Millipore Sigma Vibrant Logo
Attention: We have moved. Merck Millipore products are no longer available for purchase on MerckMillipore.com.Learn More

855019 p-Nitrophenyl carbonate Wang resin

Novabiochem®

p-Nitrophenyl carbonate Wang resin MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.
View Products on Sigmaaldrich.com
855019
Purchase on Sigma-Aldrich

Overview

Replacement Information

Products

Catalogue NumberPackaging Qty/Pack
8.55019.0001 玻璃瓶 1 g
8.55019.0005 玻璃瓶 5 g
8.55019.0025 塑膠瓶 25 g
Description
Catalogue Number855019
Replaces01-64-0123
Brand Family Novabiochem®
Background InformationResin-bound p-nitrophenyl carbonate esters react readily with amines to provide the corresponding resin-bound carbamate. Leznoff [1] was the first to demonstrate the utility of such resins in solid phase synthesis with the preparation of mono-acylated diamines from symmetrical diamines.

Similarly, Dressman, et al. [2] have used carbamate linked resin-bound amino acid amides to make hydantoins via a base-mediated cyclization/cleavage strategy.

Amines linked to p-nitrophenyl carbonate Wang resin possess similar chemical properties to methoxybenzyloxycarbonyl protected amines. The resin-bound carbamate is, therefore, cleaved with TFA or hydrogenolysis to afford the free amine [3]. Alternatively, cleavage by reduction with lithium aluminium hydride can be used to generate N-methylamines [4], and Raju & Kogan [5] have utilized this resin to prepare sulfonamides by acylation of immobilized arylamines and cleavage with LiOH or NaOMe. An analogous p-nitrophenyl carbonate resin prepared from NovaSyn® TGA resin was employed as a support for the solid phase immobilization of amidines [6]. This resin was also used to synthesize polyamines [7, 8], and to immobilize indoles [9] and guanidinylating reagents [10].

Loading of this resin can be quantified by measuring the release of p-nitrophenolate [11].

The product number for this product was previously 01-64-0123.

To obtain a certificate of analysis (CoA) of a lot that begins with the letter "A", please select the option in the right hand menu "Request a COA for Lot#s starting with A".
References
Product Information
HS Code3903 90 90
Structure formula ImageStructure formula Image
Quality LevelMQ200
Applications
Biological Information
Physicochemical Information
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Storage class10 - 13 Other liquids and solids
WGKWGK 1 slightly hazardous to water
Safety Information
Product Usage Statements
Storage and Shipping Information
StorageStore at -15°C to -25°C.
Packaging Information
Transport Information
Supplemental Information
Specifications
Color (visual)white to yellow to beige
Appearance of substance (visual)beads
Loading / photometric determination of p-nitrophenol released upon treatment with piperidine / DMF0.60 - 1.20 mmol/g
Swelling Volume (in DMF)lot specific result
The polymer matrix is copoly (styrene - 1% DVB ), 100 - 200 mesh.
Global Trade Item Number
Catalogue Number GTIN
8.55019.0001 04027269109974
8.55019.0005 04027269109981
8.55019.0025 04027269109998

Documentation

p-Nitrophenyl carbonate Wang resin MSDS

Title

Safety Data Sheet (SDS) 

Citations

Title
  • [1] D. M. Dixit, et al. (1978) Israel J. Chem., 17, 248.
  • [2] B. A. Dressman, et al. (1996) Tetrahedron Lett., 37, 937.
  • [3] J. R. Hauske, et al. (1995) Tetrahedron Lett., 36, 1589.
  • [4] C. Y. Ho & M. J. Kukla (1997) Tetrahedron Lett., 38, 2799.
  • [5] B. Raju & T. P. Kogan (1997) Tetrahedron Lett., 38, 3373.
  • [5] A. K. Ghosh, et al. (2001) J. Org. Chem., 66, 2161.
  • [6] R. Mohan, et al. (1998) Bioorg. Med. Chem. Lett., 8, 1877.
  • [7] S. Tomasi, et al. (1998) Bioorg. Med. Chem. Lett., 8, 635.
  • [8] N. D. Hone & L. J. Payne (2000) Tetrahedron Lett., 41, 6149.
  • [9] A. L. Smith, et al. (2000) Bioorg. Med. Chem. Lett., 10, 2693.
  • [10] A. K. Ghosh, et al. (2001) J. Org. Chem., 66, 2161.
  • [11] A. Paio, et al. (2003) Tetrahedron Lett., 44, 1867.