3,5-Dibromopyridine

Chemical properties

Light-Yellow Solid

The Uses of 3,5-Dibromopyridine

3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3?-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.

Definition

ChEBI: 3,5-dibromopyridine is a dibromopyridine.

What are the applications of Application

3,5-Dibromopyridine (3,5-DBP) can be used for:
(1) Spectroscopic analysis: FTIR and FT Raman spectra in the solid phase of 3,5-DBP and 3,5- dichloro-2,4,6-trifluoropyridine (3,5-DCTFP) were recorded in the regions of 4000-400 cm-1 and 3500-100 cm-1, respectively^[1].
(2) Chemical reactions: 3,5-DBP can be reacted with phenyl isocyanate. chemoselective Staudinger-Phosphite reaction of 2,4,6-triazido-3,5-dibromopyridine azide moiety^[2-3].
(3) Organic synthesis: Using 3,5-dibromopyridine as raw material can be used to prepare 3-acetamido-5-ethoxypyridine^[4].

General Description

3,5-Dibromopyridine undergoes lithiation with lithium diisopropylamide and on subsequent reaction with electrophiles yields 4-alkyl-3,5-dibromopyridines.

References

[1] V. KRISHNAKUMAR  R. J X. Density functional theory calculations and vibrational spectra of 3,5-dibromopyridine and 3,5-dichloro-2,4,6-trifluoropyridine[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2005. DOI:10.1016/j.saa.2004.03.038.
[2] SERGEI V. CHAPYSHEV Igor K Y Alexander V Chernyak. Chemoselective Staudinger-Phosphite Reaction on the Azido Groups of 2,4,6-Triazido-3,5-dibromopyridine[J]. Journal of Heterocyclic Chemistry, 2015. DOI:10.1002/jhet.2339.
[3] T. HISANO M. I Toshikazu Matsuoka. THE REACTION OF 3,5-DIBROMOPYRIDINE N-OXIDE WITH PHENYL ISOCYANATE[J]. ChemInform, 1974. DOI:10.1002/CHIN.197448358.
[4] H. J. HERTOG  A. V D L A W M Falter. The reactivity of bromine atoms in brominated pyridines. The preparation of 3-acetylamino-5-ethoxypyridine from 3,5-dibromopyridine?[J]. Recueil des Travaux Chimiques des Pays-Bas, 1948. DOI:10.1002/RECL.19480670507.