| Identification | More | [Name]
2-Nitroaniline | [CAS]
88-74-4 | [Synonyms]
1-AMINO-2-NITROBENZENE
2-NITROANILINE
AKOS BBS-00004353
AZOIC DIAZO COMPONENT 6
LABOTEST-BB LTBB000464
O-NITRANILINE
O-NITROANILINE
ORTHO-NITROANILINE
1-amino-2-nitro-benzen
1-Nitro-2-aminobenzene
2-Aminonitrobenzene
2-nitro-benzenamin
2-Nitrobenzenamine
2-nitro-Benzenamine
2-Nitro-benzeneamine
2-Nitro-phenylamine
Aniline, o-nitro-
aniline,o-nitro-
Azoene Fast Orange GR Base
Azoene Fast Orange GR Salt | [EINECS(EC#)]
201-855-4 | [Molecular Formula]
C6H6N2O2 | [MDL Number]
MFCD00007687 | [Molecular Weight]
138.12 | [MOL File]
88-74-4.mol |
| Chemical Properties | Back Directory | [Appearance]
orange solid | [Melting point ]
70-73 °C (lit.) | [Boiling point ]
284 °C (lit.) | [bulk density]
500kg/m3 | [density ]
1,255 g/cm3 | [vapor pressure ]
8.1 at 25 °C (Mabey et al., 1982) | [refractive index ]
1.6349 (estimate) | [Fp ]
168 °C
| [storage temp. ]
2-8°C | [solubility ]
methanol: 0.1 g/mL, clear
| [Colour Index ]
37025 | [form ]
Crystals or Flakes | [pka]
-0.26(at 25℃) | [color ]
Orange to brown | [PH]
6.1 (10g/l, H2O, 20℃)(slurry) | [Stability:]
Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, chloroformates, hexanitroethane. | [Water Solubility ]
1.1 g/L (20 ºC) | [Specific Heat Capacity]
Cp(crystal):1.20185J/(g·K),at 25℃ | [Detection Methods]
GC,NMR | [Merck ]
14,6583 | [BRN ]
509275 | [Henry's Law Constant]
5.88 x 10-8 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) | [InChI]
1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 | [InChIKey]
DPJCXCZTLWNFOH-UHFFFAOYSA-N | [SMILES]
Nc1ccccc1[N+]([O-])=O | [LogP]
1.85 at 25℃ | [CAS DataBase Reference]
88-74-4(CAS DataBase Reference) | [NIST Chemistry Reference]
o-Nitroaniline(88-74-4) | [EPA Substance Registry System]
88-74-4(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS06,GHS08 | [Signal word ]
Danger | [Hazard statements ]
H301+H311+H331-H373-H412 | [Precautionary statements ]
P273-P280-P301+P310-P302+P352+P312-P304+P340+P311-P314 | [Hazard Codes ]
T,F | [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 .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [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 .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 1661 6.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
BY6650000
| [F ]
8 | [Autoignition Temperature]
521 °C | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29214210 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Aquatic Chronic 3
STOT RE 2 | [Safety Profile]
A poison. Moderately
toxic by ingestion. Mildly toxic by skin
contact. Mutation data reported. Mixtures
with magnesium are hypergolic on contact
with nitric acid. Forms extremely explosive
addltion compounds with hexanitroethane.
Vigorous reaction with sulfuric acid above
200°C. When heated to decomposition it
emits toxic fumes of NOx. See also m-
NITROANILINE, p-NITROANILINE,
and ANILINE DYES. | [Hazardous Substances Data]
88-74-4(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1600 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| Hazard Information | Back Directory | [General Description]
Orange solid with a musty odor. Sinks and mixes slowly with water. | [Reactivity Profile]
O-NITROANILINE(88-74-4) may be sensitive to prolonged exposure to light. Mixtures of this chemical with magnesium are hypergolic on contact with nitric acid. O-NITROANILINE(88-74-4) forms extremely explosive addition compounds with hexanitroethane. O-NITROANILINE(88-74-4) has a vigorous reaction with sulfuric acid above 392° F. O-NITROANILINE(88-74-4) is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. | [Air & Water Reactions]
Insoluble in water. | [Hazard]
Explosion risk. Toxic when absorbed by
skin. | [Health Hazard]
Inhalation or ingestion causes headache, nausea, methemo-globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion. | [Fire Hazard]
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. | [Chemical Properties]
orange solid | [Uses]
2-Nitroaniline is the main precursor to?phenylenediamines, which are converted to?benzimidazoles, a family of?heterocycles?that are key components in pharmaceuticals. | [Uses]
Dyestuff intermediate. | [Production Methods]
2-Chloronitrobenzene is heated with excess (10 mol/mol) strong aqueous ammonia in an autoclave. The temperature is gradually increased to 180 ℃ over 4 h and held there for 5 h more. The pressure builds up to around 4 MPa and is released to an ammonia recycle loop before the product is isolated by filtration and washing. The reaction is extremely exothermic, and too rapid heating or inadequate temperature control can result in a runaway reaction. Because of this hazard, I.G. Farbenindustrie developed a continuous amination unit for amination of chloronitrobenzenes; the process is summarized under 4-nitroaniline. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 77, p. 5688, 1955 DOI: 10.1021/ja01626a066
Organic Syntheses, Coll. Vol. 1, p. 388, 1941 | [Environmental Fate]
Biological. Under aerobic and anaerobic conditions using a sewage inoculum, 2-nitroaniline
degraded to 2-methylbenzimidazole and 2-nitroacetanilide (Hallas and Alexander, 1983). A
Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 2-nitroaniline as
the sole source of carbon. However, in the presence of 4-nitroaniline, approximately 50% of the
applied 2-nitroaniline metabolized to nonvolatile products which could not be identified by HPLC
(Zeyer and Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, no
degradation was observed (Pitter, 1976).
Plant. 2-Nitroaniline was degraded by tomato cell suspension cultures (Lycopericon
lycopersicum). Transformation products identified were 2-nitroanilino-β-D-glucopyranoside, β-(2-
amino-3-nitrophenyl)glucopyranoside, and β-(4-amino-3-nitrophenyl)-glucopyranoside (Pogány et
al., 1990). | [Purification Methods]
Crystallise the aniline from hot water (charcoal), then from aqueous 50% EtOH, or EtOH, and dry it in a vacuum desiccator. It has also been chromatographed on alumina, then recrystallised from *benzene. [Beilstein 12 IV 1563.] |
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