Triphenylmethyl chloride

Triphenylmethyl chloride

Names
IUPAC name [chloro-di(phenyl)methyl]benzene
Other names 1,1',1"-(chloromethanetriyl)tribenzene
Identifiers
CAS Number	76-83-5
ChemSpider	17344583
Jmol 3D image	Interactive graph
PubChem	6456
InChI 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 Key: TXMWQDFQVWGFTQ-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl
Properties
Chemical formula	C19H15Cl
Molar mass	278.7754 g/mol
Appearance	white to yellow solid
Density	1.141g/cm^3
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
Safety data sheet	Corvine Chemicals MSDS
Flash point	177.9 °C (352.2 °F; 451.0 K)
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.

Preparation

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]

Reactions

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

• Triphenylmethyl radical
• Triphenylmethane
• Triphenylmethyl hexafluorophosphate
• Triphenylmethanol

References

1. http://www.sciencelab.com/msds.php?msdsId=9925340
2. http://www.scbt.com/datasheet-258321-trityl-chloride.html
3. W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Org. Synth.; Coll. Vol. 3, p. 841
4. W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Org. Synth.; Coll. Vol. 2, p. 607