|
Diamine
A diamine is an amine with two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to Primary (chemistry), primary diamines, as those are the most reactive. In terms of quantities produced, 1,6-diaminohexane (a precursor to Nylon 6-6) is most important, followed by ethylenediamine. Vicinal (chemistry), Vicinal diamines (1,2-diamines) are a structural motif in many biological compounds and are used as ligands in coordination chemistry. Aliphatic diamines Linear * 2 carbon backbone: ethylenediamine (1,2-diaminoethane). Related derivatives include the N-alkylated compounds, 1,1-dimethylethylenediamine, 1,2-dimethylethylenediamine, ethambutol, tetrakis(dimethylamino)ethylene, TMEDA. Many 1,2-diamine derivatives are of practical interest such as penicillin. * 3 carbon backbone: 1,3-diaminopropane (propane-1,3-diamine) * 4 carbon backbone: putrescine (butane-1,4-diamine) * 5 carbon backbone: cadaverine (pen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethylenediamine
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines. Synthesis Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 °C in an aqueous medium (EDC process): : In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by fractional distillation. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products. Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH : Th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexamethylenediamine
Hexamethylenediamine or hexane-1,6-diamine, is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. Synthesis Hexamethylenediamine was first reported by Theodor Curtius. It is produced by the hydrogenation of adiponitrile: :NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2 The hydrogenation is conducted on molten adiponitrile diluted with ammonia, typical catalysts being based on cobalt and iron. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriamine). An alternative process uses Raney nickel as the catalyst and adiponitrile that is diluted with hexamethylenediamine itself (as the solvent ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
2,3-Butanediamine
2,3-Butanediamine are organic compounds with the formula CH3CH(NH2)CH(NH2)CH3. Three stereoisomers exist, meso and a pair of enantiomers. These diamines form complexes with transition metals. Synthesis 2,3-Butanediamines can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide. Alternative, it is produced by reduction of dimethylglyoxime with lithium aluminium hydride. The meso and the d,l diastereomers can be separated by fractional crystallization of the hydrochlorides. The enantiomers have been resolved using tartrate salts. Reactions In coordination chemistry, 2,3-butanediamine (abbreviated bn) has illuminates aspects of the stereochemistry. The structure of o(meso-2,3-butanediamine)2CO3sup>+ confirms the presence of the rarely observed axial methyl groups on each of the diamine-cobalt rings. Related compounds *1,2-Diaminopropane 1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CHCH(NH)CHNH. A col ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,2-diaminopropane
1,2-Diaminopropane (propane-1,2-diamine) is organic compound with the formula CHCH(NH)CHNH. A colorless liquid, it is the simplest chiral diamine. Preparation Industrially, this compound is synthesized by the ammonolysis of 1,2-dichloropropane: :CHCHClCHCl + 4 NH → CHCH(NH)CHNH + 2 NHCl This preparation allows for the use of waste chloro-organic compounds to form useful amines using inexpensive and readily available ammonia. The racemic mixture of this chiral compound may be separated into enantiomers by conversion into the diastereomeric tartaric acid ammonium salt. After purification of the diastereomer, the diamine can be regenerated by treatment of the ammonium salt with sodium hydroxide. Alternate reagents for chiral resolution include N-p-toluenesulfonylaspartic acid, N-benzenesulfonylaspartic acid, or N-benzoylglutamic acid. Uses 1,2-Diaminopropane is used in the synthesis of ''N'',''N''-disalicylidene-1,2-propanediamine, a salen-type ligand, usually abbreviated as s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
TMEDA
Tetramethylethylenediamine (TMEDA or TEMED) is a chemical compound with the formula (CH3)2NCH2CH2N(CH3)2. This species is derived from ethylenediamine by replacement of the four amine hydrogens with four methyl groups. It is a colorless liquid, although old samples often appear yellow. Its odor is similar to that of rotting fish. As a reagent in synthesis TMEDA is widely employed as a ligand for metal ions. It forms stable complexes with many metal halides, e.g. zinc chloride and copper(I) iodide, giving complexes that are soluble in organic solvents. In such complexes, TMEDA serves as a bidentate ligand. TMEDA has an affinity for lithium ions. When mixed with n-Butyllithium, ''n''-butyllithium, TMEDA's nitrogen atoms coordinate to the lithium, forming a cluster of higher reactivity than the tetramer or hexamer that ''n''-butyllithium normally adopts. BuLi/TMEDA is able to metallate or even doubly metallate many substrates including benzene, furan, thiophene, ''N''-alkylpyrroles ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pentane-1,5-diamine 200
Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor. It is present in small quantities in living organisms but is often associated with the putrefaction of Tissue (biology)#Animal tissue, animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors. Production Cadaverine is produced by decarboxylation of lysine.Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane. History Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). It was named from the English adjective ''cadaverous''. Receptors In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1,3-diaminopropane
1,3-Diaminopropane, also known as , is a simple diamine with the formula H2N(CH2)3NH2. A colourless liquid with a fishy odor, it is soluble in water and many polar organic solvents. It is isomeric with 1,2-diaminopropane. Both are building blocks in the synthesis of heterocycles, such as those used in textile finishing, and coordination complexes. It is prepared by the amination of acrylonitrile followed by hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ... of the resulting aminopropionitrile.Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. The potassium salt was used in the alkyne zipper reaction. Known uses of 1,3-diaminopropane are in the synthesis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coordination Chemistry
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many metal-containing chemical compound, compounds, especially those that include transition metals (elements like titanium that belong to the periodic table's d-block), are coordination complexes. Nomenclature and terminology Coordination complexes are so pervasive that their structures and reactions are described in many ways, sometimes confusingly. The atom within a ligand that is bonded to the central metal atom or ion is called the donor atom. In a typical complex, a metal ion is bonded to several donor atoms, which can be the same or different. A Ligand#Polydentate and polyhapto ligand motifs and nomenclature, polydentate (multiple bonded) ligand is a molecule or ion that bonds to the central atom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
