p-Anisidine-3-sulfonic acid supplier

Name
p-Anisidine-3-sulfonic acid
EINECS 236-224-2
CAS No. 13244-33-2
Article Data13
CAS DataBase
Density 1.467 g/cm³
Solubility
Melting Point 314-318 °C
Formula C₇H₉NO₄S
Boiling Point
Molecular Weight 203.219
Flash Point
Transport Information
Appearance beige powder
Safety 37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 1-Amino-4-methoxybenzene-2-sulfonicacid;4-Amino-3-sulfoanisole;4-Aminoanisole-3-sulfonic acid;4-Anisidine-2-sulfonic acid;4-Methoxy-1-aminobenzene-2-sulfonic acid;4-Methoxy-2-sulfoaniline;4-Methoxyaniline-2-sulfonic acid;
PSA 98.00000
LogP 2.18610

Synthetic route

: 2942-13-4
6-methoxy-1,3-benzothiazole

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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%

: 1190954-82-5
2-(2,2-dimethylpropionylamino)-5-methoxy-benzenesulfonic acid

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: C6H5NO4S(2-)*2Na(1+)

: 74-88-4
methyl iodide

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

Conditions	Yield
for 0.0666667h; microwave irradiation;	58%

: sodium 5-methoxy-2-(phenylazo)benzenesulfonate

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 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

A: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

B: 3-Amino-7-{[4-chloro-6-(3-sulfo-phenylamino)-[1,3,5]triazin-2-yl]-methyl-amino}-4-hydroxy-naphthalene-2-sulfonic acid

C: 67-64-1
acetone

Conditions

Conditions	Yield
In water Irradiation;

...Expand

acidic sulfate p-anisidine: acidic sulfate p-anisidine

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 100-17-4
para-methoxynitrobenzene

disulfite: disulfite

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: sodium 5-hydroxy-2-(phenylazo)benzenesulfonate

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 56619-94-4
4-methoxy-N-pivaloylaniline

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 104-94-9
4-methoxy-aniline

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 123-30-8
4-amino-phenol

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 108-95-2
phenol

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 100-02-7
4-nitro-phenol

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

A: 17754-90-4
4-(Diethylamino)salicylaldehyde

B: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: C7H6N2O4S

Conditions

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

: bismuth(III) tert-butoxide

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: Bi(3+)*3C7H8NO4S(1-)

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 20667-12-3
silver(l) oxide

: [Ag(6-amino-3-methoxybenzosulfonate)]

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 2835-05-4
2-amino-5-hydroxy-benzenesulfonic acid

Conditions

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

: 5329-14-6
aminosulfonic acid

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 40567-33-7
2-sulfo-4-methoxybenzoic acid

Conditions

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

: 17754-90-4
4-(Diethylamino)salicylaldehyde

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: (E)-2-((4-(diethylamino)-2-hydroxybenzylidene)amino)-5-methoxybenzenesulfonic acid

Conditions

Conditions	Yield
In methanol for 3h;	86.8%

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 2-iodo-5-methoxybenzenesulfonic acid

Conditions

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%

: 1677-46-9
4-hydroxy-1-methyl-2(1H)-quinolone

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: (E)-2-((4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)diazenyl)-5-methoxybenzenesulfonic acid

Conditions

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%

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 871831-99-1
2-azido-5-methoxybenzenesulfonic acid

Conditions

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%

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: sodium 2-iodo-5-methoxybenzenesulfonate

Conditions

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%

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 1025996-94-4
2-azido-5-methoxy-benzenesulfonyl chloride

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 871832-03-0
2-azido-5-methoxy-N-(2-methoxyethyl)benzenesulfonamide

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 2-N-(2-methoxyethyl)-3-n-butylamino-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 2-N-(2-methoxyethyl)-3-(3-fluoro-4-methylphenylamino)-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 2-N-(2-methoxyethyl)-3-(4-fluorophenylsulfonylamino)-7-methoxy-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

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

: 705980-65-0
C33H20Cl2N6O12S3

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: C40H28ClN7O16S4

Conditions

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

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: C7H7N2O4S(1+)*Cl(1-)

Conditions

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

: 95-78-3
2,5-Dimethylaniline

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 888322-60-9
C23H25N5O4S

Conditions

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;

: 95-78-3
2,5-Dimethylaniline

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

: 1204777-89-8
C15H17N3O4S

Conditions

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;

: 13244-33-2
2-amino-5-methoxybenzenesulfonic acid

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

: 1246251-58-0
N-[[[2-(chlorosulphonyl)-4-methoxyphenyl]amino]methylene]-N-methyl-methanaminium chloride

Conditions

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

p-Anisidine-3-sulfonic acid Consensus Reports

Reported in EPA TSCA Inventory.

p-Anisidine-3-sulfonic acid Specification

The 4-Aminoanisole-3-sulfonic acid is an organic compound with the formula C₇H₉NO₄S. The IUPAC name of this chemical is 2-amino-5-methoxybenzenesulfonic acid. With the CAS registry number 13244-33-2 and EINECS 236-224-2, it is also named as Benzenesulfonic acid, 2-amino-5-methoxy-. The classification code is Skin / Eye Irritant. When heated to decomposition it emits very toxic fumes of SO_x and NO_x.

The other characteristics of 4-Aminoanisole-3-sulfonic acid can be summarized as: (1)ACD/LogP: 0.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.15; (4)ACD/LogD (pH 7.4): -3.16; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 64.22 Å²; (13)Index of Refraction: 1.595; (14)Molar Refractivity: 47.08 cm³; (15)Molar Volume: 138.4 cm³; (16)Polarizability: 18.66×10^-24 cm³; (17)Surface Tension: 60.8 dyne/cm; (18)Rotatable Bond Count: 2; (19)Exact Mass: 203.025228; (20)MonoIsotopic Mass: 203.025228; (21)Topological Polar Surface Area: 98; (22)Heavy Atom Count: 13; (23)Complexity: 258.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and 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 gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=S(=O)(O)c1c(ccc(OC)c1)N
2. 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)
3. InChIKey:KZKGEEGADAWJFS-UHFFFAOYAN

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	10gm/kg (10000mg/kg)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1055, 1986.

Product Name

p-Anisidine-3-sulfonic acid

Synthetic route

p-Anisidine-3-sulfonic acid Consensus Reports

p-Anisidine-3-sulfonic acid Specification

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