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8.55046 EMD Millipore

IIDQ-polystyrene

Novabiochem®

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Properties

brand family   Novabiochem
packaging   25 g in Plastic bottle (8550460025)
  5 g in Glass bottle (8550460005)
shipped in   ambient
storage temp.   Store at +2°C to +8°C.
specifications   Colour (visual): yellow to beige to amber
  Appearance of substance (visual): beads
  Loading (determined by HPLC after reaction of 3-phenylpropionic acid with cyclohexlamine): 1.3 - 1.9 mmol/g
  Swelling Volume (in DMF): lot specific result
  The polymer matrix is copoly (styrene-1 % DVB) 200 - 400 mesh.

Description

Background information

IIDQ-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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Safety & Documentation

Safety Information

HS Code 
3903 90 90
Storage class 
10 - 13 Other liquids and solids
WGK 
WGK 1 slightly water endangering
Protocols & Articles
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