88-74-4 Usage
Description
2-Nitroaniline is an orange solid with a musty odor, which sinks and mixes slowly with water. It is a chemical compound that serves as a key precursor to phenylenediamines, which are further converted to benzimidazoles, a family of heterocycles that are essential components in pharmaceuticals.
Uses
Used in Pharmaceutical Industry:
2-Nitroaniline is used as a precursor for phenylenediamines, which are crucial in the synthesis of benzimidazoles. These benzimidazoles are vital components in the development of various pharmaceuticals, making 2-Nitroaniline an important chemical intermediate in the pharmaceutical industry.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 5688, 1955 DOI: 10.1021/ja01626a066Organic Syntheses, Coll. Vol. 1, p. 388, 1941
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 88-74-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 8 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 88-74:
(4*8)+(3*8)+(2*7)+(1*4)=74
74 % 10 = 4
So 88-74-4 is a valid CAS Registry Number.
88-74-4Relevant articles and documents
Virtual Transition State for the Acylation Step of Acetylcholinesterase-Catalysed Hydrolysis of o-Nitrochloroacetanilide
Quinn, Daniel M.,Swanson, Michael L.
, p. 1883 - 1884 (1984)
-
-
Tocco,D.J. et al.
, p. 399 - 405 (1964)
-
Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives
Azadi, Sedigheh,Esmaeilpour, Mohsen,Sardarian, Ali Reza
, p. 809 - 821 (2021/07/20)
Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.