4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane
• CAS No.: 195062-57-8
• Molecular Formula: C13H19BO2
• Molecular Weight: 218.104
• Hs Code.: 2931900090
• European Community (EC) Number: 803-244-3
• DSSTox Substance ID: DTXSID90378841
• Nikkaji Number: J1.255.211D
• Wikidata: Q72494696
• Mol file: 195062-57-8.mol

Synonyms:195062-57-8;4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)toluene;4-methylphenylboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-(4-methylphenyl)-1,3,2-dioxaborolane;4,4,5,5-tetramethyl-2-p-tolyl-1,3,2-dioxaborolane;4-tolylboronic acid pinacol ester;p-Tolylboronic Acid Pinacol Ester;1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(4-METHYLPHENYL)-;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl) toluene;MFCD03453662;4,4,5,5-Tetramethyl-2-(4-methylphenyl)dioxaborolane;4-Methylphenylboronic acid pinacol ester;SCHEMBL64653;DTXSID90378841;GKSSEDDAXXEPCP-UHFFFAOYSA-N;AKOS015917412;AB15519;AS-2257;CS-W022040;AM808110;SY050591;4-methylbenzeneboronic acid, pinacol ester;FT-0643822;T2888;EN300-155808;A813781;J-012634;J-513987;2-p-Tolyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)toluene;Z1336745081;2-(biphenyl-4-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)TOLUENE;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)toluene, AldrichCPR

Chemical Property of 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 53.3-54.0 °C
• Boiling Point: 298.2 °C at 760 mmHg
• Flash Point: 134.1 °C
• PSA: 18.46000
• Density: 0.98 g/cm³
• LogP: 2.29420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Toluene
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 218.1478100
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

98% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(4-methylphenyl)dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C
• Uses: suzuki reaction 4,4,5,5-Tetramethyl-2-(4-methylphenyl)dioxaborolane is used in the synthesis of antimicrobial compounds, showing gram-negatice activity. Also used in the synthesis of component chemicals to thin-film transistors.

Technology Process of 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane

There total 161 articles about 4,4,5,5-Tetramethyl-2-(p-tolyl)-1,3,2-dioxaborolane 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: 99.5%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-methylphenylboronic acid (5720-05-8) → p-tolylboronic pinacol ester (195062-57-8)

Guidance literature:

In diethyl ether;

DOI:10.1016/j.tetlet.2010.05.104

Reference yield: 99.0%

para-bromotoluene (106-38-7) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → p-tolylboronic pinacol ester (195062-57-8)

Guidance literature:

para-bromotoluene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1002/chem.200902172

Reference yield: 99.0%

para-chlorotoluene (106-43-4) + bis(pinacol)diborane (73183-34-3) → p-tolylboronic pinacol ester (195062-57-8)

Guidance literature:

With sodium acetate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; XPhos; for 12h; Heating;

DOI:10.1002/adsc.201500844

upstream raw materials:

4-tolyl iodide

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

4-methylbenzenediazonium tetrafluoroborate

bis(pinacol)diborane

Downstream raw materials:

2-methylphenylboronic acid pinacol ester

4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane

4-(4-tolyl)anisole

(RS)-2-(2,6-dioxopiperidin-3-yl)-4-p-tolylisoindole-1,3-dione

Refernces

• 1、 Yang, Kai,Song, Qiuling. "Palladium-catalyzed arylboration of bicyclic alkenes". . p. 1000 - 1005. Retrieved 2016.
• 2、 Cameron,Pincock,Pincock,Thompson. "Phototransposition reactions of arylboronate esters in acetonitrile and 2,2,2-trifluoroethanol". . p. 4954 - 4960. Retrieved 2004.
• 3、 Zhang, Hua,Hagihara, Shinya,Itami, Kenichiro. "Aromatic C-H borylation by nickel catalysis". . p. 779 - 781. Retrieved 2015.
• 4、 Obligacion, Jennifer V.,Semproni, Scott P.,Pappas, Iraklis,Chirik, Paul J.. "Cobalt-Catalyzed C(sp2)-H Borylation: Mechanistic Insights Inspire Catalyst Design". . p. 10645 - 10653. Retrieved 2016.
• 5、 Lamola, Jairus L.,Moshapo, Paseka T.,Holzapfel, Cedric W.,Christopher Maumela, Munaka. "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands". supporting information. . Retrieved 2021/12/13.
• 6、 Du, Linlin,Sun, Li,Zhang, Hua. "Photochemical and electrochemical C-N borylation of arylhydrazines". supporting information. p. 1716 - 1719. Retrieved 2022/02/21.