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

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
• CAS No.: 878194-93-5
• Molecular Formula: C12H15BN2O2
• Molecular Weight: 230.074
• Hs Code.: 2934999090
• European Community (EC) Number: 678-954-8
• DSSTox Substance ID: DTXSID50580549
• Nikkaji Number: J2.402.418K
• Wikidata: Q72459061
• Mol file: 878194-93-5.mol

Synonyms:878194-93-5;2-Cyanopyridine-3-boronic acid pinacol ester;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile;2-Cyanopyridine-3-boronic acid, pinacol ester;MFCD08458477;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carbonitrile;2-CYANO-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)PYRIDINE;2-Pyridinecarbonitrile, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;(2-CYANOPYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;SCHEMBL10060676;DTXSID50580549;AKOS015950047;BS-2127;MB06242;s10013;EN300-101523;Z1346101319

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

Chemical Property:

• Vapor Pressure: 4.56E-06mmHg at 25°C
• Melting Point: 58-61℃
• Refractive Index: 1.506
• Boiling Point: 382.9 °C at 760 mmHg
• PKA: -0.33±0.12(Predicted)
• Flash Point: 185.4 °C
• PSA: 55.14000
• Density: 1.1 g/cm³
• LogP: 1.25248
• 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:

97% ^*data from raw suppliers

2-Cyanopyridine-3-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=C(N=CC=C2)C#N
• Uses: A pyridylborane derivative evaluated for its kinase inhibitory activity. Also used in immunodiagnostics. Used as intermediate. As syntheses material intermediates.

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

There total 4 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile 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: 82.0%

(2-cyanopyridin-3-yl)boronic acid (874290-88-7) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine-2-carbonitrile (878194-93-5)

Guidance literature:

With magnesium sulfate; In toluene; at 20 ℃; for 12h;

DOI:10.1055/s-2005-922772

Reference yield: 53.0%

2-Cyanopyridine (100-70-9,1232006-36-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine-2-carbonitrile (878194-93-5)

Guidance literature:

2-Cyanopyridine; With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; at -80 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With acetic acid; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Further stages.;

DOI:10.1055/s-2007-990810

Reference yield:

C12H17BN2O2 → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine-2-carbonitrile (878194-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. HCl / pH 6

2: 82 percent / MgSO₄ / toluene / 12 h / 20 °C

With hydrogenchloride; magnesium sulfate; In toluene;

DOI:10.1055/s-2005-922772

upstream raw materials:

(2-cyanopyridin-3-yl)boronic acid

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

2-Cyanopyridine

Downstream raw materials:

3-hydroxypyridine-2-carbonitrile

7,8,9,10-tetrahydropyrido[2,3-c]-1,5-naphthyridine

pyridine-2-carboxylic acid amide

Refernces

• 1、 Cailly, Thomas,Lemaitre, Stephane,Fabis, Frederic,Rault, Sylvain. "Straightforward access to ethyl 3-aminofuropyridine-2-carboxylates from 1-chloro-2-cyano- or 1-hydroxy-2-cyano-substituted pyridines". . p. 3247 - 3251. Retrieved 2008/04/03.