5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane

Base Information

• Chemical Name: 5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane
• CAS No.: 214360-78-8
• Molecular Formula: C14H21BO2
• Molecular Weight: 232.131
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID50465827
• Nikkaji Number: J1.429.490B
• Wikidata: Q72513920
• Mol file: 214360-78-8.mol

Synonyms:214360-78-8;2,4,6-Trimethylbenzeneboronic acid neopentyl glycol ester;5,5-dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane;2-MESITYL-5,5-DIMETHYL-1,3,2-DIOXABORINANE;2,4,6-TRIMETHYLBENZENEBORONIC ACID NEOPENTYL GLYCOL CYCLIC ESTER;2,4,6-TRIMETHYLPHENYLBORONIC ACID NEOPENTYL GLYCOL ESTER;SCHEMBL172725;DTXSID50465827;MFCD01318178;AKOS022172839;AB08673;AS-76984;CS-0175794;FT-0609900;A815371;5, 5-dimethyl-2-(2, 4, 6-trimethylphenyl)-1, 3, 2-dioxaborinane;4-Oxo-1,9a-dihydro-4H-pyrimido[1,2-a]pyrimidine-3-carboxylicacidethylester

Chemical Property of 5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 46-48 °C
• Refractive Index: 1.493
• Boiling Point: 339.91 °C at 760 mmHg
• Flash Point: 159.372 °C
• PSA: 18.46000
• Density: 0.98 g/cm³
• LogP: 2.38000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 232.1634601
• Heavy Atom Count: 17
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

2-Mesityl-5,5-dimethyl-1,3,2-dioxaborinane 95% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OCC(CO1)(C)C)C2=C(C=C(C=C2C)C)C

Technology Process of 5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane

There total 6 articles about 5,5-Dimethyl-2-(2,4,6-trimethylphenyl)-1,3,2-dioxaborinane 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%

2,4,6-trimethylphenyl bromide (576-83-0) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 2,4,6-trimethylbenzeneboronic acid neopentyl glycol cyclic ester (214360-78-8)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; cesium acetate; In 1,4-dioxane; at 20 - 110 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

Reference yield: 86.0%

mesitylboronic acid (5980-97-2) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 2,4,6-trimethylbenzeneboronic acid neopentyl glycol cyclic ester (214360-78-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 0.166667h;

DOI:10.1039/b201622b

Reference yield: 60.0%

2,4,6-trimethylphenyl bromide (576-83-0) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 2-tert-butoxy-5,5-dimethyl-1,3,2-dioxaborinane + 2,4,6-trimethylbenzeneboronic acid neopentyl glycol cyclic ester (214360-78-8)

Guidance literature:

With copper(l) iodide; tributylphosphine; potassium tert-butylate; In tetrahydrofuran; byproducts: KBr, Me3C6H3; react. of (B(OCH2)2C(CH3)2)2 (1.5 equiv.), 2,4,6-Me3C6H2Br (1 equiv.), CuI (10 mol%), nBu3P (13 mol%) and KOtBu (1.5 equiv.) at room temp.; detd. by XRD;

upstream raw materials:

mesitylboronic acid

2,2-Dimethyl-1,3-propanediol

2,4,6-trimethylphenyl bromide

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

Downstream raw materials:

4′-(2,4,6-trimethylphenyl)-2,2′:6′,2″-terpyridine

4-phenyl-3-(3,5-bis(2,4,6-trimethylphenyl)phenyldiazenyl)pyridine

N,N-dibenzyl-2,4,6-trimethylaniline

mesitylenecarboxylic acid

Refernces

• 1、 Yasuike, Shuji,Nakata, Kazuhide,Qin, Weiwei,Matsumura, Mio,Kakusawa, Naoki,Kurita, Jyoji. "Synthesis of arylboronates by boron-induced ipso-deantimonation of triarylstibanes with boron trihalides and its application in one-pot two-step transmetallation/cross-coupling reactions". . p. 9 - 16. Retrieved 2015/05/13.
• 2、 Zhao, Yigang,Snieckus, Victor. "Beyond directed ortho metalation: Ruthenium-catalyzed amide-directed C Ar-N activation/C-C coupling reaction of anthranilamides with organoboronates". supporting information. p. 3200 - 3203. Retrieved 2014/07/08.