452972-13-3

Basic information

• Product Name: 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE
• Synonyms: 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE;3-BROMOPYRIDINE-5-BORONIC ACID PINACOL ESTER;5-BROMO-3-PYRIDINEBORONIC ACID PINACOL &;5-BROMOPYRIDINE-3-BORONIC ACID, PINACOL ESTER;5-Bromo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;5-Bromo-3-pyridineboronic acid pinacol ester;3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-y98%
• CAS NO: 452972-13-3
• Molecular Formula: C₁₁H₁₅BBrNO₂
• Molecular Weight: 283.96
• Mol File: 452972-13-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 63.4-63.8°C
• Boiling Point: 341.4 °C at 760 mmHg
• Flash Point: 160.3 °C
• Appearance: /
• Density: 1.34
• Vapor Pressure: 0.000159mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.86±0.22(Predicted)
• CAS DataBase Reference: 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE(452972-13-3)
• EPA Substance Registry System: 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE(452972-13-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 452972-13-3(Hazardous Substances Data)

Usage

General Description

3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE is a chemical compound that contains a pyridine ring substituted with a bromine atom and a boron-containing group. The boron-containing group, specifically a dioxaborolane, is tetramethylated and attached to the pyridine ring, making it a unique and potentially valuable building block for organic synthesis. The compound's structure suggests that it could be used in the creation of various pharmaceuticals, agrochemicals, or other organic compounds where a boron-containing pyridine derivative is desired. Additionally, boron-containing compounds are known for their potential use in catalysis and as fluorescent probes, so 3-BROMO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE may have applications in these areas as well.

InChI:InChI=1/C11H15BBrNO2/c1-10(2)11(3,4)16-12(15-10)8-5-9(13)7-14-6-8/h5-7H,1-4H3

Upstream product

• 626-55-1 3-Bromopyridine 
• 73183-34-3 bis(pinacol)diborane 
• 625-92-3 3,5-dibromopyridine 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 233770-01-9 3-bromo-5-iodopyridine 

Downstream Products

• 74115-13-2 5-bromopyridine-3-ol 
• 15862-30-3 3-bromo-5-nitro-pyridine 
• 28232-66-8 3-bromo-5-(4-chlorophenoxy)pyridine 
• 452972-07-5 3-bromo-5-(4-methoxyphenyl)pyridine 

Relevant articles and documents

Design, synthesis and biological evaluation of 1H-indazole derivatives as novel ASK1 inhibitors

Apoptosis signal-regulating kinase 1 (ASK1, MAP3K5), a member of the mitogen-activated protein kinase (MAPK) signaling pathway, is involved in cell survival, differentiation, stress response, and apoptosis. ASK1 kinase inhibition has emerged as a promisin

Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics

A newly developed robust catalyst [Ir(COD)(Phen)Cl] (A) was used for the C-H borylation of three dozen aromatics and heteroaromatics with excellent yield and selectivity. Activation of the catalyst was identified by the use of catalytic amounts of water, alcohols, etc., when B2pin2 was used in noncoordinating solvents, while for THF catalytic use of HBpin was required. The results were on par with the in situ based expensive system [Ir(OMe)(COD)]2/dtbbpy or Me4Phen.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.