10330. N-Hydroxysuccinimide

Nomenclature

CAS number: 6066-82-6
1-Hydroxy-2,5-pyrrolidinedione; HOSu; NHS; NHSI.
C4H5NO3; mol wt 115.09.
C 41.74%, H 4.38%, N 12.17%, O 41.70%.

Description and references

Reagent utilized in amide bond synthesis and other coupling reactions. Prepn: G. Errera, Gazz. Chim. Ital. 25 II, 25 (1895). Crystal structure: P. G. Jones, Acta Crystallogr. E59, 1951 (2003) DOI. Early use in peptide synthesis: G. W. Anderson et al., J. Am. Chem. Soc. 85, 3039 (1963) DOI; and alternative prepn method: eidem, ibid. 86, 1839 DOI (1964). Synthetic applications: A. Cecchetto et al., Tetrahedron Lett. 43, 3605 (2002) DOI; A. Schulze, A. Giannis, Adv. Synth. Catal. 346, 252 DOI (2004); M. A. Mironov et al., Tetrahedron Lett. 46, 3957 (2005) DOI; H.-C. Ma, X.-Z. Jiang, J. Org. Chem. 72, 8943 (2007) DOI PubMed. Reviews: D. W. Knight in Encyclopedia of Reagents for Organic Synthesis 4, L. A. Paquette, Ed. (John Wiley & Sons, New York, 1995) pp 2780-2781; P. A. Wang, Synlett 2008, 2384-2385 DOI.

Chemical structure

Properties

White crystalline solid, mp 99-100°. Crystal density: 1.563 Mg/m3. Absorption max (ethanol): 265.5 (ε 625). pKa 6.0. Sol in water, DMF, alcohols, ethyl acetate. Insol in cold ether.

Use

Reagent in synthetic organic chemistry.