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Bis(dimethylamino)methane
Bis(dimethylamino)methane is the organic compound with the formula CH3)2Nsub>2CH2. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...: : 2 (CH3)2NH + CH2O → CH3)2Nsub>2CH2 + H2O It is used for the dimethyl aminomethylation reactions, the reaction being initiated by the addition of a strong, anhydrous acid:{{cite journal , journal=eEROS, Encyclopedia of Reagents for Organic Synthesis, title=Bis(dimethylamino)methane, doi=10.1002/047084289X.rb143, author=Allen J. Duplantier : CH3)2Nsub>2CH2 + H+ → (CH3)2NCH2+ + (CH3)2NH Related reagents * N,N,N′,N′-Tetramethylfo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aminal
In organic chemistry, an aminal or aminoacetal is a functional group or type of organic compound that has two amine groups attached to the same carbon atom: . (As is customary in organic chemistry, R can represent hydrogen or an alkyl group). A common aminal is bis(dimethylamino)methane, a colorless liquid that is prepared by the reaction of dimethylamine and formaldehyde: : 2 (CH3)2NH + CH2O -> CH3)2NCH2 + H2O Aminals are encountered in, for instance, the Fischer indole synthesis. Several examples exist in nature. Physostigmin.svg, Physostigmine,a highly toxic cholinesterase inhibitor found in the Calabar bean. Hodgkinsine.png, Hodgkinsine, an alkaloid with antiviral, antibacterial and antifungal effects 5,10-methylenetetrahydrofolic acid.svg, 5,10-Methylenetetrahydrofolate, an intermediate in one-carbon metabolism Hexahydro-1,3,5-triazine (), an intermediate in the condensation of formaldehyde and ammonia, tends to degrade to hexamethylene tetraamine. Cyclic aminal ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethylamine
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005. Structure and synthesis The molecule consists of a nitrogen atom with two methyl substituents and one proton. Dimethylamine is a weak base and the pKa of the ammonium CH3--CH3 is 10.73, a value above methylamine (10.64) and trimethylamine (9.79). Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia at elevated temperatures and high pressure: :2 CH3OH + NH3 → (CH3)2NH + 2 H2O Natural occurrence Dimethylamine is found quite widely distributed in animals and plants, and is present in many foods at the level of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
N,N,N′,N′-Tetramethylformamidinium Chloride
''N'',''N'',''N''′,''N''′-Tetramethylformamidinium chloride is the simplest representative of quaternary formamidinium cations of the general formula + with a chloride as a counterion in which all hydrogen atoms of the protonated formamidine C(=NH2)NH2sup>+ are replaced by methyl groups. Deprotonation results in the exceptionally basic bis(dimethylamino)carbene R2N−C̈−NR2. Preparation It is generated by protonation of (CH3)3COCH(N(CH3)2)2 ( Bredereck's reagent). :(CH3)3COCH(N(CH3)2)2 + H+ → (CH3)3COH + H(N(CH3)2)2sup>+ ''N'',''N'',''N''′,''N''′-Tetramethylformamidinium chloride is also obtained in high yield (95%) in the reaction of dimethylformamide (DMF) with dimethylcarbamoyl chlorideThe conversion of DMF with thionyl chloride in a ratio of 3:1 obtains the product in a is significantly lower yield (72%) which appears, however, more realistic in view of the tricky handling of the chloride salt. : Properties ''N'',''N'',''N''′,''N''′-Tetrameth ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Eschenmoser's Salt
In organic chemistry, Eschenmoser's salt (named for Albert Eschenmoser) is the ionic, organic compound . It is the iodide salt of the dimethylaminomethylene cation . The dimethylaminomethylene cation is a strong dimethylaminomethylating agent, used to prepare derivatives of the type .E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. Enolates, silyl enol ethers, and even more acidic ketones undergo efficient dimethylaminomethylation. Once prepared, such tertiary amines can be further methylated and then subjected to base-induced elimination to afford methylidenated ketones. The salt was first prepared by the group of Albert Eschenmoser after whom the reagent is named. Structure and bonding Dimethylaminomethylene cation is described as a resonance hybrid of the carbocation and an iminium cation: :(CH3)2N-CH2+ (CH3)2N+=CH2 The atoms are coplanar. The cation ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tertiary Amine
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section Forms below), hence it is stored as an aqueous solution (formalin), which is also used to store animal specimens. It is the simplest of the aldehydes (). The common name of this substance comes from its similarity and relation to formic acid. Formaldehyde is an important precursor to many other materials and chemical compounds. In 1996, the installed capacity for the production of formaldehyde was estimated at 8.7 million tons per year. It is mainly used in the production of industrial resins, e.g., for particle board and coatings. Forms Formaldehyde is more complicated than many simple carbon compounds in that it adopts several diverse forms. These compounds can often be used interchangeably and can be interconverted. *Molecular formald ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tertiary Amines
In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline; Inorganic derivatives of ammonia are also called amines, such as monochloramine (). The substituent is called an amino group. Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure , are called amides and have different chemical properties from amines. Classification of amines Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
