Triphenylmethanol
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
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)
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
- Language:English Provider:Triphenylmethanol
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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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Triphenylmethanol(76-84-6)Related Product Information
- Trimethyl orthobenzoate
- TRIPHENYL PHOSPHOROTHIONATE
- Triphenylsilanol
- Benzyl alcohol
- Ethyl acetate
- Triphenylphosphine oxide
- Benzhydrol
- ALPHA-NAPHTHOLBENZEIN
- Triphenylmethyl Chloride
- 4-Hydroxybenzyl alcohol
- TRIPHENYLBORANE
- 2-Nitrobenzyl alcohol
- Triphenylphosphine
- p-Naphtholbenzein
- 1,2,3-TRIPHENYLGUANIDINE
- ZIDOVUDINE IMPURITY A
- ZIDOVUDINE IMPURITY B
- (3S,3'S,5R,5'R)-3,3'-dihydroxy-.kappa.,.kappa.-carotene-6,6'-dione