Pyridine-4-boronic acid

Base Information

• Chemical Name: Pyridine-4-boronic acid
• CAS No.: 1692-15-5
• Molecular Formula: C5H6BNO2
• Molecular Weight: 122.919
• Hs Code.: 29339900
• European Community (EC) Number: 671-679-4
• DSSTox Substance ID: DTXSID90370269
• Nikkaji Number: J1.107.939C
• Wikidata: Q72503785
• Mol file: 1692-15-5.mol

Synonyms:4-pyridineboronic acid;pyridine-4-boronic acid

Chemical Property of Pyridine-4-boronic acid

Chemical Property:

• Appearance/Colour: light orange granular powder
• Vapor Pressure: 6.52E-05mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Boiling Point: 308.782 °C at 760 mmHg
• PKA: 7.59±0.10(Predicted)
• Flash Point: 140.547 °C
• PSA: 53.35000
• Density: 1.23 g/cm³
• LogP: -1.23860
• Storage Temp.: 0-6°C
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 123.0491586
• Heavy Atom Count: 9
• Complexity: 83

Purity/Quality:

99% ^*data from raw suppliers

4-Pyridinylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi,C,F
• Hazard Codes: Xn,Xi,C,F
• Statements: 36/37/38-22-34-11
• Safety Statements: 22-24/25-36/37/39-26-45-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC=NC=C1)(O)O
• Uses: Pyridine-4-boronic acid can be used as a candidate for Suzuki-Miyaura coupling reaction. Especially, as a N-containing building blocks, pyridine-4-boronic acid was employed to construct some heterocyclic compounds with superior biological activities. suzuki reaction Reagent used forPalladium-catalyzed Suzuki-Miyaura coupling reactions Ligand-free palladium-catalyzed Suzuki coupling reaction under microwave irradation Reagent used in Preparation of HIV-1 protease inhibitors Potential cancer threapeutics, such as PDK1 and protein kinase CK2 inhibitors Boronic acid derivatives and their binding affinities with diols.
• Description: Pyridine-4-boronic acid is a kind of boronic acid derivative. It is useful building blocks in crystal engineering. It can also be used as a catalyst to act as a dehydrative condensation agent to synthesize amides using carboxylic acid and amines as raw materials. Its derivative, polystyrene-bound 4-pyridineboronic acid, is a useful catalyst for amidation reaction and esterification of alpha-hydrocarboxylic acids.

Technology Process of Pyridine-4-boronic acid

There total 9 articles about Pyridine-4-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: 74.0%

4-bromopyridin (1120-87-2) → 4-pyridylboronic acid (1692-15-5)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1021/acs.joc.7b01765

Reference yield: 65.0%

4-bromopyridin (1120-87-2) + Trimethyl borate (121-43-7,63156-11-6) + water (7732-18-5) → 4-pyridylboronic acid (1692-15-5)

Guidance literature:

4-bromopyridin; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

water; With hydrogenchloride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

Reference yield: 60.0%

4-bromopyridine hydrochloride (19524-06-2) → 4-pyridylboronic acid (1692-15-5)

Guidance literature:

4-bromopyridine hydrochloride; With n-butyllithium; In hexanes; toluene; at -60 - -50 ℃;

With Triisopropyl borate; In tetrahydrofuran; hexanes; toluene; at -50 - -15 ℃;

With hydrogenchloride; In tetrahydrofuran; hexanes; water; toluene;

DOI:10.1016/j.bmc.2010.06.025

upstream raw materials:

4-bromopyridin

Triisopropyl borate

4-bromopyridine hydrochloride

sodium carbonate

Downstream raw materials:

methyl <3,4'-bipyridine>-5-carboxylate

4-(pyridin-4-yl)aniline

4'-(4-(pyridin-4-yl)phenyl)-[2,2':6',2]terpyridine

5-Phenyl-1H-tetrazole

Refernces

• 1、 Ohmura, Toshimichi,Morimasa, Yohei,Suginome, Michinori. "Organocatalytic diboration involving "reductive addition" of a boron-boron-bond to 4,4′-bipyridine". . p. 2852 - 2855. Retrieved 2015.
• 2、 -. "Synthetic process for pyridine-4-boronic acid". Paragraph 0017-0028. . Retrieved 2018/04/21.
• 3、 -. "Based on 4,4 the structure of the- [...][...] 9, the 9-bit [...] a main body material and its application (by machine translation)". Paragraph 0064; 0065. . Retrieved 2016/10/10.