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any organic compound containing two amino groups

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/09 09:31:16」(JST)

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A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides and polyureas. In terms of quantities produced, 1,6-diaminohexane, a precursor to Nylon 6-6, is most important, followed by ethylenediamine.^[1] Vicinal diamines (1,2-diamines) are a structural motif in many biological compounds and are used as ligands in organometallic chemistry ^[2]

Aliphatic diamines

Linear aliphatic diamines

2 carbons: ethylenediamine (1,2-diaminoethane). Related derivatives include the N-alkylated compounds ethambutol and TMEDA.
3 carbons: 1,3-diaminopropane (propane-1,3-diamine)
4 carbons: putrescine (butane-1,4-diamine)
5 carbons: cadaverine (pentane-1,5-diamine)
6 carbons: hexamethylenediamine (hexane-1,6-diamine)

Branched aliphatic diamines

Derivatives of ethylenediamine are prominent:

1,2-diaminopropane, which is chiral.
diphenylethylenediamine, which is C₂-symmetric.
diaminocyclohexane, which is C₂-symmetric.

Xylylenediamines

Xylylenediamines are classified as alkylamines since the amine is not directly attached to an aromatic ring.

o-xylylenediamine or OXD
m-xylylenediamine or MXD
p-xylylenediamine or PXD

Aromatic diamines

Three phenylenediamines are known:^[3]

o-phenylenediamine or OPD
m-phenylenediamine or MPD
p-phenylenediamine or PPD. 2,5-Diaminotoluene is related to PPD but contains a methyl group on the ring.

Various N-methylated derivatives of the phenylenediamines are known:

dimethyl-4-phenylenediamine, a reagent.
N,N'-di-2-butyl-1,4-phenylenediamine, an antioxidant.

Examples with two aromatic rings include derivatives of biphenyl and naphthalene:

4,4'-diaminobiphenyl
1,8-diaminonaphthalene

Ethylenediamine
Cadaverine
PPD (para-phenylenediamine)

References

^ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a02_001
^ Lucet, D., Le Gall, T. and Mioskowski, C. (1998), The Chemistry of Vicinal Diamines. Angew. Chem. Int. Ed., 37: 2580–2627. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2580::AID-ANIE2580>3.0.CO;2-L
^ Robert A. Smiley "Phenylene- and Toluenediamines" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a19_405

External links

Diamines at the US National Library of Medicine Medical Subject Headings (MeSH)
Synthesis of diamines

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English Journal

Simultaneous determination of 15 aminoglycoside(s) residues in animal derived foods by automated solid-phase extraction and liquid chromatography-tandem mass spectrometry.

Tao Y, Chen D, Yu H, Huang L, Liu Z, Cao X, Yan C, Pan Y, Liu Z, Yuan Z.SourceNational Reference Laboratory of Veterinary Drug Residues (HZAU)/MOA, Key Laboratory of Food Safety Evaluation, Huazhong Agricultural University, Wuhan, Hubei 430070, China.
Food chemistry.Food Chem.2012 Nov 15;135(2):676-83. Epub 2012 Apr 24.
An automated method has been developed for the simultaneous quantification of 15 aminoglycosides in muscle, liver (pigs, chicken and cattle), kidney (pigs and cattle), cow milk, and hen eggs by liquid chromatography tandem mass spectrometry. Homogenized samples were extracted by monopotassium phosph
PMID 22868145

Asymmetric construction of spirocyclohexanonerhodanines catalyzed by simple diamine derived from chiral tert-leucine.

Wu W, Huang H, Yuan X, Zhu K, Ye J.SourceEngineering Research Centre of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China. yejx@ecust.edu.cn.
Chemical communications (Cambridge, England).Chem Commun (Camb).2012 Sep 21;48(73):9180-2. Epub 2012 Aug 6.
A diamine-catalyzed asymmetric tandem reaction between α,β-unsaturated ketones and rhodanine derivatives has been developed to synthesize various spirocyclic compounds with high stereoselectivities (up to 99% ee and >20 : 1 dr). The products obtained contain two pharmaceutically relevant fe
PMID 22864403