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Merck
CN

941514

Furan-2-carboxylic acid N-hydroxysuccinimide ester

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Synonym(s):

(2,5-Dioxopyrrolidin-1-yl) furan-2-carboxylate, Furan-2-carboxylic acid NHS ester

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About This Item

Empirical Formula (Hill Notation):
C9H7NO5
CAS Number:
Molecular Weight:
209.16
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.21
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Assay

>90% (HPLC)

Quality Level

form

powder or crystals

greener alternative product score

old score: 53
new score: 19
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greener alternative product characteristics

Safer Solvents and Auxiliaries
Design for Energy Efficiency
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

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color

white to off-white

solubility

chloroform: 30 mg/mL

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storage temp.

2-8°C

SMILES string

O=C(ON1C(=O)CCC1=O)C=2OC=CC2

General description

Furan-2-carboxylic acid N-hydroxysuccinimide ester is a versatile chemical compound belonging to the class of furan derivatives. Due to its ability to form stable amide bonds with primary amines, this compound is widely utilized in organic synthesis and bioconjugation techniques. Its unique furan ring structure imparts specific chemical properties that make it particularly valuable in medicinal chemistry and biochemistry for modifying biomolecules. The efficient nucleophilic substitution reactions it undergoes enable researchers to create stable amide bonds, making it an essential tool for peptide synthesis and biomolecule modification.
We are committed to bringing you Greener Alternative Products that adhere to one of the four categories of Greener Alternatives. This product belongs to the category of Re-engineered Products, demonstrating key improvements in Green Chemistry Principles such as "Safer Sovents and Auxiliaries", "Design for Energy Efficiency", and "Inherently Safer Chemistry for Accident Prevention." Click here to view its DOZN scorecard.

Application

Furan-2-carboxylic acid N-hydroxysuccinimide ester is ideal for a variety of scientific research applications, including:
  • Organic Synthesis: Used in the synthesis of complex organic molecules and as a coupling agent in peptide synthesis.
  • Biochemical Studies: Employed for the modification of proteins and peptides in various biochemical assays.
  • Drug Development: Utilized in creating drug delivery systems and conjugating therapeutic agents to targeting molecules.
  • Diagnostic and Therapeutic Production: Applied in producing bioconjugates for diagnostic and therapeutic purposes.
Its ability to form stable amide bonds with primary amines makes Furan-2-carboxylic acid N-hydroxysuccinimide ester a highly valuable compound in advancing bioconjugation techniques and enhancing the functionality of biomolecules in research and development.

Features and Benefits

  • Stable Amide Bond Formation: Reacts efficiently with primary amines to create robust amide bonds, crucial for bioconjugation.
  • Efficient Reaction Mechanism: Forms a reactive ester intermediate that readily reacts with primary amines, ensuring high yields.
  • Unique Furan Structure: Imparts specific chemical properties that enhance its utility compared to other N-hydroxysuccinimide esters.

Pictograms

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Information

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