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Merck

130672

N-Hydroxysuccinimide

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
Molecular Weight:
115.09
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
228-001-3
Beilstein/REAXYS Number:
113913
MDL number:
Assay:
98%
Form:
solid
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Quality Level

assay

98%

form

solid

mp

95-98 °C (lit.)

functional group

imide

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

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.


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pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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PEGylation of native disulfide bonds in proteins.
Brocchini S
Nature Protocols, 1(5), 2241-2241 (2006)
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
Polycyclic Aromat. Compd., 3, 781-781 (1993)