2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 171364-79-7
• Molecular Formula: C13H19BO3
• Molecular Weight: 234.103
• Hs Code.: 2934999090
• European Community (EC) Number: 801-556-4
• DSSTox Substance ID: DTXSID00342770
• Nikkaji Number: J845.355A
• Wikidata: Q72517515
• Mol file: 171364-79-7.mol

Synonyms:171364-79-7;2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-Methoxyphenylboronic acid pinacol ester;4-METHOXYPHENYLBORONIC ACID, PINACOL ESTER;4-Methoxyphenylboronic acid , pinacol ester;MFCD05663864;2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl[1,3,2]dioxaborolane;1,3,2-DIOXABOROLANE, 2-(4-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-;(4-METHOXYPHENYL)BORONIC ACID PINACOL ESTER;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)anisole;4-METHOXYPHENYLBORONIC ACID,PINACOL ESTER;SCHEMBL464505;DTXSID00342770;AKOS015910437;AB21973;AS-2574;CS-W003231;AM808107;SY030139;FT-0671325;T3196;EN300-1425743;A848369;p-Anisylboronic acid 2,3-dimethyl-2,3-butanediyl;J-506043;4-methoxyphenylboronic acid, pinacol ester, AldrichCPR;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anisole;2-(4-Methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Chemical Property of 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.000571mmHg at 25°C
• Melting Point: 26-28 °C
• Refractive Index: 1.49
• Boiling Point: 321.1 °C at 760 mmHg
• Flash Point: 148 °C
• PSA: 27.69000
• Density: 1.02 g/cm³
• LogP: 1.99440
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 234.1427246
• Heavy Atom Count: 17
• Complexity: 254

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)OC
• Uses: suzuki reaction 4-Methoxyphenylboronic Acid Pinacol Ester is an arylboronate ester used in the copper-catalyzed alkylation and arylation of chiral propargylic phosphates as well as in Suzuki-Miyaura coupling reaction . 4-Methoxyphenylboronic Acid Pinacol Ester is an arylboronate ester used in the copper-catalyzed alkylation and arylation of chiral propargylic phosphates as well as in Suzuki-Miyaura coupling reaction.

Technology Process of 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 139 articles about 2-(4-Methoxyphenyl)-4,4,5,5-tetramethyl-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: 91.0%

1-bromo-4-methoxy-benzene (104-92-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methoxybenzene (100-66-3) + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7)

Guidance literature:

With triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 6h;

DOI:10.1055/s-2006-947365

Reference yield: 90.0%

1-bromo-4-methoxy-benzene (104-92-7) + bis(pinacol)diborane (73183-34-3) → methoxybenzene (100-66-3) + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7)

Guidance literature:

With {meso-1,3-bis(1-methylethyl)-4,5-(9,10-dihydroanthraceno)imidazolin-2-ylidene}copper(I) chloride; potassium tert-butylate; In tetrahydrofuran; tert-butyl methyl ether; at 0 - 25 ℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1021/acs.joc.5b01721

Reference yield: 89.0%

4-chloromethoxybenzene (623-12-1) + bis(pinacol)diborane (73183-34-3) → methoxybenzene (100-66-3) + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7)

Guidance literature:

With p-phenylpyridine; sodium methylate; In acetonitrile; at 20 ℃; for 12h; Reagent/catalyst; Solvent; Wavelength; Catalytic behavior; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.9b00917

upstream raw materials:

Phenyl triflate

4-methoxyphenyl triflate

bis(pinacol)diborane

para-iodoanisole

Downstream raw materials:

4'-methoxybiphenyl-4-carbonitrile

ethyl p-methoxyphenylacetate

4-methoxyphenylboronic acid

4-methoxy-phenol

Refernces

• 1、 Esteruelas, Miguel A.,Martínez, Antonio,Oliván, Montserrat,O?ate, Enrique. "Direct C?H Borylation of Arenes Catalyzed by Saturated Hydride-Boryl-Iridium-POP Complexes: Kinetic Analysis of the Elemental Steps". . p. 12632 - 12644. Retrieved 2020.
• 2、 Chun, Wang-Jae,Maeda, Kyogo,Manaka, Yuichi,Motokura, Ken,Nakajima, Kiyotaka,Satter, Shazia Sharmin,Uemura, Yohei. "Controllable factors of supported IR complex catalysis for aromatic C?H borylation". . p. 14552 - 14559. Retrieved 2020.
• 3、 Varni, Anthony J.,Bautista, Michael V.,Noonan, Kevin J.T.. "Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes under Mild Conditions". . p. 6770 - 6777. Retrieved 2020.
• 4、 Kim, Kyoung-Rok,Kim, Hoon Jun,Hong, Jong-In. "Electrogenerated Chemiluminescent Chemodosimeter Based on a Cyclometalated Iridium(III) Complex for Sensitive Detection of Thiophenol". . p. 1353 - 1359. Retrieved 2019.
• 5、 Chotana, Ghayoor A.,Rak, Michael A.,Smith, Milton R.. "Sterically directed functionalization of aromatic C-H bonds: Selective borylation ortho to cyano groups in arenes and heterocycles". . p. 10539 - 10544. Retrieved 2005.
• 6、 Ding, Wei,García, Felipe,Ho, Chang Chin,León, Felix,Tan, Jie Ren,Wang, Chen,Yoshikai, Naohiko. "Site-selective aromatic C-H λ3-iodanation with a cyclic iodine(iii) electrophile in solution and solid phases". . p. 7356 - 7361. Retrieved 2020.
• 7、 Pandarus, Valerica,Marion, Olivier,Gingras, Genevieve,Beland, Francois,Ciriminna, Rosaria,Pagliaro, Mario. "SiliaCat diphenylphosphine palladium(II) catalyzed borylation of aryl halides". . p. 1340 - 1348. Retrieved 2014.
• 8、 Pandarus, Valerica,Gingras, Genevive,Bland, Franois,Ciriminna, Rosaria,Pagliaro, Mario. "Fast and clean borylation of aryl halides under flow using sol-gel entrapped silia cat DPP-Pd". . p. 1556 - 1559. Retrieved 2014.
• 9、 Qi, Xinxin,Li, Hao-Peng,Peng, Jin-Bao,Wu, Xiao-Feng. "Borylation of aryldiazonium salts at room temperature in an aqueous solution under catalyst-free conditions". . p. 3851 - 3853. Retrieved 2017.
• 10、 Melaimi, Mohand,Mathey, Fran?ois,Le Floch, Pascal. "Bis(diphosphaferrocene) palladium(II) dimer complexes as efficient catalysts in the synthesis of arylboronic esters". . p. 197 - 199. Retrieved 2001.