Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
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.
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
1,1′,1′′-(Chloromethanetriyl)tribenzene | |||
Other names
(Chloromethanetriyl)tribenzene [Chloro(diphenyl)methyl]benzene | |||
Identifiers | |||
3D model (JSmol) |
|||
ChemSpider | |||
ECHA InfoCard | 100.000.898 | ||
PubChem CID |
|||
UNII | |||
CompTox Dashboard (EPA) |
|||
| |||
| |||
Properties | |||
C19H15Cl | |||
Molar mass | 278.7754 g/mol | ||
Appearance | white 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] | ||
Hazards | |||
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).
|
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]
Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.
Trityl chloride reacts with zinc in nonpolar solvents (e.g. benzene) to form Gomberg's dimer.[5]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.