3,5-Dibromopyridine Chemical Properties

Melting point:

110-115 °C (lit.)

Boiling point:

222 °C

Density 

2.0383 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

pka

0.52±0.20(Predicted)

form 

Needle-Like Crystals

color 

White to light beige

Water Solubility 

Soluble in Chloroform and Methanol. Insoluble in water.

BRN 

108477

InChIKey

SOSPMXMEOFGPIM-UHFFFAOYSA-N

CAS DataBase Reference

625-92-3(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Dibromopyridine(625-92-3)

EPA Substance Registry System

3,5-Dibromopyridine (625-92-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

UN2811

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:3,5-Dibromopyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dibromopyridine Usage And Synthesis

Chemical Properties

Light-Yellow Solid

Uses

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.

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.

3,5-Dibromopyridine(625-92-3)Related Product Information

• 2-Chloro-3-cyanopyridine
• 2,2-Bis(bromomethyl)propane-1,3-diol
• 2,3-Dibromopropionic acid
• 2,5-DIBROMOPYRIDINE 2,5-DIBROMOPYRIDINE,2,5-DIBROMOPYRIDINE
• 1,3-Dibromo-5,5-dimethylhydantoin
• 1,2-Dibromopropane
• 3-Aminopyridine
• 2,4-DIBROMOPENTANE
• 2-PHENYL-1,3,2-DIOXABORINANE
• PeraMpanel
• PeraMpanel
• 6'-Methoxy-2,3'-bipyridine
• PeraMpanel
• PeraMpanel
• PeraMpanel
• 2-Cyanophenylboronic acid
• Phenylboronic acid
• 3,5-Dimethoxypyridine