Sulfanilic acid

Base Information

• Chemical Name: Sulfanilic acid
• CAS No.: 121-57-3
• Deprecated CAS: 856062-06-1
• Molecular Formula: C6H7NO3S
• Molecular Weight: 173.192
• Hs Code.: H2N)C6H4SO3H MOL WT. 173.19
• European Community (EC) Number: 285-231-7,204-482-5,290-689-6,290-691-7,286-256-6,305-460-9
• ICSC Number: 0569
• NSC Number: 7170
• UN Number: 2585
• UNII: 434Z8C2635
• DSSTox Substance ID: DTXSID6024464
• Nikkaji Number: J2.924F
• Wikipedia: Sulfanilic Acid
• Wikidata: Q253746
• Metabolomics Workbench ID: 51344
• ChEMBL ID: CHEMBL1566888
• Mol file: 121-57-3.mol

Synonyms:4-aminobenzenesulfonic acid;4-aminobenzenethiol;4-sulfanilic acid;4-sulfanilic acid, sodium salt;4-sulfanilic acid, zinc (2:1) salt;para-aminobenzenesulfonic acid

Chemical Property of Sulfanilic acid

Chemical Property:

• Appearance/Colour: greyish-white crystals or powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 500oC
• PKA: 3.24(at 25℃)
• PSA: 88.77000
• Density: 1.512 g/cm³
• LogP: 2.17750
• Storage Temp.: Store in dark!
• Solubility.: 10g/l
• Water Solubility.: 0.1 g/100 mL (20 ºC)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 173.01466426
• Heavy Atom Count: 11
• Complexity: 211
• Transport DOT Label: Corrosive

Purity/Quality:

99%min ^*data from raw suppliers

Sulfanilic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: C,Xi
• Statements: 36/38-43-34
• Safety Statements: 26-36/37/39-45-37-24-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: UVCB,Nitrogen Compounds -> Aminobenzenesulfonic Acids
• Canonical SMILES: C1=CC(=CC=C1N)S(=O)(=O)O
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance is mildly irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Chemical Composition and Structure: Sulfanilic acid typically exists as a white to off-white crystalline solid with a slight odor. It is soluble in water and has a melting point around 288-290°C. Sulfanilic acid has the chemical formula C6H7NO3S, with a molecular weight of 173.19 g/mol. It contains an amino group (NH2) and a sulfonic acid group (SO3H) attached to a benzene ring.
• Uses and Mechanism of Action: In chemistry, sulfanilic acid serves as a precursor in the synthesis of various compounds, including dyes, pharmaceuticals, and coordination polymers.^[4]; In dosimetry, sulfanilic acid is used as a dosimeter in low-dose ionizing radiation (<30?Gy), exhibiting electron spin resonance (ESR) signals proportional to the radiation dose.^[2]; In spectroscopic studies, sulfanilic acid is employed to explore electronic and vibrational properties through periodic and non-periodic density functional theory (DFT) calculations.^[1]; In biology and environmental science, sulfanilic acid and its derivatives are studied for potential antibacterial properties and their role in photocatalysis for environmental remediation.
• History and Development: Sulfanilic acid has been used industrially for many years, particularly in the dye industry. Its synthesis from readily available starting materials has made it a versatile compound for various applications.
• Analysis Method: The purity and identity of sulfanilic acid can be determined using various spectroscopic techniques such as FTIR, Raman spectroscopy, UV-Vis spectroscopy, and ESR spectroscopy. These methods help ensure product quality and consistency, as well as provide insights into its molecular structure and properties.
• Production Methods: Sulfanilic acid is primarily synthesized from aniline and concentrated sulfuric acid. It can also be obtained as a byproduct in the production of aniline and is widely available commercially.^[3]
• References: [1] Vibrational spectra and molecular structure of sulfanilic acid: IR and low temperature Raman studies and DFT investigation of monomeric and dimeric forms; DOI 10.1016/j.molstruc.2022.134143; [2] The study of dosimetric properties of sulfanilic acid in low radiation dose range using the ESR technique; DOI 10.1080/10420150.2024.2306609; [3] Quantum computational, spectroscopic, Hirshfeld surface, electronic state and molecular docking studies on sulfanilic acid: An anti-bacterial drug; DOI 10.1016/j.molliq.2021.117150; [4] Treatment of high salinity sulfanilic acid wastewater by bipolar membrane electrodialysis; DOI 10.1016/j.seppur.2021.119842; [5] Tailoring photocatalytic activity of graphitic carbon nitride using sulfanilic acid and incorporating in chitosan beads: Cr(VI) removal from aqueous solutions; DOI 10.1016/j.jiec.2023.09.047

Technology Process of Sulfanilic acid

There total 241 articles about Sulfanilic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.1%

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene (57-67-0,61116-95-8) → bis(4-aminophenyl)disulfide (722-27-0) + sulfanilamide (63-74-1) + aniline (62-53-3) + 4-aminobenzene sulfonic acid (121-57-3,856062-06-1)

Guidance literature:

In methanol; for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;

DOI:10.1002/ardp.19843171103

Reference yield: 39.3%

3-amino-benzenesulfonic acid, monosodium salt (1126-34-7) → 2-amino-1-benzenesulfonic acid (88-21-1) + aniline (62-53-3) + 4-aminobenzene sulfonic acid (121-57-3,856062-06-1)

Guidance literature:

With disodium hydrogenphosphate; sodium dihydrogenphosphate; In methanol; for 0.0166667h; Product distribution; Mechanism; Irradiation; effect of solvent and pH;

DOI:10.1039/c39870001571

Reference yield: 29.1%

sulphapyridine (144-83-2) → 2-aminopyridine (504-29-0) + bis(4-aminophenyl)disulfide (722-27-0) + p-nitrobenzenesulfonamide (6325-93-5) + sulfanilamide (63-74-1) + aniline (62-53-3) + 4-aminobenzene sulfonic acid (121-57-3,856062-06-1)

Guidance literature:

In methanol; for 48h; Product distribution; Mechanism; Irradiation; λ=254 nm;

DOI:10.1002/ardp.19843171103

upstream raw materials:

2-amino-1-benzenesulfonic acid

N,N'-Diphenyloxamid

succinic acid

N-phenylbenzenesulfonamide

Downstream raw materials:

4-phenylazo-benzenesulfonic acid

N-[8]quinolylmethylene-sulfanilic acid

(E)-4-((8-hydroxyquinolin-5-yl)diazenyl)benzenesulfonic acid

4-(4-ethoxy-2,6-diamino-[3]pyridylazo)-benzenesulfonic acid

Refernces

• 1、 Lebegue, Estelle,Madec, Lenaic,Brousse, Thierry,Gaubicher, Joel,Levillain, Eric,Cougnon, Charles. "Modification of activated carbons based on diazonium ions in situ produced from aminobenzene organic acid without addition of other acid". . p. 12221 - 12223. Retrieved 2011.
• 2、 Jacobs,Othmer,Hokanson. "". . p. 321. Retrieved 1943.
• 3、 Jamil, Saba,Ahmad, Zunaira,Ali, Muhammad,Rauf Khan, Shanza,Ali, Sarmed,Amen Hammami, Mohamed,Haroon, Muhammad,Saleh, Tawfik A.,Ramzan Saeed Ashraf Janjua, Muhammad. "Synthesis and characterization of polyaniline/nickel oxide composites for fuel additive and dyes reduction". . . Retrieved 2021.
• 4、 Shen, Nan,Xia, Xiu-Yang,Chen, Yun,Zheng, Hang,Zhong, Yong-Chen,Zeng, Raymond J.. "Palladium nanoparticles produced and dispersed by Caldicellulosiruptor saccharolyticus enhance the degradation of contaminants in water". . p. 15559 - 15565. Retrieved 2015.
• 5、 Alexander. "". . p. 1599,1600. Retrieved 1947.
• 6、 Lau, Yen-Yie,Wong, Yee-Shian,Teng, Tjoon-Tow,Morad, Norhashimah,Rafatullah, Mohd,Ong, Soon-An. "Degradation of cationic and anionic dyes in coagulation-flocculation process using bi-functionalized silica hybrid with aluminum-ferric as auxiliary agent". . p. 34206 - 34215. Retrieved 2015.
• 7、 Tzeng, Tai-Wei,Wang, Shan-Li,Chen, Chiing-Chang,Tan, Chen-Chung,Liu, Yu-Ting,Chen, Tsan-Yao,Tzou, Yu-Min,Chen,Hung. "Photolysis and photocatalytic decomposition of sulfamethazine antibiotics in an aqueous solution with TiO2". . p. 69301 - 69310. Retrieved 2016.
• 8、 Scott,Spillane. "". . p. 2707. Retrieved 1967.
• 9、 Xiao, Xiang,Zhu, Wen-Wen,Lei, Yu-Bin,Liu, Qiu-Yue,Li, Qian,Li, Wen-Wei. "Zwitterionic buffer-induced visible light excitation of TiO2 for efficient pollutant photodegradation". . p. 35449 - 35454. Retrieved 2016.
• 10、 -. "Preparation method of p-amino benzene sulfonic acid". Paragraph 0042; 0045-0048; 0051-0053. . Retrieved 2021/07/17.