3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile

Base Information

• Chemical Name: 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile
• CAS No.: 214360-45-9
• Molecular Formula: C₁₂H₁₄BNO₂
• Molecular Weight: 215.06
• Hs Code.: 2934999090
• European Community (EC) Number: 622-425-6
• DSSTox Substance ID: DTXSID80584636
• Wikidata: Q82476317
• Mol file: 214360-45-9.mol

Synonyms:214360-45-9;3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile;(3-Cyanophenyl)boronic acid, neopentyl glycol ester;2-(3-Cyanophenyl)-5,5mu-dimethyl-1,3,2-dioxaborinane;Benzonitrile, 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-;(3-Cyanophenyl)boronic acid neopentyl glycol ester;SCHEMBL5265998;DTXSID80584636;RTYUBKQTFNAFQC-UHFFFAOYSA-N;MFCD09750437;AKOS015999760;AC-27377;BS-25008;CS-0173780;D96358;A851934;2-(3-Cyanophenyl)-5,5|I-dimethyl-1,3,2-dioxaborinane;3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-benzonitrile;(3-Cyanophenyl)boronic acid, neopentyl glycol ester, 95%

Chemical Property of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile

Chemical Property:

• Vapor Pressure: 4.48E-05mmHg at 25°C
• Melting Point: 85-87 °C
• Refractive Index: 1.511
• Boiling Point: 350.2°C at 760 mmHg
• Flash Point: 165.6°C
• PSA: 42.25000
• Density: 1.08g/cm³
• LogP: 1.32648
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 215.1117589
• Heavy Atom Count: 16
• Complexity: 287

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3-Cyanophenyl)boronic acid, neopentyl glycol ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=CC(=CC=C2)C#N
• Uses: (3-Cyanophenyl)boronic acid, neopentyl glycol ester

Technology Process of 3-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile

There total 1 articles about 3-(5,5-Dimethyl-1,3,2-dioxaborinan-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%

2,2-Dimethyl-1,3-propanediol (126-30-7) + (3‐cyanophenyl)boronic acid (150255-96-2) → 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (214360-45-9)

Guidance literature:

In toluene; at 110 ℃; for 8h; Dean-Stark;

DOI:10.1002/anie.202104871

Reference yield: 100.0%

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (214360-45-9) + m-bromobenzoic aldehyde (3132-99-8) → 3'-formyl-[1,1'-biphenyl]-3-carbonitrile (400748-29-0)

Guidance literature:

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile; m-bromobenzoic aldehyde; With sodium carbonate; In ethanol; water; toluene; for 0.0833333h; Inert atmosphere;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene; Sealed tube; Inert atmosphere; Reflux;

Reference yield: 66.0%

3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile (214360-45-9) + potassium 2-(2-nitrophenyl)acetate (1316859-98-9) → 3-(2-nitrobenzyl)benzonitrile (886570-18-9)

Guidance literature:

With copper diacetate; at 35 ℃; for 23h; Sealed tube;

DOI:10.1002/anie.201800829

upstream raw materials:

2,2-Dimethyl-1,3-propanediol

(3‐cyanophenyl)boronic acid

Downstream raw materials:

3'-formyl-[1,1'-biphenyl]-3-carbonitrile

3-(2-nitrobenzyl)benzonitrile

methyl 3-cyanobenzoate

Refernces

• 1、 Liu, Kai,Li, Nian,Ning, Yunyun,Zhu, Chengjian,Xie, Jin. "Gold-Catalyzed Oxidative Biaryl Cross-Coupling of Organometallics". supporting information. p. 2718 - 2730. Retrieved 2019/10/09.