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Triphenylmethanol

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Triphenylmethanol Basic information

Product Name:
Triphenylmethanol
Synonyms:
  • .alpha.,.alpha.-diphenyl-Benzenemethanol
  • alpha,alpha-diphenyl-benzenemethano
  • Methanol, triphenyl-
  • Triphenylmethyl alcohol
  • Pragrelide Impurity 20
  • Tritanol
  • Triphenyl carbinol~Trityl alcohol
  • Triphenylmethanol, (Triphenyl carbinol
CAS:
76-84-6
MF:
C19H16O
MW:
260.33
EINECS:
200-988-5
Product Categories:
  • Alcohols
  • Bioactive Small Molecules
  • Building Blocks
  • C11 to C30+
  • Cell Biology
  • Chemical Synthesis
  • Aromatic alcohols and diols
  • Aromatics
  • Organic Building Blocks
  • Oxygen Compounds
  • T
  • top
Mol File:
76-84-6.mol
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Triphenylmethanol Chemical Properties

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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
38-36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
TSCA 
Yes
HS Code 
29062900

MSDS

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Triphenylmethanol Usage And Synthesis

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.

Triphenylmethanol Preparation Products And Raw materials

Raw materials

Preparation Products

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