2-Bromopyridine-3-boronic acid

Base Information

• Chemical Name: 2-Bromopyridine-3-boronic acid
• CAS No.: 452972-08-6
• Molecular Formula: C₅H₅BBrNO₂
• Molecular Weight: 201.815
• Hs Code.: 29333990
• European Community (EC) Number: 670-326-1
• ChEMBL ID: CHEMBL3236606
• DSSTox Substance ID: DTXSID40476861
• Nikkaji Number: J1.702.369A
• Wikidata: Q72511850
• Mol file: 452972-08-6.mol

Synonyms:452972-08-6;2-BROMOPYRIDINE-3-BORONIC ACID;(2-bromopyridin-3-yl)boronic acid;2-bromo-3-pyridineboronic acid;2-bromopyridin-3-ylboronic acid;2-BROMOPYRIDINE-3-YLBORONIC ACID;MFCD04113805;2-Bromopyridine-3-boronic acid(contains varying amounts of Anhydride);2-BROMO-3-PYRIDYLBORONIC ACID;2-Bromopyridine-3-boronicacid;2-BROMOPYRIDIN-3-YL-3-BORONIC ACID;SCHEMBL1920925;CHEMBL3236606;DTXSID40476861;(2-bromopyridin-3-yl)boronicacid;(2-Bromo-3-pyridinyl)boronic acid;BCP05466;AKOS004119280;AB17846;CS-W015532;GS-6577;SY029992;2-bromopyridine-3-boronic acid, AldrichCPR;A7149;AM20051189;B5170;FT-0644698;EN300-1270607;J-508542;Z1269228665;2-Bromopyridine-3-boronic acid;2-Bromopyridine-3-boronic Acid (contains varying amounts of Anhydride)

Chemical Property of 2-Bromopyridine-3-boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132 °C(dec.)
• Refractive Index: 1.602
• Boiling Point: 374.311 °C at 760 mmHg
• PKA: 6.61±0.58(Predicted)
• Flash Point: 180.177 °C
• PSA: 53.35000
• Density: 1.78 g/cm³
• LogP: -0.47610
• Storage Temp.: Keep Cold
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 200.95967
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99% ^*data from raw suppliers

2-Bromopyridine-3-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: B(C1=C(N=CC=C1)Br)(O)O

Technology Process of 2-Bromopyridine-3-boronic acid

There total 6 articles about 2-Bromopyridine-3-boronic acid 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: 60.0%

2,3-dibromopyridine (13534-89-9) → 2-bromo-3-pyridylboronic acid (452972-08-6)

Guidance literature:

2,3-dibromopyridine; With n-butyllithium; In diethyl ether; at -78 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; at -78 - 20 ℃;

With sodium hydroxide; In diethyl ether; at 20 ℃;

DOI:10.1016/S0040-4020(02)00283-1

Reference yield: 45.0%

2-bromo-pyridine (109-04-6) → 2-bromo-3-pyridylboronic acid (452972-08-6)

Guidance literature:

2-bromo-pyridine; With lithium diisopropyl amide; In diethyl ether; at -60 ℃; for 0.75h;

With Triisopropyl borate; In diethyl ether; at -60 - 20 ℃;

With sodium hydroxide; In diethyl ether; at 20 ℃;

DOI:10.1016/S0040-4020(02)00283-1

Reference yield:

3-amino-2-bromopyridine (39856-58-1) → 2-bromo-3-pyridylboronic acid (452972-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HBr 47 percent; NaNO₂

1.2: CuBr

2.1: n-BuLi / diethyl ether / 1 h / -78 °C

2.2: B(Oi-Pr)3 / diethyl ether / -78 - 20 °C

2.3: 60 percent / aq. NaOH / diethyl ether / 20 °C

With n-butyllithium; hydrogen bromide; sodium nitrite; In diethyl ether;

DOI:10.1016/S0040-4020(02)00283-1

upstream raw materials:

2-bromo-pyridine

2,3-dibromopyridine

3-amino-2-bromopyridine

2-amino-3-nitropyridine