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

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
• CAS No.: 171364-82-2
• Molecular Formula: C13H16BNO2
• Molecular Weight: 229.087
• Hs Code.: 29319090
• European Community (EC) Number: 626-346-8
• DSSTox Substance ID: DTXSID30370405
• Nikkaji Number: J845.351I
• Wikidata: Q72457884
• Mol file: 171364-82-2.mol

Synonyms:171364-82-2;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;4-Cyanophenylboronic acid pinacol ester;4-cyanophenylboronic acid, pinacol ester;MFCD03093897;4-cyanobenzeneboronic acid, pinacol ester;Benzonitrile, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile;2-(4-CYANOPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;(4-CYANOPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL476909;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile;DTXSID30370405;AKOS015950729;AB13287;AM62749;AS-2265;SY024024;CS-0030567;FT-0643642;T3350;4-Cyanophenylboronic acid pinacol ester, 97%;EN300-1706218;A811324;J-010716;J-513428;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile

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

Chemical Property:

• Appearance/Colour: light yellow to orange or light tan crystalline powder
• Vapor Pressure: 6.02E-05mmHg at 25°C
• Melting Point: 95-99 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 345.782 °C at 760 mmHg
• Flash Point: 162.923 °C
• PSA: 42.25000
• Density: 1.066 g/cm³
• LogP: 1.85748
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 229.1274089
• Heavy Atom Count: 17
• Complexity: 321

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C#N
• Uses: 4-(Cyanophenyl)boronic Acid Pinacol Ester is used to prepare arylparacyclophanes via Suzuki aryl cross-coupling of bromoparacyclophane with arylboronic acid and arylboronates. It’s also used to prepare tyrosine-modified analogs of α4β7 integrin inhibitor biotin-R8ERY.

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

There total 62 articles about 4-(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: 99.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-cyanophenylboronic acid (126747-14-6) → 4-cyanophenylboronic acid pinacol ester (171364-82-2)

Guidance literature:

With magnesium sulfate; In diethyl ether; at 25 ℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.1c08551

Reference yield: 98.0%

4-bromobenzenecarbonitrile (623-00-7) + bis(pinacol)diborane (73183-34-3) → 4-cyanophenylboronic acid pinacol ester (171364-82-2)

Guidance literature:

With C₃₇H₅₁ClFeNPPd; potassium acetate; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1002/adsc.201000085

Reference yield: 95.0%

4-Cyanochlorobenzene (623-03-0) + bis(pinacol)diborane (73183-34-3) → 4-cyanophenylboronic acid pinacol ester (171364-82-2)

Guidance literature:

With potassium acetate; palladium diacetate; (1R,3S,5S,7R)-8-([1,1'-biphenyl]-2-yl)-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phospha-adamantane; In tetrahydrofuran; at 25 ℃; for 12h; Reagent/catalyst; Time; Catalytic behavior; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2021.153572

upstream raw materials:

para-nitrophenyl triflate

Phenyl triflate

4-iodobenzonitrile

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

Downstream raw materials:

cyclopropanecarboxylic acid {8-[4-(6-cyano-pyridin-3-yl)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-amide

4-(2-chloropyridin-4-yl)benzonitrile