76-84-6

white powder

A triaryl methane derivative as antiproliferative agent.

Triphenylmethanol is used as a reagent in the research laboratory. It acts as an intermediate in the production of the commercially useful triarylmethane dyes. It is used in the preparation of triphenylmethane. It is also used as an antiproliferative agent. Further, it is used in the preparation of two-electron reduction product of pyrylogen. In addition to this, it reacts with triphenylphosphine oxide to form a 1:1 molecular complex. It serves as a specific clathrate host for methanol and dimethyl sulphoxide and forms clathrate inclusion complexes.
Triphenylmethanol was used in the synthesis of of the two-electron reduction product of pyrylogen.
It undergoes reduction to triphenylmethane by 9, 10-dihydro-10-methylacridine in the presence of perchloric acid.

Triphenylmethanol can also be prepared by the reaction of phenylmagnesium bromide with methyl benzoate (instead of benzophenone).

The first one is the formation of the triphenylmethyl bromide from the reaction of triphenylmethanol with hydrobromic acid.
The second reaction is the formation of an ether from the reaction of triphenylmethanol with methanol in acidic conditions.

Organic Syntheses, Coll. Vol. 3, p. 839, 1955
The Journal of Organic Chemistry, 57, p. 4555, 1992 DOI: 10.1021/jo00042a044

Triphenylmethanol (TPOH) is a non-fluorescent compound that emits strong fluorescence in an aggregate state or on a solid surface after irradiation by UV light at 254 nm (UV1). Interestingly, the photo-induced fluorescence of TPOH was quenched when irradiated by UV light at a longer wavelength of 365 nm (UV2) and further repeatable on and off by UV1 and UV2, respectively. The reversible activation and deactivation of fluorescence at a solid surface could be repeatable at least 5 times. TPOH is thus applied for rewritable photopatterning tuned by UV light[1].

Crystallise the carbinol from EtOH, MeOH, CCl4 (4mL/g), *benzene, hexane or pet ether (b 60-70o). Dry it at 90o. [Ohwada et al. J Am Chem Soc 108 3029 1986, Beilstein 6 IV 5014.]

[1] Zheng, Yue et al. “Photoactivatable aggregation-induced emission of triphenylmethanol?.” Chemical Communications 81 (2017): 11130–11133.