1777-84-0

Usage

General Description

Beige powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A nitrated acetamide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition N-(4-ethoxy-3-nitrophenyl)acetamide emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for N-(4-ethoxy-3-nitrophenyl)acetamide are not available; however, N-(4-ethoxy-3-nitrophenyl)acetamide is probably combustible.

Safety Profile

An eye irritant. Mutation data reported. Questionable carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

InChI:InChI=1/C10H12N2O4/c1-3-16-10-5-4-8(11-7(2)13)6-9(10)12(14)15/h4-6H,3H2,1-2H3,(H,11,13)

Upstream product

• 62-44-2 4-ethoxyacetanilide 
• 7664-93-9 sulfuric acid 

Downstream Products

• 17026-81-2 3'-amino-4'-ethoxyacetanilide 
• 15854-74-7 4-Ethoxy-3-nitro-N-nitroso-acetanilid 
• 1777-87-3 4-ethoxy-3-nitroaniline 
• 103394-60-1 2-ethoxy-5-(5-methyl-tetrazol-1-yl)-aniline 

Relevant academic research and scientific papers

Involvement of Free Nitrenium Ions, Ion Pairs, and Preassociation Trapping in the Reactions of Ester Derivatives of N-Arylhydroxylamines and N-Arylhydroxamic Acids in Aqueous Solution

Rate and product yield data for the decomposition of the ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids 1a-i in aqueous solution in the presence of N3- support a mechanistic scheme (Scheme 5) in which the trapping by N3- changes from trapping of the free ion, to trapping of an ion pair, to a preassociation process as the ion becomes more reactive.When the rate constant for trapping of the free ion by solvent, ks, 8 s-1, trapping by both N3- and solvent occurs almost exclusively at the free ion.When 108 s-1 s 10 s-1, a change in the mechanism occurs, and trapping of the ion pair by both solvent and N3- becomes important.In this range of reactivity there is also evidence, based on the apparent magnitude of kaz', the rate constant for N3- trapping of the ion pair, that some of the reaction with N3- occurs through a preassociation process.When ks > ca. 1010 s-1 essentially all of the observed N3- trapping occurs by a preassociation process because N3-, which cannot react with the ion pair faster than the diffusion limit, can no longer compete with solvent for the ion pair.This progression in trapping mechanisms as the ion becomes more reactive with solvent is apparently an important factor in determining the carcinogenic potential of aromatic amines and amides which are metabolized into sulfuric and carboxylic acid esters of N-arylhydroxylamines and N-arylhydroxamic acids.Nitrenium ions which undergo slow reactions with solvent are selectively trapped by biologically relevant nucleophiles such as 2'-deoxyguanosine.As the rate constant for reaction with solvent increases, the nitrenium ion is no longer capable of undergoing selective trapping by nonsolvent nucleophiles because these reactions are limited by diffusion, but solvent trapping is not.