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

Base Information

• Chemical Name: 2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetonitrile
• CAS No.: 936250-18-9
• Molecular Formula: C14H18BNO3
• Molecular Weight: 259.113
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00592137
• Wikidata: Q82486079
• Mol file: 936250-18-9.mol

Synonyms:936250-18-9;2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetonitrile;3-CYANOMETHOXYPHENYLBORONIC ACID, PINACOL ESTER;2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetonitrile;[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-acetonitrile;3-Cyanomethoxyphenylboronic acid pinacol ester;SCHEMBL2424699;DTXSID00592137;MFCD06795674;AKOS015960076;AB29225;DS-17990;CS-0174448;3-Cyanomethoxy-phenylboronic acid pinacol ester;C77221;A859705;3-cyanomethoxy-phenylboronic acid, pinacol ester, AldrichCPR;[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]acetonitrile

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

Chemical Property:

• Vapor Pressure: 1.59E-06mmHg at 25°C
• Boiling Point: 397.4°C at 760 mmHg
• Flash Point: 194.1°C
• PSA: 51.48000
• Density: 1.09g/cm³
• LogP: 1.88818
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 259.1379736
• Heavy Atom Count: 19
• Complexity: 358

Purity/Quality:

97% ^*data from raw suppliers

3-Cyanomethoxyphenylboronicacid,pinacolester ^*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)OCC#N
• Uses: 3-Cyanomethoxyphenylboronic acid, pinacol ester

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

There total 2 articles about 2-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)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: 95.0%

(3-Iodo-phenoxy)-acetonitrile + bis(pinacol)diborane (73183-34-3) → 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetonitrile (936250-18-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; for 18h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2017.12.053

Reference yield:

3-Iodophenol (626-02-8) → 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetonitrile (936250-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: 18 h / 20 °C

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / tetrahydrofuran / 18 h / Inert atmosphere; Reflux

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; sodium hydroxide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2017.12.053

Reference yield: 76.0%

2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetonitrile (936250-18-9) + 6-bromo-7-methylisobenzofuran-1(3H)-one → 2-(3-(4-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)phenoxy)acetonitrile

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 85 ℃; for 7h; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tet.2017.12.053

upstream raw materials:

bis(pinacol)diborane

3-Iodophenol

Downstream raw materials:

3-[3-(cyanomethoxy)phenyl]-2-oxido-4-oxo-1-(2,2,2-trifluoroethyl)-4H-pyrido[1,2-a]pyrimidinium