3-Nitroaniline

Base Information

• Chemical Name: 3-Nitroaniline
• CAS No.: 99-09-2
• Deprecated CAS: 12262-63-4
• Molecular Formula: C6H6N2O2
• Molecular Weight: 138.126
• Hs Code.: 2912.42
• European Community (EC) Number: 202-729-1
• ICSC Number: 0307
• NSC Number: 9574
• UN Number: 1661
• UNII: CM50SM561T
• DSSTox Substance ID: DTXSID6025725
• Nikkaji Number: J3.991H
• Wikipedia: 3-Nitroaniline
• Wikidata: Q2668442
• ChEMBL ID: CHEMBL14068
• Mol file: 99-09-2.mol

Synonyms:3-NA, aniline;3-nitroaniline

Chemical Property of 3-Nitroaniline

Chemical Property:

• Appearance/Colour: ochre-yellow to orange crystalline powder
• Vapor Pressure: 1 mm Hg ( 119 °C)
• Melting Point: 111-114 °C(lit.)
• Refractive Index: 1.626
• Boiling Point: 307 °C at 760 mmHg
• PKA: 2.466(at 25℃)
• Flash Point: 139.5 °C
• PSA: 71.84000
• Density: 1.333 g/cm³
• LogP: 2.28140
• Storage Temp.: Store below +30°C.
• Solubility.: 1.25g/l
• Water Solubility.: 1.25 g/L
• 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: 132
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

3-Nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-33-52/53
• Safety Statements: 28-36/37-45-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])N
• 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. Medical observation is indicated. The effects may be delayed.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in the formation of methaemoglobin.
• Physical properties: Yellow, rhombic crystals or powder. Finely dispersered particles form explosive mixtures. Combustible.
• Uses: Dyestuff intermediate. Acetylation of 3-nitroaniline followed by reduction gives 3-aminoacetanilide. Diazotization, followed by reduction of the diazosulfonate with ammonium bisulfite and subsequent hydrolysis, gives (3-nitrophenyl) hydrazine; an intermediate in the production of pyrazolone azo coupling components. 3-Nitroaniline is used as a diazo component (Fast Orange R Base) in azo dyes (e.g., C.I. Disperse Yellow 5 and C.I. Acid Orange 18). 3-Nitroaniline is commonly used as a raw material for dyes. It is also used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.

Technology Process of 3-Nitroaniline

There total 161 articles about 3-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: 52.0%

aniline (62-53-3) → 4-nitro-aniline (100-01-6,104810-17-5) + 3-nitro-aniline (99-09-2)

Guidance literature:

With sodium nitrate; sulfuric acid; at 0 - 5 ℃; for 3h;

Reference yield: 23.0%

nitrobenzene (98-95-3,26969-40-4) → 4-nitro-aniline (100-01-6,104810-17-5) + 2-nitro-aniline (88-74-4) + 3-nitro-aniline (99-09-2)

Guidance literature:

nitrobenzene; With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; trifluorormethanesulfonic acid; C₈H₉F₃NO₃S⁽¹⁺⁾*CF₃O₃S^(1-); In acetonitrile; at 23 - 25 ℃; for 24h; Sealed tube; Irradiation;

With N-butylamine; In acetonitrile; at 40 ℃; for 18h;

DOI:10.1002/anie.201810262

Reference yield:

acetic anhydride (108-24-7) + anilinium nitrate (542-15-4) → 4-nitro-aniline (100-01-6,104810-17-5) + 2-nitro-aniline (88-74-4) + 3-nitro-aniline (99-09-2)

Guidance literature:

at 0 ℃; Product distribution;

upstream raw materials:

meta-dinitrobenzene

ethanol

1-(3-nitrophenyl)-3-phenylthiourea

1-methyl-4-nitrosobenzene

Downstream raw materials:

3-[N,N-Bis(2-hydroxyethyl)amino]nitrobenzene

3'-nitroacetoacetanilide

thiophene-2-carbaldehyde-(3-nitro-phenylimine)

selenophene-2-carbaldehyde-(3-nitro-phenylimine)

Refernces

• 1、 Paul, Manidipa,Pal, Nabanita,Bhaumik, Asim. "Mesoporous nickel-aluminum mixed oxide: A promising catalyst in hydride-transfer reactions". . p. 5129 - 5134. Retrieved 2010.
• 2、 Abedi, Syed Ali Abbas,Liu, Xiaogang,Lou, Kaiyan,Ma, Huijuan,Wang, Shanshan,Wang, Wei,Xing, Wanjin,Xu, Hang,Xu, Huan,Zhang, Xingchen. "A PET-based fluorescent probe for monitoring labile Fe(ii) pools in macrophage activations and ferroptosis". supporting information. p. 2979 - 2982. Retrieved 2022/03/15.
• 3、 Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju. "Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines". supporting information. p. 1915 - 1923. Retrieved 2021/02/06.