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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.


Upon treatment with ] 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|s2cid=32185653 |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 ]. This compound used to produce perimidines by various aldehydes.<ref>{{cite journal|last=F.K. Behbahani, F.M.Golchin|doi=10.1016/j.jtusci.2015.10.004|title=A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4|journal=Journal of Taibah University for Science|year=2017|volume=11|pages=85–89|s2cid=98648448|doi-access=free|url=https://zenodo.org/records/3593823/files/A%20new%20catalyst%20for%20the%20synthesis%20of%202%20substituted%20perimidines%20catalysed%20by%20FePO4(1).pdf}}</ref> Upon treatment with ] 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|s2cid=32185653 |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 ]. This compound used to produce perimidines by various aldehydes.<ref>{{cite journal|last=F.K. Behbahani, F.M.Golchin|doi=10.1016/j.jtusci.2015.10.004|title=A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4|journal=Journal of Taibah University for Science|year=2017|volume=11|issue=1 |pages=85–89|s2cid=98648448|doi-access=free|bibcode=2017JTUS...11...85B |url=https://zenodo.org/records/3593823/files/A%20new%20catalyst%20for%20the%20synthesis%20of%202%20substituted%20perimidines%20catalysed%20by%20FePO4(1).pdf}}</ref>


==See also== ==See also==

Latest revision as of 20:51, 22 February 2024

1,8-Diaminonaphthalene
Names
Preferred IUPAC name Naphthalene-1,8-diamine
Other names Deltamin, 1,8-Naphthalenediamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.846 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2Key: YFOOEYJGMMJJLS-UHFFFAOYSA-N
  • InChI=1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2Key: YFOOEYJGMMJJLS-UHFFFAOYAU
SMILES
  • C1=CC2=C(C(=C1)N)C(=CC=C2)N
  • c1(cccc2cccc(N)c12)N
Properties
Chemical formula C10H10N2
Molar mass 158.1998
Related compounds
Related Aromatic amines 1-Naphthylamine
1,8-bis(dimethylamino)naphthalene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Synthesis and reactions

Chemical structure of 12-phthaloperinone, a derivative of 1,8-diaminonaphthalene

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. 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.

See also

References

  1. Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3527306732..
  2. 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. S2CID 32185653.
  3. F.K. Behbahani, F.M.Golchin (2017). "A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4" (PDF). Journal of Taibah University for Science. 11 (1): 85–89. Bibcode:2017JTUS...11...85B. doi:10.1016/j.jtusci.2015.10.004. S2CID 98648448.
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