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Phenolphthalein is slightly soluble in water and usually is dissolved in alcohols in experiments. It is a weak acid, which can lose H + ions in solution. The nonionized phenolphthalein molecule is colorless and the double deprotonated phenolphthalein ion is fuchsia. Further proton loss in higher pH occurs slowly and leads to a colorless form.
Chemical structure of phenolphthalein, a common phthalein dye. Phthalein dyes are a class of dyes mainly used as pH indicators, due to their ability to change colors depending on pH. [1] They are formed by the reaction of phthalic anhydride with various phenols. They are a subclass of triarylmethane dyes. Common phthalein dyes include ...
Phenolphthalein can be synthesized by the condensation of phthalic anhydride with two equivalents of phenol under acidic conditions (hence the name). It was discovered in 1871 by Adolf von Baeyer. [8] [9] [10] Synthesis of phenolphthalein [11]
Phenols are more acidic than typical alcohols. The acidity of the hydroxyl group in phenols is commonly intermediate between that of aliphatic alcohols and carboxylic acids (their pK a is usually between 10 and 12).
In organic chemistry, phthalic acid is an aromatic dicarboxylic acid, with formula C 6 H 4 (CO 2 H) 2 and structure HO(O)C−C 6 H 4 −C(O)OH.Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. [4]
The phthalide core is found a variety of more complex chemical compounds including dyes (such as phenolphthalein), fungicides (such as tetrachlorophthalide, often referred to simply as "phthalide"), and natural oils (such as butylphthalide).
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Upon reduction, the very intense pink color of the cationic form of phenolphthalein fades to a faint yellow color. It is this form of phenolphthalein that is present in Kastle–Meyer test kits. In order to generate the intense pink color indicative of a positive test, the reduced phenolphthalein must be oxidized back to its normal, colored form.