2,5-ノルボルナジエン 化学特性,用途語,生産方法
外観
無色～ほとんど無色透明液体
解説
2,5-ノルボルナジエンともいう,融点－20 ℃，沸点90 ℃．可燃性液体．加熱すれば1,3,5-シクロヘプタトリエンを生じる．光照射すれば，光のエネルギーを吸収してクアドリシクランに異性化するので，光エネルギー変換物質として注目されている．
森北出版「化学辞典（第2版）
用途
2,5-ノルボルナジエン,有機化合物である。この二環式の炭化水素は、ノルボルナンとノルボルネンから誘導される最も安定したジオレフィンである。ノルボルナジエンは、均一系触媒における配位子として主に関心が持たれたが、その高い反応性や異性化できないジエンとしての独特の構造的な特性により盛んに研究されている。
化学的特性
2,5-Norbornadiene, also known as dicycloheptadiene, is a clear colorless to slightly yellow liquid that is soluble in petroleum ether and insoluble in water. Commercially available goods usually contain 500 ppm of 2,6-di-tert-butyl-p-methylphenol (BHT) as a stabilizer. Analyzing the structural characteristics of NBD, it can be found that it has good reaction properties and can synthesize a variety of organic compounds through addition or substitution reactions at the double bond.
使用
2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.
製造方法
2,5-Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene.
一般的な説明
2,5-norbornadiene, stabilized appears as a colorless liquid. Insoluble in water and less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. When heated will polymerize and at decomposition emits acrid smoke and irritating fumes.
空気と水の反応
Highly flammable. Insoluble in water.
反応プロフィール
2,5-NORBORNADIENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Violent explosions at low temperatures in ammonia synthesis gas units have been traced to the addition products of dienes and nitrogen dioxide [Bretherick, 5th Ed., 1995].
健康ハザード
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
安全性プロファイル
Poison by intravenous
route. Moderately toxic by ingestion and
intraperitoneal routes. Mildly toxic by
inhalation. A flammable liquid. When heated
to decomposition it emits acrid smoke and
irritating fumes.
純化方法
Purify the diene by distillation from activated alumina [Landis & Halpern J Am Chem Soc 109 1746 1987]. [Beilstein 5 IV 879.]
2,5-ノルボルナジエン 上流と下流の製品情報
原材料
3,4-Diazatricyclo[4.2.1.02,5]nona-3,7-diene, (1R,2R,5S,6S)-rel- (9CI)
Bicyclo[2.2.1]hept-2-ene, 5,6-bis(phenylsulfonyl)-, (endo,endo)- (9CI)
準備製品