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

Base Information

• Chemical Name: 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile
• CAS No.: 325141-71-7
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.113
• Hs Code.: 2934999090
• European Community (EC) Number: 853-432-4
• DSSTox Substance ID: DTXSID50397058
• Nikkaji Number: J1.486.112B
• Wikidata: Q82198086
• Mol file: 325141-71-7.mol

Synonyms:325141-71-7;2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile;2-Cyanomethylphenylboronic acid, pinacol ester;2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile;(2-CYANOMETHYLPHENYL)BORONIC ACID, PINACOL ESTER;(2-Cyanomethylphenyl)boronic acid,pinacol ester;BENZENEACETONITRILE, 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;2-(Cyanomethyl)benzeneboronic acid, pinacol ester;[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile;SCHEMBL534206;DTXSID50397058;FIARMBRSPSECPP-UHFFFAOYSA-N;2-[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile;MFCD02179457;AKOS022172756;AB11169;AT16271;PS-9708;2-Cyanomethylphenylboronic acid pinacol ester;2-Cyanomethylphenylboronic acid,pinacol ester;CS-0138342;FT-0644419;EN300-212495;A875598;J-018767;(S)-2-(TOLUENE-4-SULFONYLOXY)-PROPIONICACID;Z2044743170;[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]acetonitrile;[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzeneacetonitrile

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

Chemical Property:

• Vapor Pressure: 5.99E-06mmHg at 25°C
• Refractive Index: 1.505
• Boiling Point: 379.1 °C at 760 mmHg
• Flash Point: 183.1 °C
• PSA: 42.25000
• Density: 1.05 g/cm³
• LogP: 2.05188
• Storage Temp.: 2-8°C
• Water Solubility.: Miscible with water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 243.1430590
• Heavy Atom Count: 18
• Complexity: 342

Purity/Quality:

97% ^*data from raw suppliers

2-Cyanomethylphenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2CC#N
• Uses: 2-Cyanomethylphenylboronic acid, pinacol ester

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

There total 4 articles about 2-(2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile 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%

2-(2-iodophenyl)acetonitrile (40400-15-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → phenylacetonitrile (140-29-4) + [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile (325141-71-7)

Guidance literature:

With triethylamine; CyJohnPhos; palladium diacetate; at 80 ℃; for 0.5h;

DOI:10.1021/jo005663d

Reference yield: 85.0%

2-(2-iodophenyl)acetonitrile (40400-15-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile (325141-71-7)

Guidance literature:

With palladium diacetate; triethylamine; CyJohnPhos; In 1,4-dioxane; at 80 ℃; for 0.5h;

DOI:10.1021/acs.joc.5b02378

Reference yield: 75.0%

2-(2-bromophenyl)acetonitrile (19472-74-3) + bis(pinacol)diborane (73183-34-3) → [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetonitrile (325141-71-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 3h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2011.05.116

upstream raw materials:

2-(2-bromophenyl)acetonitrile

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

2-(2-iodophenyl)acetonitrile

bis(pinacol)diborane

Downstream raw materials:

2-hydroxybenzyl cyanide