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2-Nitroaniline

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2-Nitroaniline Basic information

Product Name:
2-Nitroaniline
CAS:
88-74-4
MF:
C6H6N2O2
MW:
138.12
EINECS:
201-855-4
Mol File:
88-74-4.mol
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2-Nitroaniline Chemical Properties

Melting point:
70-73 °C(lit.)
Boiling point:
284 °C(lit.)
Density 
1,255 g/cm3
vapor pressure 
8.1 at 25 °C (Mabey et al., 1982)
refractive index 
1.6349 (estimate)
Flash point:
168 °C
storage temp. 
2-8°C
solubility 
methanol: 0.1 g/mL, clear
pka
-0.26(at 25℃)
form 
Crystals or Flakes
Colour Index 
37025
color 
Orange to brown
PH
6.1 (10g/l, H2O, 20℃)(slurry)
Water Solubility 
1.1 g/L (20 ºC)
Merck 
14,6582
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)
Stability:
Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, chloroformates, hexanitroethane.
CAS DataBase Reference
88-74-4(CAS DataBase Reference)
NIST Chemistry Reference
o-Nitroaniline(88-74-4)
EPA Substance Registry System
o-Nitroaniline (88-74-4)
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Safety Information

Hazard Codes 
T,F
Risk Statements 
23/24/25-33-52/53-39/23/24/25-11
Safety Statements 
28-36/37-45-61-28A-16-7
RIDADR 
UN 1661 6.1/PG 2
WGK Germany 
2
RTECS 
BY6650000
8
Autoignition Temperature
521 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29214210
Hazardous Substances Data
88-74-4(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1600 mg/kg LD50 dermal Rabbit > 7940 mg/kg

MSDS

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2-Nitroaniline Usage And Synthesis

Chemical Properties

orange solid

Uses

Dyestuff intermediate.

General Description

Orange solid with a musty odor. Sinks and mixes slowly with water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Nitroaniline may be sensitive to prolonged exposure to light. Mixtures of 2-Nitroaniline with magnesium are hypergolic on contact with nitric acid. 2-Nitroaniline forms extremely explosive addition compounds with hexanitroethane. 2-Nitroaniline has a vigorous reaction with sulfuric acid above 392° F. 2-Nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers.

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.

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.

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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