1,5-Diaminonaphthalene

1,5-Diaminonaphthalene
Names
	Preferred IUPAC name Naphthalene-1,5-diamine
	Other names Alphamin, 1,5-DAN
Identifiers
CAS Number	2243-62-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53003;
ChEMBL	ChEMBL538965;
ChemSpider	15851;
ECHA InfoCard	100.017.108
EC Number	218-817-8;
KEGG	C19463;
PubChem CID	16720;
RTECS number	QJ3400000;
UNII	13PD3J52LK;
UN number	3077
CompTox Dashboard (EPA)	DTXSID3020916 ;
	InChI 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;
	SMILES C1=CC2=C(C=CC=C2N)C(=C1)N;
Properties
Chemical formula	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
Crystal structure	monoclinic
Space group	P21/c
Lattice constant	a = 5.1790, b = 11.008, c = 21.238 α = 90°, β = 90.68°, γ = 90°
Lattice volume (V)	1210.7
Formula units (Z)	6
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H351, H410
Precautionary statements	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). Infobox references

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

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]

1,5-Diaminonaphthalene is a precursor imine-linked covalent organic frameworks.^[4]

Applications

Analytical matrix for MALDI/LDI. 1,5-Diaminonaphthalene (often as the hydrochloride salt) is used as a low-background matrix for MALDI mass spectrometry, including mass spectrometry imaging (MSI) of small molecules in tissue sections.^[5] It has also been reported as a highly performing electron-transfer matrix for LDI analyses of low-mass species.^[6]

Precursor to naphthalene-1,5-diisocyanate (NDI). 1,5-Diaminonaphthalene is an industrial intermediate to diisocyanates, notably naphthalene-1,5-diisocyanate (NDI), which is used to make high-performance polyurethane elastomers (marketed as Vulkollan, based on Desmodur 15).^[7]^[8]

References

^ 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.
^ 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.
^ Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2.
^ Afshari, Mohaddeseh; Dinari, Mohammad; Farrokhpour, Hossein; Zamora, Félix (2022-05-18). "Imine-Linked Covalent Organic Framework with a Naphthalene Moiety as a Sensitive Phosphate Ion Sensing". ACS Applied Materials & Interfaces. 14 (19): 22398–22406. doi:10.1021/acsami.1c24555. PMC 9121346. PMID 35503993.
^ Liu, Huihui; Chen, Rui; Wang, Jiyun; Chen, Suming; Xiong, Caiqiao; Wang, Jianing; Hou, Jian; He, Qing; Zhang, Ning; Nie, Zongxiu; Mao, Lanqun (2014). "1,5-Diaminonaphthalene hydrochloride assisted laser desorption/ionization mass spectrometry imaging of small molecules in tissues following focal cerebral ischemia". Analytical Chemistry. 86 (20): 10114–10121. doi:10.1021/ac5034566. PMID 25247713.
^ Calvano, Cosima D.; Capozzi, Maria Annunziata M.; Punzi, Angela; Farinola, Gianluca M.; Cataldi, Tommaso R. I.; Palmisano, Francesco (2018-12-19). "1,5-Diaminonaphtalene is a Highly Performing Electron-Transfer Secondary-Reaction Matrix for Laser Desorption Ionization Mass Spectrometry of Indolenine-Based Croconaines". ACS Omega. 3 (12): 17821–17827. doi:10.1021/acsomega.8b02575. PMC 6644284. PMID 31458378.
^ "Vulkollan®: The ultimate elastomer". Covestro. Retrieved 21 August 2025.
^ "NDI-based elastomers – Technology by Covestro". Covestro. Retrieved 21 August 2025.

[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.

[Ullmann-3] Booth, Gerald (2005). "Naphthalene Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 978-3-527-30673-2.

[4] Afshari, Mohaddeseh; Dinari, Mohammad; Farrokhpour, Hossein; Zamora, Félix (2022-05-18). "Imine-Linked Covalent Organic Framework with a Naphthalene Moiety as a Sensitive Phosphate Ion Sensing". ACS Applied Materials & Interfaces. 14 (19): 22398–22406. doi:10.1021/acsami.1c24555. PMC 9121346. PMID 35503993.

[5] Liu, Huihui; Chen, Rui; Wang, Jiyun; Chen, Suming; Xiong, Caiqiao; Wang, Jianing; Hou, Jian; He, Qing; Zhang, Ning; Nie, Zongxiu; Mao, Lanqun (2014). "1,5-Diaminonaphthalene hydrochloride assisted laser desorption/ionization mass spectrometry imaging of small molecules in tissues following focal cerebral ischemia". Analytical Chemistry. 86 (20): 10114–10121. doi:10.1021/ac5034566. PMID 25247713.

[6] Calvano, Cosima D.; Capozzi, Maria Annunziata M.; Punzi, Angela; Farinola, Gianluca M.; Cataldi, Tommaso R. I.; Palmisano, Francesco (2018-12-19). "1,5-Diaminonaphtalene is a Highly Performing Electron-Transfer Secondary-Reaction Matrix for Laser Desorption Ionization Mass Spectrometry of Indolenine-Based Croconaines". ACS Omega. 3 (12): 17821–17827. doi:10.1021/acsomega.8b02575. PMC 6644284. PMID 31458378.

[7] "Vulkollan®: The ultimate elastomer". Covestro. Retrieved 21 August 2025.

[8] "NDI-based elastomers – Technology by Covestro". Covestro. Retrieved 21 August 2025.

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Synthesis and reactions

Applications

See also

References