1,8-ビス(ジメチルアミノ)ナフタレン 化学特性,用途語,生産方法
外観
白色〜褐色, 結晶又は塊
溶解性
酢酸に溶け、水にほとんど溶けない。
用途
有機合成において、微量のプロトン源によって反応が妨害される場合、プロトンスポンジの添加が効果的な場合がある。
用途
有機合成原料。
化学的特性
1,8-Bis(dimethylamino)naphtalene is pale brownish-pink crystalline powder
使用
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.
一般的な説明
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-C
2B
8H
14 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.
純化方法
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-ビス(ジメチルアミノ)ナフタレン 上流と下流の製品情報
原材料
準備製品