Skip to Content
Merck
CN
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:
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

Signal Word

Danger

Hazard Statements

H315,H318

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solution stability of Product 130672, N-Hydroxysuccinimide?

    Sigma-Aldrich does not evaluate 130672 for solution stability. Therefore, it is advisable to prepare a solution fresh for each use. Please note, the product is moisture sensitive.

  6. What is the purity of Product 130672, N-Hydroxysuccinimide?

    The purity is lot specific and will be stated on the Specification Sheet.

  7. Does N-Hydroxysuccinimide go by any other names?

    Yes, N-Hydroxysuccinimide is also referred to by the acronym NHS and is also referred to by the synonyms 1-Hydroxy-2,5-pyrrolidinedione and HOSu.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Polycyclic Aromat. Compd., 3, 781-781 (1993)
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
Preparation of N-succinimidyl 3-[* I] iodobenzoate: an agent for the indirect radioiodination of proteins.
Vaidyanathan G
Nature Protocols, 1(2), 707-707 (2006)
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
View All Related Papers

Articles

Molecular Monolayers on Silicon Surfaces

Explore methods for molecular monolayers on silicon surfaces, their properties, and applications in molecular electronics and sensing.

Functionalized Graphene Oxide: Properties & Applications

Professor Aran discusses engineering graphene-based materials through careful functionalization, enabling diverse applications.

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