3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Base Information

• Chemical Name: 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• CAS No.: 479411-96-6
• Molecular Formula: C13H15BBrNO2
• Molecular Weight: 307.983
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00464885
• Nikkaji Number: J1.803.293G
• Wikidata: Q82290422
• Mol file: 479411-96-6.mol

Synonyms:479411-96-6;3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;3-Bromo-5-cyanophenylboronic acid pinacol ester;C13H15BBrNO2;SCHEMBL12522631;(3-BROMO-5-CYANOPHENYL)BORONIC ACID PINACOL ESTER;DTXSID00464885;RXYJIHWLAKWJTK-UHFFFAOYSA-N;MFCD11846465;3-Bromo-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile;AKOS015999355;MB10097;BS-28886;CS-0175567;A872010;3-Bromo-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Chemical Property of 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Chemical Property:

• Boiling Point: 374.2±32.0 °C(Predicted)
• PSA: 42.25000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 2.61998
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 307.03792
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

97% ^*data from raw suppliers

3-Bromo-5-cyanophenylboronicacidpinacolester ^*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(=CC(=C2)Br)C#N

Technology Process of 3-Bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

There total 2 articles about 3-Bromo-5-(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: 90.0%

3-cyanobromobenzene (6952-59-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (479411-96-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In neat (no solvent); at 50 ℃; for 2.5h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.5b01588

Reference yield: 55.0%

3-cyanobromobenzene (6952-59-6) + bis(pinacol)diborane (73183-34-3) → 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (479411-96-6)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 125 ℃; for 48h; Schlenk technique; Inert atmosphere;

DOI:10.1021/jacs.5b05252

Reference yield: 72.0%

Ph3In + 3-bromo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (479411-96-6) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-carbonitrile

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; at 65 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.joc.1c01978

upstream raw materials:

3-cyanobromobenzene

bis(pinacol)diborane

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

Downstream raw materials:

C₁₅H₁₀BrNO₂

5'-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-3-ethoxycarbonyl-3''-methoxy-1,1':3',1''-terphenyl