4-Aminophenol

Base Information

• Chemical Name: 4-Aminophenol
• CAS No.: 123-30-8
• Deprecated CAS: 52985-09-8,1309774-68-2
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 2922.29 Oral rat LD50: 375 mg/kg
• European Community (EC) Number: 204-616-2
• NSC Number: 1545
• UN Number: 2512
• UNII: R7P8FRP05V
• DSSTox Substance ID: DTXSID3024499
• Nikkaji Number: J3.620J
• Wikipedia: 4-Aminophenol
• Wikidata: Q2548040
• RXCUI: 1435279
• Metabolomics Workbench ID: 37637
• ChEMBL ID: CHEMBL1142
• Mol file: 123-30-8.mol

Synonyms:Phenol,p-amino- (8CI);1-Amino-4-hydroxybenzene;4-Amino-1-hydroxybenzene;4-Hydroxy-1-aminobenzene;4-Hydroxyaniline;4-Hydroxybenzenamine;4-Hydroxyphenylamine;Activol;Azol;BASF Ursol P Base;Benzofur P;C.I. 76550;C.I. Oxidation Base 6;Certinal;Citol;Durafur Brown RB;Fouramine P;Fourrine84;Fourrine P Base;Furro P base;NSC 1545;Nako Brown R;Paranol;PelagolGrey P Base;Pelagol P Base;Renal AC;Rodinal;Tertral P Base;Unal;Ursol P;Ursol P Base;Zoba Brown P Base;p-Aminophenol;p-Hydroxyaniline;p-Hydroxyphenylamine;p-Amino phenol;4-Aminophenol, para amino phenol;4-Aminophenol;

Chemical Property of 4-Aminophenol

Chemical Property:

• Appearance/Colour: Off white granular powder
• Vapor Pressure: 0.00202mmHg at 25°C
• Melting Point: 188 °C
• Refractive Index: 1.637
• Boiling Point: 281.984 °C at 760 mmHg
• PKA: 5.48, 10.30(at 25℃)
• Flash Point: 124.34 °C
• PSA: 46.25000
• Density: 1.21 g/cm³
• LogP: 1.55560
• Storage Temp.: Refrigerator
• Sensitive.: Air & Light Sensitive
• Solubility.: water: slightly soluble
• Water Solubility.: 1.5 g/100 mL (20 ºC)
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 66.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Aminophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 20/22-50/53-68-40-R68-R50/53-R20/22
• Safety Statements: 28-36/37-60-61-28A-S61-S60-S36/37-S28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Phenols
• Canonical SMILES: C1=CC(=CC=C1N)O
• description: 4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H2NC6H4OH, belongs to the class of organic compounds known as aniline and substituted anilines.Typically available as a white powder, it was commonly used as a developer for black-and-white film, marketed under the name Rodinal.Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.
• Uses: 4-Aminophenol is widely used in the synthesis of pharmaceuticals, dyes and other organic products and is mainly for the synthesis of paracetamol, clofibrate ketone, vitamin B1 and compound nicotinamide. It can be used for the production of Sulphur Blue FBG and weak acid dyes such as yellow 5G.The product is the intermediate of pharmaceutical intermediates, dyes and other fine chemicals. It can be used for the production of paracetamol, azo dyes, sulfur dyes, acid dyes, fur dye and developer, antioxidants as well as oil additive.It can be used for gold assay as well as determination of copper, iron, magnesium, vanadium, nitrite and cyanate, antioxidants.p-Aminophenol is an oxidative hair dye precursor. It is incorporated in oxidative hair dye formulations and in the bottle on the market at a maximum concentration of 1.8% and is typically mixed in a 1:1 ratio with an oxidative agent thereby reaching a concentration of 0.9% for in use application. 4-Aminophenol is suitable for use in the synthesis of 2,2-bis(4-aminophenoxy) benzonitrile [4-APBN], a monomer required for the preparation of series of polyamides and poly(amide-imide)s. It may be used as derivatization reagent to improve the ionization of aliphatic and aromatic aldehydes by paper spray ionization mass spectrometry.
• Description: 4-Aminophenol, also known as 4-hydroxyaniline, is an organic building block. Its quantification in water samples upto the detection limit of 8×10-10mol l-1 has been proposed by employing single-wall carbon nanotubes (SWNT)-nafion film coated glassy carbon electrodes. It is present as the main contaminant in pharmaceutical formulations of paracetamol. High-performance liquid chromatographic (HPLC) method with amperometric detection has been reported for its determination in various analgesic formulations. It has been reported to be formed from the reduction of 4-nitrophenol (Nip) under metal-free conditions catalyzed by N-doped graphene (NG).

Technology Process of 4-Aminophenol

There total 395 articles about 4-Aminophenol 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: 70.0%

1-allyloxy-4-nitrobenzene (1568-66-7) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 4-amino-phenol (123-30-8)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In methanol; for 0.5h; Heating;

DOI:10.1016/j.tetlet.2006.05.176

Reference yield: 56.0%

benzyl 4-nitrophenyl ether (1145-76-2) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + p-benzyloxyaniline (6373-46-2) + 4-amino-phenol (123-30-8)

Guidance literature:

With potassium fluoride; polymethylhydrosiloxane; palladium diacetate; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1055/s-2006-950231

Reference yield: 15.0%

aniline (62-53-3) → 4-amino-phenol (123-30-8) + Azobenzene (1227476-15-4) + azoxybenzene (495-48-7,55599-32-1) + p-benzoquinone (106-51-4)

Guidance literature:

With peroxomonophosphoric acid; In water; at 35 ℃; for 5h; Rate constant; Kinetics; Mechanism; various pH, various initial PMPA concentration, other temp., ΔH(excit.), ΔS(excit.), other solvents;

DOI:10.1021/jo00333a013

upstream raw materials:

4-nitro-phenol

4-bromo-phenol

p-nitrosophenol

p-benzoquinone oxime

Downstream raw materials:

p-phenol

2-[(4-hydroxyphenyl)amino]ethanol

4-(dibenzylamino)phenol

acetoacetic acid-(4-hydroxy-anilide)

Refernces

• 1、 Jacquesy, Jean-Claude,Jouannetaud, Marie-Paule,Morellet, Guy,Vidal, Yves. "DIRECT CONVERSION OF ANILINES INTO AMINOPHENOLS". . p. 1479 - 1482. Retrieved 1984.
• 2、 Patil, Pravin O.,Mahale, Sanchita S.,More, Mahesh P.,Bhandari, Pravin V.,Deshmukh, Prashant K.,Bari, Sanjay B.. "Eco-Friendly In Situ Fabrication of Reduced Graphene Oxide Gold Nanocomposites for Catalysis and Dye Degradation". . p. 2750 - 2756. Retrieved 2018.
• 3、 Sasaki,Kaiser. "Helichrome: Synthesis and enzymatic activity of a designed hemeprotein". . p. 380 - 381. Retrieved 1989.
• 4、 Borah, Biraj Jyoti,Bharali, Pankaj. "Direct Hydrogenation of Nitroaromatics at Room Temperature Catalyzed by Magnetically Recoverable Cu@Fe2O3 Nanoparticles". . . Retrieved 2020.
• 5、 Bassett,O'Leary. "". . p. 2945. Retrieved 1932.
• 6、 Adkins, Jaclyn A.,Noviana, Eka,Henry, Charles S.. "Development of a Quasi-Steady Flow Electrochemical Paper-Based Analytical Device". . p. 10639 - 10647. Retrieved 2016.
• 7、 Kohnstam, George,Petch, W. Andrew,Williams, D. Lyn H.. "KINETIC SUBSTITUENT AND ISOTOPE EFFECTS IN THE ACID-CATALYSED REARRANGEMENT OF N-PHENYLHYDROXYLAMINES. ARE NITRENIUM IONS INVOLVED?". . p. 423 - 428. Retrieved 1984.
• 8、 Hamachi, Itaru,Fujita, Akio,Kunitake, Toyoki. "Aniline-Hydroxylase Activity of Myoglobin by Coupling with a Membrane-Bound Electron Transport System". . p. 657 - 658. Retrieved 1995.
• 9、 Kumari, Mitlesh,Gupta, Ragini,Jain, Yachana. "Fe3O4 – Glutathione stabilized Ag nanoparticles: A new magnetically separable robust and facile catalyst for aqueous phase reduction of nitroarenes". . . Retrieved 2019.
• 10、 Kumar, Alok,Purkait, Kallol,Dey, Suman Kr.,Sarkar, Amrita,Mukherjee, Arindam. "A hydroquinone based palladium catalyst for room temperature nitro reduction in water". . p. 35233 - 35237. Retrieved 2014.