4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzonitrile

Base Information

• Chemical Name: 4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzonitrile
• CAS No.: 863868-30-8
• Molecular Formula: C13H15BClNO2
• Molecular Weight: 263.52800
• DSSTox Substance ID: DTXSID80696920
• Wikidata: Q82626688
• Mol file: 863868-30-8.mol

Synonyms:863868-30-8;2-Chloro-5-cyanophenyl boronic acid pinacol ester;4-CHLORO-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE;Benzonitrile, 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;DTXSID80696920;MFCD11617917;CS-0189702;E82305;EN300-6482377;A841629;Z2049750577;4-chloro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile;4-CHLORO-3-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZONITRILE

Chemical Property of 4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzonitrile

Chemical Property:

• Boiling Point: 364.9±32.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 2.51088
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 263.0884366
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloro-5-cyanophenylboronicacidpinacolester 95% ^*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(C=CC(=C2)C#N)Cl

Technology Process of 4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzonitrile

There total 2 articles about 4-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzonitrile 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: 70.0%

3-bromo-4-chlorobenzonitrile (948549-53-9) + bis(pinacol)diborane (73183-34-3) → 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-30-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 12h; Reflux;

DOI:10.1002/chem.201904477

Reference yield:

4-Cyanochlorobenzene (623-03-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (863868-30-8) + 4-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 25 ℃; for 36h; Title compound not separated from byproducts;

DOI:10.1021/ja0428309

upstream raw materials:

4-Cyanochlorobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

3-bromo-4-chlorobenzonitrile

bis(pinacol)diborane

Refernces

• 1、 Miller, Susanne L.,Chotana, Ghayoor A.,Fritz, Jonathan A.,Chattopadhyay, Buddhadeb,Maleczka, Robert E.,Smith, Milton R.. "C-H Borylation Catalysts that Distinguish between Similarly Sized Substituents like Fluorine and Hydrogen". supporting information. p. 6388 - 6392. Retrieved 2019/08/26.
• 2、 Chotana, Ghayoor A.,Rak, Michael A.,Smith, Milton R.. "Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles". . p. 10539 - 10544. Retrieved 2007/10/03.