Cyano-4-(dimethylamino)pyridinium tetrafluoroborate

CAS 59016-56-7, Cat. No EN300-6731863
Reagent for cyanation

Cyano-4-(dimethylamino)pyridinium tetrafluoroborate

1-Cyano-4-(dimethylamino)pyridinium tetrafluoroborate is capable of selective cyanation of thiols. It is a bench-stable solid, soluble in most common organic solvents, both protic and aprotic. The reaction occurs with many nucleophiles but specifically prioritizes thiols in the presence of hydroxy or amino group[1], [2]. This reagent finds its uses in selective cyanation of the peptides, which is often completed without any problem and with good yield[2]. Also, this reagent is known to be used for cyanation of Grignard reagents[3].

Synonyms: Borate(1-), tetrafluoro-, 1-cyano-4-(dimethylamino)pyridinium (ZCI); Pyridinium, 1-cyano-4-(dimethylamino)-, tetrafluoroborate(1-) (9CI); 1-Cyano-4-dimethylammoniumpyridinium tetrafluoroborate; 1-Cyano-N,N-dimethyl-1,4-dihydropyridin-4-iminium; tetrafluoroboranuide

Selected publication

  1. A Novel Methodology for Assignment of Disulfide Bond Pairings in Proteins.

    Wu J.; Watson J. T. Protein Science 1997, 6 (2), 391–398. DOI: 10.1002/pro.5560060215

  2. 1-Cyano-4-Dimethylamino-Pyridinium Salts: New Water-Soluble Reagents for the Cyanylation of Protein Sulphydryl Groups.

    Wakselman M.; Guibé-Jampel E.; Raoult A.; Busse W. D. J. Chem. Soc. Chem. Commun. 1976, 1, 21–22. DOI: 10.1039/C39760000021

  3. Convenient Synthesis of Benzonitriles via Electrophilic Cyanation with N ‐Cyanobenzimidazole.

    Anbarasan P.; Neumann H.; Beller M. A Chemistry 2010, 16 (16), 4725–4728. DOI: 10.1002/chem.201000086