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1,8-Diaminonaphthalene

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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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