Triphenylmethanol Property

Melting point:

160-163 °C (lit.)

Boiling point:

360 °C (lit.)

Density 

d40 1.199

refractive index 

1.6220 (estimate)

Flash point:

360-380°C

storage temp. 

2-8°C

solubility 

dioxane: 0.1 g/mL, clear

pka

12.73±0.29(Predicted)

form 

Fine Crystalline Powder

color 

White to light yellow

Water Solubility 

INSOLUBLE

Merck 

14,9739

BRN 

1460837

Stability:

Stable. Combustible. Incompatible with oxidizing agents, acids, acid chlorides, acid anhydrides.

CAS DataBase Reference

76-84-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzenemethanol, «alpha»,«alpha»-diphenyl-(76-84-6)

EPA Substance Registry System

Benzenemethanol, .alpha.,.alpha.-diphenyl- (76-84-6)

Safety

Hazard Codes 

Xi

Risk Statements 

38-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29062900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

Triphenylmethanol Chemical Properties,Usage,Production

Luminescence performance

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].

Chemical Properties

white powder or colorless trisolated crystals. Soluble in alcohol, ether and benzene, dark yellow when dissolved in concentrated sulfuric acid, colorless when dissolved in glacial acetic acid, insoluble in water and petroleum ether. Distilled at 360-380℃ without decomposition.

Uses

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.

Uses

Triphenylmethanol (Zidovudine EP Impurity D) is a triaryl methane derivative as antiproliferative agent.

Preparation

Triphenylmethanol synthesis: Triphenylmethanol was prepared by the action of benzene with carbon tetrachloride in the presence of Aluminum chloride, followed by acidification and hydrolysis.
Triphenylmethanol can also be prepared by the reaction of phenylmagnesium bromide with methyl benzoate (instead of benzophenone).
Synthesis of Triphenylmethanol

Reactions

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.

Synthesis Reference(s)

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

General Description

Triphenylmethanol forms 1:1 molecular complex with triphenylphosphine oxide. It is a specific clathrate host for methanol and dimethyl sulphoxide and forms clathrate inclusion complexes. It undergoes reduction to triphenylmethane by 9, l0-dihydro-10-methylacridine in the presence of perchloric acid.

Purification Methods

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.]

References

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