2,4,6-Triisopropylbenzenesulfonyl azide

2,4,6-Triisopropylbenzenesulfonyl azide
Names
	IUPAC name N-diazo-2,4,6-tri(propan-2-yl)benzenesulfonamide
Identifiers
CAS Number	36982-84-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1995382;
ChemSpider	2391566;
ECHA InfoCard	100.124.728
EC Number	609-323-7;
PubChem CID	371707;
CompTox Dashboard (EPA)	DTXSID80327323;
	InChI 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;
	SMILES CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C;
Properties
Chemical formula	C15H23N3O2S
Molar mass	309.43 g·mol−1
Melting point	39–44 °C (102–111 °F; 312–317 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H241, H301
Precautionary statements	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). Infobox references

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

^ "2,4,6-Triisopropylbenzenesulfonyl azide". pubchem.ncbi.nlm.nih.gov. Retrieved 1 May 2022.
^ 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.

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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