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2-Nitroaniline

Base Information
  • Chemical Name:2-Nitroaniline
  • CAS No.:88-74-4
  • Molecular Formula:C6H6N2O2
  • Molecular Weight:138.126
  • Hs Code.:29214210
  • European Community (EC) Number:201-855-4
  • ICSC Number:0306
  • NSC Number:9796
  • UN Number:1661
  • UNII:2519U0541L
  • DSSTox Substance ID:DTXSID1025726
  • Nikkaji Number:J812.451E,J3.908J
  • Wikipedia:2-Nitroaniline
  • Wikidata:Q2590230
  • ChEMBL ID:CHEMBL274009
  • Mol file:88-74-4.mol
2-Nitroaniline

Synonyms:2-nitroaniline;o-nitroaniline;ortho-nitroaniline

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of 2-Nitroaniline
Chemical Property:
  • Appearance/Colour:orange solid 
  • Vapor Pressure:0.00289mmHg at 25°C 
  • Melting Point:70-73 °C(lit.) 
  • Refractive Index:1.634 
  • Boiling Point:284.9 °C at 760 mmHg 
  • PKA:-0.26(at 25℃) 
  • Flash Point:126.1 °C 
  • PSA:71.84000 
  • Density:1.333 g/cm3 
  • LogP:2.28140 
  • Storage Temp.:2-8°C 
  • Solubility.:methanol: 0.1 g/mL, clear 
  • Water Solubility.:1.1 g/L (20 ºC) 
  • XLogP3:1.9
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:138.042927438
  • Heavy Atom Count:10
  • Complexity:132
  • Transport DOT Label:Poison
Purity/Quality:
Safty Information:
  • Pictogram(s): ToxicT, Flammable
  • Hazard Codes:T,F 
  • Statements: 23/24/25-33-52/53-39/23/24/25-11 
  • Safety Statements: 28-36/37-45-61-28A-16-7 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Nitrogen Compounds -> Nitroanilines
  • Canonical SMILES:C1=CC=C(C(=C1)N)[N+](=O)[O-]
  • Inhalation Risk:No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
  • 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:The substance may have effects on the blood. This may result in the formation of methaemoglobin.
  • Uses 2-Nitroaniline is the main precursor to?phenylenediamines, which are converted to?benzimidazoles, a family of?heterocycles?that are key components in pharmaceuticals.
Technology Process of 2-Nitroaniline

There total 214 articles about 2-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:
Guidance literature:
With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 4h;
DOI:10.1081/SCC-100103545
Guidance literature:
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h; Product distribution; Mechanism; other sulfenamide reagents, other nitroarenes;
DOI:10.1021/jo00044a002
Refernces

Synthesis of 3-arylazo-1H-pyridazin-4-ones from difluoroboron chelates of 1,3-diketones

10.1007/s11172-007-0243-5

The research presents a novel method for synthesizing 6-R-3-arylazo-1H-pyridazin-4-ones from difluoroboron chelates of 1,3-diketones. The study is based on the reactivity of the methyl group in these chelates with two equivalents of a diazonium salt. The synthesis involves a two-step process: first, the reaction of difluoroboron complexes of ?-diketones with diazonium salts at low temperatures to form dark red crystalline intermediates, followed by their decomposition upon refluxing in a pyridine-butanol mixture to yield the final 3-arylazo-1H-pyridazin-4-one derivatives. Acetylacetone and aroylacetones as the starting 1,3-diketones. Boron trifluoride etherate and tributyl borate for the preparation of difluoroboron chelates. The researchers utilized various spectroscopic techniques, including 1H and 13C NMR, IR, and mass spectrometry, to identify and analyze the structures of the synthesized compounds. The study also explored the possibility of structural isomers and confirmed the formation of the desired compounds through 2D NMR spectroscopy.

Synthesis of axially chiral oxazoline-carbene ligands with an N-naphthyl framework and a study of their coordination with AuCl·SMe2

10.3762/bjoc.8.81

The research focuses on the synthesis and coordination behavior of axially chiral oxazoline-carbene ligands with an N-naphthyl framework, specifically their interaction with AuCl·SMe2 to form Au(I) complexes. The main reactants used in the synthesis include methyl 1-hydroxy-2-naphthoate, trifluoromethylation reagents, 2-nitroaniline, Pd/C for reduction, triethyl orthoformate, TsOH for cyclization, and (S)-2-amino-2-phenylethanol, among others. The synthesis process involved several steps, including trifluoromethylation, coupling reactions, reduction, cyclization, and amide formation, leading to the formation of axially chiral ligands. The coordination study with AuCl·SMe2 was conducted using NaOAc in acetonitrile, and the Au(I) complexes were isolated by flash column chromatography. The analysis of the complexes was performed using 1H NMR spectroscopy to compare the chemical shifts of protons on the oxazoline ring before and after complexation, and single-crystal X-ray diffraction studies were employed to confirm the structure of the complexes, revealing a nearly linear coordination geometry around the gold(I) center. The study found that the geometry of the chiral N-naphthyl axis significantly influenced the yields of the Au(I) complexes, with (Sa,S)-7 yielding higher complex yields than (Ra,S)-7.

Oxidation-reduction reactions of 1,3-dithioles and their ions [7]

10.1007/s10593-006-0272-2

The research discusses the oxidation-reduction reactions of 1,3-dithioles and their ions, focusing on the transfer of hydrogen from the C-H group of organic compounds to electrophilic substrates as a model for fermentation processes. The study explores the reduction potential of 1,3-benzodithiole and its derivatives, comparing their hydride-ion donating abilities. Experiments involved the reduction of dibenzopyrilium perchlorate by 1,3-benzodithiole to form dibenzopyran, and the subsequent reduction of 1,3-benzodithiolium cation by dibenzothiopyran. The reactions were carried out in tetrahydrofuran (THF) at 80°C, and the products were analyzed using 1H NMR spectroscopy and mass spectrometry. Key reactants included 1,3-benzodithiole, dibenzopyrilium perchlorate, and dibenzothiopyran, along with various 4-aryl-1,3-dithiolium perchlorates and 10-methyl-9,10-dihydroacridine. The analyses confirmed the formation of the expected products, such as 4-aryl-1,3-dithioles, and provided insights into the relative hydride-donating abilities of the compounds involved.