Trityl chloride

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of trityl chloride
General
Surname Trityl chloride
other names
  • Triphenylchloromethane
  • Triphenylmethyl chloride
  • α-chlorotriphenylmethane
  • Chlorotriphenylmethane
Molecular formula C 19 H 15 Cl
Brief description

light yellow powder with a pungent odor

External identifiers / databases
CAS number 76-83-5
EC number 200-986-4
ECHA InfoCard 100,000,898
PubChem 6456
Wikidata Q2790082
properties
Molar mass 278.78 g mol −1
Physical state

firmly

Melting point

109-112 ° C

boiling point

230–235 ° C (at 27 hPa )

safety instructions
GHS labeling of hazardous substances
05 - Corrosive 09 - Dangerous for the environment

danger

H and P phrases H: 314-410
P: 280-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-310
Toxicological data

180 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trityl chloride is a reactive organic chemical substance that is used as a protective group for primary alcohols .

Manufacturing

Trityl chloride is commercially available. To produce it, triphenylmethanol is reacted with acetyl chloride . Alternatively, Friedel-Crafts alkylation of benzene with carbon tetrachloride yields a salt of trityl chloride and aluminum chloride , which upon hydrolysis yields trityl chloride.

Synthesis of trityl chloride

properties

The most important thermodynamic properties are listed in the following table:

property Formula symbol Value (remark)
Standard enthalpy of formation Δ f H 0 (s) 183 kJ mol −1
Enthalpy of combustion Δ c H 0 (s) −9826 kJ mol −1
Heat capacity c p 367.27 J mol −1 K −1 (as a solid at 25 ° C)
Enthalpy of fusion Δ f H 0 27.9 kJ mol −1 (at the melting point)
Entropy of fusion Δ f S 0 74.1 kJ mol −1 (at the melting point)

use

To synthesize trityl ethers , an alcohol is reacted with trityl chloride (Ph 3 CCl, abbreviated as TrCl) in the presence of a base (e.g. pyridine ). For steric reasons, only primary alcohols are etherified with trityl chloride and, in the case of monosaccharides , for example, it is possible to selectively protect the hydroxyl group at C-6 in addition to all others.

In addition, the triphenylmethyl radical can be prepared from trityl chloride.

Individual evidence

  1. ↑ a b c d e data sheet Trityl chloride, purum at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
  2. ↑ a b c Entry on chlorotriphenylmethane in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  3. ^ WE Bachmann, CR Hauser, Boyd E. Hudson, Jr .: Triphenylchloromethane In: Organic Syntheses . 23, 1943, p. 100, doi : 10.15227 / orgsyn.023.0100 ; Coll. Vol. 3, 1955, p. 841 ( PDF ).
  4. ↑ a b Schmidlin, MJ: Recherches chimiques et thermochimiques sur la constitution des rosanilines in Ann. Chim. Phys., 1906, 1, 195-256.
  5. ↑ a b c Naoki, M .; Seki, M .; Kugo, H .; Saito, F .; Taioka, T .: Dielectric relaxation in supercooled triphenylchloromethane and intrinsic factor determining mobility in molecular liquids in J. Phys. Chem. 95 (1991) 5628-5633.
  6. ↑ Jonathan Clayden, Nick Greeves, Stuart Warren, Peter Wothers: Organic Chemistry . Oxford University Press, 2001, p. 1370. ISBN 978-0-19-850346-0 .
  7. ↑ P. Collins, R. Ferrier: Monosacharides - Their Chemistry and their Roles in Natural Products. Wiley West Sussex 1995, ISBN 0-471-95343-1 .
  8. ↑ PJ Kocienski: Protecting Groups. Georg Thieme Verlag, Stuttgart 1994, ISBN 3-13-135601-4 .
  9. ↑ Jerry March, 1929–1997 .: Advanced organic chemistry: reactions, mechanisms, and structure . 3rd ed. Wiley, New York 1985, ISBN 0-471-88841-9 .