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(R)-(+)-NBD-Pro-COCl [=(R)-(+)-4-Nitro-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole] [HPLC Labeling Reagent for e.e. Determination]
(CAS RN:159717-69-8 Product Number:A5566)

Structure

(R)-(+)-NBD-Pro-COCl
Synonym (R)-(+)-4-Nitro-7-(2-chloroformylpyrrolidin-1-yl)benzofurazan
Synonym (R)-(+)-4-Nitro-7-(2-chloroformylpyrrolidin-1-yl)-2,1,3-benzoxadiazole

General Information

Product Number A5566

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Purity/Analysis Method
Storage Temperature 0-10°C
M.F. / M.W. C11H9ClN4O4=296.67
CAS RN 159717-69-8
Related CAS RN
MDL Number MFCD00191511
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Effect test of HPLC derivatization Effective as labeling agent fo 2-Hexanol

References

PubChem SID 87563183

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 2934999090

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 wavelengths of 470 nm and 540 nm, respectively. And the diastereomers derived from racemic alcohol or amine and 1 can be separated by HPLC (The separation factor α:2-hexanol and 1-phenylethylamine = 1.2 and 1.37, respectively). 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)-(-)-NBD-Pro-COCl] of 1. The detection limit for the alcohols is sub-picomol. A highly sensitive detection can be done by using laser induced fluorescence detector.

Application example:1)
Add 0.5 mL of 40 mM labeling reagent 1 / dry benzene solution and 0.5 mL of 1 mM alcholol (or amine) / dry benzene (containing 2% of pyridine) solution to a vessel. Close the cap of the reaction vessel and incubate the mixture at 80 ºC for 1~2 h (50 ºC for 1h, in the case of amine). 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

  • 1)Tokyo Kasei Kogyo Co. Ltd., Jpn. Kokai Tokkyo Koho 95 188224, 1995.

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