1,5-Diaminonaphthalene

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1,5-Diaminonaphthalene
1,5-DAN.svg
Names
Preferred IUPAC name
Naphthalene-1,5-diamine
Other names
Alphamin, 1,5-DAN
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.108 Edit this at Wikidata
EC Number
  • 218-817-8
KEGG
RTECS number
  • QJ3400000
UNII
UN number 3077
  • InChI=1S/C10H10N2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6H,11-12H2
    Key: KQSABULTKYLFEV-UHFFFAOYSA-N
  • C1=CC2=C(C=CC=C2N)C(=C1)N
Properties
C10H10N2
Molar mass 158.204 g·mol−1
Appearance white solid
Density 1.4
Melting point 185–187 °C (365–369 °F; 458–460 K)
Structure[1]
monoclinic
P21/c
a = 5.1790, b = 11.008, c = 21.238
α = 90°, β = 90.68°, γ = 90°[2]
1210.7
6
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Warning
H351, H410
P201, P202, P273, P281, P308+P313, P391, P405, P501
Flash point 226 °C (439 °F; 499 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,5-Diaminonaphthalene is an organic compound with the formula C10H6(NH2)2. It is one of several diaminonaphthalenes. It is a colorless solid that darkens in air due to oxidation.

Synthesis and reactions[edit]

It is prepared by reduction of 1,5-dinitronaphthalene, which in turn is obtained with the 1,8-isomers by nitration of 1-nitronaphthalene. It can also be prepared by treatment of 1,5-dihydroxynaphthalene with ammonium sulfite. It is a precursor to naphthalene-1,5-diisocyanate, a precursor to specialty polyurethanes.[3]

See also[edit]

References[edit]

  1. ^ Bernes, S.; Pastrana, M.R.; Sanchez, E.H.; Perez, R.G. (2004). "Crystal Structure". CCDC 232143: Experimental Crystal Structure Determination. Cambridge Crystallographic Data Centre. doi:10.5517/cc7skh1.
  2. ^ Bernès, Sylvain; Pastrana, Modesto Rodríguez; Sánchez, Enrique Huerta; Pérez, René Gutiérrez (12 December 2003). "1,5-Diaminonaphthalene". Acta Crystallographica Section E. 60 (1): o45–o47. doi:10.1107/S1600536803026643.
  3. ^ Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.