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(R)-(-)-NBD-Py-NCS [=(R)-(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole] [HPLC Labeling Reagent for e.e. Determination]
(CAS RN:163927-29-5 Product Number:A5577)

Structure

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(R)-(-)-NBD-Py-NCS
Synonym (R)-(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitrobenzofurazan
Synonym (R)-(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-nitro-2,1,3-benzoxadiazole

General Information

Product Number A5577

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Purity/Analysis Method >98.0%(HPLC)
Storage Temperature 0-10°C
M.F. / M.W. C11H9N5O3S=291.29
CAS RN 163927-29-5
Related CAS RN
MDL Number MFCD02093434
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Purity(HPLC) min. 98.0 area%
Optical purity(LC) min. 99.0 ee%
Specific rotation [a]20/D -520 to -550 deg(C=0.2, CH3CN)
Effect test of HPLC derivatization Effective as labeling agent for DL-Valine, DL-Phenylalanine

Data of Reference

ee >99.0%(HPLC)

References

PubChem SID 87563194

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H302+H332
  • :Harmful by inhalation and if swallowed.
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
  • H335
  • :May cause respiratory irritation.
Precautionary Statements
  • P261
  • :Avoid breathing dust/fume/gas/mist/vapours/spray.
  • P270
  • :Do not eat, drink or smoke when using this product.
  • 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.
  • P304+P340+P312
  • :IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER or doctor if you feel unwell.
  • 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 Amines

The compound 1 is an HPLC fluorescence labeling reagent for optical purity determination. This compound easily reacts with amino groups, which are directly linked to an asymmetric carbon atom, and produces diastereomers of thiourea. These diasteromers can be separated by reversed phase HPLC, and an excellent chromatogram can be obtained by fluorescence detection at the excitation and emission wavelengths of 488 nm and 590 nm, respectively.
Since both (R)- and (S)-isomers of the derivatization reagents are commercially available on the market, it is possible to change the elution order of the derivatized diastereomers by selecting either enantiomer of the derivatization reagent. Thus, an enantiomer of the aminocompound, whose existing quantity is very small, can be eluted out first and quantified with high precision. Moreover, there are reports for the application of these isomers to Edman Degradation.

Application example:
Add 10 μL of 5 mM HPLC labeling reagent 1 / acetonitrile solution in 10 μL of 1 mM amine / acetonitrile-H2O (1:1) solution (containing 2% triethylamine) to a vessel. Close the cap of the reaction vessel and incubate the mixture at 55 ºC for 10 min. Then, add 480 μL of a mixture solution of 1 M acetic acid and acetonitrile-H2O (1:1) solution, and dilute this reactant mixture 10x by acetonitrile. Use 5 μL of this diluted solution as an HPLC sample solution.

References

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