1,8-Diaminonaphthalene

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]

1,8-Diaminonaphthalene

Names
IUPAC name naphthalene-1,8-diamine
Other names deltamin, 1,8-naphthalenediamine
Identifiers
CAS Number	479-27-6^Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL595537^Y
ChemSpider	61381^Y
ECHA InfoCard	100.006.846
PubChem CID	68067
UNII	IKA7029YH9^Y
CompTox Dashboard (EPA)	DTXSID6044432
InChI InChI=1S/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2^Y Key: YFOOEYJGMMJJLS-UHFFFAOYSA-N^Y InChI=1/C10H10N2/c11-8-5-1-3-7-4-2-6-9(12)10(7)8/h1-6H,11-12H2 Key: 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 [77 °F], 100 kPa).
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Infobox references

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.[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.

See also

• C₁₀H₁₀N₂

References

1. Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH..
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.