1896年,氟代乙酸乙酯的合成标志着有机氟化学研究的开端,至今已整整一个世纪。在此期间,几次重要的突破极大地推动了这一领域的发展,例如20世纪30年代氟里昂在制冷工业中的应用、二战期间曼哈顿工程的实施以及50年代高生理活性5-氟脲嘧啶的合成等。
我国拥有丰富的氟资源,已探明萤石储量约占世界总量的四分之一。然而直到20世纪50年代,中国在此领域的研究一片空白。当时国际形势的变化促使我国开始自主开发原子能技术,并急需一批特殊的含氟材料。从此,有机氟化学在中国的研究逐渐展开。中国科学院上海有机化学研究所因其在有机氟化学基础研究方面的卓越成就,被国际氟化学界誉为“上海氟化学”。
有机氟化合物又称氟碳化合物,是指分子结构中含C-F键的化合物,如四氟乙烯(CF2=CF2)。若碳氢化合物中的所有氢原子均被氟原子取代,则称为全氟化合物。由于氟是元素周期表中最电负、氧化性最强的原子,因此氟聚合物不易发生氧化裂解。此外,氟原子半径接近C-C键原子间距的一半,能紧密排列在碳原子周围,形成对C-C键的保护屏障,确保化学稳定性。C-F键具有极高的键能,赋予有机氟化物良好的热稳定性和抗氧化性。
许多含氟化合物被用于药物中,如全身麻醉剂氟烷、抗癌药5-氟尿嘧啶、镇静药氟奋乃静和抗精神病药氟哌啶醇等。根据结构不同,有机氟化合物大致可分为三类:
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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2-氟苯氧乙腈 | (2-Fluoro-phenoxy)-acetonitrile | 137988-23-9 | C8H6FNO |
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2-氟苯基乙酸乙酯 | ethyl 2-(2-fluorophenyl)acetate | 584-74-7 | C10H11FO2 |
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2-氟苯基乙腈 | 2-fluorophenyl acetonitrile | 326-62-5 | C8H6FN |
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2-氟苯基乙基异腈 | 2-Fluorophenethylisocyanide | 730964-62-2 | C9H8FN |
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2-氟苯乙酸 | (2-fluorophenyl)acetic acid | 451-82-1 | C8H7FO2 |
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2-氟苄醇 | 2-fluorobenzyl alcohol | 446-51-5 | C7H7FO |
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2-氟芴 | 2-fluoro-9H-fluorene | 343-43-1 | C13H9F |
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2-氟甲苯 | 2-Fluorotoluene | 95-52-3 | C7H7F |
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2-氟丙烷 | 2-propylfluoride | 420-26-8 | C3H7F |
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2-氟三氟甲苯 | 1-fluoro-2-trifluoromethylbenzene | 392-85-8 | C7H4F4 |
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2-氟-6-羟基苯腈 | 2-fluoro-6-hydroxybenzonitrile | 140675-43-0 | C7H4FNO |
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2-氟-6-羟基苯甲酸 | 6-fluorosalicylic acid | 67531-86-6 | C7H5FO3 |
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2-氟-6-甲氧基苯腈 | 2-fluoro-6-methoxybenzonitrile | 94088-46-7 | C8H6FNO |
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2-氟-6-甲基苯腈 | 2-fluoro-6-methylbenzonitrile | 198633-76-0 | C8H6FN |
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2-氟-6-溴苯腈 | 2-bromo-6-fluorobenzonitrile | 79544-27-7 | C7H3BrFN |
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2-氟-6-(三氟甲基)苯腈 | 2-fluoro-6-(trifluoromethyl)benzonitrile | 133116-83-3 | C8H3F4N |
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2-氟-6-(4-甲基苯氧基)苯甲腈 | 2-fluoro-6-(p-tolyloxy)benzonitrile | 175204-08-7 | C14H10FNO |
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2-氟-5-碘苯甲醛 | 2-Fluoro-5-iodo-benzaldehyde | 146137-76-0 | C7H4FIO |
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2-氟-5-碘苯甲腈 | 2-fluoro-5-iodobenzonitrile | 351003-36-6 | C7H3FIN |
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2-氟-5-碘-三氟甲苯 | 1-chloro-2-fluoro-5-iodo-3-(trifluoromethyl)benzene | 928783-87-3 | C7H2ClF4I |
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2-氟-5-硝基苯腈 | 2-fluoro-5-nitrobenzonitrile | 17417-09-3 | C7H3FN2O2 |
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2-氟-5-硝基苯甲醚 | 1-fluoro-2-methoxy-4-nitrobenzene | 454-16-0 | C7H6FNO3 |
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2-氟-5-硝基三氟甲苯 | 2-Fluoro-5-nitrobenzotrifluoride | 400-74-8 | C7H3F4NO2 |
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2-氟-5-甲酰基苯腈 | 2-fluoro-5-formylbenzonitrile | 218301-22-5 | C8H4FNO |
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2-氟-5-甲氧基苯甲酸 | 2-fluoro-5-methoxybenzoic acid | 367-83-9 | C8H7FO3 |
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2-氟-5-甲氧基-苯酚 | 2-fluoro-5-methoxyphenol | 117902-16-6 | C7H7FO2 |
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2-氟-5-甲基苯腈 | 2-fluoro-5-methylbenzonitrile | 64113-84-4 | C8H6FN |
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2-氟-5-甲基苯乙酮 | 1-(2-fluoro-5-methylphenyl)ethan-1-one | 446-07-1 | C9H9FO |
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2-氟-5-溴苯腈 | 5-Bromo-2-fluoro-benzonitrile | 179897-89-3 | C7H3BrFN |
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2-氟-5-乙酰基苯甲腈 | 5-acetyl-2-fluorobenzonitrile | 288309-07-9 | C9H6FNO |
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2-氟-5-[(3-氧代-1(3H)-异苯并呋喃亚基)甲基]苯腈 | 2-fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile | 763114-25-6 | C16H8FNO2 |
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2-氟-5-(三氟甲氧基)苯腈 | 2-fluoro 5-(trifluoromethoxy)benzonitrile | 886498-08-4 | C8H3F4NO |
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2-氟-5-(三氟甲基)苯乙酮 | 2-fluoro-5-trifluoromethyl-acetophenone | 202664-53-7 | C9H6F4O |
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2-氟-4-羟基苯腈 | 2-fluoro-4-hydroxybenzonitrile | 82380-18-5 | C7H4FNO |
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2-氟-4-碘苯腈 | 2-fluoro-4-iodobenzonitrile | 137553-42-5 | C7H3FIN |
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2-氟-4-硝基苯腈 | 2-fluoro-4-nitrobenzonitrile | 34667-88-4 | C7H3FN2O2 |
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2-氟-4-甲酰基苯硼酸 | (2-fluoro-4-formylphenyl)boronic acid | 871126-22-6 | C7H6BFO3 |
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2-氟-4-甲酰基苯甲腈 | 4-cyano-3-fluorobenzaldehyde | 101048-76-4 | C8H4FNO |
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2-氟-4-甲氧基苯腈 | 2-fluoro-4-methoxybenzonitrile | 94610-82-9 | C8H6FNO |
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2-氟-4-甲氧基苯胺 | 2-fluoro-4-(methoxy)aniline | 458-52-6 | C7H8FNO |
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2-氟-4-甲基苯酚 | 2-fluoro-4-methylphenole | 452-81-3 | C7H7FO |
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2-氟-4-甲基苯腈 | 2-fluoro-4-methylbenzonitrile | 85070-67-3 | C8H6FN |
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2-氟-4-甲基三氟甲苯 | 2-fluoro-4-methylbenzotrifluoride | 158364-83-1 | C8H6F4 |
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2-氟-4-溴苯腈 | 4-bromo-6-fluorobenzonitrile | 105942-08-3 | C7H3BrFN |
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2-氟-4-溴苯乙腈 | (4-bromo-2-fluorophenyl)acetonitrile | 114897-91-5 | C8H5BrFN |
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2-氟-4-溴-5-氯苯胺 | 4-bromo-5-chloro-2-fluoroaniline | 116369-24-5 | C6H4BrClFN |
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2-氟-4-三氟甲基苯腈 | 2-fluoro-4-(trifluoromethyl)benzonitrile | 146070-34-0 | C8H3F4N |
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2-氟-4-(三氟甲基)苯乙酸 | 2-(2-fluoro-4-(trifluoromethyl)phenyl)acetic acid | 209991-64-0 | C9H6F4O2 |
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2-氟-4,5-二甲氧基苯基氰 | 2-fluoro-4,5-dimethoxybenzonitrile | 119396-88-2 | C9H8FNO2 |
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2-氟-3-(三氟甲基)苯乙酸 | 2-Fluoro-3-(trifluoromethyl)phenylacetic acid | 194943-83-4 | C9H6F4O2 |
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