21190-88-5

Basic information

• Product Name: 6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: Ethyl 6-bromopicolinate, 2-Bromo-6-(ethoxycarbonyl)pyridine;ETHYL 6-BROMOPYRIDINE-2-CARBOXYLATE;ETHYL-6-BROMO-2-PYRIDINECARBOXYLATE;6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER;6-BROMOPYRIDINE-2-ETHYL CARBOXYLATE;RARECHEM AL BI 0899;Ethyl 6-bromo-2-piperidinecarboxylate;ETHYL 6-BROMOPICOLINATE
• CAS NO: 21190-88-5
• Molecular Formula: C₈H₈BrNO₂
• Molecular Weight: 230.06
• EINECS: 1312995-182-4
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridine Series;NULL;Heterocycle-Pyridine series
• Mol File: 21190-88-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 41-42°C
• Boiling Point: 302.7 °C at 760 mmHg
• Flash Point: 136.9 °C
• Appearance: /
• Density: 1.501 g/cm³
• Vapor Pressure: 0.000973mmHg at 25°C
• Refractive Index: 1.544
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -0.89±0.10(Predicted)
• CAS DataBase Reference: 6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER(21190-88-5)
• EPA Substance Registry System: 6-BROMOPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER(21190-88-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 21190-88-5(Hazardous Substances Data)

Usage

Uses

ethyl 6-bromopicolinate is a model compound for the preliminary screening of dimerization reaction.

Preparation

Ethyl 6-bromopicolinate was prepared by monolithiation of 2,6-dibromopyridine followed by a reaction with ethyl formate and subsequently by a reaction with iodine in ethanol (Scheme 57). This three-step procedure furnished the required ethyl 6-bromopicolinate in 45% yield.Synthesis of Ethyl 6-bromopicolinate

InChI:InChI=1/C8H8BrNO2/c1-2-12-8(11)6-4-3-5-7(9)10-6/h3-5H,2H2,1H3

Upstream product

• 626-05-1 2,6-Dibromopyridine 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 109-94-4 formic acid ethyl ester 
• 21190-87-4 6-bromo-pyridine-2-carboxylic acid 
• 5315-25-3 2-bromo-6-methylpyridine 
• 1824-81-3 2-Amino-6-methylpyridine 

Downstream Products

• 855300-98-0 6-(2-chloro-phenyl)-pyridine-2-carboxylic acid ethyl ester 
• 850897-40-4 ethyl 6-(2-{5-chloro-2-[(phenylmethyl)oxy]phenyl}-1-cyclohexen-1-yl)-2-pyridinecarboxylate 
• 1258269-05-4 C₁₅H₁₂F₃NO₃ 
• 1449292-75-4 2-[1-(phenylimino)ethyl]-6-(3,5-dimethylpyrazol-1-yl)pyridine 
• 1449292-76-5 2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-(3,5-dimethylpyrazol-1-yl)pyridine 
• 1190071-25-0 (2,6-diisopropylphenyl)-{1-[6-(3,5-dimethyl-pyrazol-1-yl)pyridin-2-yl]ethylidene} amine 
• 1449292-77-6 2-[1-(2,6-diisopropylphenylimino)ethyl]-6-(3,5-diisopropylpyrazol-1-yl)pyridine 
• 1449292-82-3 2-[1-(phenylimino)ethyl]-6-(3,5-dimethylpyrazol-1-yl)pyridine cobaltdichloride 
• 1449292-83-4 2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-(3,5-dimethylpyrazol-1-yl)pyridine cobaltdichloride 
• 1449292-85-6 2-[1-(2,6-diisopropylphenylimino)ethyl]-6-(3,5-diisopropylpyrazol-1-yl)pyridine cobaltdichloride 
• 1449292-70-9 ethyl 6-(3,5-diphenylpyrazol-1-yl)pyridine-2-carboxylate 
• 1204747-45-4 C₂₂H₁₇N₃O₂ 
• 89465-52-1 6-Hydrazino-picolinsaeure-hydrazid 

Relevant articles and documents

A convenient synthetic route to polypyridine-esters by palladium- promoted carboalkoxylation

Pyridine and oligopyridines bearing halide or triflate groups react smoothly with CO (1 atm) and n-butanol in the presence of a tertiary amine and a catalytic amount of bis(triphenylphosphine)palladium dichloride to afford the corresponding esters. When ethanol and a disubstituted substrate are used under milder conditions, selective mono-carboalkoxylation occurs. Amidation is effected using a primary amine as nucleophile.

Facile synthesis of polypyridine esters: A route to functionalized aldehydes

A wide range of ester-substituted oligopyridines, based on pyridine, 1,8-naphthyridine, 1,10-phenanthroline, 2,2'-bipyridine, and 2,2':6',6-terpyridine units, has been synthesized and fully characterized. The principal reaction involves the palladium(0)-catalyzed carboalkoxylation of the bromo-, chloro- or triflate-substituted pyridine unit with carbon monoxide in the presence of a primary alcohol as nucleophile and a tertiary amine as base. Monofunctionalization of disubstituted compounds is realized by reaction in ethanol under mild conditions (70 °C, 1 atm CO). Stepwise reduction of selected esters with sodium borohydride, followed by Swern oxidation, affords the corresponding carbaldehydes in good yield. Several products are reported for the first time. The synthetic methods reported herein represent a valuable approach to the large-scale preparation of ester-functionalized oligopyridines that can be subsequently transformed to the corresponding alcohols or acids. These procedures also provide a practical methodology to the rational design of ligands bearing different kinds of functionalities.

Structure-activity relationship studies for the development of inhibitors of murine adipose triglyceride lipase (ATGL)

High serum fatty acid (FA) levels are causally linked to the development of insulin resistance, which eventually progresses to type 2 diabetes and non-alcoholic fatty liver disease (NAFLD) generalized in the term metabolic syndrome. Adipose triglyceride lipase (ATGL) is the initial enzyme in the hydrolysis of intracellular triacylglycerol (TG) stores, liberating fatty acids that are released from adipocytes into the circulation. Hence, ATGL-specific inhibitors have the potential to lower circulating FA concentrations, and counteract the development of insulin resistance and NAFLD. In this article, we report about structure–activity relationship (SAR) studies of small molecule inhibitors of murine ATGL which led to the development of Atglistatin. Atglistatin is a specific inhibitor of murine ATGL, which has proven useful for the validation of ATGL as a potential drug target.

Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium

Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with methanol, molecular iodine, and K2CO3. Some aromatics could be also converted into the corresponding aromatic esters in good yields by the treatment with n-BuLi, and subsequently with ethyl formate or DMF, followed by the reaction with molecular iodine and K2CO3. The present reactions offer a novel route for the transition-metal-free, carbon-monoxide-free, and therefore environmentally benign one-pot conversion of aromatic bromides and aromatics into aromatic esters.