1,8-Bis(dimethylamino)naphthalene

1,8-Bis(dimethylamino)naphthalene
Names
Preferred IUPAC name
N1,N1,N8,N8-Tetramethylnaphthalene-1,8-diamine
Other names
N,N,N′,N′-Tetramethylnaphthalene-1,8-diamine
Proton Sponge
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.039.986 Edit this at Wikidata
UNII
  • InChI=1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3 checkY
    Key: GJFNRSDCSTVPCJ-UHFFFAOYSA-N checkY
  • InChI=1/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3
    Key: GJFNRSDCSTVPCJ-UHFFFAOYAM
  • CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C
  • c1(cccc2cccc(N(C)C)c12)N(C)C
Properties
C14H18N2
Molar mass 214.312 g·mol−1
Appearance White crystalline powder
Melting point 47.8 °C (118.0 °F; 320.9 K)
Acidity (pKa) 12.1 (in water)[1]

18.62 (in acetonitrile)[2]
(acidity of the conjugate acid C14H18N2H+)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

1,8-Bis(dimethylamino)naphthalene is an organic compound with the formula C10H6(NMe2)2 (Me = methyl). It is classified as a peri-naphthalene, i.e. a 1,8-disubstituted derivative of naphthalene. Owing to its unusual structure, it exhibits exceptional basicity. It is often referred by the trade name Proton Sponge, a trademark of Sigma-Aldrich.[3]

  1. ^ R. W. Alder; P. S. Bowman; W. R. S. Steele & D. R. Winterman (1968). "The remarkable basicity of 1,8-bis(dimethylamino)naphthalene". Chem. Commun. (13): 723. doi:10.1039/C19680000723.
  2. ^ I. Kaljurand, A. Kütt, L. Sooväli, T. Rodima, V. Mäemets, I. Leito, I. A. Koppel. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales. J. Org. Chem., 2005, 70, 1019–1028. doi:10.1021/jo048252w
  3. ^ Cite error: The named reference Alder was invoked but never defined (see the help page).