6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile

Base Information

• Chemical Name: 6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile
• CAS No.: 425379-22-2
• Molecular Formula: C₁₉H₁₈BF₂NO₂
• Molecular Weight: 341.165
• DSSTox Substance ID: DTXSID001120160
• Mol file: 425379-22-2.mol

Synonyms:SCHEMBL2658918;JGEHOZIBWQGIAS-UHFFFAOYSA-N;DTXSID001120160;6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile;425379-22-2;6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile;2',6-Difluoro-5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-2-carbonitrile;6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-biphenyl-2-carbonitrile

Chemical Property of 6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 341.1398653
• Heavy Atom Count: 25
• Complexity: 531

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)F)C3=C(C=CC=C3F)C#N

Technology Process of 6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile

There total 5 articles about 6,2'-Difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile 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: 95.0%

5'-bromo-6,2'-difluorobiphenyl-2-carbonitrile (425379-21-1) + bis(pinacol)diborane (73183-34-3) → 6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (425379-22-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃;

DOI:10.1016/j.bmcl.2005.12.027

Reference yield:

2-bromo-1-fluoro-4-nitrobenzene (701-45-1) → 6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (425379-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / AcOK; dichloro[1,1'-bis(diphenylphosphino)ferrocene]Pd(II)*CH₂Cl₂; DMSO / dioxane / 14 h / 90 °C

2: KF; tris(dibenzylideneacetone)dipalladium; tri-tert-butylphosphine / tetrahydrofuran; dioxane / 1.5 h / 20 - 50 °C

3: SnCl₂*2H₂O / ethanol; tetrahydrofuran / 12 h / 20 °C

4: aq. HBr; NaNO₂; CuBr / dioxane / 0.5 h / 5 - 50 °C

5: AcOK; dichloro[1,1'-bis(diphenylphosphino)ferrocene]Pd(II)*CH₂Cl₂; DMSO / dioxane / 16 h / 90 °C

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tri-tert-butyl phosphine; hydrogen bromide; potassium acetate; dimethyl sulfoxide; tin(ll) chloride; copper(I) bromide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; ethanol; 1: Miyaura reaction / 4: Sandmeyer reaction / 5: Miyaura reaction;

DOI:10.1021/jm051065l

Reference yield:

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (425378-68-3) → 6,2'-difluoro-5'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile (425379-22-2)

Guidance literature:

Multi-step reaction with 4 steps

1: KF; tris(dibenzylideneacetone)dipalladium; tri-tert-butylphosphine / tetrahydrofuran; dioxane / 1.5 h / 20 - 50 °C

2: SnCl₂*2H₂O / ethanol; tetrahydrofuran / 12 h / 20 °C

3: aq. HBr; NaNO₂; CuBr / dioxane / 0.5 h / 5 - 50 °C

4: AcOK; dichloro[1,1'-bis(diphenylphosphino)ferrocene]Pd(II)*CH₂Cl₂; DMSO / dioxane / 16 h / 90 °C

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; tri-tert-butyl phosphine; hydrogen bromide; potassium acetate; dimethyl sulfoxide; tin(ll) chloride; copper(I) bromide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; ethanol; 3: Sandmeyer reaction / 4: Miyaura reaction;

DOI:10.1021/jm051065l

upstream raw materials:

5'-bromo-6,2'-difluorobiphenyl-2-carbonitrile

bis(pinacol)diborane

2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-bromo-1-fluoro-4-nitrobenzene

Downstream raw materials:

5'-(8-chloro-imidazo[1,2-a]pyrazin-3-yl)-6,2'-difluoro-biphenyl-2-carbonitrile

6,2'-difluoro-5'-(8-oxo-7,8-dihydro-imidazo[1,2-a]pyrazin-3-yl)-biphenyl-2-carbonitrile

6,2'-difluoro-5'-(8-methoxy-imidazo[1,2-a]pyrazin-3-yl)-biphenyl-2-carbonitrile