h / 15 °C / pH 6 1.2: 0.83 h / 20 - 30 °C / 11251.1 Torr / Sealed tube 2.1: zinc; hydrogenchloride / water / 0.17 h / 85 - 100 °C 3.1: sulfuric acid / 1.75 h / 40 °C / 11251.1 Torr 4.1: sodium hydroxide / 0.83 h / 55 °C 5.1: 0.67 h / 20 °C / 760.05 Torr 5.2: 1.17 h / 115 °C View Scheme

4-nitro-phenol (100-02-7) → 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: zinc; hydrogenchloride / water / 0.17 h / 85 - 100 °C 2.1: sulfuric acid / 1.75 h / 40 °C / 11251.1 Torr 3.1: sodium hydroxide / 0.83 h / 55 °C 4.1: 0.67 h / 20 °C / 760.05 Torr 4.2: 1.17 h / 115 °C View Scheme

(E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid → 4-(Diethylamino)salicylaldehyde (17754-90-4) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2)

Conditions	Yield
With sodium hypochlorite In aq. phosphate buffer; N,N-dimethyl-formamide pH=7.4;

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → C7H6N2O4S

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 10℃; for 3h;	98%

bismuth(III) tert-butoxide + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → Bi(3+)*3C7H8NO4S(1-)

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	97%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) + silver(l) oxide (20667-12-3) → [Ag(6-amino-3-methoxybenzosulfonate)]

Conditions	Yield
In water acid (2 mmol0 and Ag2O (1 mmol) stirred for 2 h; filtered, crystd. on slow evapn. overnight, elem. anal.;	93%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-amino-5-hydroxy-benzenesulfonic acid (2835-05-4)

Conditions	Yield
With hydrogen bromide at 100℃; for 18h;	92.3%

aminosulfonic acid (5329-14-6) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-sulfo-4-methoxybenzoic acid (40567-33-7)

Conditions	Yield
With sulfuric acid; sodium nitrite; palladium(II) chloride In water; acetonitrile	88%

4-(Diethylamino)salicylaldehyde (17754-90-4) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → (E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid

Conditions	Yield
In methanol for 3h;	86.8%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-iodo-5-methoxybenzenesulfonic acid

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With sodium carbonate In water Stage #2: With sodium nitrite In water at 0℃; for 0.75h; Further stages;	85%

4-hydroxy-1-methyl-2(1H)-quinolone (1677-46-9) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → (E)-2-((4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)diazenyl)-5-methoxybenzenesulfonic acid

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With sodium carbonate In water at 0 - 5℃; Stage #2: With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.833333h; Stage #3: 4-hydroxy-1-methyl-2(1H)-quinolone With sodium hydroxide at 0 - 5℃; for 4h; pH=6 - 7;	64%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-azido-5-methoxybenzenesulfonic acid (871831-99-1)

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 12h;	60%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → sodium 2-iodo-5-methoxybenzenesulfonate

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: With sodium iodide In water at 0 - 50℃;	40%

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-azido-5-methoxy-benzenesulfonyl chloride (1025996-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: 60 percent / NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating View Scheme

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-azido-5-methoxy-N-(2-methoxyethyl)benzenesulfonamide (871832-03-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: 60 percent / NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C View Scheme

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-N-(2-methoxyethyl)-3-n-butylamino-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: 60 percent / NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2 / 16 h / 25 °C 4.2: 71 percent / 1,2-dichloro-ethane / 24 h / 80 °C View Scheme

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-N-(2-methoxyethyl)-3-(3-fluoro-4-methylphenylamino)-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: 60 percent / NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2 / 16 h / 25 °C 4.2: 54 percent / 1,2-dichloro-ethane / 24 h / 80 °C View Scheme

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → 2-N-(2-methoxyethyl)-3-(4-fluorophenylsulfonylamino)-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: 60 percent / NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2 / 16 h / 25 °C 4.2: 66 percent / 1,2-dichloro-ethane / 24 h / 80 °C View Scheme

C33H20Cl2N6O12S3 (705980-65-0) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → C40H28ClN7O16S4

Conditions	Yield
With sodium hydroxide; Lipal OH In water at 60 - 70℃; for 0.5h; pH=5 - 6;

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → C7H7N2O4S(1+)*Cl(1-)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 5 - 10℃; Product distribution / selectivity;

2,5-Dimethylaniline (95-78-3) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → C23H25N5O4S (888322-60-9)

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 25 - 30℃; for 2h; Stage #2: 2,5-Dimethylaniline With sodium carbonate In water at 20 - 30℃; pH=3;

2,5-Dimethylaniline (95-78-3) + 2-amino-5-methoxybenzenesulfonic acid (13244-33-2) → C15H17N3O4S (1204777-89-8)

Conditions	Yield
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 5 - 10℃; for 1h; Stage #2: 2,5-Dimethylaniline With sodium carbonate In water at 30 - 40℃; pH=3;
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 5 - 10℃; for 1h; Stage #2: 2,5-Dimethylaniline With hydrogenchloride; sodium carbonate In water at 30 - 40℃; pH=3;
Stage #1: 2-amino-5-methoxybenzenesulfonic acid With sodium hydroxide In water Stage #2: With hydrogenchloride; sodium nitrite In water at 5 - 10℃; for 1h; Stage #3: 2,5-Dimethylaniline With sodium carbonate In water pH=3;

2-amino-5-methoxybenzenesulfonic acid (13244-33-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride (1246251-58-0)

Conditions	Yield
With thionyl chloride at 70℃; for 1.5h;

Upstream product

• 70865-26-8 trisodium 7-({4-chloro-6-[(3-sulphonatophenyl)amino]-1,3,5-triazin-2-yl}methylamino)-4-hydroxy-3-[(4-methoxy-2-sulphonatophenyl)azo]naphthalene-2-sulphonate 
• 67-63-0 isopropyl alcohol 
• 100-17-4 para-methoxynitrobenzene 
• 2942-13-4 6-methoxy-1,3-benzothiazole 
• 1190954-82-5 2-(2,2-dimethylpropionylamino)-5-methoxy-benzenesulfonic acid 
• 56619-94-4 4-methoxy-N-pivaloylaniline 
• 104-94-9 4-methoxy-aniline 
• 123-30-8 4-amino-phenol 
• 74-88-4 methyl iodide 
• 108-95-2 phenol 
• 100-02-7 4-nitro-phenol 

Downstream Products

• 871831-99-1 2-azido-5-methoxybenzenesulfonic acid 
• 888322-60-9 C₂₃H₂₅N₅O₄S 
• 1204777-89-8 C₁₅H₁₇N₃O₄S 
• 1246251-58-0 N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride 
• 2835-05-4 2-amino-5-hydroxy-benzenesulfonic acid 
• 25254-23-3 C₂₀H₁₄Cl₂N₆O₈S₂ 
• 16452-06-5 Gamma Acid 
• 40567-33-7 2-sulfo-4-methoxybenzoic acid 

Relevant articles and documents

An imine-based colorimetric chemodosimeter for the detection of hypochlorite (ClO -) in aqueous media: its application in test strips and real water samples

Abstract: A highly selective colorimetric chemodosimeter ASAD, (E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid, was readily synthesized and characterized. The probe ASAD could selectively recognize hypochlorite (ClO -) through an oxidative cleavage of C=N bond with a color change from yellow to colorless and detected it down to a low concentration of 0.95 μ M. Importantly, ASAD could be employed as a practical and efficient optical sensor for ClO - in test strips and water samples. Moreover, the detection process of ASAD to hypochlorite was demonstrated by UV-vis spectroscopy, NMR titration and theoretical calculations. Graphical abstract: A highly selective colorimetric chemodosimeter ASAD was developed to selectively recognize hypochlorite (ClO -) through an oxidative cleavage of C=N bond with color change from yellow to colorless and could detect it down to a low concentration of 0.95 μ M.

Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids

Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting phenyl ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H2O-D2O and the reactions were carried out at different temperatures. Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (KC) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced.

Preparation, crystal structure and microwave studies on ring-substituted arylammonium hydrogen sulfate salts

Three ring substituted arylammonium hydrogen sulfates (RSAHS)/ring substituted dianilinium sulfates (RDAS) have been prepared from corresponding arylamines by treatment with excess conc. H2SO4 and characterized by X-ray crystallography, elemental, gravimetric and spectral analyses. The RSAHS/RDAS salts yield the corresponding ring substituted amino benzene sulfonic acids (RSABSA) when subjected to microwave irradiation. It is observed that these salts undergo transformation to acid in solid state via proton transfer reaction prior to sulfonation.