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

Description

Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate is a chemical compound derived from nicotinic acid, featuring a methoxy group and a boron-containing dioxaborolane functional group. It serves as a valuable intermediate in organic synthesis and pharmaceutical research, contributing to the development of complex molecules and new drugs.

Uses

Used in Pharmaceutical Research:
Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate is used as a building block for the production of various pharmaceuticals, leveraging its unique structure and properties to facilitate the synthesis of biologically active compounds.
Used in Organic Synthesis:
In the field of organic synthesis, Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate is employed as an important reagent, enabling the creation of complex molecules through its versatile functional groups.
Used in Drug Development:
Methyl2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate is utilized in the development of new drugs, where its boron-containing dioxaborolane group plays a crucial role in enhancing the synthesis and properties of potential therapeutic agents.

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.