25843-45-2

Usage

Uses

Used in Pharmaceutical Research:
Azoxymethane is used as a gene mutation agent for inducing mutations in laboratory animals. This application is crucial for creating cancer models that help researchers understand the underlying mechanisms of cancer progression and develop chemoprevention strategies.
Used in Cancer Research:
Azoxymethane is used in combination with dextran sulfate sodium (DSS) to create cancer models in laboratory animals. These models are essential for studying the effects of various treatments and potential therapeutic agents on cancer cells, ultimately contributing to the development of novel cancer treatments.
Used in Toxicology Studies:
Azoxymethane is also used in toxicology studies to evaluate the potential mutagenic and carcinogenic effects of various substances. By understanding how AOM interacts with different compounds, researchers can assess the safety and potential risks associated with exposure to these substances.

Air & Water Reactions

AZOXYMETHANE is sensitive to prolonged exposure to air and elevated temperatures . Soluble in water.

Reactivity Profile

AZOXYMETHANE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Health Hazard

ACUTE/CHRONIC HAZARDS: AZOXYMETHANE is highly flammable and sensitive to elevated temperatures. Upon decomposition it emits toxic fumes.

Fire Hazard

Flash point data for AZOXYMETHANE are not available. AZOXYMETHANE is probably highly flammable.

Biochem/physiol Actions

Carcinogen that induces O6-methylguanine adducts in DNA leading to G→A transitions. Induces tumorigenesis in the colon of laboratory animals and is used to study the mechanism of cancer progression and chemoprevention.

Safety Profile

Suspected carcinogen with experimental carcinogenic and mmorigenic data. Poison by subcutaneous route. An experimental teratogen. Mutation data reported. When heated to decomposition it emits toxic fumes of Nox

InChI:InChI=1/C2H6N2O/c1-3-4(2)5/h1-2H3/b4-3+

Synthetic route

MeN((15)NO)OH → Azoxymethane (25843-45-2)

Upstream product

• 4143-42-4 (Z)-azomethane 
• 16339-12-1 N-nitroso-O,N-dimethylhydroxylamine 
• 917-54-4 methyllithium 
• 42963-41-7 6-hydroxyamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 41106-11-0 N-[2-furylmethylene]methanamine N-oxide 

Relevant academic research and scientific papers

Nitrosation of N-methylhydroxylamine by nitroprusside. A kinetic and mechanistic study

The kinetics of the reaction between aqueous solutions of Na 2[Fe(CN)5NO]?2H2O (sodium pentacyanonitrosylferrate(ii), nitroprusside, SNP) and MeN(H)OH (N-methylhydroxylamine, MeHA) has been studied by means of UV-vis spectroscopy, using complementary solution techniques: FTIR/ATR, EPR, mass spectrometry and isotopic labeling (15NO), in the pH range 7.1-9.3, I = 1 M (NaCl). The main products were N-methyl-N-nitrosohydroxylamine (MeN(NO)OH) and [Fe(CN)5H2O]3-, characterized as the [Fe(CN)5(pyCONH2)]3- complex (pyCONH 2 = isonicotinamide). No reaction occurred with Me2NOH (N,N-dimethylhydroxylamine, Me2HA) as nucleophile. The rate law was: R = kexp [Fe(CN)5NO2-] × [MeN(H)OH] × [OH-], with kexp = 1.6 ± 0.2 × 105 M-2 s-1, at 25.0 °C, and ΔH # = 34 ± 3 kJ mol-1, ΔS# = -32 ± 11 J K-1 mol-1, at pH 8.0. The proposed mechanism involves the formation of a precursor associative complex between SNP and MeHA, followed by an OH--assisted reversible formation of a deprotonated adduct, [Fe(CN)5(N(O)NMeOH)]3-, and rapid dissociation of MeN(NO)OH. In excess SNP, the precursor complex reacts through a competitive one-electron-transfer path, forming the [Fe(CN)5NO]3- ion with slow production of small quantities of N2O. The stoichiometry and mechanism of the main adduct-formation path are similar to those previously reported for hydroxylamine (HA) and related nucleophiles. The nitrosated product, MeN(NO)OH, decomposes thermally at physiological temperatures, slowly yielding NO. The Royal Society of Chemistry 2008.

Chemistry of unsaturated arenetricarbonylchromium compounds 1. Reaction of (η6-arene)tricarbonylchromium complexes of nitrones with methyl phenylpropiolate

The reactions of nitrones of the composition (CO)3CrC6H5CH=N+(O-)R (R = Me, Ph, or But) with substituted acetylene were studied. The reactions proceed with high regioselectivity and give 4-

Studies on Annelated Pyrimidines: Reaction of 6-Hydroxylamino-1,3-dimethylpyrimidine-2,4-dione with Aldonitrones

Reaction of 6-hydroxylamino-1,3-dimethylpyrimidine-2,4-dione (I) with aldonitrones (II) affords isoxazolopyrimidines in good yields.

THE FORMATION OF AZOXYALKANES IN REACTIONS OF SOME ORGANOMETALLIC REAGENTS WITH N-nitroso-O,N-DIALKYLHYDROXYLAMINES: THE NONPHOTOCHEMICAL SYNTHESIS OF AN ACYCLIC (E)-AZOXYALKANE

Azoxyalkanes were found to be regiospecifically formed in the reactions of some alkyllithium and Grignard reagents with N-nitroso-O,N-dialkylhydroxylamines.Remarkably, although (Z)-stereomers were usually produced, in one case the (E)-isomer was predominant.