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Basic Information

Molecular Structure:
CAS No.:	121-57-3
Name:	Sulfanilic acid
Article Data:	241

Formula:	C₆H₇NO₃S
Molecular Weight:	173.192
Synonyms:	Benzenesulfonic acid,4-amino-;Benzenesulfonic acid, 4-amino-;4-Aminobenzenesulfonic acid;4-Aminobenzenesulfonate;p-aminophenylsulfonic acid;aniline-p-sulphonic acid;Aniline-4-sulfonic acid;p-Aminobenzenesulfonic acid;aniline-p-sulfonic acid;Rough sulfanilic acid;P-Aminobenzene Sulfonic acid;Para amino benzene sulphonic acid;4-Aminobenzene Sulfonic Acid;4-Anilinesulfonic acid;p-Amino Benzene Sulfonic acid;
EINECS:	204-482-5
Density:	1.512 g/cm³
Melting Point:	>300 °C(lit.)
Boiling Point:	500oC
Solubility:	0.1 g/100 mL (20 °C) in water
Appearance:	greyish-white crystals or powder
Hazard Symbols:	Xi,C
Risk Codes:	36/38-43-34
Safety:	26-36/37/39-45-37-24
Transport Information:	UN 2790 8/PG 3
PSA:	88.77000
LogP:	2.17750

Synthetic route

: 138-42-1
p-nitrobenzenesulfonic acid

: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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

: 62-53-3
aniline

: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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%

: 62-53-3
aniline

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

B: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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;

: 57-67-0
1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

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

B: 63-74-1
sulfanilamide

C: 62-53-3
aniline

D: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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%

...Expand

: 123-30-8
4-amino-phenol

: 121-57-3
4-aminobenzene sulfonic acid

Conditions

Conditions	Yield
With aluminum (III) chloride; o-toluenesulfonic acid at 110℃; for 2h; Temperature;	94%

: 2369-25-7
4-amino-3-fluorobenzenesulfonic acid

: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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

: 542-16-5, 2424-53-5, 20305-50-4, 29961-02-2
dianilunium sulphate

A: 62-53-3
aniline

B: 121-57-3
4-aminobenzene sulfonic acid

Conditions

Conditions	Yield
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

A: 77747-65-0
C20H20N6S2

B: 121-57-3
4-aminobenzene sulfonic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium dithionite In methanol; water	A 60% B 28%

: 1126-34-7
3-amino-benzenesulfonic acid, monosodium salt

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

B: 62-53-3
aniline

C: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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.

...Expand

: 144-83-2
sulphapyridine

A: 504-29-0
2-aminopyridine

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

C: 6325-93-5
p-nitrobenzenesulfonamide

D: 63-74-1
sulfanilamide

E: 62-53-3
aniline

F: 121-57-3
4-aminobenzene sulfonic acid

Conditions

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%

...Expand

Raw Materials

98-95-3

6343-76-6

3989-50-2

17040-79-8

103-71-9

98-11-3

2484-88-0

7553-56-2

Downstream Products

147-82-0

712-24-3

608-33-3

137-51-9

121-47-1

118-79-6

97-02-9

103-50-4

Total:164 Page 1 of 5 1 2 3 4 5 Next>>

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

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.