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| | N-ACRYLOXYSUCCINIMIDE Basic information |
| Product Name: | N-ACRYLOXYSUCCINIMIDE | | Synonyms: | N-ACRYLOXYSUCCINIMIDE;ACRYLIC ACID N-HYDROXY-SUCCINIMIDE ESTER;AKOS MSC-0123;1-[(1-OXO-2-PROPENYL)OXY]-2,5-PYRROLIDINEDIONE;1-(ACRYLOYLOXY)-2,5-PYRROLIDINEDIONE;N-Acryloxysuccinimide (NAS);Acrylic acid 2,5-dioxo-1-pyrrolidinyl ester;Acrylic acid 2,5-dioxopyrrolidine-1-yl ester | | CAS: | 38862-24-7 | | MF: | C7H7NO4 | | MW: | 169.13 | | EINECS: | | | Product Categories: | | | Mol File: | 38862-24-7.mol |  |
| | 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 | | Major Application | peptide synthesis | | 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) |
| 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 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2 |
| | 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 |
| | N-ACRYLOXYSUCCINIMIDE Preparation Products And Raw materials |
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