英文互译镜像站

1,5-Diaminonaphthalene

Last updated
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-817-8
KEGG
PubChem CID
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
Appearancewhite 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:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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.

Contents

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]

See also

References

  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. 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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.
镜像程序 镜像软件 站点核心词加权 站点核心词加权 小偷程序