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

Base Information

• Chemical Name: Methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 929626-17-5
• Molecular Formula: C15H21BO4
• Molecular Weight: 276.14
• Hs Code.: 2931900090
• European Community (EC) Number: 802-076-8
• DSSTox Substance ID: DTXSID30581635
• Nikkaji Number: J2.438.841G
• Wikidata: Q82472827
• Mol file: 929626-17-5.mol

Synonyms:929626-17-5;Methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;3-Methyl-5-methoxycarbonylphenylboronic acid, pinacol ester;3-Methoxycarbonyl-5-methylphenylboronic acid pinacol ester;SCHEMBL7475416;3-methyl-5-methoxycarbonylphenylboronic acid pinacol ester;3-Methyl-5-methoxycarbonylphenylboronic acid,pinacol ester;DTXSID30581635;methyl 3-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;(3-(METHOXYCARBONYL)-5-METHYLPHENYL)BORONIC ACID PINACOL ESTER;MFCD11858366;AKOS016003693;AS-3266;SB40006;METHYL3-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;CS-0175810;EN300-363391;Z2044754882

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

Chemical Property:

• Boiling Point: 389.4±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% ^*data from raw suppliers

Methyl3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate ^*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(=CC(=C2)C(=O)OC)C
• Uses: Methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate is used in the preparation of phenanthroline iridium complexes.

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

There total 2 articles about Methyl 3-methyl-5-(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: 96.0%

→ methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (929626-17-5)

Guidance literature:

With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate; In 1,4-dioxane; Reflux; Inert atmosphere;

Reference yield: 91.0%

1-methoxycarbonyl-3-methylbenzene (99-36-5) + bis(pinacol)diborane (73183-34-3) → methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (929626-17-5)

Guidance literature:

bis(pinacol)diborane; With C₂₄H₂₈ClIrN₂O; In n-heptane; isopropyl alcohol; at 75 ℃; for 1h; Sealed tube; Inert atmosphere;

1-methoxycarbonyl-3-methylbenzene; In n-heptane; isopropyl alcohol; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04210

Reference yield: 90.0%

methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (929626-17-5) + methyl iodide (74-88-4) → methyl 3,5-dimethylbenzoate (25081-39-4)

Guidance literature:

With C₂₁H₃₀ClNPPd; potassium tert-butylate; In tert-Amyl alcohol; at 65 ℃; for 18h; Sealed tube; Inert atmosphere; Glovebox;

DOI:10.1021/acs.orglett.9b00025

upstream raw materials:

1-methoxycarbonyl-3-methylbenzene

bis(pinacol)diborane

Downstream raw materials:

(3-methoxycarbonyl-5-methyl-phenyl)boronic acid

methyl 3-bromo-5-methylbenzoate

methyl 3-chloro-5-methylbenzoate

methyl 5-methyl-3-cyanobenzoate

Refernces

• 1、 Slack, Eric D.,Colacot, Thomas J.. "Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics". supporting information. p. 1561 - 1565. Retrieved 2021/02/20.
• 2、 Gao, Pengcheng,Szostak, Michal. "Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation". supporting information. p. 6010 - 6015. Retrieved 2020/07/30.