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Trityl chloride (CAS 76-83-5)

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Alternate Names:
Chlorotriphenylmethane; Triphenylchloromethane; Triphenylmethyl chloride
Application:
Trityl chloride is a protecting reagent
CAS Number:
76-83-5
Purity:
≥97%
Molecular Weight:
278.78
Molecular Formula:
C19H15Cl
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Trityl chloride functions as a versatile protecting group in organic synthesis. It is used to selectively protect hydroxyl groups in the presence of other functional groups, such as carboxylic acids and amines. The mechanism of action of trityl chloride involves the formation of a covalent bond with the hydroxyl group, leading to the formation of a trityl ether. This reaction occurs under acidic conditions, allowing for the selective protection of hydroxyl groups in the presence of other reactive functional groups. The trityl group can be easily removed under mild conditions, making it useful in the synthesis of complex organic molecules.


Trityl chloride (CAS 76-83-5) References

  1. Trityl isothiocyanate support for solid-phase synthesis.  |  Pirrung, MC. and Pansare, SV. 2001. J Comb Chem. 3: 90-6. PMID: 11148069
  2. Homogeneous tritylation of cellulose in 1-butyl-3-methylimidazolium chloride.  |  Erdmenger, T., et al. 2007. Macromol Biosci. 7: 440-5. PMID: 17429805
  3. Covalency in Ce(IV) and U(IV) halide and N-heterocyclic carbene bonds.  |  Arnold, PL., et al. 2010. Chemistry. 16: 9623-9. PMID: 20658507
  4. Cascade reaction of β,γ-unsaturated α-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications.  |  Wu, YC., et al. 2011. Org Biomol Chem. 9: 2868-77. PMID: 21387069
  5. Cerium(III/IV) formamidinate chemistry, and a stable cerium(IV) diolate.  |  Werner, D., et al. 2014. Chemistry. 20: 4426-38. PMID: 24643972
  6. Cerium tetrakis(diisopropylamide)--a useful precursor for cerium(IV) chemistry.  |  Schneider, D., et al. 2014. Chem Commun (Camb). 50: 14763-6. PMID: 25317924
  7. Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin.  |  Yoshikiyo, K., et al. 2015. Beilstein J Org Chem. 11: 1530-40. PMID: 26425212
  8. Monoanionic bis(carbene) pincer complexes featuring cobalt(I-III) oxidation states.  |  Ibrahim, AD., et al. 2016. Dalton Trans. 45: 9805-11. PMID: 26778113
  9. Synthesis and derivatisation of ceric tris(tert-butoxy)siloxides.  |  Friedrich, J., et al. 2017. Chem Commun (Camb). 53: 12044-12047. PMID: 29063097
  10. Trivalent Rare-Earth-Metal Bis(trimethylsilyl)amide Halide Complexes by Targeted Oxidations.  |  Bienfait, AM., et al. 2018. Inorg Chem. 57: 5204-5212. PMID: 29630356
  11. Single C-F Transformations of o-Hydrosilyl Benzotrifluorides with Trityl Compounds as All-in-One Reagents.  |  Idogawa, R., et al. 2020. Org Lett. 22: 9292-9297. PMID: 33180503
  12. Expanding the Rare-Earth Metal BINOLate Catalytic Multitool beyond Enantioselective Organic Synthesis.  |  Panetti, GB., et al. 2021. Acc Chem Res. 54: 2637-2648. PMID: 34014657
  13. Carbocation catalysis in confined space: activation of trityl chloride inside the hexameric resorcinarene capsule.  |  De Rosa, M., et al. 2022. Chem Sci. 13: 8618-8625. PMID: 35974771
  14. A Shelf Stable Fmoc Hydrazine Resin for the Synthesis of Peptide Hydrazides.  |  Bird, MJ. and Dawson, PE. 2022. Pept Sci (Hoboken). 114: PMID: 36387422
  15. Synthesis and Characterization of Functional Cellulose-Ether-Based PCL- and PLA-Grafts-Copolymers.  |  Sommer, K., et al. 2023. Polymers (Basel). 15: PMID: 36679334

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Trityl chloride, 25 g

sc-258321
25 g
$21.00

Trityl chloride, 100 g

sc-258321A
100 g
$41.00