4-Amino-3-nitrophenol

Base Information

• Chemical Name: 4-Amino-3-nitrophenol
• CAS No.: 610-81-1
• Molecular Formula: C6H6N2O3
• Molecular Weight: 154.125
• Hs Code.: 29222900
• European Community (EC) Number: 210-236-8
• NSC Number: 400380
• UNII: R5WY41Q95Z
• DSSTox Substance ID: DTXSID50209864
• Nikkaji Number: J96.210D
• Wikidata: Q27287833
• Mol file: 610-81-1.mol

Synonyms:4-Amino-3-nitrophenol;610-81-1;4-Hydroxy-2-nitroaniline;Phenol, 4-amino-3-nitro-;3-Nitro-4-aminophenol;4-amino-3-nitro-phenol;MFCD00066310;2-Nitro-4-hydroxyaniline;Phenol, 4-amino-3-nitro;UNII-R5WY41Q95Z;R5WY41Q95Z;EINECS 210-236-8;NSC 400380;NSC-400380;3-NITRO-4-AMINO PHENOL;NSC400380;4-amino-3-nitropbenol;3-nitro-4-amino-phenol;4-amino-3-nitro phenol;4-azanyl-3-nitro-phenol;4- amino- 3- nitrophenol;SCHEMBL24928;2-amino-5-hydroxynitrobenzene;4-Amino-3-nitrophenol, 98%;SCHEMBL14547836;IQXUIDYRTHQTET-UHFFFAOYSA-;DTXSID50209864;1-amino-4-hydroxy-2-nitrobenzene;CS-D1352;STR02932;NSC 40038;AKOS005151894;4-AMINO-3-NITROPHENOL [INCI];CS-T-03148;AC-16153;BP-20101;SY004683;A8485;AM20060868;FT-0617506;EN300-42789;A833037;W-105201;Q27287833;Z431554226;InChI=1/C6H6N2O3/c7-5-2-1-4(9)3-6(5)8(10)11/h1-3,9H,7H2

Chemical Property of 4-Amino-3-nitrophenol

Chemical Property:

• Appearance/Colour: dark red powder
• Vapor Pressure: 3.87E-06mmHg at 25°C
• Melting Point: 150-154 °C(lit.)
• Refractive Index: 1.688
• Boiling Point: 374.4 °C at 760 mmHg
• PKA: 9.21±0.10(Predicted)
• Flash Point: 180.3 °C
• PSA: 92.07000
• Density: 1.511 g/cm³
• LogP: 1.98700
• Storage Temp.: Store below +30°C.
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: soluble
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 154.03784206
• Heavy Atom Count: 11
• Complexity: 156

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-3-nitrophenol ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1O)[N+](=O)[O-])N
• Uses: 4-Amino-3-nitrophenol is an aminonitrophenol isomer used in hair dyes, potent human skin sensitizers and other cosmetic products with very low levels of mutagenic activity. 4-Amino-3-nitrophenol was used in the synthesis of benzimidazole based Factor Xa (trypsin-like serine protease) inhibitors and 4-(4-amino-3-nitrophenoxy)phthalonitrile. It was also employed as matrix during visible matrix-assisted laser desorption/ionization mass spectrometry.

Technology Process of 4-Amino-3-nitrophenol

There total 22 articles about 4-Amino-3-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: 50.0%

4-amino-phenol (123-30-8) → 4-amino-2-nitrophenol (119-34-6) + 4-hydroxy-2-nitroaniline (610-81-1)

Guidance literature:

With bromine; silver nitrate; triphenylphosphine; In acetonitrile; at 20 ℃; for 0.0833333h;

DOI:10.1016/j.tetlet.2006.07.054

Reference yield:

1-benzoylamino-4-benzoyloxy-2-nitro-benzene → 4-hydroxy-2-nitroaniline (610-81-1)

Guidance literature:

With sulfuric acid;

Reference yield:

N-(4-hydroxy-2-nitrophenyl)-acetamide (7403-75-0) → 4-hydroxy-2-nitroaniline (610-81-1)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

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

4-acetamido-3-nitrophenyl acetate

o-azidonitrobenzene

sulfuric acid

Downstream raw materials:

N-(4-benzyloxy-2-nitrobenzenesulfonyl)-N-(bromoethylene)-D-alanine methyl ester

N-(4-benzyloxy-2-aminobenzenesulfonyl)-N-(bromoethylene)-D-alanine methyl ester

2-[7-(3-nitro-phenoxy)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-propionic acid methyl ester

methyl 2(R)-[7-(4-nitrophenoxy)-2,3,4,5-tetrahydrobenzo[1,2,5-f]thiadiazepine-1,1-dioxide]propanoate

Refernces

• 1、 Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh,Firouzabadi, Dena. "Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system". . p. 6879 - 6881. Retrieved 2007/10/03.