Skip to Content
MilliporeSigma
All Photos(5)

Documents

130672

Sigma-Aldrich

N-Hydroxysuccinimide

98%

Synonym(s):

1-Hydroxy-2,5-pyrrolidinedione, HOSu, NHS

Sign Into View Organizational & Contract Pricing
All Photos(5)

About This Item

Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
6066-82-6
Molecular Weight:
115.09
Beilstein/REAXYS Number:
113913
EC Number:
228-001-3
MDL number:
MFCD00005516
UNSPSC Code:
12352115
PubChem Substance ID:
24847975
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

mp

95-98 °C (lit.)

SMILES string

ON1C(=O)CCC1=O

InChI

1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2

InChI key

NQTADLQHYWFPDB-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

N-Hydroxysuccinimide can be used in the synthesis of N-hydroxysuccinimide ester via dehydration reaction in the presence of dicyclohexylcarbodiimide in carboxylic acid.
N-Hydroxysuccinimide has been used in the synthesis of intermediates such as:
  • N

  • -succinimidyl 3-(di-tert-butylfluorosilyl)benzoate
  • 4-[2,2-bis[(p-tolylsulfonyl)-methyl] acetyl]benzoic acid-NHS ester
  • N-succinimidyl 3-iodobenzoate

It has also been used in a protocol for the surface modification of microchannels of a microfluidic-integrated surface plasmon resonance (SPR) platform for the detection and quantification of bacterial pathogens.
Additive used in the carbodiimide method for improved amidations and peptide couplings.

pictograms

Corrosion
GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Pico Y et al.
Food Toxicants Analysis: Techniques, Strategies and Developments (2007)
Cong Li et al.
Journal of the American Chemical Society, 128(47), 15072-15073 (2006-11-23)
The conjugate of bacterial cytosine deaminase (bCD) and poly-l-lysine (PLL) that was functionalized with biotin, rhodamine, and Gd3+-DOTA was synthesized and characterized. It demonstrated high relaxivity, improved enzymatic specificity to prodrug 5-fluorocytosine, low cytotoxicity, efficient cell uptake, and high enzymatic
D Sehgal et al.
Analytical biochemistry, 218(1), 87-91 (1994-04-01)
Water-soluble carbodiimides are widely used for carboxyl-amine conjugation. However, extremely variable and low yields, obtained under a variety of conditions, have been a serious problem in the coupling. A simple method, optimizing various parameters of the coupling reaction, in which
Zbigniew Czajgucki et al.
Journal of peptide science : an official publication of the European Peptide Society, 12(10), 653-662 (2006-07-19)
Edeines are pentapeptide amide antibiotics composed of four nonprotein amino acids, glycine, and polyamine. They exhibit antimicrobial and immunosuppressive activities and are universal inhibitors of translation. Moreover, it was proven that the free ionizable carboxy group in the (2R, 6S
PEGylation of native disulfide bonds in proteins.
Brocchini S
Nature Protocols, 1(5), 2241-2241 (2006)
View All Related Papers

Articles

Molecular Monolayers on Silicon Surfaces

This article briefly reviews the methods and mechanisms for the formation of molecular monolayers on silicon surfaces, the properties of these monolayers and current perspectives regarding their application in molecular electronic and sensing applications.

Properties and Applications of Functionalized Graphene Oxide

Professor Aran (Claremont University, USA) thoroughly discusses the engineering of graphene based materials through careful functionalization of graphene oxide, a solution processable form of graphene.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service