88-74-4

Name	2-Nitroaniline
CAS	88-74-4
EINECS(EC#)	201-855-4
Molecular Formula	C6H6N2O2
MDL Number	MFCD00007687
Molecular Weight	138.12
MOL File	88-74-4.mol

Chemical Properties

Appearance	orange solid
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)
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)
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)
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

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. less more
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 . less more
RIDADR	UN 1661 6.1/PG 2
WGK Germany	2
RTECS	BY6650000
F	8
Autoignition Temperature	521 °C
TSCA	Yes
HazardClass	6.1
PackingGroup	II
HS Code	29214210
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. less more
Hazardous Substances Data	88-74-4(Hazardous Substances Data)
Toxicity	LD50 orally in Rabbit: 1600 mg/kg LD50 dermal Rabbit > 7940 mg/kg less more

Raw materials And Preparation Products

Hazard Information

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.

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.]

Material Safety Data Sheet(MSDS)

Spectrum Detail

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