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

Base Information

• Chemical Name: Methyl 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 1073371-99-9
• Molecular Formula: C14H19BO5
• Molecular Weight: 278.113
• Hs Code.: 2934999090
• European Community (EC) Number: 691-570-5
• DSSTox Substance ID: DTXSID90592146
• Wikidata: Q82486095
• Mol file: 1073371-99-9.mol

Synonyms:1073371-99-9;Methyl 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;3-HYDROXY-4-METHOXYCARBONYLPHENYLBORONIC ACID, PINACOL ESTER;3-Hydroxy-4-methoxycarbonylphenylboronic acid pinacol ester;MFCD08458200;SCHEMBL2697552;YSZC1595;DTXSID90592146;SRYGMLVCVMGUTB-UHFFFAOYSA-N;YSB37199;AKOS015960150;Methyl2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;FS-5869;SY029124;DB-112065;CS-0100676;NS00015793;W18499;A895460;J-001886;Methyl 2-hydroxybenzoate-4-boronic acid pinacol ester;3-Hydroxy-4-(methoxycarbonyl)phenylboronic acid pinacol ester;methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)salicylate;3-Hydroxy-4-methoxycarbonylphenylboronic acid pinacol ester, AldrichCPR;Benzoic acid, 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester

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

Chemical Property:

• Boiling Point: 383.9±32.0 °C(Predicted)
• PKA: 9.80±0.10(Predicted)
• PSA: 64.99000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 1.47800
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 278.1325539
• Heavy Atom Count: 20
• Complexity: 366

Purity/Quality:

97% ^*data from raw suppliers

3-Hydroxy-4-methoxycarbonylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)C(=O)OC)O
• Uses: 3-Hydroxy-4-methoxycarbonylphenylboronic acid, pinacol ester

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

There total 6 articles about Methyl 2-hydroxy-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: 81.0%

methyl 4-iodosalicylate (18179-39-0) + bis(pinacol)diborane (73183-34-3) → methyl 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1073371-99-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 20 - 120 ℃; for 16.5h; Inert atmosphere;

DOI:10.1021/ja503296c

Reference yield: 80.0%

bis(pinacol)diborane (73183-34-3) + 2-hydroxy-4-trifluoromethanesulfonyloxybenzoic acid methyl ester (149878-72-8) → methyl 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1073371-99-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 100 ℃; for 3.5h;

DOI:10.1016/j.ejmech.2020.112770

Reference yield: 41.1%

4-bromo-2-Hydroxybenzoic Acid Methylester (22717-56-2) + bis(pinacol)diborane (73183-34-3) → methyl 2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1073371-99-9)

Guidance literature:

4-bromo-2-Hydroxybenzoic Acid Methylester; bis(pinacol)diborane; With potassium acetate; In 1,4-dioxane; for 0.166667h; Inert atmosphere;

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 60 - 80 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2015.03.010

upstream raw materials:

4-hydroxysalicylic acid

methyl 2,4-dihydroxybenzoate

bis(pinacol)diborane

2-hydroxy-4-trifluoromethanesulfonyloxybenzoic acid methyl ester

Downstream raw materials:

methyl 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]-2-hydroxybenzoate

methyl 4-[5-(2,2,3,3,13,13-hexamethyl-11-oxo-4,7,12-trioxa-10-aza-3-silatetradecan-10-yl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-hydroxybenzoate

methyl 4-(5-{[(tert-butoxy)carbonyl][2-(2-hydroxyethoxy)ethyl]amino}pyrazolo[1,5-a]pyrimidin-3-yl)-2-hydroxybenzoate

C₂₈H₃₇N₅O₈