1,8-Diaminonaphthalene: Difference between revisions
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It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene. |
It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene. |
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Upon treatment with [[phthalic anhydride]] derivatives, the diamine converts to phthaloperinones.<ref>{{cite journal |doi=10.1021/ol201973w|title=Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors|year=2011|last1=Mamada|first1=Masashi|last2=PéRez-BolíVar|first2=César|last3=Anzenbacher|first3=Pavel|journal=Organic Letters|volume=13|issue=18|pages=4882–4885|pmid=21863817|url=https://scholarworks.bgsu.edu/chem_pub/145}}</ref> The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to [[1,8-bis(dimethylamino)naphthalene]]. This compound used to produce perimidines by various aldehydes.<ref>{{Cite journal|last=F.K. Behbahani, F.M.Golchin|first=|date=|doi= |
Upon treatment with [[phthalic anhydride]] derivatives, the diamine converts to phthaloperinones.<ref>{{cite journal |doi=10.1021/ol201973w|title=Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors|year=2011|last1=Mamada|first1=Masashi|last2=PéRez-BolíVar|first2=César|last3=Anzenbacher|first3=Pavel|journal=Organic Letters|volume=13|issue=18|pages=4882–4885|pmid=21863817|url=https://scholarworks.bgsu.edu/chem_pub/145}}</ref> The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to [[1,8-bis(dimethylamino)naphthalene]]. This compound used to produce perimidines by various aldehydes.<ref>{{Cite journal|last=F.K. Behbahani, F.M.Golchin|first=|date=|doi=10.1016/j.jtusci.2015.10.004|title=A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4|url=https://www.sciencedirect.com/science/article/pii/S1658365515001508|journal=Journal of Taibah University for Science|volume=11|pages=85-89|via=ScienceDirect}}</ref> |
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==See also== |
==See also== |
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Revision as of 14:21, 10 November 2021
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| Names | |
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| Preferred IUPAC name
Naphthalene-1,8-diamine | |
| Other names
Deltamin, 1,8-Naphthalenediamine
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.006.846 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H10N2 | |
| Molar mass | 158.1998 |
| Related compounds | |
Related Aromatic amines
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1-Naphthylamine 1,8-bis(dimethylamino)naphthalene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,8-Diaminonaphthalene is an organic compound with the formula C10H6(NH2)2. It is one of several isomeric naphthalenediamines. It is a colorless solid that darkens in air due to oxidation. It is a precursor to commercial pigments.[1]
Synthesis and reactions
It is prepared by reduction of 1,8-dinitronaphthalene, which in turn is obtained as a mixture of isomers by nitration of 1-nitronaphthalene.
Upon treatment with phthalic anhydride derivatives, the diamine converts to phthaloperinones.[2] The derivative from phthalic anhydride itself, Solvent Orange 60, is a useful orange pigment. It is a precursor to 1,8-bis(dimethylamino)naphthalene. This compound used to produce perimidines by various aldehydes.[3]
See also
References
- ^ Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..
- ^ Mamada, Masashi; PéRez-BolíVar, César; Anzenbacher, Pavel (2011). "Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors". Organic Letters. 13 (18): 4882–4885. doi:10.1021/ol201973w. PMID 21863817.
- ^ F.K. Behbahani, F.M.Golchin. "A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4". Journal of Taibah University for Science. 11: 85–89. doi:10.1016/j.jtusci.2015.10.004 – via ScienceDirect.