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N-Bromosuccinimide
N-Bromosuccinimide (NBS) is a crystalline organic brominating reagent used chiefly for selective allylic and benzylic bromination, the Wohl–Ziegler reaction, introduced by Ziegler in the late 1930s.
n-Butyl acetate
n-Butyl acetate, also called butyl ethanoate, is a colorless, flammable liquid ester with a fruity odor, used mainly as a solvent for coatings and lacquers.
N-Butyllithium
N-Butyllithium (n-BuLi) is an organolithium compound sold as solutions in hydrocarbon solvents, used as a strong base and to initiate anionic polymerization of butadiene, isoprene, and styrene.
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-Formylmethionine Leucyl-Phenylalanine
N-Formylmethionine leucyl-phenylalanine (fMLF, also written fMLP) is a formylated tripeptide, first isolated from bacteria in 1976, that powerfully attracts mammalian phagocytes such as neutrophils.
N-heterocyclic carbene
An N-heterocyclic carbene (NHC) is a cyclic molecule containing a carbene carbon and a ring nitrogen, widely used as a ligand for transition-metal catalysts and as an organocatalyst.
N-heterocyclic carbene catalysis
N-heterocyclic carbene catalysis, also known as heterocyclic carbene catalysis, is an organocatalysis method in which carbenes from azolium salts invert carbonyl reactivity, enabling benzoin, Stetter, and annulation reactions.
N-heterocyclic carbene radical catalysis
N-heterocyclic carbene radical catalysis is a branch of organocatalysis in which an N-heterocyclic carbene generates radical intermediates through single-electron transfer, inspired by thiamine diphosphate enzymes and developed since 2008.
N-hydroxyphthalimide esters
N-hydroxyphthalimide esters, also called NHPI esters or N-(acyloxy)phthalimides, are redox-active esters of carboxylic acids that release alkyl radicals and carbon dioxide on single-electron reduction, and are a standard radical feedstock in modern organic synthesis.
N-Methyl-2-pyrrolidone
N-Methyl-2-pyrrolidone (NMP), also called 1-methyl-2-pyrrolidone or N-methylpyrrolidone, is a water-miscible polar aprotic solvent used in petrochemical extraction, polymer processing, and battery manufacturing, and restricted in the European Union as a reproductive toxicant.
N-Methyl-D-glucamine
N-Methyl-D-glucamine, widely known as meglumine, is an amino sugar derived from sorbitol whose main use is as a salt-forming counterion for acidic drugs, most prominently radiographic contrast media.
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-Methylaniline
N-Methylaniline, also called monomethyl aniline or NMA, is a secondary aromatic amine, an oily liquid used in organic synthesis and as a gasoline octane booster since the 1920s.
N-Methylethanolamine
N-Methylethanolamine, also called methyl beta-hydroxyethylamine, is a viscous, colorless, water-miscible secondary amino alcohol and strong base used in acid gas scrubbing, coatings, surfactants, and pharmaceutical synthesis.
N-Methylformamide
N-Methylformamide, or NMF, is a colorless liquid organic amide (CH₃NHCHO) and polar protic solvent more polar than water, intermediate between formamide and the common solvent DMF.
N-Methylmorpholine N-oxide
N-Methylmorpholine N-oxide (NMMO, also NMO) is a cyclic tertiary amine oxide used as the direct solvent for cellulose in the lyocell process and as a co-oxidant in alkene dihydroxylation.
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.
N-Phenyl-1-naphthylamine
N-Phenyl-1-naphthylamine, usually sold as PANA or antioxidant A and known in China as T531, is a crystalline arylamine used as an antioxidant in rubber compounds and lubricating oils.
N-Phenylcarbazole
N-Phenylcarbazole, also known as 9-phenyl-9H-carbazole, is an aromatic amine with a phenyl ring attached to carbazole's nitrogen atom, valued in organic electronics for its high triplet energy and use as an OLED host material.
n-propyl acetate
n-Propyl acetate, also 1-propyl acetate, is the acetate ester of acetic acid and propan-1-ol, a flammable liquid with a fruity, pear-like odor used as a solvent.
n-Propylamine
n-Propylamine, also known as propan-1-amine, is the straight-chain primary aliphatic amine of propane, a clear, highly flammable liquid with an ammonia-like odor used mainly as an intermediate in agricultural chemicals and pharmaceuticals.
N-ray
N-rays were a purported form of radiation announced in 1903 by French physicist René Blondlot, debunked in 1904 by Robert W. Wood and now a classic case of pathological science.
N-sphere
An n-sphere, also called a hypersphere, is the set of points at a fixed distance from a center in (n + 1)-dimensional space; the 1-sphere is the circle.
N-Trifluoromethylthiosaccharin
N-Trifluoromethylthiosaccharin is an electrophilic trifluoromethylthiolating reagent developed at the Shanghai Institute of Organic Chemistry and reported in 2014 by Chunfa Xu, Bingqing Ma, and Qilong Shen.
N-Vinylpyrrolidone
N-Vinylpyrrolidone (1-vinyl-2-pyrrolidone) is a colorless liquid lactam monomer made from 2-pyrrolidone and acetylene by the Reppe process, polymerized to polyvinylpyrrolidone, used in pharmaceuticals, cosmetics, and UV-curable inks.
N,N-Diisopropylethylamine
N,N-Diisopropylethylamine, also called Hünig's base or DIPEA, is a sterically hindered, non-nucleophilic tertiary amine named for Siegfried Hünig and widely used in peptide couplings and other organic syntheses.
N,N'-Dicyclohexylcarbodiimide
N,N'-Dicyclohexylcarbodiimide (DCC, C13H22N2) is a carbodiimide coupling reagent that joins carboxylic acids with amines or alcohols to form amide and ester bonds, introduced for peptide synthesis in 1955.