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Chemical Structure| 10199-89-0 Chemical Structure| 10199-89-0
Chemical Structure| 10199-89-0

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NBD-Cl is a nonfluorescent reagent which becomes highly fluorescent after reaction with thiol or amino groups.

Synonyms: NBD chloride

4.5 *For Research Use Only !

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Product Details of NBD-Cl

CAS No. :10199-89-0
Formula : C6H2ClN3O3
M.W : 199.55
SMILES Code : O=[N+](C1=CC=C(Cl)C2=NON=C21)[O-]
Synonyms :
NBD chloride
MDL No. :MFCD00005808
InChI Key :IGHBXJSNZCFXNK-UHFFFAOYSA-N
Pubchem ID :25043

Safety of NBD-Cl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of NBD-Cl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 10199-89-0 ]

[ 10199-89-0 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 463-71-8 ]
  • [ 10199-89-0 ]
  • [ 17417-09-3 ]
  • [ 39835-09-1 ]
  • [ 57381-56-3 ]
  • 5-Nitro-2-(trifluoromethylthio)benzonitrile [ No CAS ]
  • 4
  • [ 90-41-5 ]
  • [ 10199-89-0 ]
  • [ 413611-93-5 ]
YieldReaction ConditionsOperation in experiment
90% With tertiary amine; In acetonitrile; for 16.0h;Reflux; Inert atmosphere; General procedure: To a solution of 4-chloro-7-nitrobenzofurazan (NBD-Cl, 2; 1 eq.) in acetonitrile (0.1 M) was added the requisite amine (1.1 eq.) followed by triethylamine (2 eq.) The reaction mixture was then stirred at reflux under an inert atmosphere (N2) for 16 h. The solvent was removed in vacuo, then the residue was re-dissolved in EtOAc, washed with 1 M HCl, water, brine, dried (Na2SO4), filtered and concentrated. The crude material was purified over silica gel, eluting with a gradient of EtOAc in Hexanes.
90% With triethylamine; In acetonitrile; for 16.0h;Reflux; Inert atmosphere; General procedure: To a solution of 4-chloro-7-nitrobenzoliirazan (NBD-Cl, 2; 1 eq.) in acetonitrile (0.1 M) was added the requisite amine (1.1 eq.) followed by triethylamine (2 eq.). The reaction mixture was then stirred at reflux under an inert atmosphere (N2) for 16 h. The solyent was remoyed in yacuo, then the residue was re-dissolyed in EtOAc, washed with 1 M HC1, water, brine, dried (Na2 S04), fltered and concentrated. The crude material was purifed oyer silica gel, eluting with a gradient ofEtOAc in Hexanes.
  • 5
  • [ 10199-89-0 ]
  • [ 137215-27-1 ]
  • [ 1558669-86-5 ]
YieldReaction ConditionsOperation in experiment
86% With triethylamine; In ethanol; at 20℃; NBD-Cl (0.24 g, 1.2 mmol) was added to a solution of7-mercapto-4-methylcoumarin (0.23 g, 1.2 mmol) and triethylamine (0.36 g, 3.6 mmol) in ethanol(50 mL). The reaction mixture was stirred at room temperature for overnight,and the resulting yellow precipitates were filtered and washed with ethanol. The crude product was dried undervacuum to afford compound 2 (86%yield) as a yellow powder; mp: 298 C. 1H NMR (600 MHz, DMSO-d6) delta 8.50 (d, J = 7.9 Hz, 1H), 7.97 (d, J= 8.2 Hz, 1H), 7.80 (d, J = 1.8 Hz,1H), 7.68 (dd, J = 8.2, 1.8 Hz, 1H),7.19 (d, J = 7.9 Hz, 1H), 6.55 (d, J = 1.3 Hz, 1H), 2.49 (d, J = 1.3 Hz, 3H); 13C NMR (150 MHz,DMSO-d6) delta 159.5, 153.9, 153.1, 149.4, 143.4, 137.7, 134.2, 132.8,131.7, 129.9, 127.7, 126.5, 122.2, 121.6, 116.2, 18.5; HRMS: (EI+); m/z calcdfor C16H9N3O5S [M]+:355.0263,found 355.0263.
  • 6
  • [ 10199-89-0 ]
  • [ 117976-90-6 ]
  • C24H22N6O6S [ No CAS ]
  • 7
  • [ 57184-23-3 ]
  • [ 10199-89-0 ]
  • 4-[4-(cyclohexylmethyl)piperazin-1-yl]-7-nitro-2,1,3-benzoxadiazole [ No CAS ]
  • 8
  • [ 13108-19-5 ]
  • [ 10199-89-0 ]
  • 10-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)decanoic acid [ No CAS ]
  • 9
  • [ 39987-25-2 ]
  • [ 10199-89-0 ]
  • dimethyl 2,2'-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)azanediyl)diacetate [ No CAS ]
 

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