90050-70-7

Basic information

• Product Name: Ethyl 2,6-dibromopyridine-4-carboxylate
• Synonyms: Ethyl 2,6-dibromopyridine-4-carboxylate;4-Pyridinecarboxylic acid, 2,6-dibroMo-, ethyl ester;Ethyl 2,6-dibromoisonicotinate
• CAS NO: 90050-70-7
• Molecular Formula: C₈H₇Br₂NO₂
• Molecular Weight: 308.95
• Mol File: 90050-70-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 333.5°Cat760mmHg
• Flash Point: 155.5°C
• Appearance: /
• Density: 1.823g/cm³
• Vapor Pressure: 0.000136mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: Ethyl 2,6-dibromopyridine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2,6-dibromopyridine-4-carboxylate(90050-70-7)
• EPA Substance Registry System: Ethyl 2,6-dibromopyridine-4-carboxylate(90050-70-7)

Safety Data

• Hazardous Substances Data: 90050-70-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H7Br2NO2/c1-2-13-8(12)5-3-6(9)11-7(10)4-5/h3-4H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 99-11-6 citrazinic acid 
• 2016-99-1 2,6-dibromoisonicotinic acid 

Downstream Products

• 485815-52-9 ethyl 6-bromo-6'-methyl-4-(2,2'-bipyridine)carboxylate 
• 1148-79-4 2,2':6,2''-terpyridine 
• 316800-46-1 2,6-Dibromopyridine-4-carbaldehyde 
• 108295-45-0 4′-formyl-2,2′:6′2″-terpyridine 
• 372520-85-9 ethyl 6,6''-bis-(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate 
• 372520-84-8 6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester 
• 223463-02-3 2,6-dibromo-4-(hydroxymethyl)pyridine 
• 294211-85-1 5,5''-Dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid 
• 294211-86-2 5,5''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester 
• 148332-36-9 [2,2′:6′,2′′-terpyridine]-4′-carboxylic acid 
• 148332-31-4 4’-ethoxycarbonyl-2,2’:6’,2’’-terpyridine 
• 294211-87-3 6-Bromo-2,2'-bipyridine-4-carboxylic acid 
• 294211-88-4 Ethyl 6-bromo-2,2'-bipyridine-4-carboxylate 

Relevant articles and documents

Bi-stable spin-crossover in charge-neutral [Fe(R-ptp)2] (ptp = 2-(1: H -pyrazol-1-yl)-6-(1 H -tetrazol-5-yl)pyridine) complexes

Bi-stable charge-neutral iron(ii) spin-crossover (SCO) complexes are a class of switchable molecular materials proposed for molecule-based switching and memory applications. In this study, we report on the SCO behavior of a series of iron(ii) complexes composed of rationally designed 2-(1H-pyrazol-1-yl)-6-(1H-tetrazol-5-yl)pyridine (ptp) ligands. The powder forms of [Fe2+(R-ptp-)2]0 complexes tethered with less-bulky substituents - R = H (1), R = CH2OH (2), and R = COOCH3 (3; previously reported) - at the 4-position of the pyridine ring of the ptp skeleton showed abrupt and hysteretic SCO at or above room temperature (RT), whereas complex 5 featuring a bulky pyrene substituent showed incomplete and gradual SCO behavior. The role of intermolecular interactions, lattice solvent, and electronic nature of the chemical substituents (R) in tuning the SCO of the complexes is elucidated.

Synthesis of 2,6-di(pyrazol-1-yl)-4-bromomethylpyridine, and its conversion to other 2,6-di(pyrazol-1-yl)pyridines substituted at the pyridine ring

Two routes to 2,6-di(pyrazol-1-yl)-4-hydroxymethylpyridine (1) from 2,6-dihydroxy-isonicotinic acid, in four and six steps, are reported. Reaction of 1 with 48% HBr yields 2,6-di(pyrazol-1-yl)-4-bromomethylpyridine (2), which is a powerful precursor to a range of new tridentate ligands for transition metals functionalised at the pyridine ring. As a proof of principle, we describe the further elaboration of 2 to give two 2,6-di(pyrazol-1-yl)pyridines bearing nucleobase substituents, and the back-to-back ligand 1,2-bis[2,6-di(pyrazol-1-yl)pyrid-4-yl]ethane. Crystal structures of two of these new derivatives are presented.

Carboxylate derivatives of oligopyridines

The key compound ethyl 2,6-dibromopyridine-4-carboxylate was prepared in two steps starting from the commercially available citrazinic acid. By using the Stille coupling reaction ethyl 2,6- dibromopyridine-4-carboxylate was converted to 2,2'-bipyridines, 2,2':6',2''-terpyridines and 2,2':6',2'':6'',2''':6''',2''''- quinquepyridines which bear a carboxylate functional group directly attached to the central pyridine ring.