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4-Dimethylaminopyridine (CAS 1122-58-3)

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Alternate Names:
DMAP; N,N′-Dimethyl-4-pyridinamine
Application:
4-Dimethylaminopyridine is a highly efficient catalyst for acylation reactions
CAS Number:
1122-58-3
Molecular Weight:
122.17
Molecular Formula:
C7H10N2
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Dimethylaminopyridine (4-DMAP) is a versatile organic compound widely employed as a catalyst in chemical reactions, particularly in organic synthesis for the creation of amines and other nitrogen-containing compounds. This odorless, white crystalline solid possesses a boiling point of 285°C and a melting point of 75-77°C. With a strong base nature and a pKa of 13.3, 4-Dimethylaminopyridine significantly aids in the synthesis of esters and amides, as well as heterocyclic compounds like pyridines and quinolines. Acting as a catalyst, it enhances the formation of carbon-nitrogen bonds by functioning as a nucleophile that attacks the electrophilic carbon atom of the substrate, resulting in the establishment of a covalent bond between the carbon and nitrogen atoms. Consequently, 4-Dimethylaminopyridine remains widely employed in scientific research to expedite various chemical reactions of significance.


4-Dimethylaminopyridine (CAS 1122-58-3) References

  1. 4-Dimethylaminopyridine as a catalyst in heroin synthesis.  |  Klemenc, S. 2002. Forensic Sci Int. 129: 194-9. PMID: 12372690
  2. Structure and reactivity in neutral organic electron donors derived from 4-dimethylaminopyridine.  |  Garnier, J., et al. 2010. Beilstein J Org Chem. 6: PMID: 20703372
  3. 2,3;5,6-Di-O-isopropyl-idene-1-O-(2-phenyl-acet-yl)-α-d-mannofuran-ose.  |  Sacui, IA., et al. 2010. Acta Crystallogr Sect E Struct Rep Online. 66: o2341. PMID: 21588686
  4. 4-Dimethylaminopyridine promoted interfacial polymerization between hyperbranched polyesteramide and trimesoyl chloride for preparing ultralow-pressure reverse osmosis composite membrane.  |  Qin, J., et al. 2013. ACS Appl Mater Interfaces. 5: 6649-56. PMID: 23796005
  5. A silyliumylidene cation stabilized by an amidinate ligand and 4-dimethylaminopyridine.  |  Yeong, HX., et al. 2013. Chemistry. 19: 11786-90. PMID: 23853083
  6. Semisynthetic lectin-4-dimethylaminopyridine conjugates for labeling and profiling glycoproteins on live cell surfaces.  |  Hayashi, T., et al. 2013. J Am Chem Soc. 135: 12252-8. PMID: 23889132
  7. A comparison of the effects of 4-dimethylaminopyridine and 4-aminopyridine on isolated cardiac and skeletal muscle preparations.  |  Savage, AO. 1985. Arch Int Pharmacodyn Ther. 273: 262-76. PMID: 2860880
  8. 4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl α-Halo Esters to Aryl α-Keto Esters.  |  Jung, Y., et al. 2020. ACS Omega. 5: 22951-22957. PMID: 32954144
  9. New Charge Transfer Complex between 4-Dimethylaminopyridine and DDQ: Synthesis, Spectroscopic Characterization, DNA Binding Analysis, and Density Functional Theory (DFT)/Time-Dependent DFT/Natural Transition Orbital Studies.  |  Varukolu, M., et al. 2022. ACS Omega. 7: 810-822. PMID: 35036748
  10. Cyclodextrins Initiated Ring-Opening Polymerization of Lactide Using 4-Dimethylaminopyridine (DMAP) as Catalyst: Study of DMAP/β-CD Inclusion Complex and Access to New Structures.  |  Meimoun, J., et al. 2022. Molecules. 27: PMID: 35164347
  11. 4-Dimethylaminopyridine (DMAP), A Superior Mediator for Morita-Balylis-Hillman Reaction-Triggered Annulative Condensation of Salicylaldehydes and Acrylonitrile to Form 3-Cyano-2H-chromenes.  |  Kang, B. and Ikeda, K. 2023. Chem Pharm Bull (Tokyo). 71: 318-325. PMID: 36805528
  12. Solvent effects on the cinnamoylation of n-propyl alcohol catalyzed by N-methylimidazole and 4-dimethylaminopyridine.  |  Connors, KA. and Eboka, CJ. 1983. J Pharm Sci. 72: 369-72. PMID: 6864472
  13. Enhancement of peptide coupling reactions by 4-dimethylaminopyridine.  |  Wang, SS., et al. 1981. Int J Pept Protein Res. 18: 459-67. PMID: 7341528

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Dimethylaminopyridine, 10 g

sc-210031
10 g
$56.00