| Identification | More | [Name]
3-Nitroaniline | [CAS]
99-09-2 | [Synonyms]
1-AMINO-3-NITROBENZENE
3-NITROANILINE
AURORA KA-7785
FAST ORANGE BASE R
LABOTEST-BB LTBB000465
m-Aminonitrobenzene
M-NITRANILINE
M-NITROANILINE
3-nitro-benzenamin
3-Nitrobenzenamine
3-nitro-Benzenamine
3-Nitrobenzeneamine
3-Nitrophenylamine
3-Nitro-phenylamine
Amarthol Fast Orange R Base
amartholfastorangerbase
Aniline, m-nitro-
aniline,m-nitro-
Azobase MNA
azobasemna | [EINECS(EC#)]
202-729-1 | [Molecular Formula]
C6H6N2O2 | [MDL Number]
MFCD00007782 | [Molecular Weight]
138.12 | [MOL File]
99-09-2.mol |
| Chemical Properties | Back Directory | [Appearance]
ochre-yellow to orange crystalline powder | [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) | [Fp ]
196 °C
| [storage temp. ]
Store below +30°C. | [solubility ]
1.25g/l | [Colour Index ]
37030 | [form ]
Crystals, Crystalline Powder and/or Chunks | [pka]
2.466(at 25℃) | [color ]
Yellow to ochre-yellow to orange | [Specific Gravity]
0.901 | [Water Solubility ]
1.25 g/L | [Merck ]
14,6582 | [BRN ]
636962 | [Henry's Law Constant]
1.93 x 10-5 atm?m3/mol at 25 °C (approximate - calculated from water solubility and vapor pressure) | [CAS DataBase Reference]
99-09-2(CAS DataBase Reference) | [NIST Chemistry Reference]
m-Nitroaniline(99-09-2) | [EPA Substance Registry System]
99-09-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R33:Danger of cumulative effects.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 1661 6.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
BY6825000
| [F ]
8 | [Autoignition Temperature]
521℃ | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29214210 | [Hazardous Substances Data]
99-09-2(Hazardous Substances Data) | [Toxicity]
Acute LD50 for guinea pigs 450 mg/kg, mice 308 mg/kg, quail 562 mg/kg, rats 535 mg/kg
(quoted, RTECS, 1985). |
| Hazard Information | Back Directory | [General Description]
Yellow needles or yellow powder. | [Reactivity Profile]
Thermal stability of this compound is reduced by various impurities. This compound may be sensitive to prolonged exposure to light. This compound may react explosively with ethylene oxide at 266° F. M-NITROANILINE(99-09-2) is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . Unstable when heated. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Moderate fire risk. Toxic when absorbed by
skin. | [Fire Hazard]
Flash point data for this chemical are not available; however, M-NITROANILINE is probably combustible. | [Chemical Properties]
3-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 properties]
Yellow, rhombic crystals or powder. Finely dispersered particles form explosive mixtures.
Combustible. | [Uses]
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. | [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). | [Preparation]
M-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 | [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.] |
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