1,8-Bis(dimethylamino)naphthalene Chemical Properties

Melting point:

49-51 °C(lit.)

Boiling point:

144-145°C (3.7505 mmHg)

Density 

1.12

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in organic solvents.

form 

Crystalline Powder

pka

12.1(at 25℃)

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

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,8-Bis(dimethylamino)naphthalene 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.

Uses

Very strong base with weak nucleophilic character due to steric effects.

Definition

ChEBI: N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine is a member of naphthalenes.

General Description

Proton-sponge is also referred as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C₂B₈H₁₄ and selected acyl chlorides. It has been tested as an effective H⁺ scavenger.

Solubility in organics

Soluble in most organic solvents, such as methanol and chloroform.

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.]

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