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

Base Information

• Chemical Name: Methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 473596-87-1
• Molecular Formula: C15H21BO4
• Molecular Weight: 276.14
• Hs Code.: 2934999090
• European Community (EC) Number: 801-040-9
• DSSTox Substance ID: DTXSID90454770
• Wikidata: Q82276492
• Mol file: 473596-87-1.mol

Synonyms:473596-87-1;Methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-(Methoxycarbonyl)-2-methylphenylboronic acid pinacol ester;2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester;MFCD08669595;2-Methyl-4-methoxycarbonylphenylboronic acid pinacol ester;(4-(METHOXYCARBONYL)-2-METHYLPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL203450;4-(Methoxycarbonyl)-2-methylphenylboronicacidpinacolester;DTXSID90454770;RDBWYSWPXDSHOE-UHFFFAOYSA-N;AKOS016007672;MB06451;AM803937;AS-39538;SY075773;CS-0046846;FT-0746857;10.14272/RDBWYSWPXDSHOE-UHFFFAOYSA-N;EN300-314468;10.14272/RDBWYSWPXDSHOE-UHFFFAOYSA-N.1;A872177;doi:10.14272/RDBWYSWPXDSHOE-UHFFFAOYSA-N;doi:10.14272/RDBWYSWPXDSHOE-UHFFFAOYSA-N.1;J-522198;Z2037320387;METHYL 3-METHYL-4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester

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

Chemical Property:

• Boiling Point: 377.5±35.0 °C(Predicted)
• PSA: 44.76000
• Density: 1.07±0.1 g/cm3(Predicted)
• LogP: 2.08080
• Storage Temp.: 2-8°C
• 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%,99%, ^*data from raw suppliers

2-Methyl-4-methoxycarbonylphenylboronic 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=C(C=C2)C(=O)OC)C

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

There total 6 articles about Methyl 3-methyl-4-(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: 99.0%

4-Bromo-3-methylbenzoic acid methyl ester (148547-19-7) + bis(pinacol)diborane (73183-34-3) → 4-methoxycarbonyl-2-methylbenzeneboronic acid pinacol ester (473596-87-1)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 18h;

DOI:10.1002/chem.201903460

Reference yield: 89.0%

methanol (67-56-1) + 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (269409-74-7) → 4-methoxycarbonyl-2-methylbenzeneboronic acid pinacol ester (473596-87-1)

Guidance literature:

With thionyl chloride; at 20 ℃; for 4h;

Reference yield: 87.0%

→ 4-methoxycarbonyl-2-methylbenzeneboronic acid pinacol ester (473596-87-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 20h;

upstream raw materials:

4-Bromo-3-methylbenzoic acid methyl ester

bis(pinacol)diborane

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

methanol

Downstream raw materials:

C₁₅H₁₅NO₂

methyl 4-(4-(2-(((4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-2-oxooxazolidin-3-yl)methyl)-4,4-dimethylcyclohex-1-enyl)-5-methoxypyrimidin-2-yl)-3-methylbenzoate

methyl 4-(3-(2-(((4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-2-oxooxazolidin-3-yl)methyl)-4,4-dimethylcyclohex-1-enyl)-2-methoxypyridin-5-yl)-3-methylbenzoate

4-(2-(2-(((4S,5R)-5-(3,5-bis(trifluoromethyl)phenyl)-4-methyl-2-oxooxazolidin-3-yl)methyl)-4,4-dimethylcyclohex-1-enyl)-3-methoxypyridin-6-yl)-3-methylbenzoic acid

Refernces

• 1、 Zhao, Jia-Hui,Zhou, Zhao-Zhao,Zhang, Yue,Su, Xuan,Chen, Xi-Meng,Liang, Yong-Min. "Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex". supporting information. p. 4390 - 4394. Retrieved 2020/10/20.
• 2、 Priem, Christoph,Geyer, Armin. "Reversible Covalent End-Capping of Collagen Model Peptides". supporting information. p. 14278 - 14283. Retrieved 2019/11/03.