N-Hydroxysuccinimide

N-Hydroxysuccinimide
Skeletal formula of N-hydroxysuccinimide
Ball-and-stick model of the N-hydroxysuccinimide molecule
Names
Preferred IUPAC name
1-Hydroxypyrrolidine-2,5-dione
Other names
HOSu, HSI.
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.025.456 Edit this at Wikidata
UNII
  • InChI=1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2 ☒N
    Key: NQTADLQHYWFPDB-UHFFFAOYSA-N ☒N
  • InChI=1/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2
    Key: NQTADLQHYWFPDB-UHFFFAOYAM
  • O=C1N(O)C(=O)CC1
Properties
C4H5NO3
Molar mass 115.09 g/mol
Appearance Colourless solid
Melting point 96.3 °C (205.3 °F; 369.4 K)[1]
Related compounds
Related imides
 Succinimide
N-Bromosuccinimide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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N-Hydroxysuccinimide (NHS) is an organic compound with the formula (CH2CO)2NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.[2]

  1. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.316. ISBN 9781498754293.
  2. ^ Knight, David W. (2001). "N-Hydroxysuccinimide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rh069. ISBN 0471936235.