5-Bromopyridine-3-boronic acid

Base Information

• Chemical Name: 5-Bromopyridine-3-boronic acid
• CAS No.: 452972-09-7
• Molecular Formula: C5H5BBrNO2
• Molecular Weight: 201.815
• Hs Code.: 2933399090
• European Community (EC) Number: 625-866-2
• DSSTox Substance ID: DTXSID00396798
• Nikkaji Number: J1.702.376D
• Wikidata: Q72511840
• Mol file: 452972-09-7.mol

Synonyms:452972-09-7;5-bromopyridine-3-boronic acid;(5-bromopyridin-3-yl)boronic acid;3-Bromopyridine-5-boronic acid;5-bromopyridin-3-ylboronic acid;3-bromo-5-pyridineboronic acid;3-bromopyridyl-5-boronic acid;BORONIC ACID, (5-BROMO-3-PYRIDINYL)-;MFCD02685634;5-Bromopyridine-3-boronicacid;(5-bromo-3-pyridyl)boronic acid;5-Bromo-3-pyridylboronic acid;SCHEMBL1479937;5-bromo-pyridine-3-boronic acid;3-Bromo-5-pyridine boronic acid;DTXSID00396798;(5-bromopyridin-3-yl)boronicacid;3-bromo-pyridin-5-ylboronic acid;ICCGFOKNFZWCTJ-UHFFFAOYSA-N;AMY11563;AKOS002663089;AB12651;GS-6279;5-Bromopyridine-3-boronic acid, >=95%;AC-27943;SY026619;(3-BROMOPYRIDIN-5-YL)BORONIC ACID;A7150;FT-0644699;EN300-251407;J-517202

Chemical Property of 5-Bromopyridine-3-boronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Melting Point: >300 ºC
• Refractive Index: 1.602
• Boiling Point: 351.5 ºC at 760 mmHg
• PKA: 5.91±0.10(Predicted)
• Flash Point: 166.4 ºC
• PSA: 53.35000
• Density: 1.78 g/cm³
• LogP: -0.47610
• Storage Temp.: Keep Cold
• 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

5-Bromopyridine-3-boronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CN=C1)Br)(O)O
• Uses: Reactant for preparation of:? ;Thienylpyridyl garlands via cross-coupling with heteroaryl halides1? ;Arenes via nickel-catalyzed cross-coupling with potassium aryl- and heteroaryl trifluoroborates2? ;Meso-substituted ABCD-type porphyrins by functionalization reactions3? ;Analogs of (acetylamino)(dimethylpyrazol)(pyridyl)pyrimidines as A2A adenosine receptor antagonists for the treatment of Parkinson′s disease4? ;5-hydroxy-1,3,2-dioxaborolan-4-ones boronate-amine complexes via heterocyclization with α-oxocarboxylic acids followed by subsequent complexation5&

Technology Process of 5-Bromopyridine-3-boronic acid

There total 3 articles about 5-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: 87.4%

3-bromo-5-fluoropyridine (407-20-5) → (5-bromopyridin-3-yl)boronic acid (452972-09-7)

Guidance literature:

3-bromo-5-fluoropyridine; With n-butyllithium; isopropoxyboronic acid; In tetrahydrofuran; at -90 - -80 ℃; for 2.5h;

With hydrogenchloride; water; In tetrahydrofuran; at -20 - 10 ℃; for 0.5h; pH=1 - 2;

Reference yield: 74.0%

3,5-dibromopyridine (625-92-3) → (5-bromopyridin-3-yl)boronic acid (452972-09-7)

Guidance literature:

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

With Triisopropyl borate; In diethyl ether; hexane; at -78 ℃; for 2h;

DOI:10.1055/s-2003-39158

Reference yield:

→ (5-bromopyridin-3-yl)boronic acid (452972-09-7)

Guidance literature:

upstream raw materials:

3,5-dibromopyridine

3-bromo-5-fluoropyridine

Downstream raw materials:

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

3-bromo-5-thiophen-3-yl-pyridine

3-bromo-5-thiophen-2-yl-pyridine

C₁₆H₁₀Br₂N₂