2,4,6-Triisopropylbenzenesulfonyl azide

2,4,6-Triisopropylbenzenesulfonyl azide
Names
IUPAC name
N-diazo-2,4,6-tri(propan-2-yl)benzenesulfonamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.124.728 Edit this at Wikidata
EC Number
  • 609-323-7
  • InChI=1S/C15H23N3O2S/c1-9(2)12-7-13(10(3)4)15(14(8-12)11(5)6)21(19,20)18-17-16/h7-11H,1-6H3
    Key: AEMWUHCKKDPRSK-UHFFFAOYSA-N
  • CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C
Properties
C15H23N3O2S
Molar mass 309.43 g·mol−1
Melting point 39–44 °C (102–111 °F; 312–317 K)
Hazards
GHS labelling:[1]
GHS01: ExplosiveGHS06: Toxic
Danger
H241, H301
P210, P234, P240, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P380+P375+P378, P403, P403+P233, P405, P410, P411, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,4,6-Triisopropylbenzenesulfonyl azide (trisyl azide) is an organic chemical used as a reagent to supply azide for electrophilic amination reactions, such as for the asymmetric synthesis of unnatural amino acids.[2] Introduction of an azide on the α carbon of carboxylic acid derivative using trisyl azide is an efficient alternative to electrophilic halogenation followed by nucleophilic substitution using anionic azide. Using an oxazolidinone as chiral auxiliary typically gives good induction of the stereochemistry at the α position. Subsequent reduction converts the α-azide to an α-amine.

References

[edit]
  1. ^ "2,4,6-Triisopropylbenzenesulfonyl azide". pubchem.ncbi.nlm.nih.gov. Retrieved 1 May 2022.
  2. ^ Evans, David A.; Britton, Thomas C. (1987). "Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of α-amino acids". J. Am. Chem. Soc. 109 (22): 6881–3. doi:10.1021/ja00256a069.

Further reading

[edit]
  • Calmes, M.; Daunis, J. (1999). "How to build optically active α-amino acids". Amino Acids. 16 (3–4): 215–250. doi:10.1007/BF01388170. PMID 10399014. S2CID 36591079.
  • Han, Y.; Lin, J.; Liao, S.; Qiu, W.; Cai, C.; Hruby, V.J. (2002). "Stereoselective synthesis of highly topographically constrained β-isopropyl substituted aromatic amino acids". In Tam, J.P.; Kaumaya, P.T.P. (eds.). Peptides Frontiers of Peptide Science. American Peptide Symposia. Vol. 5. Springer. pp. 241–243. doi:10.1007/0-306-46862-X_98. ISBN 0-7923-5160-6.
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