三氟乙醇

2,2,2-三氟乙醇
骨架式
3D模型
IUPAC名
2,2,2-Trifluroroethanol
2,2,2-三氟乙醇
别名 TFE
识别
CAS号 75-89-8  checkY
PubChem 6409
ChemSpider 21106169
SMILES
 
  • OCC(F)(F)F
InChI
 
  • 1/C2H3F3O/c3-2(4,5)1-6/h6H,1H2
InChIKey RHQDFWAXVIIEBN-UHFFFAOYAH
ChEBI 42330
DrugBank DB03226
性质
化学式 C2H3F3O
摩尔质量 100.04 g·mol⁻¹
外观 無色液體
密度 1.373 g/mL,液體
熔点 −45.0 °C
沸点 78.0 °C
溶解性 可混溶
溶解性乙醇 可混溶
危险性
警示术语 R:R10, R20/21/22, R36/38, R62
安全术语 S:S16, S36/37/39, S45
欧盟分类 有害 (Xn)
NFPA 704
3
2
1
 
相关物质
相关 六氟-2-丙醇
相关化学品 1,1,1-三氟乙烷
三氟乙酸
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

三氟乙醇2,2,2-三氟乙醇化學式:CF3CH2OH),是一種有機化合物 ,缩写為TFE,它是無色、能與水相溶的液體,帶有跟乙醇相似的氣味。由于三氟甲基的强吸电子效应,三氟乙醇的酸性乙醇强得多,可与杂环化合物生成氢键键连的穩定配合物(例如:THF吡啶)。

生產

三氟乙醇在工業生產中的制取常采用氫化氢化物还原三氟乙酸的衍生物,如酰氯[1]

TFE亦可從氫化通式为CF3−CHOH−OR(R=或1-8个碳原子的烷基)製備,以沉积在活性炭上的催化劑。此外还常加入脂肪叔胺,如三乙胺共催化。

用途

作為溶劑

三氟乙醇在有機化學中用作溶劑。[2][3]过氧化氢对硫化合物的氧化反应常采用TFE作溶剂。[4]

在生物學中,TFE可於用NMR光譜學研究蛋白質折疊時作為一種聯合溶劑。此溶劑能有效地把蛋白質溶解。在一定濃度下,TFE可強烈地影響蛋白質的三維結構

工業上,三氟乙醇是生产尼龍和医药时用的溶剂。

反應

三氟乙醇可被氧化为三氟乙醛三氟乙酸。它也可提供三氟甲基,参与化學反應如Horner-Wadsworth-Emmons反应的Still-Gennari改进。

2,2,2-三氟乙基乙烯基醚是三氟乙醇的乙烯基醚,用作通過臨床診斷的可吸入藥品。可由三氟乙醇與乙炔加成製備。[1]

參考資料

  1. ^ 1.0 1.1 Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons,(2007年)
  2. ^ Review: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synthesis,(2004年),(1), pp. 18-29.
  3. ^ Review: Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin , Synthesis,(2007年), pp. 2925-2943
  4. ^ Kabayadi S. Ravikumar, Venkitasamy Kesavan, Benoit Crousse, Danièle Bonnet-Delpon, and Jean-Pierre Bégué (2003年). "Mild and Selective Oxidation of Sulfur Compounds in Trifluroroethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide". Org. Synth. 80: 184. 
  • United States Patent number 4,647,706 "Process for the synthesis of 2,2,2-Trifluoroethanol and 1,1,1,3,3,3-Hexafluoroisopropanol"

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