4-Nitroaniline

Base Information

• Chemical Name: 4-Nitroaniline
• CAS No.: 100-01-6
• Deprecated CAS: 1309774-69-3
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.126
• Hs Code.: 2921.42 Oral rat LD50: 750 mg/kg
• European Community (EC) Number: 202-810-1
• ICSC Number: 0308
• NSC Number: 9797
• UN Number: 1661
• UNII: 1MRQ0QZG7G
• DSSTox Substance ID: DTXSID8020961
• Nikkaji Number: J2.508.693G,J4.000B
• Wikipedia: 4-Nitroaniline
• Wikidata: Q419842
• Metabolomics Workbench ID: 50755
• ChEMBL ID: CHEMBL14282
• Mol file: 100-01-6.mol

Synonyms:4-nitroaniline;4-nitroaniline monohydrochloride;4-nitroaniline sulfate (2:1);4-nitroaniline, mercury (2+) salt (2:1);p-nitroaniline;para-nitroaniline;paranitronaniline

Chemical Property of 4-Nitroaniline

Chemical Property:

• Appearance/Colour: Yellow solid with a mild odor
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 147 °C
• Refractive Index: 1.634
• Boiling Point: 333.1 °C at 760 mmHg
• PKA: 1(at 25℃)
• Flash Point: 165 °C
• PSA: 71.84000
• Density: 1.333 g/cm³
• LogP: 2.28140
• Storage Temp.: Store at R.T.
• Solubility.: ethanol: soluble25mg/mL, slightly hazy, yellow to brownish-yellow
• Water Solubility.: 0.8 g/L (20℃)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 138.042927438
• Heavy Atom Count: 10
• Complexity: 124
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F
• Hazard Codes: T:Toxic
• Statements: R23/24/25:; R33:; R52/53:
• Safety Statements: S28A:; S36/37:; S45:; S61:

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC(=CC=C1N)[N+](=O)[O-]
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C , on spraying or dispersing much faster.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes. 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: The substance may have effects on the blood. This may result in the formation of methaemoglobin.
• Physical properties: Bright yellow crystalline powder or flakes with a faint, ammonia-like, slightly pungent odor. Combustible.
• Uses: Product of chromogenic reactions. 4-Nitroaniline is used in the synthesis of photorefractive polymers, as novel chromophores in analytical study. As well, due to the absorption spectrum associated with 4-Nitroaniline, it is used to de termine catechol derivatives in syntheses. Dyestuff intermediate.

Technology Process of 4-Nitroaniline

There total 883 articles about 4-Nitroaniline 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: 95%

3-methyl-5-nitro-1-(p-nitrophenyl)uracil (108047-30-9) + methylamine (74-89-5) → 1,3-dimethyl-5-nitrouracil (41613-26-7) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

In methanol; for 0.5h; Ambient temperature;

DOI:10.1039/P19900000367

Reference yield: 92.5%

3,5-dinitro-1-(p-nitrophenyl)-4-pyridone (74197-40-3) + methylamine (74-89-5) → 3,5-dinitro-1-methyl-4-pyridone (19872-97-0) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

DOI:10.1016/0040-4039(81)80143-8

Reference yield: 91.4%

3,5-dinitro-1-(p-nitrophenyl)-4-pyridone (74197-40-3) + o-toluidine (95-53-4) → 3,5-Dinitro-1-o-tolyl-1H-pyridin-4-one (78641-63-1) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

DOI:10.1016/0040-4039(81)80143-8

upstream raw materials:

pyridine

para-dinitrobenzene

1-Amino-1-deoxy-D-glucitol

N-phenylphthalimide

Downstream raw materials:

N,N-bis(2-hydroxyethyl)-4-nitroaniline

p-nitroformanilide

5-(4-nitro-anilino)-penta-2,4-dienal-(4-nitro-phenylimine); hydrobromide

2-(4-nitro-phenyl)-pyrimidine

Refernces

• 1、 Torres, Cecilia C.,Jiménez, Verónica A.,Campos, Cristian H.,Alderete, Joel B.,Dinamarca, Robinson,Bustamente, Tatiana M.,Pawelec, Barbara. "Gold catalysts supported on TiO2-nanotubes for the selective hydrogenation of p-substituted nitrobenzenes". . p. 21 - 27. Retrieved 2018.
• 2、 Yamauchi, Yasuo,Ejiri, Yukinori,Tanaka, Kiyoshi. "Purification of an aminopeptidase preferentially releasing N-terminal alanine from cucumber leaves and its identification as a plant aminopeptidase N". . p. 2802 - 2805. Retrieved 2001.
• 3、 Syroeshkin, Mikhail A.,Mendkovich, Andrei S.,Mikhalchenko, Ludmila V.,Rusakov, Alexander I.,Gul'tyai, Vadim P.. "Self-protonation upon the electroreduction of 2- and 4-nitrophenylhydroxylamines in aprotic media". . p. 258 - 259. Retrieved 2009.
• 4、 Kamal, Ahmed,Shankaraiah,Reddy, K. Laxma,Devaiah. "Selective reduction of aromatic azides in solution/solid-phase and resin cleavage by employing BF3·OEt2/EtSH. Preparation of DC-81". . p. 4253 - 4257. Retrieved 2006.
• 5、 Beardsell,Hinchliffe,Wood,Wilmouth,Schofield,Page. "β-Sultams - A novel class of serine protease inhibitors". . p. 497 - 498. Retrieved 2001.
• 6、 Asano, Minao,Nakamura, Nami,Kawai, Misako,Miwa, Tetsuya,Nio, Noriki. "Purification and characterization of an N-terminal acidic amino acid-specific aminopeptidase from soybean cotyledons (glycine max)". . p. 113 - 118. Retrieved 2010.
• 7、 Pagoti, Sreenivasarao,Surana, Subham,Chauhan, Ajay,Parasar, Bibudha,Dash, Jyotirmayee. "Reduction of organic azides to amines using reusable Fe3O 4 nanoparticles in aqueous medium". . p. 584 - 588. Retrieved 2013.
• 8、 Iyer, Suresh,Kulkarni, Girish M.. "Mo(CO)6 Mediated Selective Reduction of Azides and Nitro Compounds to Amines under Neutral Conditions". . p. 721 - 725. Retrieved 2004.
• 9、 Sultane, Prakash R.,Mete, Trimbak B.,Bhat, Ramakrishna G.. "Chemoselective N-deacetylation under mild conditions". . p. 261 - 264. Retrieved 2014.
• 10、 Saito, Shinichi,Koizumi, Yuichiro. "Copper-catalyzed coupling of aryl halides and nitrite salts: A mild Ullmann-type synthesis of aromatic nitro compounds". . p. 4715 - 4717. Retrieved 2005.