99-09-2

Basic information

• Product Name: 3-Nitroaniline
• Synonyms: 3-nitro-benzenamin;3-Nitrobenzenamine;3-nitro-Benzenamine;3-Nitrobenzeneamine;3-Nitrophenylamine;3-Nitro-phenylamine;Amarthol Fast Orange R Base;amartholfastorangerbase
• CAS NO: 99-09-2
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.12
• EINECS: 202-729-1
• Product Categories: Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Organics;Functional Materials;Organic Nonlinear Optical Materials;C2 to C6;Alpha Sort;Analytical Standards;AromaticsChemical Class;AromaticsVolatiles/ Semivolatiles;Chemical Class;N;NA - NIAnalytical Standards;Nitro Compounds;N-OAlphabetic;C2 to C6Photonic and Optical Materials;Amines;Nitrogen Compounds;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;NA - NI;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Photonic and Optical Materials;Building Blocks;C6;Chemical Synthesis;Materials Science;Nitrogen Compounds;Organic and Printed Electronics;Organic Building Blocks;Dyestuff Intermediates
• Mol File: 99-09-2.mol

Chemical Properties

• Melting Point: 111-114 °C(lit.)
• Boiling Point: 306 °C
• Flash Point: 196 °C
• Appearance: Yellow to ochre-yellow to orange/Crystals, Crystalline Powder and/or Chunks
• Density: 0,901 g/cm3
• Vapor Pressure: 1 mm Hg ( 119 °C)
• Refractive Index: 1.6396 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 1.25g/l
• PKA: 2.466(at 25℃)
• Water Solubility: 1.25 g/L
• Merck: 14,6581
• BRN: 636962
• CAS DataBase Reference: 3-Nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitroaniline(99-09-2)
• EPA Substance Registry System: 3-Nitroaniline(99-09-2)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-33-52/53
• Safety Statements: 28-36/37-45-61-28A
• RIDADR: UN 1661 6.1/PG 2
• WGK Germany: 2
• RTECS: BY6825000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 99-09-2(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
3-Nitroaniline is used as a dyestuff intermediate for the production of various dyes. It is an essential component in the synthesis of 3-aminoacetanilide, which is obtained through acetylation followed by reduction. 3-Nitroaniline is further used in the production of pyrazolone azo coupling components.
Additionally, 3-Nitroaniline is utilized as a diazo component in azo dyes, such as Fast Orange R Base. It plays a crucial role in the synthesis of dyes like C.I. Disperse Yellow 5 and C.I. Acid Orange 18.
Used in Chemical Intermediates:
3-Nitroaniline is commonly used as a raw material for dyes and serves as a chemical intermediate for azo coupling component 17. It is also involved in the synthesis of dyes such as disperse yellow 5 and acid blue 29. During the dyeing process, 3-Nitroaniline is transformed into other substances, including dyestuffs and m-nitrophenol, which contribute to the coloration and properties of the final product.

Preparation

M-nitroaniline partial reduction.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 4992, 1980 DOI: 10.1021/jo01312a039Tetrahedron Letters, 30, p. 251, 1989 DOI: 10.1016/S0040-4039(00)95173-6Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Thermal stability of 3-Nitroaniline is reduced by various impurities. 3-Nitroaniline may be sensitive to prolonged exposure to light. 3-Nitroaniline may react explosively with ethylene oxide at 266° F. 3-Nitroaniline is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . Unstable when heated.

Hazard

Moderate fire risk. Toxic when absorbed by skin.

Fire Hazard

Flash point data for 3-Nitroaniline are not available; however, 3-Nitroaniline is probably combustible.

Synthesis

1,3-Dinitrobenzene is added towarmwater containing magnesium sulfate. An aqueous solution of sodium hydrogen sulfide (6molar equivalents) is added gradually to the vigorously stirred emulsion, and reduction is completed by heating to 90℃. The 3-nitroaniline produced solidifies on cooling and is separated by filtration.

Environmental fate

Biological. A bacterial culture isolated from the Oconee River in North Georgia degraded 3- nitroaniline to the intermediate 4-nitrocatechol (Paris and Wolfe, 1987). A Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 3-nitroaniline as the sole source of carbon. However, in the presence of 4-nitroaniline, all of the applied 3-nitroaniline metabolized completely to carbon dioxide (Zeyer and Kearney, 1983). In the presence of suspended natural populations from unpolluted aquatic systems, the second-order microbial transformation rate constant determined in the laboratory was reported to be 4.6 ± 0.1 x 10-13 L/organism?h (Steen, 1991). In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976). Chemical/Physical. Reacts with acids forming water soluble salts.

Purification Methods

Purify it as for o-nitroaniline. Warning: it is absorbed through the skin. [Beilstein 12 IV 1589.]

InChI:InChI=1/C6H6N2O2/c9-8(10)7-6-4-2-1-3-5-6/h1-5,7H

Upstream product

• 99-65-0 meta-dinitrobenzene 
• 64-17-5 ethanol 
• 13140-66-4 1-(3-nitrophenyl)-3-phenylthiourea 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 33322-43-9 3-nitro-benzoic acid bromoamide 
• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 15999-30-1 (3-nitro-phenyl)-carbonimidic acid dichloride 
• 20829-97-4 5-nitroisatonic anhydride 
• 122-28-1 N-(3-nitrophenyl)acetanilide 
• 3532-31-8 3-nitrobenzoyl azide 
• 108-24-7 acetic anhydride 
• 542-15-4 anilinium nitrate 
• 99-61-6 3-nitro-benzaldehyde 
• 108-45-2 m-phenylenediamine 

Downstream Products

• 24812-82-6 3-[N,N-Bis(2-hydroxyethyl)amino]nitrobenzene 
• 102-38-5 N-(3-nitrophenyl)formamide 
• 25233-49-2 3'-nitroacetoacetanilide 
• 32116-47-5 2,4-bis-(3-nitro-anilino)-cyclopent-2-enone 
• 32116-48-6 trans-4,5-bis((3-nitrophenyl)amino)cyclopent-2-enone 
• 78662-36-9 thiophene-2-carbaldehyde-(3-nitro-phenylimine) 
• 121761-12-4 selenophene-2-carbaldehyde-(3-nitro-phenylimine) 
• 36847-90-2 3-(3-nitro-phenylcarbamoyl)-acrylic acid 
• 42537-57-5 N-(3-nitrophenyl)maleamic acid 
• 90736-46-2 3-[2]furyl-acrylaldehyde-(3-nitro-phenylimine) 
• 1797-93-9 3-(3-nitrophenylaminocarbonyl)propionic acid 
• 52109-85-0 furan-2-carboxylic acid-(3-nitro-anilide) 
• 64745-45-5 3-[1-(3-nitro-phenylimino)-ethyl]-dihydro-furan-2-one 
• 132466-85-4 N-[8]quinolylmethylene-3-nitro-aniline 

Relevant articles and documents

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