2-Amino-5-nitrophenol

Base Information

• Chemical Name: 2-Amino-5-nitrophenol
• CAS No.: 121-88-0
• Molecular Formula: C6H6N2O3
• Molecular Weight: 154.125
• Hs Code.: 29222900
• European Community (EC) Number: 204-503-8
• UNII: 0149H05U82
• UN Number: 2811
• ChEMBL ID: CHEMBL164989
• DSSTox Substance ID: DTXSID1020063
• Nikkaji Number: J3.256E
• NSC Number: 7087
• Wikidata: Q27155913
• Mol file: 121-88-0.mol

Synonyms:2-amino-5-nitrophenol;2-hydroxy-4-nitroaniline;3-hydroxy-4-aminonitrobenzene;3-nitro-6-aminophenol;5-nitro-2-aminophenol;Rodol YBA;Ursol Yellow Brown A

Chemical Property of 2-Amino-5-nitrophenol

Chemical Property:

• Appearance/Colour: brown to rust crystalline powder
• Vapor Pressure: 8.29E-06mmHg at 25°C
• Melting Point: 198-202 ºC (dec.)
• Refractive Index: 1.688
• Boiling Point: 364 ºCat 760 mmHg
• PKA: 8.08±0.19(Predicted)
• Flash Point: 173.9 ºC
• PSA: 92.07000
• Density: 1.511 g/cm³
• LogP: 1.98700
• Water Solubility.: insoluble
• XLogP3: 1.5
• 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:

99% ^*data from raw suppliers

2-Amino-5-nitrophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68-20/21/22
• Safety Statements: 26-36/37-45-36/37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrophenols
• Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])O)N
• Uses: Reactant for:? ;Diazotation and coupling reactions1? ;Preparation of biologically and pharmacologically active molecules2 2-Amino-5-nitrophenol is used in hair dyes and as an intermediate in preparing azo dyes. 2-Amino-5-nitrophenol has been used as starting material in the synthesis of series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides, as semi permanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products, in synthesis of series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones, anticonvulsant agents. Also used as a reactant for, diazotation and coupling reactions, preparation of biologically and pharmacologically active molecules. It is also applied in hair dyes and to make azo dyes.

Technology Process of 2-Amino-5-nitrophenol

There total 32 articles about 2-Amino-5-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: 93.5%

C6H4N2O4S → 5-Nitro-2-aminophenol (121-88-0)

Guidance literature:

With methanol; sodium hydroxide; at 85 ℃; for 7h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 84.4%

6-nitro-3H-benzooxazol-2-one (4694-91-1) → 5-Nitro-2-aminophenol (121-88-0)

Guidance literature:

With sodium hydroxide; at 95 ℃; for 2h;

Reference yield: 54.0%

2,5-dinitrophenol (329-71-5) → 2-hydroxy-4-amino-1-nitrobenzene (16292-86-7) + 5-Nitro-2-aminophenol (121-88-0)

Guidance literature:

With 1-methylcyclohex-1-ene; palladium on activated charcoal; In methanol; at 80 ℃; for 0.166667h; microwave irradiation;

DOI:10.1055/s-2006-939062

upstream raw materials:

2-methyl-1,3-benzoxazole

2-Benzoxazolinone

N-(2-hydroxy-4-nitrophenyl)acetamide

2-acetoxy-1-acetylamino-4-nitro-benzene

Downstream raw materials:

5-nitro-2-anisalamino-phenol

toluene-4-sulfonic acid-(2-amino-5-nitro-phenyl ester)

4-nitro-1-(toluene-4-sulfonylamino)-2-(toluene-4-sulfonyloxy)-benzene

8-hydroxy-6-nitroquinoline

Refernces

• 1、 -. "Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound". . . Retrieved 2019/09/14.
• 2、 Chapman, Nicholas,Conway, Benjamin,O'Grady, Fiona,Wall, Michael D.. "A convenient method to aniline compounds using microwave-assisted transfer hydrogenation". . p. 1043 - 1046. Retrieved 2007/10/03.