2-Aminophenol

Base Information

• Chemical Name: 2-Aminophenol
• CAS No.: 95-55-6
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 2922.29
• European Community (EC) Number: 202-431-1
• ICSC Number: 0824
• NSC Number: 1534
• UN Number: 2512
• UNII: 23RH73DZ65
• DSSTox Substance ID: DTXSID8024498
• Nikkaji Number: J3.955A
• Wikipedia: 2-Aminophenol
• Wikidata: Q1089204
• Metabolomics Workbench ID: 51159
• ChEMBL ID: CHEMBL28319
• Mol file: 95-55-6.mol

Synonyms:2-aminophenol;2-aminophenol, hydrochloride;2-aminophenol, ion (1+);2-aminophenol, monopotassium salt;2-aminophenol, monosodium salt;o-aminophenol;ortho-aminophenol

Chemical Property of 2-Aminophenol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 14 hPa (153 °C)
• Melting Point: 172 °C
• Refractive Index: 1.5444 (estimate)
• Boiling Point: 234.496 °C at 760 mmHg
• PKA: 4.78, 9.97(at 20℃)
• Flash Point: 95.62 °C
• PSA: 46.25000
• Density: 1.211 g/cm³
• LogP: 1.55560
• Storage Temp.: Store below +30°C.
• Solubility.: 17 g/L (20°C)
• Water Solubility.: 17 g/L (20 ºC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 74.9
• Transport DOT Label: Poison

Purity/Quality:

≥98% ^*data from raw suppliers

2-Aminophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, C
• Hazard Codes: Xn,C
• Statements: 20/22-68-34-20/21/22
• Safety Statements: 28-36/37-28A-45-36/37/39-26-68-20/22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Phenols
• Canonical SMILES: C1=CC=C(C(=C1)N)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 may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• General Description: 2-Aminophenol (o-aminophenol) is a versatile compound used in multicomponent reactions to synthesize biologically active heterocycles, such as tetrahydrobenzo[b][1,4]oxazepines and malonamide derivatives, under mild conditions with high yields. It also serves as a precursor for bioinspired catalytic systems, where its oxidized form, o-iminoquinone, facilitates aerobic oxidative C-H functionalization of primary amines to produce pharmacologically relevant benzimidazoles. These applications highlight its importance in medicinal chemistry and sustainable synthetic methodologies.

Technology Process of 2-Aminophenol

There total 233 articles about 2-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: 94.0%

N-acetyl-2-(m-chlorobenzoyloxy)-3,4-dihydro-3-hydroxy-2,3-diphenyl-2H-1,4-benzoxazine (85969-43-3) → 2-amino-phenol (95-55-6) + benzil (134-81-6) + 3-chlorobenzoate (535-80-8)

Guidance literature:

With sulfuric acid; In methanol; for 2.5h; Heating;

Reference yield: 83.0%

2-(acetylamino)phenol (614-80-2) → 2-amino-phenol (95-55-6) + 2-ethylaminophenol (614-70-0)

Guidance literature:

With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; In dibutyl ether; at 130 ℃; for 24h;

DOI:10.1002/adsc.201900406

Reference yield: 7.4%

N-Phenyl-N-benzhydrylhydroxylamine (4657-41-4) → Diphenylmethane (101-81-5) + 4-amino-phenol (123-30-8) + 2-amino-phenol (95-55-6) + azoxybenzene (495-48-7,55599-32-1)

Guidance literature:

at 180 - 200 ℃; for 20h; Further byproducts given;

upstream raw materials:

2-hydroxy-phenoxazin-3-one

(2-oxo-4H-benzo[1,4]oxazin-3-ylidene)-acetic acid ethyl ester

sodium ethanolate

2-(phenyl-NNO-azoxy)-phenol

Downstream raw materials:

2-[bis-(2-hydroxy-ethyl)-amino]-phenol

N-(β-hydroxyethyl)-o-aminophenol

2-methoxy-phenylamine

N'-(2-hydroxy-phenyl)-N-methyl-N-phenyl-urea

Refernces

Behavior of Mixed Halogenated Phenols in the Zincke Method of Nitration

10.1021/ja01332a059

The study investigates the behavior of mixed halogenated phenols and cresols in the Zincke method of nitration. Various mixed halogenated phenols, such as 2-bromo-4-chlorophenol, 2-chloro-4-bromophenol, and their derivatives, were prepared and subjected to nitration. The researchers observed that when bromine occupies both ortho and para positions in a phenol or cresol, isomeric mononitro compounds can be formed. For the first time, it was shown that a phenol with hydrogen in one ortho position and bromine in the other can undergo nitration at both positions in the same experiment. Chlorine was found not to be replaceable by the nitro group under the studied conditions. The study also provided further evidence supporting the view that only one acetyl-benzoyl derivative can be prepared from an o-aminophenol regardless of the order of introduction of the acyl radicals.

Novel isocyanide-based one-pot multicomponent syntheses of tetrahydrobenzo[ b][1,4]oxazepine and malonamide derivatives

10.1021/cc100032d

The study presents a novel one-pot multicomponent reaction for the synthesis of tetrahydrobenzo[b][1,4]oxazepine and malonamide derivatives. The reaction involves 2-aminophenols, Meldrum’s acid, and isocyanides, and it proceeds at ambient temperature with good to excellent yields. These chemicals serve to create a new class of substituted malonamide and tetrahydrobenzo[b][1,4]oxazepine derivatives, which are significant in medicinal chemistry due to their potential as ionophores for selective electrodes, liquid-liquid extractants for nuclear waste management, and pharmaceutical compounds with diverse biological activities, including anticancer properties.

A Bioinspired Catalytic Aerobic Oxidative C-H Functionalization of Primary Aliphatic Amines: Synthesis of 1,2-Disubstituted Benzimidazoles

10.1002/chem.201502487

The study presents a bioinspired catalytic aerobic oxidative C-H functionalization of primary aliphatic amines, leading to the synthesis of 1,2-disubstituted benzimidazoles, which are significant in drug discovery. The process employs a biomimetic cooperative catalytic system that includes a copper(II) salt (CuBr2) as an electron transfer mediator and an o-iminoquinone organocatalyst (1ox) derived from o-aminophenol (1red), to activate the α-C-H bond of primary amines under ambient air. This atom-economical multistep reaction proceeds under mild conditions and is environmentally friendly, offering a convenient strategy for functionalizing non-activated aliphatic amines. The study also explores the reactions of various primary amine substrates with o-aminoanilines, resulting in the formation of benzimidazoles with different substituents. The synthesized benzimidazoles are important as they are found in pharmaceutical products such as antihypertensives and antihistaminic agents.