1,8-Bis(dimethylamino)naphtalene CAS NO.20734-58-1

Product Name:    1,8-Bis(dimethylamino)naphtalene
Synonyms:    N1,N1,N8,N8-TETRAMETHYLNAPHTHALENE-1,8-DIAMINE;N,N,N',N'-TETRAMETHYL-1,8-DIAMINONAPHTHALENE;N,N,N',N'-TETRAMETHYL-1,8-NAPHTHALENEDIAMINE;N,N,N',N'-BIS(DIMETHYLAMINO) NAPHTHALENE;PROTON SPONGE;PROTON-SPONGE(R);N,N,N',N'-TetraMethyl-1,8-naphthalenediaMine puruM, >=99.0% (NT);N-N-N-Tetramethyl-1-8-naphthalenediamine
CAS:    20734-58-1
MF:    C14H18N2
MW:    214.31
EINECS:    244-001-6
Mol File:    20734-58-1.mol

1,8-Bis(dimethylamino)naphtalene Chemical Properties
Melting point     49-51 °C(lit.)
Boiling point     144-145°C (3.7505 mmHg)
density     1.12
Fp     >230 °F
storage temp.     Keep in dark place,Inert atmosphere,Room temperature
solubility     Soluble in organic solvents.
pka    12.1(at 25℃)
form     Crystalline Powder
color     Pale brownish-pink
Water Solubility     insoluble
Sensitive     Light Sensitive
Merck     14,3388
BRN     396782
InChIKey    GJFNRSDCSTVPCJ-UHFFFAOYSA-N
CAS DataBase Reference    20734-58-1(CAS DataBase Reference)
NIST Chemistry Reference    1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1)
Safety Information
Hazard Codes     Xn,C
Risk Statements     22-36/37/38-34
Safety Statements     26-45-36/37/39
RIDADR     3259
WGK Germany     3
F     8-10-23
HazardClass     8
HS Code     29215900
MSDS Information
Provider    Language
ACROS    English
SigmaAldrich    English
ALFA    English
1,8-Bis(dimethylamino)naphtalene Usage And Synthesis
Chemical Properties    1,8-Bis(dimethylamino)naphtalene is pale brownish-pink crystalline powder
Uses    1,8-Bis(dimethylamino)naphthalene, also referred to as protone sponge, is a lipophilic proton trapping agent. 1,8-Bis(dimethylamino)naphthalene is used in the matrix for mass spectroscopy analysis of lipids and fatty acids.
Uses    Very strong base in organic synthesis and catalysis.
Purification Methods    It is prepared by methylating 1,8-diaminonaphthalene, and likely impurities are methylated products. The tetramethyl compound is a stronger base than the unmethylated, di and trimethylated derivatives. The pKa values are: 1,8-(NH2)2 = 4.61, 1,8-(NHMe)2 = 5.61, 1-NHMe-8-NHMe2 = 6.43 and 1,8-(NMe2)2 = 12.34. The mixture is then treated with H2O at pH 8 (where all but the required base are protonated) and extracted with Et2O or CHCl3. The dried extract (K2CO3) yields the tetramethyldiamine on evaporation which can be distilled. It is a strong base with weak nucleophilic properties, e.g. it could not be alkylated by refluxing with EtI in MeCN for 4 days; and on treatment with methyl fluorosulfonate only the fluorosulfonate salt of the base is obtained. [NMR: Adler et al. J Chem Soc, Chem Commun 723 1968, Brown & Letang J Am Chem Soc 63 358 1941, Brzezinski et al. J Chem Soc Perkin Trans 2 857 1991.] Alternatively, crystallise proton sponge from EtOH and dry it in a vacuum oven. Store it in the dark in a CO2-free atmosphere. [Benoit et al. Can J Chem 65 996 1987, Beilstein 13 IV 344.]
1,8-Bis(dimethylamino)naphtalene Preparation Products And Raw materials
Preparation Products    Hexamethylene Diisocyanate