1083168-93-7

Basic information

• Product Name: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate
• Synonyms: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate;2-Methoxy-3-(carbomethoxy)pyridine-5-boronic acid, pinacol ester;Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)
• CAS NO: 1083168-93-7
• Molecular Formula: C₁₄H₂₀BNO₅
• Molecular Weight: 293.1233
• Mol File: 1083168-93-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate(1083168-93-7)
• EPA Substance Registry System: Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate(1083168-93-7)

Safety Data

• Hazardous Substances Data: 1083168-93-7(Hazardous Substances Data)

Usage

General Description

Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate is a chemical compound that is commonly used in organic synthesis and pharmaceutical research. It is a derivative of nicotinic acid, also known as niacin, and is often employed as a building block in the production of various pharmaceuticals. Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate contains a methoxy group and a boron-containing dioxaborolane functional group, which makes it a valuable intermediate for the synthesis of complex molecules. Additionally, its unique structure and properties make it an important reagent in the development of new drugs and biologically active compounds.

Upstream product

• 67367-26-4 2-methoxynicotinic acid methyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 122433-41-4 methyl 5-bromo-2-methoxy-3-pyridinecarboxylate 

Relevant articles and documents

Exploiting C–H borylation for the multidirectional elaboration of 2-halopyridines

Regioselectively polysubstituted pyridines can be efficiently accessed from 2-halopyridines via a sequence involving C–H borylation, Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution chemistry.

Iridium-catalyzed C-H borylation of pyridines

The iridium-catalysed C-H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring. This journal is the Partner Organisations 2014.