502485-28-1Relevant articles and documents
In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System
Nahide, Pradip D.,Ramadoss, Velayudham,Juárez-Ornelas, Kevin A.,Satkar, Yuvraj,Ortiz-Alvarado, Rafel,Cervera-Villanueva, Juan M. J.,Alonso-Castro, ángel J.,Zapata-Morales, Juan R.,Ramírez-Morales, Marco A.,Ruiz-Padilla, Alan J.,Deveze-álvarez, Martha A.,Solorio-Alvarado, César R.
, p. 485 - 493 (2018/02/09)
A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.
Mild synthesis of asymmetric 2′-carboxyethyl-substituted fluoresceins
Lukhtanov, Eugeny A.,Vorobiev, Alexei V.
, p. 2424 - 2427 (2008/09/19)
(Chemical Equation Presented) Asymmetric fluoresceins bearing a carboxyethyl group in the chromophoric portion of the dyes were prepared by a reaction of substituted phthalic anhydride with a carboxyethyl substituted resorcinol analogue followed by a condensation with a second resorcinol analogue. In order to avoid an accumulation of symmetric side products, the second step was performed in two substeps: acid-catalyzed formation of a triphenylmethyl intermediate followed by base-catalyzed cyclization which furnished the desired dyes.
Compounds and methods for fluorescent labeling
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Page/Page column 35, (2008/06/13)
Compounds useful in the fluorescent labeling of biological materials are provided along with methods for their use and preparation.