N-ACRYLOXYSUCCINIMIDE Chemical Properties

Melting point:

69 °C

Boiling point:

298.4°C (rough estimate)

Density 

1.4523 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

2-8°C

solubility 

soluble in Toluene

form 

Crystals and Chunks

color 

Yellow

InChI

InChI=1S/C7H7NO4/c1-2-7(11)12-8-5(9)3-4-6(8)10/h2H,1,3-4H2

InChIKey

YXMISKNUHHOXFT-UHFFFAOYSA-N

SMILES

C(ON1C(=O)CCC1=O)(=O)C=C

CAS DataBase Reference

38862-24-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-40-48/20/22-36-22

Safety Statements 

36-26-37/39

WGK Germany 

2

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

N-ACRYLOXYSUCCINIMIDE Usage And Synthesis

Chemical Properties

yellow crystals and chunks

Uses

sulfhydryl reactive cross-linking reagent affording sulfides and HI, can subsequently be radio-iodinated, the phenylazide function can then be photo-activated with long wavelength UV light to couple with another molecule

Uses

Acrylic acid N-hydroxysuccinimide ester (NAS) is a general acrylating agent that is used in the synthesis of:

• Acrylated hyaluronic acid (HA) hydrogel for bone regeneration applications.
• Injectable, biodegradable, and thermosensitive copolymers for tissue engineering.
• Imidazole-based biocompatible, aqueous quantum dots (QDs).

Synthesis

N-hydroxysuccinimide (10 g, 0.086 mol) and triethylamine (13.2 g, 0.129 mol) were dissolved in chloroform (130 mL) at 0 °C. Stirring was maintained and acryloyl chloride (8.6 g, 0.094 mol) was slowly added dropwise to the reaction mixture, the dropwise process was controlled to be completed within 2 hours. After the reaction was completed, stirring was continued at 0 °C for 30 min. Subsequently, the reaction solution was washed twice with 60 mL of saturated aqueous NaCl, and the organic phase was dried with MgSO4, filtered and concentrated to a residual volume of about 30 mL. to the concentrate was added a solvent mixture of ethyl acetate/pentane (14 mL, 1:3, v/v/v), and the mixture was kept at 0 °C to promote the crystallization of N-acryloyloxysuccinimide overnight, resulting in the target 70% yield of the Product. The structure of the product was confirmed by 1H NMR (CDCl3) with chemical shifts of 2.95 (s, 4H, CH2CH2), 6.20 (m, 1H, CH=CH2), 6.4 (m, 1H, CH=CH2) and 6.75 (m, 1H, CH=CH2), respectively.

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 10, p. 4528 - 4560
[2] Chemical Communications, 2014, vol. 50, # 95, p. 15045 - 15048
[3] Organic Letters, 2002, vol. 4, # 5, p. 737 - 740
[4] Chemical Communications, 2009, # 46, p. 7107 - 7109
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4179 - 4190

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