Date published: 2026-4-30

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2-(Dimethylamino)pyridine (CAS 5683-33-0)

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CAS Number:
5683-33-0
Molecular Weight:
122.17
Molecular Formula:
C7H10N2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-(Dimethylamino)pyridine is a transparent liquid ranging from colorless to pale yellow. When combined with toluene at ambient temperature and in the company of 1.1 equivalents of methyl trifluoromethanesulfonate, it generates the (2-pyridyl)-trimethylammonium trifluoromethanesulfonate salt. This compound is used as a model substrate in crafting chelate carbenes through cyclometalation, H2 elimination, and reversible α-elimination.


2-(Dimethylamino)pyridine (CAS 5683-33-0) References

  1. Double geminal C-H activation and reversible alpha-elimination in 2-aminopyridine iridium(III) complexes: the role of hydrides and solvent in flattening the free energy surface.  |  Clot, E., et al. 2004. J Am Chem Soc. 126: 8795-804. PMID: 15250733
  2. Assessment of 4-(dimethylamino)pyridine as a capping agent for gold nanoparticles.  |  Gandubert, VJ. and Lennox, RB. 2005. Langmuir. 21: 6532-9. PMID: 15982063
  3. Iridium(III)-induced isomerization of 2-substituted pyridines to N-heterocyclic carbenes.  |  Alvarez, E., et al. 2006. J Am Chem Soc. 128: 13060-1. PMID: 17017779
  4. 2,2',2''-Terpyridine-catalyzed synthesis of cyclic carbonates from epoxides and carbon dioxide under solvent-free conditions.  |  Liu, H., et al. 2014. Int J Mol Sci. 15: 9945-51. PMID: 24901525
  5. Csp3 -H Activation without Chelation Assistance in an Iridium Pincer Complex Forming Cyclometallated Products.  |  Ahlstrand, DA., et al. 2017. Chemistry. 23: 1748-1751. PMID: 27982473
  6. Synthesis of 4-trifluoromethyl 2-pyrones and pyridones through the Brønsted base-catalyzed Pechmann-type reaction with cyclic 1,3-diones.  |  Yan, W., et al. 2018. Org Biomol Chem. 16: 9440-9445. PMID: 30515497
  7. Towards the enzymatic formation of artificial metal base pairs with a carboxy-imidazole-modified nucleotide.  |  Röthlisberger, P., et al. 2019. J Inorg Biochem. 191: 154-163. PMID: 30529723
  8. Preferential protonation and methylation at the nitrogen atoms of N, N‐dimethylamino derivatives of pyridine  |  Barbieri, G., Benassi, R., Grandi, R., Pagnoni, U. M., & Taddei, F. 1979. Organic Magnetic Resonance. 12(3): 159-162.
  9. Karramkam, M., Hinnen, F., Vaufrey, F., & Dollé, F. (2003). 2‐, 3‐and 4‐[18F] Fluoropyridine by no‐carrier‐added nucleophilic aromatic substitution with K [18F] F‐K222–a comparative study.  |  Karramkam, M., Hinnen, F., Vaufrey, F., & Dollé, F. 2003. Journal of Labelled Compounds and Radiopharmaceuticals: The Official Journal of the International Isotope Society. 46(10): 979-992.
  10. Synthesis and pH-dependent micellization of sulfonamide-modified diblock copolymer  |  Pal, R. R., Kim, M. S., & Lee, D. S. 2005. Macromolecular Research. 13: 467-476.
  11. Expedient Synthesis of (R)‐Curcuphenol: A Chiral Pool Strategy  |  Feng, J., Zhu, G., Liu, B., & Zhou, X. 2013. Chinese Journal of Chemistry. 31(1): 23-26.
  12. Pincer complexes, leading characters in C–H bond activation processes. Synthesis and catalytic applications  |  Valdés, H., Rufino-Felipe, E., & Morales-Morales, D. 2019. Journal of Organometallic Chemistry. 898: 120864.
  13. Preparation and characterization of modified starches obtained in acetic anhydride/tartaric acid medium  |  Tupa, M. V., Altuna, L., Herrera, M. L., & Foresti, M. L. 2020. Starch‐Stärke. 72(5-6): 1900300.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-(Dimethylamino)pyridine, 25 g

sc-237868
25 g
$91.00