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855046 IIDQ-polystyrene

Novabiochem®

IIDQ-polystyrene MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.
CAS #: 9003-70-7
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855046
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Overview

Replacement Information

Key Spec Table

CAS #
9003-70-7
Description
Catalogue Number855046
Replaces01-64-0469
Brand Family Novabiochem®
Background InformationIIDQ-polystyrene (IIDQ-PS) [1] is a polymer-supported version of the IIDQ coupling reagent [2]. IIDQ has many advantages over conventional carbodiimide- or uronium-based reagents: no preactivation step is required, and acid, amine and coupling reagent can be added in any order; in contrast to uronium-based reagents like HBTU, it cannot form guanidinium by-products; and it is totally stable to base.

The treatment of a carboxylic acid with IIDQ-PS in DCM or MeCN rapidly generates in situ the corresponding isobutoxycarbonyl mixed anhydride [3]. Attack by nucleophiles preferentially takes place at the less hindered and more electrophilic carbonyl of the carboxylic acid moiety, releasing only volatile carbon dioxide and isobutanol as by-products. If reaction is carried out in the presence of an amine, amide bond formation occurs concurrently with generation of the anhydride. Alternatively, addition of NaBH4 or polymer-supported borohydride to the anhydride will lead directly to the corresponding alcohol.

IIDQ-PS appears to be particularly effective for mediating the acylation for anilines, and has also been found to couple peptide fragments without epimerization. In a comparative study, IIDQ-PS was found to give higher yields and greater purities than HATU, EDC-PS or DCC-PS [4]. Occasionally, with some secondary amines the formation of isobutyl carbamate by-products has been observed, resulting from attack by the amine at the carbonyl group.

The product number for this product was previously 01-64-0469.

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References
Product Information
CAS number9003-70-7
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 +2°C to +8°C.
Packaging Information
Transport Information
Supplemental Information
Specifications
Color (visual)yellow to orange to dark brown
Appearance of substance (visual)beads
Loading (determined by HPLC after reaction of 3-phenylpropionic acid with cyclohexlamine)1.2 - 1.9 mmol/g
Swelling Volume (in DMF)lot specific result
The polymer matrix is copoly (styrene-1 % DVB) 200 - 400 mesh.

Documentation

IIDQ-polystyrene SDS

Title

Safety Data Sheet (SDS) 

Citations

Title
  • [1] E. Valeur, et al. (2005) Chem. Commun., 1164.
  • [2] Y. Kiso, et al. (1973) Chem. Pharm. Bull., 21, 2507.
  • [3] J. R. Vaughan (1951) J. Am. Chem. Soc., 73, 3547.
  • [4] E. Valeur & M. Bradley, unpublished results.