5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile
• CAS No.: 402718-29-0
• Molecular Formula: C12H15 B N2 O2
• Molecular Weight: 230.074
• Hs Code.: 2934999090
• European Community (EC) Number: 833-838-8
• DSSTox Substance ID: DTXSID20585960
• Wikidata: Q72459085
• Mol file: 402718-29-0.mol

Synonyms:402718-29-0;3-CYANOPYRIDINE-5-BORONIC ACID PINACOL ESTER;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile?;MFCD07780755;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-Pyridinecarbonitrile;3-Cyano-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine;3-Pyridinecarbonitrile, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;SCHEMBL137719;DTXSID20585960;BOIKCRIMIQAFQJ-UHFFFAOYSA-N;2-Pyrrolidinone,3-amino-1-hydroxy-;AC1997;3-CYANO-5-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE;AKOS016003071;AB42552;DS-16249;SY024859;AM20051161;CS-0041845;T3514;A25366;EN300-318545;(5-Cyanopyridin-3-yl)boronic acid pinacol ester;J-516199;3-Cyanopyridine-5-boronic acid pinacol ester, AldrichCPR;Z1391882724;2-(5-Cyano-3-pyridyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinonitrile;5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile;Nicotinonitrile-5-boronic acid pinacol ester

Chemical Property of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 122-124℃
• Boiling Point: 352.638ºC at 760 mmHg
• Flash Point: 167.07ºC
• PSA: 86.37000
• Density: 1.107g/cm3
• LogP: 0.20688
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 230.1226579
• Heavy Atom Count: 17
• Complexity: 332

Purity/Quality:

≥99% ^*data from raw suppliers

3-Cyanopyridine-5-boronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CN=C2)C#N

Technology Process of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile

There total 3 articles about 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile 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: 98.0%

5-bromopyridine-3-carbonitrile (35590-37-5) + bis(pinacol)diborane (73183-34-3) → 3-cyanopyridine-5-boronic acid pinacol ester (402718-29-0)

Guidance literature:

With potassium acetate; palladium dichloride; In dichloromethane; dimethyl sulfoxide; at 90 ℃; for 6h;

DOI:10.1021/jm400508e

Reference yield:

pyridine-3-carbonitrile (100-54-9,121697-66-3,1232169-17-3,68271-95-4) + bis(pinacol)diborane (73183-34-3) → 3-cyanopyridine-5-boronic acid pinacol ester (402718-29-0)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 80 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.9b03296

Reference yield:

→ 3-cyanopyridine-5-boronic acid pinacol ester (402718-29-0)

Guidance literature:

upstream raw materials:

5-bromopyridine-3-carbonitrile

bis(pinacol)diborane

pyridine-3-carbonitrile

Downstream raw materials:

5-[6-(4-methanesulfonyl-phenyl)-2-methyl-imidazo[1,2-b]pyridazin-3-yl]-nicotinonitrile

5-(4-(7'-methoxy-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]-1-ylcarbonyl)phenyl)nicotinonitrile hydrochloride

5-(3-(4-amino-2-(4-methoxyphenyl)-5-methyl-2H-imidazol-2-yl)phenyl)nicotinonitrile

5'-(5-cyano-pyridin-3-yl)-3'-(4-methoxy-phenoxy)-2,3,5,6-tetrahydro-[1,2]bipyrazinyl-4-carboxylic acid tert-butyl ester