55304-83-1

Basic information

• Product Name: 2,6-Dibromopyridine-3-carboxaldehyde
• Synonyms: 2,6-Dibromopyridine-3-carboxaldehyde;2,6-Dibromo-3-pyridinecarbaldehyde;2,6-DibroMopyridine-3-car...;2,6-DibroMo-pyridine-3-carbaldehyde;2,6-dibroMonicotinaldehyde;2,6-Dibromo-3-pyridinecarboxaldehyde;2,6-Dibromo-3-formylpyridine
• CAS NO: 55304-83-1
• Molecular Formula: C₆H₃Br₂NO
• Molecular Weight: 264.90212
• Mol File: 55304-83-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 331.6 °C at 760 mmHg
• Flash Point: 154.3 °C
• Appearance: /
• Density: 2.09 g/cm³
• Vapor Pressure: 0.000154mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2,6-Dibromopyridine-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromopyridine-3-carboxaldehyde(55304-83-1)
• EPA Substance Registry System: 2,6-Dibromopyridine-3-carboxaldehyde(55304-83-1)

Safety Data

• Hazardous Substances Data: 55304-83-1(Hazardous Substances Data)

Usage

General Description

2,6-Dibromopyridine-3-carboxaldehyde is a chemical compound with the molecular formula C7H4Br2NO. It is a brominated derivative of pyridine-3-carboxaldehyde and is used in various chemical reactions and synthesis processes. 2,6-Dibromopyridine-3-carboxaldehyde is primarily used as a building block in the production of pharmaceuticals and agrochemicals. It is also used in the manufacturing of dyes and in the field of materials science. 2,6-Dibromopyridine-3-carboxaldehyde is a highly reactive compound and should be handled with care in a controlled laboratory environment.

InChI:InChI=1/C6H3Br2NO/c7-5-2-1-4(3-10)6(8)9-5/h1-3H

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 55304-85-3 2,6-dibromonicotinic acid 

Relevant articles and documents

Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction

An efficient synthesis of a structurally unique, novel M3 antagonist 1 is described. Compound 1 is conveniently disconnected retrosynthetically at the amide bond to reveal the acid portion 2 and the amine fragment 3. The synthesis of key intermediate 2 is highlighted by a ZnCl2-MAEP complex 19 catalyzed diastereoselective Michael reaction of dioxolane 7 with 2-cyclopenten-1-one (5) to establish the contiguous quaternary-tertiary chiral centers and a subsequent geminal difluorination of ketone 17 using Deoxofluor in the presence of catalytic BF3·OEt2. The synthesis of the amine moiety 3 is highlighted by the discovery of a novel n-Bu3MgLi magnesium-halogen exchange reaction for selective functionalization of 2,6-dibromopyridine. This new and practical metalation protocol obviated cryogenic conditions and upon quenching with DMF gave 6-bromo-2-formylpyridine (26) in excellent yield. Further transformations afforded the amine fragment 3 via reductive amination with 35, Pd-catalyzed aromatic amination, and deprotection. Finally, the highly convergent synthesis of 1 was accomplished by coupling of the two fragments. This synthesis has been used to prepare multi-kilogram quantities of the bulk drug.