von Braun reaction

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The von Braun reaction is an organic reaction in which a tertiary amine reacts with cyanogen bromide to an organocyanamide.[1] An example is the reaction of dimethyl-α-naphthylamine:[2]

von Braun reaction

The reaction mechanism consists of two nucleophilic substitutions: the amine is the first nucleophile displacing the bromine atom which then acts as the second nucleophile.[3][4]

See also[edit]


  1. ^ von Braun, Heider, and Muller, Ber., 51, 281 (1918).
  2. ^ Organic Syntheses, Coll. Vol. 3, p.608 (1955); Vol. 27, p.56 (1947). http://www.orgsynth.org/orgsyn/pdfs/CV3P0608.pdf
  3. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7 
  4. ^ Hageman, H. A. Org. React. 1953, 7.