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532304

Sigma-Aldrich

2-Chlorotrityl chloride, polymer-bound

100-200 mesh, extent of labeling: 1.0-1.5 mmol/g

Synonym(s):

2,α-Dichlorobenzhydryl-polystyrene crosslinked with divinylbenzene

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About This Item

CAS Number:
Beilstein/REAXYS Number:
1983914
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Quality Level

extent of labeling

1.0-1.5 mmol/g

particle size

100-200 mesh

application(s)

peptide synthesis

SMILES string

Clc1ccccc1C(Cl)(c2ccccc2)c3ccccc3

InChI

1S/C19H14Cl2/c20-18-14-8-7-13-17(18)19(21,15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H

InChI key

JFLSOKIMYBSASW-UHFFFAOYSA-N

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Application

  • Acid labile resin used in Fmoc-based solid phase peptide synthesis.
  • Mild acidic cleavage conditions lead to the release of the peptide acid where fully protected peptides can be released if desired.
  • 2-Chlorotrityl chloride resins prevent racemization of the first amino acid and are thus very useful when racemic mixtures are forming (common with residues such as His or Cys).
  • This resin also prevents diketopiperazide formation, which can be an issue with proline C-terminal peptide sequences.

Use:
  • Attachment of the first amino acid residue is effected by stirring the resin, the protected amino acid, and excess diisopropylethylamine (DIEA) in dichloromethane.
  • Cleavage of the final protected peptide fragment is achieved under very mild conditions using either acetic acid/trifluoroethanol (TFE)/dichloromethane (1:1:8; v/v/v), hexafluoroisopropanol (HFIP)/dichloromethane (1:4; v/v) or simply 0.5% trifluoroacetic acid/dichloromethane (v/v).
  • Higher concentrations of TFA can be used if retention of peptide side chaing protecting groups is unimportant. Note that trityl chloride is moisture-sensitive, and, therefore, should be stored and handled appropriately.
  • If the resin becomes deactivated, treatment with acetyl chloride or SOCl2 in toluene before use is recommended to restore its activity.

pictograms

CorrosionExclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Met. Corr. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible, corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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