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1-Benzyl-1,4-dihydronicotinamide (CAS 952-92-1)

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Alternate Names:
1,4-Dihydro-1-(phenylmethyl)-3-pyridinecarboxamide; 1-Benzyl-1,4-dihydro-nicotinamide; N-Benzyl-3-carbamoyl-1,4-dihydropyridine; N-Benzyldihydronicotinamide; NSC 26899
CAS Number:
952-92-1
Purity:
≥95%
Molecular Weight:
214.26
Molecular Formula:
C13H14N2O
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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1-Benzyl-1,4-dihydronicotinamide is a synthetic compound that is used in research focused on redox chemistry and enzymatic reactions. As an analog of the reduced form of nicotinamide adenine dinucleotide (NADH), this molecule is of particular interest in studies involving electron transfer processes. Researchers employ 1-Benzyl-1,4-dihydronicotinamide to gain insights into the mechanisms of NADH-dependent enzymes, given its structural similarity to NADH. It is also used as a model compound in the development of biomimetic catalysts that aim to replicate the behavior of redox-active enzymes. Additionally, the compound is a useful tool in the study of oxidation-reduction reactions in organic synthesis, where it can serve as a hydride donor in various chemical transformations. The benzyl group in the structure of 1-Benzyl-1,4-dihydronicotinamide makes it more resistant to oxidation than NADH, which is beneficial for certain experimental conditions where increased stability is required.


1-Benzyl-1,4-dihydronicotinamide (CAS 952-92-1) References

  1. Is there a deuterium kinetic isotope effect in the one-electron transfer from 1-benzyl-1,4-dihydronicotinamide to 9-fluorenylidenemalononitrile?  |  Anne, A., et al. 2000. J Org Chem. 65: 7213-4. PMID: 11031053
  2. Determination of the C4-H bond dissociation energies of NADH models and their radical cations in acetonitrile.  |  Zhu, XQ., et al. 2003. Chemistry. 9: 871-80. PMID: 12584702
  3. Polysiloxane-supported NAD(P)H model 1-benzyl-1,4-dihydronicotinamide: synthesis and application in the reduction of activated olefins.  |  Zhang, B., et al. 2003. J Org Chem. 68: 3295-8. PMID: 12688805
  4. Hydricities of BzNADH, CH5Mo(PMe3)(CO)2H, and C5Me5Mo(PMe3)(CO)2H in acetonitrile.  |  Ellis, WW., et al. 2004. J Am Chem Soc. 126: 2738-43. PMID: 14995190
  5. Transition metal complexes coordinated by an NAD(P)H model compound and their enhanced hydride-donating abilities in the presence of a base.  |  Kobayashi, A., et al. 2005. Chemistry. 11: 4219-26. PMID: 15864798
  6. Cupric superoxo-mediated intermolecular C-H activation chemistry.  |  Peterson, RL., et al. 2011. J Am Chem Soc. 133: 1702-5. PMID: 21265534
  7. Magnetic nano-Fe3O4-supported 1-benzyl-1,4-dihydronicotinamide (BNAH): synthesis and application in the catalytic reduction of α,β-epoxy ketones.  |  Xu, HJ., et al. 2012. Org Lett. 14: 1210-3. PMID: 22324403
  8. In situ formation of H2O2 for P450 peroxygenases.  |  Paul, CE., et al. 2014. Bioorg Med Chem. 22: 5692-6. PMID: 24984939
  9. Changing the electron donor improves azoreductase dye degrading activity at neutral pH.  |  Qi, J., et al. 2017. Enzyme Microb Technol. 100: 17-19. PMID: 28284307
  10. Precious-metal free photocatalytic production of an NADH analogue using cobalt diimine-dioxime catalysts under both aqueous and organic conditions.  |  Kwok, CL., et al. 2020. Chem Commun (Camb). 56: 7491-7494. PMID: 32497158
  11. Electrochemical Properties and Reactivity Study of [MnV(O)(μ-OR-Lewis Acid)] Cores.  |  Gupta, G., et al. 2021. Inorg Chem. 60: 18006-18016. PMID: 34813300
  12. Cell-Free Protein Synthesis for the Screening of Novel Azoreductases and Their Preferred Electron Donor.  |  Rolf, J., et al. 2022. Chembiochem. 23: e202200121. PMID: 35593146
  13. Catalysis in reactions of 1-benzyl-1,4-dihydronicotinamide.  |  Anderson, BM., et al. 1965. Arch Biochem Biophys. 110: 577-82. PMID: 4221029

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

1-Benzyl-1,4-dihydronicotinamide, 100 mg

sc-208609
100 mg
$312.00