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

Base Information

• Chemical Name: Methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoate
• CAS No.: 882679-40-5
• Molecular Formula: C15H21 B O4
• Molecular Weight: 276.14
• Hs Code.: 2934999090
• European Community (EC) Number: 690-925-1
• DSSTox Substance ID: DTXSID90682238
• Wikidata: Q82606545
• Mol file: 882679-40-5.mol

Synonyms:882679-40-5;METHYL 4-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;5-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester;MFCD11520530;Dichloroaceticacid;5-(Methoxycarbonyl)-2-methylphenylboronic acid pinacol ester;SCHEMBL960031;DTXSID90682238;HAPIXNBOBZHNCA-UHFFFAOYSA-N;BCP24698;AKOS015891571;AS-2552;MB09925;SY104644;AM20041300;CS-0041218;FT-0704967;EN300-303787;N10591;A842524;J-522373;Z1947345606;5-Methoxycarbonyl-2-methylphenylboronic-acid pinacol ester;methyl 4-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;5-(Methoxycarbonyl)-2-methylphenylboronic acid pinacol ester, AldrichCPR;methyl 4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoate;4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester;METHYL4-METHYL-3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;4-(1/4)x>>u-3-(4,4,5,5-EA(1/4)x>>u-1,3,2- paragraph signthornNoOO>>.IiAethIe-2->>u)+/-(1/2)(1/4)xEa(1/4)xo yen

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

Chemical Property:

• Boiling Point: 383.1±35.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 2.08080
• Storage Temp.: Room temperature.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 276.1532893
• Heavy Atom Count: 20
• Complexity: 364

Purity/Quality:

98%min ^*data from raw suppliers

5-Methoxycarbonyl-2-Methylphenylboronic 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=C(C=CC(=C2)C(=O)OC)C

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

There total 9 articles about Methyl 4-methyl-3-(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: 92.0%

methyl 3-bromo-4-methylbenzoate (104901-43-1) + bis(pinacol)diborane (73183-34-3) → methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (882679-40-5)

Guidance literature:

methyl 3-bromo-4-methylbenzoate; bis(pinacol)diborane; With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II); potassium acetate; In 1,4-dioxane; at 100 ℃; for 0.0833333h; Inert atmosphere;

With triethylamine; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c2cc30230f

Reference yield: 71.0%

methyl 3-iodo-4-methylbenzoate (90347-66-3) + bis(pinacol)diborane (73183-34-3) → methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (882679-40-5)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 80 ℃; Inert atmosphere;

Reference yield: 65.0%

CF3C6H4SO2O(C6H3(CH3)COOCH3) (1350764-46-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (882679-40-5)

Guidance literature:

With Et₃N; tetrabutylammonium iodide; 1,1'-bis(di-tertbutylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; 100°C, 96 h; GC;

DOI:10.1246/cl.2011.962

upstream raw materials:

CF₃C₆H₄SO₂O(C₆H₃(CH₃)COOCH₃)

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

methyl 3-bromo-4-methylbenzoate

bis(pinacol)diborane

Downstream raw materials:

1-(hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)carboxylic acid

(R)-methyl 3-(5-amino-6-(1-(4-chlorophenyl)ethylamino)pyrazin-2-yl)-4-methylbenzoate

methyl 4-methyl-3-(1H-pyrazol-5-yl)benzoate

[5-(methoxycarbonyl)-2-methylphenyl]boronic acid

Refernces

• 1、 -. "1, 1 '-biphenyl-2, 6-diphenol compound and application thereof". Paragraph 0044; 0046. . Retrieved 2021/03/18.
• 2、 Furukawa, Takayuki,Tobisu, Mamoru,Chatani, Naoto. "C-H borylation by platinum catalysis". supporting information. p. 332 - 342. Retrieved 2017/05/09.