ブロモシクロプロパン

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H225：引火性の高い液体および蒸気

• 注意書き

  P210：熱/火花/裸火/高温のもののような着火源から遠ざ けること。－禁煙。

  P233：容器を密閉しておくこと。

  P240：容器を接地すること/アースをとること。

  P241：防爆型の電気機器/換気装置/照明機器/．．．機器を使 用すること。

  P242：火花を発生させない工具を使用すること。

  P243：静電気放電に対する予防措置を講ずること。

ブロモシクロプロパン 価格

MSDS Information

• Bromocyclopropane

ブロモシクロプロパン 化学特性,用途語,生産方法

• 外観

  無色～わずかにうすい黄色, 澄明の液体

• 溶解性

  水に不溶。エタノールに混和。エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。

• 用途

  有機合成原料。

• 説明

  Cyclopropyl bromide is also named as Bromocyclopropane. It is used in organic synthesis, for instance, for the formation of a Grignard Reagent, cyclopropyllithium. It is also used as an intermediate in the manufacture of pharmaceutical and agrochemical products.

• 化学的特性

  Light yellow to clear colourless liquid, boiling point 67-69°C, refractive index (nD20) 1.4605, density (d420) 1.5120, flash point -6°C.

• 使用

  Bromocyclopropane is primarily used an intermediate in the manufacture of pharmaceutical and agrochemical products. It is also used in the production of cyclopropyl boric acid. It is used as an intermediate in organic synethesis.

• 製造方法

  Bromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at ?29° (53% yield) or in tetrachloroethane at ?20° to ?25° (15–20% yield). Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield. An attempt to prepare the bromide via the von Braun reaction was unsuccessful. Ten percent yields are reported for the photobromination of cyclopropane and the photochemical rearrangement of allyl bromide. Treatment of 1,1,3-tribromopropane with methyllithium prepared from methyl bromide furnishes a 60–65% yield of bromocyclopropane.

• 主な応用

  Bromocyclopropane have anti-angiogenic effects that inhibits the growth of new blood vessels by interfering with the production of prostaglandins and nitric oxide, which are important for the formation of new blood vessels. Bromocyclopropane binds to cyclopropyl and hydrochloric acid, forming a hydrogen bond. It also forms a hydrogen bond with fatty acids and an a-type hydroxyl group.

• 参考文献

  Science of Synthesis: Houben-Weyl Methods of Molecular Transformation Vol. 7: Compounds of Group 13 and 2 (Al, Ga, In, Tl, Be…Ba), 2007, ISBN: 9783131484819
  D. Seyferth, H. M. Cohen, The Stability of Cyclopropyllithium in diethyl ether and in tetrahydrofuran, Journal of Organometallic Chemistry, 1963, vol. 1, pp. 15-21
  “Formal Nucleophilic Substitution of Bromocyclopropanes with Azoles”, Ryabchuk, P.; Rubina, M.; Xu, J.; Rubin, M. Org. Lett. 2012, 14, 1752.
  “Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles”, Banning, J. E.; Gentillon, J.; Ryabchuk, P. G.; Prosser, A. R.; Rogers, A.; Edwards, A.; Holtzen, A.; Babkov, I.; Rubina, M.; Rubin, M. J. Org. Chem., 2013, 78, 7601.

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