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(R)-(+)-DBD-Pro-COCl [=(R)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole] [HPLC Labeling Reagent for e.e. Determination]
(CAS RN:150993-62-7 Product Number:A5565)

Structure

(R)-(+)-DBD-Pro-COCl
Synonym (R)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)benzofurazan
Synonym (R)-(+)-4-(N,N-Dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole

General Information

Product Number A5565

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Purity/Analysis Method >95.0%(HPLC)
Storage Temperature 0-10°C
M.F. / M.W. C13H15ClN4O4S=358.80
CAS RN 150993-62-7
Related CAS RN
MDL Number MFCD00221513
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Purity(HPLC) min. 95.0 area%
Optical purity(LC) min. 99.0 ee%
Specific rotation [a]20/D +42.0 to +45.0 deg(C=0.2, CHCl3)
Effect test of HPLC derivatization Effective as labeling agent fo 2-Hexanol

Data of Reference

ee >99.0%(HPLC)

References

Reaxys-RN 11148085
PubChem SID 87563182

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2935909099

Application

HPLC Labeling Reagent for Chiral Alcohols and Amines

The compound 1 is an HPLC fluorescence labeling reagent for optical purity determination, which easily reacts with optical active alcohols or amines to form the corresponding esters or amides, respectively. The resultant esters or amides are stable and can reach the detector without any decomposition under reversed and normal phase HPLC. An excellent chromatogram can be obtained by fluorescence detection at the excitation and emission wavelength of 450 nm and 560 nm, respectively. And the diastereomers derived from racemic alcohol and 1 can be separated by HPLC (The separation factor α: 2-hexanol = 1.2). Since no racemization can occur with derivatization reaction, it is possible to change an elution order of the labeled diastereomeres by selecting the enantiomer [(S)-(-)-DBD-Pro-COCl] of 1. The detection limit for the alcohols is sub-picomol. A highly sensitive analysis can be done by peroxyoxalate chemiluminescence detection.

Application example:
[Secondary alcohols] 1)
Add 1 mL of 10 mM labeling reagent 1 / dry benzene solution, 1 mL of 2 mM alcholol / dry benzene (containing 1% of pyridine) solution to a vessel. Close the cap of the reaction vessel and incubate the mixture at 80 ºC for 3 h. After cooling to room temperature, excess of 1 is removed by liquid-liquid extraction (e.g. washing with 5% NaHCO3 solution) or solid phase extraction. Use the resultant as an HPLC sample solution.

References

PubMed Literature

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