ChemicalBook > Product Catalog > Organic Chemistry > Amides > Naphthenic amines derivatives > 3-Nitroaniline
3-Nitroaniline Chemical Properties
- Melting point:111-114 °C (lit.)
- Boiling point:306 °C
- Density 0,901 g/cm3
- vapor pressure 1 mm Hg ( 119 °C)
- refractive index 1.6396 (estimate)
- Flash point:196 °C
- storage temp. Store below +30°C.
- solubility 1.25g/l
- pka2.466(at 25℃)
- form Crystals, Crystalline Powder and/or Chunks
- Colour Index 37030
- Specific Gravity0.901
- color Yellow to ochre-yellow to orange
- Water Solubility 1.25 g/L
- Merck 14,6581
- BRN 636962
- Henry's Law Constant1.93 x 10-5 atm?m3/mol at 25 °C (approximate - calculated from water solubility and vapor pressure)
- CAS DataBase Reference99-09-2(CAS DataBase Reference)
- NIST Chemistry Referencem-Nitroaniline(99-09-2)
- EPA Substance Registry Systemm-Nitroaniline (99-09-2)
- Hazard Codes T
- Risk 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
- Autoignition Temperature521℃
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29214210
- Hazardous Substances Data99-09-2(Hazardous Substances Data)
- ToxicityAcute LD50 for guinea pigs 450 mg/kg, mice 308 mg/kg, quail 562 mg/kg, rats 535 mg/kg (quoted, RTECS, 1985).
3-Nitroaniline Usage And Synthesis
- Chemical Properties3-Nitroaniline is a ochre-yellow to orange crystalline powder, crystallizes as yellow needles from water. It is moderately soluble in organic solvents and sparingly soluble in water (0.11 %).
- Physical propertiesYellow, rhombic crystals or powder. Finely dispersered particles form explosive mixtures. Combustible.
- UsesDyestuff 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).
- PreparationM-nitroaniline partial reduction.
- Synthesis Reference(s)The Journal of Organic Chemistry, 45, p. 4992, 1980 DOI: 10.1021/jo01312a039
Tetrahedron Letters, 30, p. 251, 1989 DOI: 10.1016/S0040-4039(00)95173-6
Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013
- General DescriptionYellow needles or yellow powder.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileThermal 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.
- HazardModerate fire risk. Toxic when absorbed by skin.
- Fire HazardFlash point data for 3-Nitroaniline are not available; however, 3-Nitroaniline is probably combustible.
- Chemical Synthesis1,3-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 FateBiological. 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,
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 MethodsPurify it as for o-nitroaniline. Warning: it is absorbed through the skin. [Beilstein 12 IV 1589.]
3-Nitroaniline Preparation Products And Raw materials
- Preparation Products3-Bromoaniline3-Fluoroaniline1,3-Difluorobenzene 1-(3-NITROPHENYL)-PIPERAZINEN-(3-Aminophenyl)methanesulfamide5-AminoquinolineN1-(3-Aminophenyl)acetamide3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide3-NitrophenolDisperse Red 744-hydroxy-1-methyl-3-[(3-nitrophenyl)azo]-2-quinolone Mordant Yellow 13-NITROBIPHENYL2-[N-(2-acetoxyethyl)-4-chloro-2-nitro-5-[2-(propionamido)anilino]anilino]ethyl acetate 3'-NITROACETANILIDE
- Raw materialsSulfuric acid Nitric acidSulfurSodium sulfiteSodium sulfideNitrobenzene1,3-DinitrobenzeneSODIUM TETRASULFIDECALCIUM SULFIDE
- 4-BROMO-3-FLUORO-2-NITROANILINE 4-NITROANILINE [14C(U)],4-NITROANILINE-UL-14C 4-BROMO-2-FLUORO-5-NITROANILINE 2,4,5,7-TETRANITRO-9-FLUORENONE 9-DICYANOMETHYLENE-2,4,7-TRINITROFLUORENE CYCLOHEXANONE 2,4-DINITROPHENYLHYDRAZONE 2,4,7-TRINITRO-9-FLUORENONE ACID ORANGE 74 Nitroaniline 4-METHOXY-2-NITROANILINE 2-Methyl-6-nitroaniline 3,5-Dinitrosalicylic acid N-Methyl-4-nitroaniline 3-Nitroacetophenone 5-Nitroanthranilonitrile 5-Chloro-2-nitroaniline 4-FLUORO-3-NITROANILINE 2-Methyl-3-nitroaniline