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Safety Information

130672

Sigma-Aldrich

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
Beilstein:
113913
EC Number:
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22

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

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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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

130672-100G:
130672-5KG:
130672-5G:
130672-CH:
130672-25G:
130672-250G:
130672-VAR:
130672-1KG:
130672-BULK:


Certificates of Analysis (COA)

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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)
Polycyclic Aromat. Compd., 3, 781-781 (1993)
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

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