Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 653589-95-8
• Molecular Formula: C14H19 B O4
• Molecular Weight: 262.113
• Hs Code.: 2934999090
• European Community (EC) Number: 675-007-0
• DSSTox Substance ID: DTXSID30375011
• Nikkaji Number: J1.968.990E
• Wikidata: Q72489519
• Mol file: 653589-95-8.mol

Synonyms:653589-95-8;Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;2-Methoxycarbonylphenylboronic acid pinacol ester;2-methoxycarbonylphenylboronic acid, pinacol ester;2-(methoxycarbonyl)benzeneboronic acid pinacol ester;MFCD05663866;2-(methoxycarbonyl)benzeneboronic acid, pinacol ester;2-Methoxycarbonyl phenylboronic acid pinacol ester;SCHEMBL9986523;methyl 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;DTXSID30375011;GWSGJWIUSIAFOP-UHFFFAOYSA-N;(2-(METHOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER;methyl2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;AKOS015852330;AB21978;AS-3257;CS-W000957;AM804198;SY003284;FT-0644817;M3233;EN300-363379;J-521832;2-Methoxycarbonylphenylboronic acid, pinacol ester, AldrichCPR;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid methyl ester;Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, AldrichCPR

Chemical Property of Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

• Vapor Pressure: 1.77E-05mmHg at 25°C
• Melting Point: 49-51oC
• Boiling Point: 363.7°C at 760 mmHg
• Flash Point: 173.8°C
• PSA: 44.76000
• Density: 1.08g/cm³
• LogP: 1.77240
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 262.1376392
• Heavy Atom Count: 19
• Complexity: 337

Purity/Quality:

98% ^*data from raw suppliers

2-Methoxycarbonylphenylboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C(=O)OC

Technology Process of Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 15 articles about Methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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: 93.0%

o-iodo-methyl-benzoic acid (610-97-9) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester (653589-95-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium acetate; In polyethylene glycol 600; at 90 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/aoc.1799

Reference yield: 92.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + bis(pinacol)diborane (73183-34-3) → methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (480425-35-2) + methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (171364-80-0) + 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester (653589-95-8)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 90 ℃; for 40h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jacs.6b06239

Reference yield: 89.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid methyl ester (653589-95-8)

Guidance literature:

With silica-SMAP-Ir(OCH₃)(C₈H₁₂); In hexane; ligand reacted with B-compound in hexane in presence of Ir-complex as catalyst at 25°C for 2 h;

upstream raw materials:

o-iodo-methyl-benzoic acid

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

2-bromobenzoic acid methyl ester

methyl 2-oxo-2H-pyrane-3-carboxylate

Downstream raw materials:

methyl 2-(3-acetylpyridin-2-yl)benzoate

2,3-diphenyl-1H-inden-1-one

methyl salicylate

4-chlorophenyl 2-methoxycarbonylphenyl sulfide

Refernces

• 1、 Gurusingha Arachchige, Harshani S.,Herath Mudiyanselage, Poornima D.H.,VanHecke, Garrett C.,Patel, Kush,Cheaito, Hassan A.,Dou, Q. Ping,Ahn, Young-Hoon. "Synthesis and evaluation of tiaprofenic acid-derived UCHL5 deubiquitinase inhibitors". supporting information. . Retrieved 2020/12/25.
• 2、 -. "Carbazole derivatives and organoelectro luminescent device using the same". Paragraph 0366; 0403-0408; 0429-0435. . Retrieved 2020/11/28.