Triphenylmethane

Triphenylmethane

Names
Preferred IUPAC name 1,1',1''-Methanetriyltribenzene
Other names Triphenylmethane 1,1',1"-Methylidynetrisbenzene
Identifiers
CAS Number	519-73-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:76212 N
ChemSpider	10169 Y
ECHA InfoCard	100.007.524
EC Number	208-275-0
PubChem	10614
InChI InChI=1S/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H Y Key: AAAQKTZKLRYKHR-UHFFFAOYSA-N Y InChI=1/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H Key: AAAQKTZKLRYKHR-UHFFFAOYAF
SMILES c1c(cccc1)C(c2ccccc2)c3ccccc3
Properties
Chemical formula	C19H16
Molar mass	244.33 g/mol
Appearance	Colorless solid
Density	1.014 g/cm3
Melting point	92 to 94 °C (198 to 201 °F; 365 to 367 K)
Boiling point	359 °C (678 °F; 632 K)
Solubility in water	insoluble
Solubility	soluble in dioxane and hexane
Acidity (pKa)	33
Magnetic susceptibility (χ)	-165.6·10−6 cm3/mol
Hazards
Safety data sheet	External MSDS
R-phrases	R36 R37 R38
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C₆H₅)₃CH. This colorless solid is soluble in nonpolar organic solvents and not in water. 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 Ph₃C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

Triphenylmethane was first synthesized in 1872 by the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) by heating diphenylmercury (Hg(C₆H₅)₂, Quecksilberdiphenyl) with benzal chloride (C₆H₅CHCl₂, Benzylenchlorid).

Triphenylmethane can be synthesized by Friedel-Crafts reaction from benzene and chloroform with aluminium chloride catalyst:

Alternatively, benzene may react with carbon tetrachloride using the same catalyst to obtain the trityl chloride-aluminium chloride adduct, which is hydrolyzed with dilute acid:

Synthesis from benzylidene chloride, prepared from benzaldehyde and phosphorus pentachloride, is used as well.