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HomeProduct name listTriphenylmethanol

Triphenylmethanol

Synonym(s):Triphenyl carbinol;Triphenylcarbinol;Triphenylmethanol;Trityl alcohol

  • CAS NO.:76-84-6
  • Empirical Formula: C19H16O
  • Molecular Weight: 260.33
  • MDL number: MFCD00004445
  • EINECS: 200-988-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:52
Triphenylmethanol Structural

What is Triphenylmethanol?

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.

The Uses of Triphenylmethanol

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.

The Uses of Triphenylmethanol

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.
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 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.]

Properties of Triphenylmethanol

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
form  Fine Crystalline Powder
pka 12.73±0.29(Predicted)
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 for Triphenylmethanol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for Triphenylmethanol

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