5-Methoxycarbonyl-2-methylphenylboronic acid

Base Information

• Chemical Name: 5-Methoxycarbonyl-2-methylphenylboronic acid
• CAS No.: 876189-18-3
• Molecular Formula: C9H11BO4
• Molecular Weight: 193.995
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID30478955
• Nikkaji Number: J2.277.270H
• Wikidata: Q82312717
• Mol file: 876189-18-3.mol

Synonyms:876189-18-3;5-METHOXYCARBONYL-2-METHYLPHENYLBORONIC ACID;(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid;(5-methoxycarbonyl-2-methylphenyl)boronic acid;[5-(methoxycarbonyl)-2-methylphenyl]boronic acid;SCHEMBL2417938;DTXSID30478955;Methyl 3-borono-4-methylbenzoate;PGNCKSWGMBDXGE-UHFFFAOYSA-N;BCP24695;BKB18918;MFCD11111429;AKOS006308731;AS-17689;3-borono-4-methyl-benzoic acid methyl ester;5-methoxycarbonyl-2-methylbenzeneboronic acid;CS-0042974;EN300-303788;Y10593;J-517700

Chemical Property of 5-Methoxycarbonyl-2-methylphenylboronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Boiling Point: 375.353 °C at 760 mmHg
• PKA: 7.81±0.58(Predicted)
• Flash Point: 180.807 °C
• PSA: 66.76000
• Density: 1.219 g/cm³
• LogP: -0.53860
• Storage Temp.: Room temperature.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.0750390
• Heavy Atom Count: 14
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxycarbonyl-2-methylphenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=CC(=C1)C(=O)OC)C)(O)O

Technology Process of 5-Methoxycarbonyl-2-methylphenylboronic acid

There total 6 articles about 5-Methoxycarbonyl-2-methylphenylboronic acid 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: 98.0%

methanol (67-56-1) + 3-carboxy-6-methylphenylboronic acid (170230-88-3) → [5-(methoxycarbonyl)-2-methylphenyl]boronic acid (876189-18-3)

Guidance literature:

With sulfuric acid; In water; for 16h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201510321

Reference yield: 95.0%

sulfuric acid (7664-93-9) + methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (882679-40-5) → [5-(methoxycarbonyl)-2-methylphenyl]boronic acid (876189-18-3)

Guidance literature:

With methanol; for 12h; Reflux;

Reference yield: 71.0%

methyl 3-iodo-4-methylbenzoate (90347-66-3) → [5-(methoxycarbonyl)-2-methylphenyl]boronic acid (876189-18-3)

Guidance literature:

methyl 3-iodo-4-methylbenzoate; With Bis<2-(N,N-dimethylamino)aethyl>aether; isopropylmagnesium chloride; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran;

DOI:10.1021/ol052704p

upstream raw materials:

methyl 3-iodo-4-methylbenzoate

methanol

3-carboxy-6-methylphenylboronic acid

3-bromo-4-methylbenzoic acid

Downstream raw materials:

methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-methylbenzoate

N-cyclopropyl-4-methyl-3-{1-oxo-2-[3-(2-pyrrolidin-1-ylethoxy)benzyl]-1,2-dihydroisoquinolin-6-yl}benzamide

4-{4-[6-(5-methoxycarbonyl-2-methylphenyl)-1-oxo-1H-isoquinolin-2-ylmethyl]phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

N-cyclopropyl-3-(2-(4-((2-(dimethylamino)ethyl)(methyl)carbamoyl)benzyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide

Refernces

• 1、 Akgun, Burcin,Hall, Dennis G.. "Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation". supporting information. p. 3909 - 3913. Retrieved 2016/03/19.
• 2、 Pal, Arnab,Berube, Marie,Hall, Dennis G.. "Design, synthesis, and screening of a library of peptidyl bis(boroxoles) as oligosaccharide receptors in water: Identification of a receptor for the tumor marker TF-antigen disaccharide". supporting information; experimental part. p. 1492 - 1495. Retrieved 2010/06/16.