4-Amino-2-nitrophenol

Base Information

• Chemical Name: 4-Amino-2-nitrophenol
• CAS No.: 119-34-6
• Molecular Formula: C6H6N2O3
• Molecular Weight: 154.125
• Hs Code.: 29222990
• European Community (EC) Number: 204-316-1
• NSC Number: 56809
• UN Number: 2811
• UNII: N3499RCQ6B
• DSSTox Substance ID: DTXSID6020064
• Nikkaji Number: J3.252B
• Wikidata: Q27155914
• ChEMBL ID: CHEMBL1516868
• Mol file: 119-34-6.mol

Synonyms:4-amino-2-nitrophenol

Chemical Property of 4-Amino-2-nitrophenol

Chemical Property:

• Appearance/Colour: Dark brown fine crystalline powder
• Vapor Pressure: 6.57E-05mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Refractive Index: 1.688
• Boiling Point: 334.486 °C at 760 mmHg
• PKA: 7.90±0.14(Predicted)
• Flash Point: 156.092 °C
• PSA: 92.07000
• Density: 1.511 g/cm³
• LogP: 1.98700
• Storage Temp.: 2-8°C(protect from light)
• Water Solubility.: <0.01 g/100 mL at 21℃
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 154.03784206
• Heavy Atom Count: 11
• Complexity: 156
• Transport DOT Label: Poison

Purity/Quality:

4-?Amino-?2-?nitrophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-45
• Safety Statements: 22-24/25-37/39-26-53-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC(=C(C=C1N)[N+](=O)[O-])O
• Uses: 4-Amino-2-nitrophenol has been used in dyeing human hair and animal fur. The typical concentration in the “semipermanent” hair dyes was estimated to be on the order of 0.1–1.0%. 4-Amino-2-nitrophenol was used in determination of aminonitrophenols in hair dyes by differential pulse voltammetry and HPLC with electrochemical detection. It is commonly used as semipermanent (nonoxidative) hair colorant and toner in permanent (oxidative) hair dye products.

Technology Process of 4-Amino-2-nitrophenol

There total 27 articles about 4-Amino-2-nitrophenol 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: 100.0%

1-[(2-hydroxyethyl)amino]-2-nitro-4-aminobenzene (2871-01-4) → 4-amino-2-nitrophenol (119-34-6)

Guidance literature:

With sodium hydroxide; In methanol; at 70 ℃; for 4.8h;

DOI:10.1016/S0040-4020(98)00181-1

Reference yield: 98.0%

4-amino-phenol (123-30-8) → 4-amino-2-nitrophenol (119-34-6)

Guidance literature:

With magnesium(II) nitrate hexahydrate; AMA; at 20 ℃; for 6h; regioselective reaction; Neat (no solvent);

DOI:10.3184/030823408X390181

Reference yield: 92.0%

2,4-Dinitrophenol (51-28-5) → 4-amino-2-nitrophenol (119-34-6) + 2-hydroxy-5-nitroaniline (99-57-0)

Guidance literature:

With nickel; hydrazine hydrate; In ethanol; 1,2-dichloro-ethane; at 50 - 60 ℃; for 4h;

DOI:10.1246/bcsj.56.3159

upstream raw materials:

2,4-Dinitrophenol

3-nitrophenyl azide

N-(4-hydroxy-3-nitrophenyl)acetamide

2-nitro-4-azidophenol

Downstream raw materials:

4-diazo-2-nitrophenol

N-(4-hydroxy-3-nitrophenyl)acetamide

N-acetyl-sulfanilic acid-(4-hydroxy-3-nitro-anilide)

7-chloro-4-(4-hydroxy-3-nitrophenylamino)quinoline

Refernces

• 1、 Forbes,E.J.,Gregory,M.J.. "-". . p. 207 - 209. Retrieved 1968.
• 2、 Sriram, Y. Hemanth,Fatima, Touheeth,Rajanna,Kumar, M. Satish,Raju, R. Madhusudan. "Potassium Periodate/NaNO2/KHSO4-Mediated Nitration of Aromatic Compounds and Kinetic Study of Nitration of Phenols in Aqueous Acetonitrile". supporting information. p. 622 - 632. Retrieved 2017/06/30.