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Triphenylmethanol

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Triphenylmethanol Basic information
Product Name:Triphenylmethanol
Synonyms:alpha,alpha-diphenyl-benzenemethano;Methanol, triphenyl-;Triphenyl carbinol~Trityl alcohol;Triphenylmethanol,>95%;Triphenylmethanol,98%;Benzenemethanol, a,a-diphenyl-;Hydroxytriphenylmethane;1,1,1-Triphenylmethanol
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;Organic Building Blocks;Oxygen Compounds;T;Aromatic alcohols and diols;Aromatics;top
Mol File:76-84-6.mol
Triphenylmethanol Structure
Triphenylmethanol Chemical Properties
Melting point 160-163 °C (lit.)
Boiling point 360 °C (lit.)
density d40 1.199
refractive index 1.6220 (estimate)
Fp 360-380°C
storage temp. 2-8°C
solubility dioxane: 0.1 g/mL, clear
pka12.73±0.29(Predicted)
form Fine Crystalline Powder
color White to light yellow
AppearanceWhite to Light yellow to Light orange powder to crystal
Water Solubility INSOLUBLE
Merck 14,9739
BRN 1460837
Stability:Stable. Combustible. Incompatible with oxidizing agents, acids, acid chlorides, acid anhydrides.
CAS DataBase Reference76-84-6(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenemethanol, «alpha»,«alpha»-diphenyl-(76-84-6)
EPA Substance Registry SystemBenzenemethanol, .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 Information
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Triphenylmethanol English
SigmaAldrich English
ACROS English
ALFA English
Triphenylmethanol Usage And Synthesis
Chemical PropertiesTriphenylmethanol is a white powder or colorless, isolated crystals that are soluble in alcohol, ether, and benzene. It turns dark yellow when dissolved in concentrated sulfuric acid, colorless when dissolved in glacial acetic acid, and is insoluble in water and petroleum ether. It distills at 360-380°C without decomposition.
UsesTriphenylmethanol (Zidovudine EP Impurity D) is a triaryl methane derivative as antiproliferative agent.
UsesTriphenylmethanol 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.
PreparationTriphenylmethanol 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
ReactionsThe 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.
reaction of triphenylmethanol
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 DescriptionTriphenylmethanol 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.
Materials UsesTriphenylmethanol (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].
Purification MethodsCrystallise 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.
Tag:Triphenylmethanol(76-84-6) Related Product Information
Triphenylsilanol TRIPHENYL PHOSPHOROTHIONATE Trimethyl orthobenzoate 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 ZIDOVUDINE RELATED COMPOUND B (25 MG) (3'-CHLORO-3'-DEOXYTHYMIDINE)

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