57442-24-7

Usage

Physical state

Yellowish oily liquid

Odor

Strong

Usage

Intermediate in the synthesis of various organic compounds

Classification

Nitroaromatic compound

Additional uses

Flavor and fragrance agent, production of dyes and pharmaceuticals

Toxicity

Toxic, can cause irritation to skin, eyes, and respiratory system

Carcinogenicity

Possible carcinogen

Safety precautions

Handle with caution, store and handle in a well-ventilated area with appropriate protective equipment

InChI:InChI=1/C10H13NO2/c1-3-8-6-5-7-9(4-2)10(8)11(12)13/h5-7H,3-4H2,1-2H3

Upstream product

• 579-66-8 2,6-diethylaniline 

Downstream Products

• 108562-69-2 3-methyl-7-ethylanthranil 
• 33696-10-5 2,4-diethyl-1-nitro-benzene 

Relevant academic research and scientific papers

Selective oxidation of aromatic amines to nitro derivatives using potassium iodide-tert-butyl hydroperoxide catalytic system

The direct oxidation of aromatic primary amines to the corresponding nitro compounds selectively in 47-98% yields has been achieved by using potassium iodide as catalyst and tert-butyl hydroperoxide as the external oxidant. The present catalytic system works well for both electron-rich and electron-poor substrates.

Cobalt schiff base complex-catalyzed oxidation of anilines with tert-butyl hydroperoxide

Cobalt Schiff base complexes [Co(SB)] catalyze the oxidation of anilines (1) with tert-butyl hydroperoxide to give nitrobenzenes 2 and 4-(tert-butylperoxy)-2,5-cyclohexadien-1-imine derivatives 3 in yield distributions depending on the substitution mode of the substrate. 4-Alkyl- and 4-aryl-2,6-di-tert-butylanilines gave mixtures of 2 and 3, where the higher the bulkiness of the 4-substituent, the higher the yield of 2. With 2,4,6-trimethylaniline, the ratio of oxidations of the nitrogen and C-4 atoms was almost the same; but a hydrolyzed product 5 of the imine was obtained. 2,4,6-Triphenylaniline gave only 2. Nitrobenzene derivatives were also obtained from 2,6-dialkylanilines and 4-substituted anilines. The catalytic activity of Co(SB) depended on the nature of the SB ligand: the formal potential E° and steric factors seem to affect the reaction rate. Kinetic studies showed that the key step may involve hydrogen abstraction from the aniline, presumably by t-BuO? generated from homolytic decomposition of initially formed CoIII(SB)(OO-t-Bu). A precursor of 2 was found to be the nitrosobenzene derivative.

THE CYCLISATION AND REARRANGEMENT OF THE NITRO DERIVATIVES OF AROMATIC HYDROCARBONS IN TRIFLUOROMETHANESULPHONIC ACID

A number of the nitro derivatives of aromatic hydrocarbons undergo reactions in trifluoromethanesulphonic acid at ca. 100 deg C in which either the nitro group undergoes a 1,3-rearrangement or cyclisation occurs to form an anthranil.The rates and product composition have been determined for reactions in which the subsituents ortho to the nitro group are methyl or ethyl.For the rearrangement reaction to occur, it appears necessary that the nitro group should be initially between two alkyl substituents.The cyclisation reaction is significant only when one of the ortho-substituents is an ethyl group.