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
CAS Number	20734-58-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	80012 ;
ECHA InfoCard	100.039.986
PubChem CID	88675;
UNII	6S79D2P9H8 ;
CompTox Dashboard (EPA)	DTXSID10174807 ;
	InChI 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 Key: GJFNRSDCSTVPCJ-UHFFFAOYSA-N ; 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;
	SMILES CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C; c1(cccc2cccc(N(C)C)c12)N(C)C;
Properties
Chemical formula	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); 18.62 (in acetonitrile); (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). verify (what is ?) Infobox references

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.

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
CAS Number	20734-58-1^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	80012^Y
ECHA InfoCard	100.039.986
PubChem CID	88675
UNII	6S79D2P9H8^Y
CompTox Dashboard (EPA)	DTXSID10174807
InChI 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^Y Key: GJFNRSDCSTVPCJ-UHFFFAOYSA-N^Y 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
SMILES CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C c1(cccc2cccc(N(C)C)c12)N(C)C
Properties
Chemical formula	C₁₄H₁₈N₂
Molar mass	214.312 g·mol⁻¹
Appearance	White crystalline powder
Melting point	47.8 °C (118.0 °F; 320.9 K)
Acidity (pK_a)	12.1 (in water) 18.62 (in acetonitrile) (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 ^YN ?) Infobox references