每周分子 | Molecule of the Week
每周分子 | Molecule of the Week
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每周分子： 六氟-2-丙醇
Molecule of the Week:
Hexafluoro-2-propanol
六氟-2-丙醇 (又称“六氟异丙醇”，缩写为HFIP) 是一种低沸点溶剂，在化工领域中应用广泛。最早提及六氟-2-丙醇的化学文献发表于1960年，是由前苏联化学家Ivan L. Knunyants和M. P. Krasuskaya公开的一项瑞士专利，他们利用硼氢化钠还原六氟丙酮 1 的方法合成了六氟-2-丙醇 。
此后40多年中，对HFIP的研究一直停留在实验室阶段，随后才开始受到化学家们的关注。2017年，牛津大学 (英国) 的Ignacio Colomer、Timothy J. Donohoe及其同事在发表的前瞻性文章中，称HFIP是一种高通用溶剂。2022年，北卡罗来纳大学 (教堂山和威尔明顿) 的Hashim F. Motiwala、Jeffrey Aubé及其同事在论文中综述了HFIP在有机合成中的应用。他们认为HFIP是一种供氢能力较强的极性溶剂，“能稳定离子、转移质子，并能参与多种其他分子间相互作用” 。
Motiwala和Aubé等人在介绍了HFIP的物理性质并将其与常用溶剂进行对比之后，探讨了将其用于20种有机反应中的优势，包括溶剂分解、碳碳键形成、碳氢键官能团化、缩合反应和环合反应等。文章中有一张十分特别的图示，汇总了以HFIP为溶剂或反应物的629种反应 。
Colomer和Donohue等人在随后的原创论文中指出HFIP“不仅仅是一种极性质子溶剂”。除了与Motiwala和Aubé等人相同的观点外，他们还深入探讨了HFIP在电化学方法、有机金属化学和无机化学、生物学、材料学及聚合物科学中的应用。两篇文章的作者都认为HFIP将在多个科学领域获得更多应用 。
1. CAS登记号：684-16-2
六氟-2-丙醇 信息速览
CAS 登记号 |
920-66-1 |
CAS SciFinder命名 |
2-Propanol, 1,1,1,3,3,3-hexafluoro- |
分子式 |
C 3 H 2 F 6 O |
摩尔质量 |
168.04 g/mol |
外观 |
无色液体 |
沸点 |
59°C |
水溶性 |
易溶 |
六氟-2-丙醇危害信息
危险等级：急性毒性，经口，类别4 |
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H302-吞咽有害 |
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危险等级：皮肤腐蚀/刺激，分类1A |
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H314-导致严重皮肤灼伤和眼损伤 |
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危险等级：严重眼损伤/眼刺激，分类1 |
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H318-导致严重眼损伤 |
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危险等级：急性毒性，吸入，分类4 |
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H332-吸入有害 |
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危险等级：特异性靶器官毒性，单次接触，呼吸道刺激，分类3 |
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H335-可引起呼吸道刺激 |
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危险等级：生殖毒性，分类2 |
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H361-疑似对生育能力或胎儿造成损害 |
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危险等级：特异性靶器官毒性，重复接触，分类2 |
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H373-长期或重复接触可能对器官造成伤害 |
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【 关于每周分子 】
自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的CAS SciFinder n 中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。 发送邮件至motw@acs.org推荐您感兴趣的分子吧 。
Hexafluoro-2-propanol (erroneously called “hexafluoroisopropanol”, abbreviated HFIP) is a low-boiling solvent used in a variety of chemical applications. It first appeared in the chemical literature in a 1960 Swiss patent to Soviet Union chemists Ivan L. Knunyants and M. P. Krasuskaya, who synthesized it by reducing hexafluoroacetone 1 with sodium borohydride.
After 40 years or so of being considered a laboratory curiosity, HFIP began to receive chemists’ attention. A 2017 perspective by Ignacio Colomer, Timothy J. Donohoe, and co-workers at the University of Oxford (UK) described HFIP as a highly versatile solvent. Then, in 2022, Hashim F. Motiwala, Jeffrey Aubé, and colleagues at the University of North Carolina (Chapel Hill and Wilmington) reviewed the use of HFIP in organic synthesis. They described HFIP as a polar, strongly hydrogen bond–donating solvent with the “ability to stabilize ionic species, transfer protons, and engage in a range of other intermolecular interactions”.
After describing the physical properties of HFIP and comparing it with common solvents, Motiwala, Aubé et al. discussed the advantages of using it in 20 types of organic reactions, including solvolysis, carbon–carbon bond formation, carbon–hydrogen functionalization, condensation, and cyclization. The article includes an extraordinary 629 reaction schemes in which HFIP is used as the solvent, or in some cases as a reactant .
Not to be outdone, Colomer, Donohue et al. followed up their original article by describing HFIP as “more than a polar protic solvent”. In addition to covering the same ground as Motiwala, Aubé et al., they delved into its use in electrochemical methods, organometallic and inorganic chemistry, biology, and materials and polymer science. Both author sets predict that HFIP will continue to garner many more applications in multiple scientific fields.
1. CAS Reg. No. 684-16-2
Hexafluoro-2-propanol fast facts
CAS Reg. No. |
920-66-1 |
|
SciFinder nomenclature |
2-Propanol, 1,1,1,3,3,3-hexafluoro- |
|
Empirical formula |
C 3 H 2 F 6 O |
Molar mass |
168.04 g/mol |
Appearance |
Colorless liquid |
Boiling point |
59°C |
Water solubility |
Miscible |
Hexafluoro-2-propanol hazard information
Acute toxicity, oral, category 4 |
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H302-Harmful if swallowed |
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Skin corrosion/irritation, category 1A |
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H314-Causes severe skin burns and eye damage |
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Serious eye damage/eye irritation, category 1 |
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H318-Causes serious eye damage |
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Acute toxicity, inhalation, category 4 |
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H332-Harmful if inhaled |
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Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 |
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H335-May cause respiratory irritation |
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Reproductive toxicity, category 2 |
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H361-Suspected of damaging fertility or the unborn child |
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Specific target organ toxicity, repeated exposure, category 2 |
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H373-Causes damage to organs through prolonged or repeated exposure |
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About Molecule of the Week
MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using CAS SciFinder n . Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org .
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