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Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph 3 C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).
After the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) first synthesized triphenylmethane in 1872, [2] the Russian doctoral student Walerius Hemilian (1851–1914) first synthesized triphenylmethanol in 1874 by reacting triphenylmethyl bromide with water as well as by oxidizing triphenylmethane.
Triarylmethane dyes can be grouped into families according to the nature of the substituents on the aryl groups. In some cases, the anions associated with the cationic dyes (say crystal violet) vary even though the name of the dye does not.
The radical was discovered by Moses Gomberg in 1900 at the University of Michigan. [10] [11] [12] He tried to prepare hexaphenylethane from triphenylmethyl chloride and zinc in benzene in a Wurtz reaction and found that the product, based on its behaviour towards iodine and oxygen, was far more reactive than anticipated.
Triphenylmethanethiol is an organosulfur compound with the formula (C 6 H 5) 3 CSH. It is the thiol derivative of the bulky substituent triphenylmethyl (called trityl). [1] [2]The compound forms a number of unusual derivatives that are more stable than less bulky analogues.
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Gomberg's classical organic synthesis shown below starts by reacting triphenylmethyl bromide 1 with phenylhydrazine 2 to the hydrazine 3. Oxidation with nitrous acid then produces the azo compound 4 from which on heating above the melting point, nitrogen gas evolves with formation of tetraphenylmethane 5.
The methylene group in diphenylmethane is mildly acidic with a pK a of 32.2, and so can be deprotonated with sodium amide. [3](C 6 H 5) 2 CH 2 + NaNH 2 − → (C 6 H 5) 2 CHNa + NH 3. The resulting carbanion can be alkylated.