Triphenylmethyl chloride

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Triphenylmethyl chloride
Triphenylmethyl chloride.png
Preferred IUPAC name
Other names
3D model (JSmol)
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PubChem CID
  • InChI=1S/C19H15Cl.C10H10.C8H8/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-3-9-5-7-10(4-2)8-6-9;1-2-8-6-4-3-5-7-8/h1-15H;3-8H,1-2H2;2-7H,1H2 Yes check.svgY
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl
Molar mass 278.7754 g/mol
Appearancewhite to yellow solid
Density 1.141 g/cm3
Melting point 109 to 112 °C (228 to 234 °F; 382 to 385 K)
Boiling point 230 °C (446 °F; 503 K)(at 20 mmHg) and 374.3 °C (at 760 mmHg)
Solubility soluble in chloroform, benzene, acetone, [1] ether, THF, hexane [2]
Flash point 177.9 °C (352.2 °F; 451.0 K)
Safety data sheet (SDS) Corvine Chemicals MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group.



Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed. [3]


Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium: [4]

(C6H5)3CCl + 2 Na → (C6H5)3CNa + NaCl

Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.

See also

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Triphenylmethane Chemical compound

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

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Oxalyl chloride Chemical compound

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Thionyl chloride Chemical compound

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Permanganate Chemical compound

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Phosphorus pentachloride Chemical compound

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Palladium(II) chloride Chemical compound

Palladium(II) chloride, also known as palladium dichloride and palladous chloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value in organic synthesis. It is prepared by the reaction of chlorine with palladium metal at high temperatures.

Triphenylmethanol Chemical compound

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

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Hexafluorophosphate Anion with the chemical formula PF6–

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. It is an octahedral species that imparts no color to its salts. PF
is isoelectronic with sulfur hexafluoride, SF6, and the hexafluorosilicate dianion, SiF2−
, and fluoroantimonate SbF
. Being poorly nucleophilic, hexafluorophosphate is classified as a non-coordinating anion.

Triphenylarsine Chemical compound

Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.

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Sulfenyl chloride

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Triphenylmethyl hexafluorophosphate Chemical compound

Triphenylmethyl hexafluorophosphate is an organic salt with the formula C
or (C
, consisting of the triphenylmethyl cation [(C
and the hexafluorophosphate anion] [PF
. The cation is also called triphenylcarbenium, trityl cation, or tritylium.


In chemistry, triphenylcarbenium, triphenylmethyl cation, tritylium , or trityl cation is an ion with formula [C
or (C
, consisting of a carbon atom with a positive charge connected to three phenyl groups. It is a charged version of the triphenylmethyl radical (C
. The name is often abbreviated to triphenylmethyl or trityl in salts, although these names also denote the chemical group in compounds like triphenylmethyl chloride that do not contain the cation.


  1. [ dead link ]
  2. "Trityl chloride | CAS 76-83-5".
  3. W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Organic Syntheses .{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 3, p. 841.
  4. W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses .; Collective Volume, vol. 2, p. 607