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(S)-(+)-NBD-APy [=(S)-(+)-4-Nitro-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole] [HPLC Labeling Reagent for e.e. Determination]
(CAS RN:143112-52-1 Product Number:A5562)

Structure

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(S)-(+)-NBD-APy
Synonym (S)-(+)-4-Nitro-7-(3-aminopyrrolidin-1-yl)benzofurazan
Synonym (S)-(+)-4-Nitro-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole

General Information

Product Number A5562

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Purity/Analysis Method
Storage Temperature
M.F. / M.W. C10H11N5O3=249.23
CAS RN 143112-52-1
Related CAS RN
MDL Number MFCD00191509
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Optical purity(LC) min. 99.0 ee%
Specific rotation [a]20/D +12.0 to +17.0 deg(C=0.2, CH3CN)
Effect test of HPLC derivatization Effective as labeling agent fo Ibuprofen.

Data of Reference

ee >99.0%(HPLC)

References

PubChem SID 87563179

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 Carboxylic Acids

The compound 1 is an optically active HPLC fluorescence labeling reagent, which has a 2,1,3-benzoxadiazole skeleton and an amino group, and is used for optical purity determination of carboxylic acids. Labeling of racemic carboxylic acids can be done by using a mild condition such as the Mukaiyama-Corey method, and produces diastereomers without inducing racemization. These diastereomers can be separated by reversed phase HPLC, and an excellent chromatogram can be obtained by fluorescence detection at the excitation and emission wavelengths of 470 nm and 540 nm, respectively. Since their excitation and fluorescence wavelengths are at longer wavelengths, detection has less interference by contaminants. A highly sensitive detection can be done by using laser induced fluorescence detector.

Application example:2)
Add 0.1 mL of 10 mM labeling reagent 1 / acetonitrile solution, 0.25 mL of 2 μM carboxylic acid / acetonitrile solution, and 0.15 mL of 10 mM 2,2’-dipyridyl disulfide-triphenylphosphine / acetonitrile solution to a vessel, and react the mixture at room temperature for 4 h. Use the resultant as an HPLC sample solution.
For example, the detection limit (S/N=2) for naproxen is 15 fmol.

References

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