N-碘代丁二酰亚胺
化合物
N-碘代丁二酰亚胺(NIS)是一种有机化合物,化学式为C4H4INO2。它最初由Bunge于1870年通过丁二酰亚胺银和碘的反应制得。[1]它可用作烯烃[2]和芳香烃[3][4]的碘化试剂及温和的氧化剂[5]。
N-碘代丁二酰亚胺 | |
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IUPAC名 1-Iodopyrrolidine-2,5-dione | |
识别 | |
CAS号 | 516-12-1 |
PubChem | 120273 |
ChemSpider | 107372 |
SMILES |
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Beilstein | 113917 |
Gmelin | 122896 |
ChEBI | 53204 |
性质 | |
化学式 | C4H4INO2 |
摩尔质量 | 224.98 g·mol−1 |
外观 | 白色固体 |
密度 | 2.245 g/cm3 |
熔点 | 202-206 °C(分解) |
溶解性(水) | 可溶于二氧六环、THF、MeCN;难溶于乙醚、四氯化碳 |
危险性 | |
GHS危险性符号 | |
GHS提示词 | 警告 |
H-术语 | H302, H315, H319, H335 |
P-术语 | P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
参考文献
编辑- ^ N. Bunge: Einwirkung der Haloïde auf Metallderivate einiger Kohlenstoffverbindungen. In: Friedrich Wöhler, Justus Liebig, Hermann Kopp (Hrsg.): Annalen der Chemie und Pharmacie. 7. Supplementband. C. F. Winter’sche Verlagshandlung, Leipzig und Heidelberg 1870, S. 117.
- ^ Piotr Pawluć, Grzegorz Hreczycho, Justyna Szudkowska, Maciej Kubicki, Bogdan Marciniec: New One-Pot Synthesis of (E)-β-Aryl Vinyl Halides from Styrenes. In: Organic Letters. Band 11, Nr. 15, 6. August 2009, S. 3390–3393, doi:10.1021/ol901233j
- ^ Daugirdas T. Racys, Catherine E. Warrilow, Sally L. Pimlott, Andrew Sutherland: Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide. In: Organic Letters. Band 17, Nr. 19, 2. Oktober 2015, S. 4782–4785, doi:10.1021/acs.orglett.5b02345.
- ^ G. K. Surya Prakash, Thomas Mathew, Dushyanthi Hoole, Pierre M. Esteves, Qi Wang: N-Halosuccinimide/BF3−H2O, Efficient Electrophilic Halogenating Systems for Aromatics. In: Journal of the American Chemical Society. Band 126, Nr. 48, Dezember 2004, S. 15770–15776, doi:10.1021/ja0465247.
- ^ Scott C. Virgil, Ying Zeng, Fanzuo Kong, Julie A. Pigza: N -Iodosuccinimide. In: Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd, Chichester, UK 2007, ISBN 978-0-471-93623-7, S. ri038.pub3, doi:10.1002/047084289x.ri038.pub3.