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

Base Information

• Chemical Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• CAS No.: 214360-48-2
• Molecular Formula: C₁₃H₁₆BNO₂
• Molecular Weight: 229.087
• Hs Code.: 2931900090
• European Community (EC) Number: 678-824-0
• DSSTox Substance ID: DTXSID40393746
• Nikkaji Number: J1.635.709J
• Wikidata: Q72458787
• Mol file: 214360-48-2.mol

Synonyms:214360-48-2;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;2-Cyanophenylboronic acid pinacol ester;2-Cyanophenylboronic acid, pinacol ester;2-CYANOBENZENEBORONIC ACID PINACOL ESTER;MFCD04038747;Benzonitrile, 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;2-Cyanobenzeneboronic acid, pinacol ester;(2-CYANOPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL520252;DTXSID40393746;SKQNWSBNAIOCOC-UHFFFAOYSA-N;BCP10609;2-Cyanophenylboronicacid,pinacolester;BBL103621;STL557431;AKOS004115186;AB17166;AM62757;AS-2723;CS-W000901;SY023526;C2621;FT-0647958;2-Cyanophenylboronic acid pinacol ester, 97%;EN300-1706435;A815360;J-509229;2-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzonitrile;2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile;2-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)benzonitrile

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

Chemical Property:

• Vapor Pressure: 2.79E-05mmHg at 25°C
• Melting Point: 88-90°C
• Refractive Index: 1.507
• Boiling Point: 357.1 °C at 760 mmHg
• Flash Point: 169.8 °C
• PSA: 42.25000
• Density: 1.06g/cm³
• LogP: 1.85748
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 229.1274089
• Heavy Atom Count: 17
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

2-Cyanophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C#N
• Uses: suzuki reaction

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

There total 15 articles about 2-(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: 100.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-Cyanophenylboronic acid (138642-62-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (214360-48-2)

Guidance literature:

DOI:10.1016/S0022-328X(02)01175-0

Reference yield: 98.0%

2-Chlorobenzonitrile (873-32-5) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (214360-48-2)

Guidance literature:

With sodium acetate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; for 12h; Heating;

DOI:10.1002/adsc.201500844

Reference yield: 86.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + bis(N,N-diisopropylamine)boron bromide (79988-34-4) + o-cyanobromobenzene (2042-37-7) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (214360-48-2)

Guidance literature:

bis(N,N-diisopropylamine)boron bromide; o-cyanobromobenzene; With lithium; In 2-methyltetrahydrofuran; at -10 - 0 ℃; for 6h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; Reflux;

upstream raw materials:

2-Chlorobenzonitrile

bis(pinacol)diborane

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

2-Cyanophenylboronic acid

Downstream raw materials:

phenanthridine

2'-bromo-[1,1'-biphenyl]-2-carbonitrile

5-(4-isopropylphenyl)imidazo[1,2-f]phenanthridine

6-aminophenanthridine

Refernces

• 1、 Lamola, Jairus L.,Moshapo, Paseka T.,Holzapfel, Cedric W.,Christopher Maumela, Munaka. "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands". supporting information. . Retrieved 2021/12/13.
• 2、 Pezzetta, Cristofer,Folli, Andrea,Matuszewska, Oliwia,Murphy, Damien,Davidson, Robert W. M.,Bonifazi, Davide. "peri-Xanthenoxanthene (PXX): a Versatile Organic Photocatalyst in Organic Synthesis". supporting information. p. 4740 - 4753. Retrieved 2021/04/09.