2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Base Information

• Chemical Name: 2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
• CAS No.: 214360-62-0
• Molecular Formula: C11H15BBrNO2
• Molecular Weight: 283.961
• Hs Code.: 2934999090
• European Community (EC) Number: 681-888-2
• DSSTox Substance ID: DTXSID00383345
• Nikkaji Number: J2.329.219J
• Wikidata: Q72511857
• Mol file: 214360-62-0.mol

Synonyms:214360-62-0;2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;2-Bromopyridine-5-boronic acid pinacol ester;2-Bromo-5-pyridylboronic acid pinacol ester;6-Bromopyridine-3-boronic acid pinacol ester;MFCD03412794;2-Bromopyridine-5-boronic acid, pinacol ester;Pyridine, 2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL2099623;(6-BROMOPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;2-bromo-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;DTXSID00383345;MEGBELYYUPCOIQ-UHFFFAOYSA-N;BCP14071;AKOS004116431;AB14440;CS-W010032;DS-1500;AC-33503;SY032176;2-Bromo-5-pyridineboronic acid pinacol ester;AM20050945;FT-0611470;A25318;A25360;EN300-187911;J-014065;Z1741972826;2-(6-bromopyridin-3-yl)-4,4,5,5-tetramethyl-1,3-dioxaborolane;2-bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine;2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)pyridine;2-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, AldrichCPR;AKOS BRN-0197;2-Bromopyridine-5-boronic acid pinacolate;6-Bromopyridine-3-boronic Acid Pinacol Ester

Chemical Property of 2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Chemical Property:

• Vapor Pressure: 0.000126mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 345.1 °C at 760 mmHg
• PKA: 0.78±0.12(Predicted)
• Flash Point: 162.5 °C
• PSA: 31.35000
• Density: 1.34 g/cm³
• LogP: 2.14330
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 283.03792
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

99% ^*data from raw suppliers

2-Bromopyridine-5-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN=C(C=C2)Br

Technology Process of 2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

There total 8 articles about 2-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 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: 83.0%

2,5-dibromopyridine (624-28-2) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → 2-[(6-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (214360-62-0)

Guidance literature:

2,5-dibromopyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 3h;

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; at -78 - 20 ℃; for 12h; regioselective reaction;

DOI:10.1039/c4sc01025f

Reference yield: 79.0%

2,5-dibromopyridine (624-28-2) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 2-[(6-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (214360-62-0)

Guidance literature:

2,5-dibromopyridine; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 3h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In diethyl ether; hexane; at -78 - 20 ℃; for 16h;

DOI:10.1021/acs.inorgchem.0c00735

Reference yield: 78.0%

2,5-dibromopyridine (624-28-2) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-[(6-bromo)pyridin-3-yl]-4,4',5,5'-tetramethyl-1,3-dioxaborolane (214360-62-0)

Guidance literature:

2,5-dibromopyridine; With n-butyllithium; Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In diethyl ether;

DOI:10.1016/S0040-4020(02)00152-7

upstream raw materials:

2,5-dibromopyridine

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

2-bromo-5-iodo-pyridine

2-aminopyridine

Downstream raw materials:

2-bromo-5-phenyl-pyridine

(S)-1-(6-bromopyridin-3-yl)-1-phenylethanol