100366-66-3

Basic information

• Product Name: 6,6-DIBROMO-2,2:6,2-TERPYRIDINE
• Synonyms: 6,6``-DibroMo-2,2`:6`,2``-terpyridine,90%;6,6''-Dibromo-2,2':6',2''-terpyridine 90%;2,6-bis(6-bromopyridin-2-yl)pyridine;6,6''-DIBROMO-2,2':6',2''-TERPYRIDINE;6,6-DIBROMO-2,2:6,2-TERPYRIDINE
• CAS NO: 100366-66-3
• Molecular Formula: C₁₅H₉Br₂N₃
• Molecular Weight: 391.06
• Product Categories: C9 to C46Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines
• Mol File: 100366-66-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 257-263 °C(lit.)
• Boiling Point: 473 °C at 760 mmHg
• Flash Point: 239.9 °C
• Appearance: /
• Density: 1.685 g/cm³
• PKA: 0.17±0.41(Predicted)
• CAS DataBase Reference: 6,6-DIBROMO-2,2:6,2-TERPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,6-DIBROMO-2,2:6,2-TERPYRIDINE(100366-66-3)
• EPA Substance Registry System: 6,6-DIBROMO-2,2:6,2-TERPYRIDINE(100366-66-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 100366-66-3(Hazardous Substances Data)

Usage

Uses

6,6′′-Dibromo-2,2′:6′,2′′-terpyridine may be used in the synthesis of a novel disubstituted terpyridine ligand.

General Description

6,6′′-Dibromo-2,2′:6′,2′′-terpyridine is a substituted terpyridine that can be synthesized from 2,6-dibromopyridine.

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 10495-73-5 2-bromo-6-(pyridin-2-yl)pyridine 
• 366-18-7 [2,2]bipyridinyl 
• 109-04-6 2-bromo-pyridine 
• 49669-13-8 1-(6-bromopyridin-2-yl)-ethanone 
• 37709-55-0 1,5-bis(6-bromo-2-pyridyl)-1,5-dioxopentane 
• 100366-65-2 N,N-dimethyl<3-(6'-bromo-2'-pyridyl)-3-oxopropyl>ammonium chloride 
• 84488-18-6 1-(2-(6-bromopyridin-2-yl)-2-oxoethyl)pyridinium iodide 
• 1148-79-4 2,2':6,2''-terpyridine 

Downstream Products

• 85575-96-8 6,6''-diphenyl 2,2',6',2''-terpyridine 
• 1234799-68-8 6,6''-bis(2-methylphenyl)-2,2':6',2''-terpyridine 
• 938470-08-7 C₄₁H₂₇N₇O₂ 
• 162151-66-8 6,6-Bis(2-methoxyphenyl)-2,2':6',2-terpyridine 
• 129077-54-9 2,2':6',2''-terpyridine-6,6''-dicarbonitrile 

Relevant articles and documents

The Preparation and Co-ordination Chemistry of 2,2':6',2"-Terpyridine Macrocycles. Part 5. Unsubstituted Fifteen-membered-ring Macrocycles containing 2,2':6',2"-Terpyridine

The preparation of a simple unsubstituted quinquedentate macrocycle incorporating a 2,2':6',2"-terpyridine moiety by a transient template reaction is described.The cobalt(II), nickel(II), copper(II), and zinc(II) complexes of the ligand are described, as is the oxidation-reduction chemistry of these compounds.E.s.r. studies indicate that pentagonal-bipyramidal complexes, with solvent molecules occupying the axial sites, are formed.

Synthesis of Halogenated Terpyridines and Incorporation of the Terpyridine Nucleus into a Polyetheral Macrocycle

Two synthetic approaches to haloterpyridines are herein described.The first method involved direct halogenation of terpyridine N-oxides with POCl3 to generate a mixture of polyhalogenated terpyridines.A more efficient approach to 6,6''-dibromo-2,2':6',2''-terpyridine utilized the Kroehnke synthesis to form the terpyridine moiety from appropriately halosubstituted precursors.Direct nucleophilic substitution on terpyridine was found to give low yields of macrocyclic products; however, if 1,5-bis(6-bromo-2-pyridyl)-1,5-dioxopentane was employed, macrocyclization afforded improved yields of the desired terpyridines.

Synthesis of some 2,2′:6′,2″-terpyridines disubstituted in positions 6 and 6″ with head-to-tail oriented amino acids and dipeptides: A simple entry to a reversible inducer of folding in amino acid sequences

The 2,2′:6′,2″-terpyridine scaffold has been identified as a conformationally discrete structural element potentially capable of inducing reversible folding in substituents, attached through suitable spacers to its 6,6″-positions, by metal complexation/de