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

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)toluene
• CAS No.: 253342-48-2
• Molecular Formula: C13H19BO2
• Molecular Weight: 218.104
• Hs Code.: 2934999090
• European Community (EC) Number: 675-045-8
• DSSTox Substance ID: DTXSID70375252
• Nikkaji Number: J1.491.104I
• Wikidata: Q82163777
• Mol file: 253342-48-2.mol

Synonyms:2-(3-TOLYL)-4,4,6-TRIMETHYL-1,3,2-DIOXABORINATE;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)TOLUENE;3-TOLYLBORONIC ACID, HEXYLENE GLYCOL CYCLIC ESTER;3-METHYLPHENYLBORONIC ACID, PINACOL ESTER;2-dioxaborolan-2-yl)toluene;3-Methylbenzeneboronic acid, pinacol ester;4,4,5,5-Tetramethyl-2-m-tolyl-1,3,2-dioxaborolane;4,4,5,5-tetraMethyl-2-(3-Methylphenyl)-1,3,2-dioxaborolane

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

Chemical Property:

• Vapor Pressure: 0.00134mmHg at 25°C
• Melting Point: 34.0 to 38.0 °C
• Refractive Index: 1.491
• Boiling Point: 307.2 °C at 760 mmHg
• Flash Point: 139.6 °C
• PSA: 18.46000
• Density: 0.98 g/cm³
• LogP: 2.29420
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 218.1478100
• Heavy Atom Count: 16
• Complexity: 247

Purity/Quality:

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

3-Tolylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)C
• Uses: suzuki reaction

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

There total 81 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)toluene 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%

meta-bromotoluene (591-17-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane (253342-48-2)

Guidance literature:

meta-bromotoluene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; With iodine; magnesium; In tetrahydrofuran; at 25 ℃; for 3.083h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 25 ℃; for 0.666667h;

Reference yield: 94.0%

meta-bromotoluene (591-17-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane (253342-48-2)

Guidance literature:

With C₂₆H₂₅Cl₂FeN₂PPd; potassium acetate; In isopropyl alcohol; at 85 ℃; for 6h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.organomet.9b00398

Reference yield: 92.0%

1-chloro-3-methylbenzene (108-41-8) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane (253342-48-2)

Guidance literature:

With p-phenylpyridine; sodium methylate; In acetonitrile; at 20 ℃; for 12h; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.9b00917

upstream raw materials:

toluene

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

bis(pinacol)diborane

2-(3-chloro-5-methylphenyl)-4,4,5,5-tetra methyl-1,3,2-dioxaborolane

Downstream raw materials:

2-(2-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-acetyl-3'-methylbiphenyl

3-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)-5-methylphenol

2-(3-bromo-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Hu, Jiefeng,Huang, Mingming,Marder, Todd B.,Radius, Udo,Tang, Man,Westcott, Stephen A.. "Cu-mediated: vs. Cu-free selective borylation of aryl alkyl sulfones". supporting information. p. 395 - 398. Retrieved 2022/01/19.
• 2、 Du, Linlin,Sun, Li,Zhang, Hua. "Photochemical and electrochemical C-N borylation of arylhydrazines". supporting information. p. 1716 - 1719. Retrieved 2022/02/21.