947249-41-4

Basic information

• Product Name: 6-AMINOPYRAZINE-2-BORONIC ACID PINACOL ESTER
• Synonyms: 6-AMINOPYRAZINE-2-BORONIC ACID PINACOL ESTER;5-AMINOPYRAZINE-3-BORONIC ACID PINACOL ESTER;(5-AMinopyrazin-2-yl)boronic acid pinacol ester;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen (5-aminopyrazin-2-yl)boronate
• CAS NO: 947249-41-4
• Molecular Formula: C₁₀H₁₆BN₃O₂
• Molecular Weight: 221.06394
• Mol File: 947249-41-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 375.438 °C at 760 mmHg
• Flash Point: 180.859 °C
• Appearance: /
• Density: 1.138 g/cm³
• PKA: 3.23±0.10(Predicted)
• CAS DataBase Reference: 6-AMINOPYRAZINE-2-BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINOPYRAZINE-2-BORONIC ACID PINACOL ESTER(947249-41-4)
• EPA Substance Registry System: 6-AMINOPYRAZINE-2-BORONIC ACID PINACOL ESTER(947249-41-4)

Safety Data

• Hazardous Substances Data: 947249-41-4(Hazardous Substances Data)

Usage

General Description

6-Aminopyrazine-2-boronic acid pinacol ester is a chemical compound with the molecular formula C12H18B N3O3. It is commonly used in organic synthesis as a reagent for the construction of various pharmaceutical and agrochemical compounds. The pinacol ester moiety in its structure makes it a useful building block for cross-coupling reactions, and its boronic acid group enables it to participate in Suzuki-Miyaura coupling reactions. Additionally, it has been explored for its potential as a fluorescent probe in biological imaging applications due to its unique properties. Overall, 6-aminopyrazine-2-boronic acid pinacol ester is a versatile compound with a range of applications in both research and industry.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 59489-71-3 5-amino-2-bromopyrazine 

Downstream Products

• 1313026-84-4 5-(9-benzyl-2-chloro-9H-purin-6-yl)-pyrazin-2-yl-amine 

Relevant articles and documents

A Conformational Restriction Strategy for the Identification of a Highly Selective Pyrimido-pyrrolo-oxazine mTOR Inhibitor

The mechanistic target of rapamycin (mTOR) plays a pivotal role in growth and tumor progression and is an attractive target for cancer treatment. ATP-competitive mTOR kinase inhibitors (TORKi) have the potential to overcome limitations of rapamycin derivatives in a wide range of malignancies. Herein, we exploit a conformational restriction approach to explore a novel chemical space for the generation of TORKi. Structure-activity relationship (SAR) studies led to the identification of compound 12b with a ～450-fold selectivity for mTOR over class I PI3K isoforms. Pharmacokinetic studies in male Sprague Dawley rats highlighted a good exposure after oral dosing and a minimum brain penetration. CYP450 reactive phenotyping pointed out the high metabolic stability of 12b. These results identify the tricyclic pyrimido-pyrrolo-oxazine moiety as a novel scaffold for the development of highly selective mTOR inhibitors for cancer treatment.

Efficient synthesis of pyrazine boronic esters via palladium-catalyzed Miyaura borylation

A facile and efficient protocol for palladium-catalyzed Miyaura borylation reaction of chloropyrazines with B2pin2has been developed. A certain range of difficult-to-access pyrazine boronic esters can be easily prepared from the corresponding chloropyrazines in moderate to good yields.

Synthesis and in vitro and in vivo evaluation of phosphoinositide-3-kinase inhibitors

Phospoinositide-3-kinases (PI3K) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. A series of 2-morpholino, 4-substituted, 6-(3-hydroxyphenyl) pyrimidines have been reported as potent inh