(2-ブロモエチル)ベンゼン 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
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
ベータ-フェネチル誘導体、医薬品、香料、その他精密化学品の重要な出発物質
用途
有機合成原料。
使用上の注意
アルゴン封入
説明
Phenethylbromide is an analytical reference material that is structurally categorized as an organobromide. It is used in the synthesis of a variety of compounds, including fentanyl. Phenethylbromide is combined with 4-piperidinone to produce N-phenethyl-4-piperidone, which, as a precursor in the synthesis of fentanyl, is scheduled as a List I chemical in the United States. Phenethylbromide may be found as in impurity in samples of fentanyl produced using this pathway.
化学的特性
colourless to yellow liquid. It is miscible with ether and benzene, but insoluble in water.
使用
(2-Bromoethyl)benzene is used in the preparation of phenelzine by reacting with hydrazine. It is also used as a starting material to prepare various beta-phenethyl derivatives, active pharmaceutical ingredients, and fragrances. It finds application as a flame retardant.
使用
(2-Bromoethyl)benzene is an important
starting material for the production of various
b-phenethyl derivatives, pharmaceuticals, fragrances, and other fine chemicals.
製造方法
(2-Bromoethyl)benzene is synthesized by the reaction of phenethyl alcohol with hydrogen bromide.
Reaction: The phenethyl alcohol was heated to 110°C, hydrogen bromide was slowly introduced, and the reaction was refluxed. The reaction was completed, cooled, washed with water, 10% sodium carbonate solution, and water in turn. After drying with anhydrous potassium carbonate, fractional distillation under reduced pressure was carried out to collect fractions at 97-99°C (2.0 kPa) with a yield of over 90%.
安全性
Store at 2-8° C in a tightly closed container in a dry, well-ventilated place. Containers that are opened must be carefully resealed and kept upright to prevent leakage. (2-Bromoethyl)benzene is incompatible with strong oxidizing agents. This chemical is harmful if swallowed and causes severe eye irritation.
純化方法
Wash the bromide with conc H2SO4, water, aqueous 10% Na2CO3 and water again, then dry it with CaCl2 and fractionally distil it just before use. [Beilstein 5 IV 907.]
参考文献
1. Shukla, P.; Sharma, A.; Pallavi, B.; Cheng, C. H. Nickel-catalyzed reductive Heck type coupling of saturated alkyl halides with acrylates and oxabenzonorbornadiene. Tetrahedron 2015, 71 (15), 2260-2266. DOI:
10.1016/J.TET.2015.02.0672. Huang, Y. B.; Yan, L.; Chen, M. Y.; Guo, Q. X.; Fu, Y. Selective hydrogenolysis of phenols and phenyl ethers to arenes through direct C-O cleavage over ruthenium-tungsten bifunctional catalysts. Green Chem. 2015, 17 (5), 3010-3017. DOI:
10.1039/C5GC00326A3. Justice, D.E.A.D.o. Control of a chemical precursor used in the illicit manufacture of fentanyl as a List I chemical. Final rule. Federal Register 73(144), 43355-43357 (2008). PMID:
18949877
(2-ブロモエチル)ベンゼン 上流と下流の製品情報
原材料
準備製品
フェニルエチレングリコール
1-フェネチルピペラジン
4-(クロロメチル)スチレン
N-メチル-2-フェニルエチルアミン
カルフェンタニル
Benzene, [dimethyl(2-phenylethyl)silyl]-
5-フェニル吉草酸メチル
2-アセトアミド-2-フェネチルマロン酸ジエチル
2-フェネチル-4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン
1-フェニル-2-ニトロエタン
1-フェノキシ-2-フェニルエタン
4-(2-ブロモエチル)安息香酸
2,2-ジメチルプロパン酸2-フェニルエチル
1,2-ビスベンジルエタン
4-フェニルブチルブロミド
プロピオン酸フェネチル
1,2-Ethanediyl, 1-phenyl- (9CI)