2-Chloropyrimidine-5-boronic acid pinacol ester

Base Information

• Chemical Name: 2-Chloropyrimidine-5-boronic acid pinacol ester
• CAS No.: 1003845-08-6
• Molecular Formula: C10H14BClN2O2
• Molecular Weight: 240.497
• Hs Code.: 2934999090
• Mol file: 1003845-08-6.mol

Synonyms:2-Chloropyrimidine-5-Boronic Acid Pinacol Ester;2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine;

Chemical Property of 2-Chloropyrimidine-5-boronic acid pinacol ester

Chemical Property:

• Melting Point: 65.0 to 69.0 °C
• Boiling Point: 369.1±15.0 °C(Predicted)
• PKA: -1.68±0.22(Predicted)
• PSA: 44.24000
• Density: 1.19±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 1.42920
• Storage Temp.: Refrigerated.

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloropyrimidine-5-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: 2-Chloropyrimidine-5-boronic acid pinacol ester finds versatile applications across various fields. In organic chemistry, it serves as a crucial building block for the synthesis of complex organic compounds, particularly in medicinal chemistry, where it can be used to create pharmaceuticals. This compound plays a significant role in drug discovery, enabling the development of novel medications by chemists and researchers. Additionally, it has applications in agrochemicals, aiding in the creation of pesticides and herbicides. In materials science, it contributes to the development of advanced materials with tailored properties, such as polymers and catalysts. Overall, 2-Chloropyrimidine-5-boronic acid pinacol ester is a valuable tool in the hands of chemists and scientists across multiple disciplines, driving innovation and scientific progress.

Technology Process of 2-Chloropyrimidine-5-boronic acid pinacol ester

There total 5 articles about 2-Chloropyrimidine-5-boronic acid pinacol ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (2-chloropyrimidin-5-yl)boronic acid (1003845-06-4) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1003845-08-6)

Guidance literature:

With magnesium sulfate; In toluene; at 20 ℃; for 15h;

Reference yield: 65.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 5-Bromo-2-chloropyrimidine (32779-36-5) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1003845-08-6)

Guidance literature:

5-Bromo-2-chloropyrimidine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 5h;

Reference yield: 63.0%

2-chloropyrimidine (1722-12-9,1195939-87-7) + bis(pinacol)diborane (73183-34-3) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (1003845-08-6)

Guidance literature:

bis(pinacol)diborane; With C₂₄H₂₈ClIrN₂O; In n-heptane; isopropyl alcohol; at 75 ℃; for 1h; Sealed tube; Inert atmosphere;

2-chloropyrimidine; In n-heptane; isopropyl alcohol; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04210

upstream raw materials:

2,3-dimethyl-2,3-butane diol

(2-chloropyrimidin-5-yl)boronic acid

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

5-Bromo-2-chloropyrimidine

Downstream raw materials:

C₂₃H₃₉BN₄O₄

2-chloro-5-(trifluoromethyl)pyrimidine

5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine

1-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl]piperidin-4-one

Refernces

• 1、 -. "Nitrogen-containing heterocyclic derivative and organic electroluminescent device thereof". Paragraph 0154-0157; 0173-0174. . Retrieved 2021/11/26.
• 2、 -. "Preparation of 2-amino-pyrimidine-5-boronic acid frequency that ester method". Paragraph 0018. . Retrieved 2017/01/02.