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Nitriles, nitro, diazo, and related nitrogen groups

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Cyanohydrin

A cyanohydrin, also called a hydroxynitrile, is an organic compound bearing a hydroxyl and a nitrile group on the same carbon, formed by adding HCN to aldehydes or ketones.

Diazomethane

Diazomethane (CH₂N₂) is the simplest diazo compound, a yellow gas that is highly toxic and explosive, so it is freshly prepared in dilute ether solution to methylate acids in the laboratory.

Dinitrobenzene

Dinitrobenzene is any of three isomers of benzene bearing two nitro groups, pale crystalline solids used chiefly in dye manufacture and known for causing methemoglobinemia.

Environmental and toxicological effects of nitro compounds

Environmental and toxicological effects of nitro compounds: military explosives such as TNT, RDX, and HMX persist in soil and water, and microbial reduction of nitro groups produces metabolites that damage hemoglobin and DNA.

Formazan

A formazan is a highly colored nitrogen-rich organic compound, known since the late 1800s, used as a dye and formed in tetrazolium assays of cell viability such as the MTT assay.

Hydrazoic acid

Hydrazoic acid, also called hydrogen azide or hydronitric acid, is the colorless, volatile, toxic and explosive liquid nitrogen hydride (HN₃) used to make heavy metal azides for shell detonators.

Hydroxylamine

Hydroxylamine (NH2OH, also called oxammonium) is an inorganic compound of ammonia bearing a hydroxy group, a white solid that is thermally unstable and used mainly to make caprolactam for nylon.

Isobutyronitrile

Isobutyronitrile, also called 2-methylpropanenitrile or isopropyl cyanide, is a branched four-carbon nitrile, a colorless liquid with an almond-like odor, detected in interstellar space in 2014.

Isocyanate

An isocyanate, also known as an isocyanate group, is an organic compound containing the highly reactive N=C=O group, making it the reactive half of nearly all polyurethane chemistry.

Isocyanide

An isocyanide, also called an isonitrile or carbylamine, is an organic functional group R–N≡C, isomeric with nitriles but far more reactive, serving in multicomponent reactions and metal coordination.

Kolbe nitrile synthesis

The Kolbe nitrile synthesis is an organic reaction that prepares alkyl nitriles by reacting alkyl halides with metal cyanides, extending the carbon chain by one atom.

Lomustine

Lomustine (CCNU) is an oral nitrosourea chemotherapy drug that crosses the blood-brain barrier, used mainly for brain tumors and relapsed Hodgkin's lymphoma; approved in 1976, it is marketed as Gleostine.

Malononitrile

Malononitrile (propanedinitrile) is an organic dinitrile with two cyano groups on one carbon, a white crystalline solid used as a building block in organic synthesis.

Methacrylonitrile

Methacrylonitrile (2-methylpropenenitrile) is a colorless, flammable liquid acrylic monomer with a bitter almond odor, the methyl-substituted analog of acrylonitrile, polymerized to make plastics, coatings, and elastomers.

N-Ethyl-N-nitrosourea

N-Ethyl-N-nitrosourea (ENU), also called 1-ethyl-1-nitrosourea, is an alkylating N-nitrosourea compound and potent mutagen and carcinogen, used since the 1970s as the standard mutagen for forward genetic screens in mice.

N-Methyl-N-nitrosourea

N-Methyl-N-nitrosourea (MNU), also called N-nitroso-N-methylurea, is an N-nitrosourea alkylating agent classified as probably carcinogenic to humans, used in research to induce rat mammary cancer and retinal degeneration.

N-Methyl-N'-nitro-N-nitrosoguanidine

N-Methyl-N'-nitro-N-nitrosoguanidine (MNNG) is a synthetic N-nitroso compound that directly methylates DNA. Used for decades to study DNA repair, it induced the 1970s discovery of the adaptive response in E. coli.

N-Nitrosodiethylamine

N-Nitrosodiethylamine, also called diethylnitrosamine or NDEA, is a volatile nitrosamine and extensively studied carcinogen that causes tumors in all tested animals; since 2018 it has been monitored as a drug impurity.

N-Nitrosodimethylamine

N-Nitrosodimethylamine, also known as dimethylnitrosamine or NDMA, is a water-miscible nitrosamine classified as a probable human carcinogen, formed during water disinfection and found as an impurity in recalled drugs.

N-Nitrosonornicotine

N-Nitrosonornicotine (NNN) is a tobacco-specific nitrosamine, formed from nornicotine during tobacco curing, that causes esophageal and oral tumors and is classified by IARC as carcinogenic to humans.

Nickel-catalyzed cyanation

Nickel-catalyzed cyanation is a family of organic reactions in which a nickel catalyst installs a cyano group onto organic molecules, first reported by the Cassar group in 1973.

Nitrile

A nitrile, also called a carbonitrile, is an organic compound carrying a strongly polarized cyano group, −C≡N, found in solvents like acetonitrile, polymers, superglues, and medicines.

Nitrile anion

A nitrile anion is a stabilized carbanion formed by deprotonating the carbon adjacent to a nitrile group, widely used in organic synthesis to form carbon–carbon bonds.

Nitrile oxide

A nitrile oxide is a reactive organic functional group of formula R–C≡N⁺–O⁻, a nearly linear 1,3-dipole usually generated in situ and trapped in cycloadditions that build isoxazoles and isoxazolines for synthesis and medicinal chemistry.

Nitrile reduction

Nitrile reduction is the chemical conversion of an organic nitrile into a primary amine or, with partial reduction, an aldehyde, and is a major route to amines.

Nitro blue tetrazolium chloride

Nitro blue tetrazolium chloride (NBT) is a yellow tetrazolium salt reduced to a blue formazan, used in histochemistry and the NBT test for chronic granulomatous disease.

Nitro compound

A nitro compound is an organic molecule bearing the nitro group, –NO₂, valued in synthesis because it reduces readily to amines; the simplest is nitromethane, and multiple nitro groups often make compounds explosive.

Nitrobenzene

Nitrobenzene, also known as oil of mirbane, is a synthetic oily liquid with an odor of bitter almonds, produced from benzene and used almost entirely to make aniline.

Nitrobenzoxadiazole

Nitrobenzoxadiazole (NBD), systematically 7-nitro-2,1,3-benzoxadiazole, is a small environmentally sensitive fluorophore first reported in 1968, now widely used as a scaffold for fluorescent probes sensing analytes such as hydrogen sulfide.

Nitroethane

Nitroethane is a colorless, oily nitroalkane liquid with the formula CH₃CH₂NO₂ and a fruity odor, used as a solvent and chemical intermediate and regulated in the United States as a DEA List I chemical.