4-Methoxycarbonylphenylboronic acid

Base Information

• Chemical Name: 4-Methoxycarbonylphenylboronic acid
• CAS No.: 99768-12-4
• Molecular Formula: C8H9BO4
• Molecular Weight: 179.968
• Hs Code.: 29163990
• European Community (EC) Number: 619-459-9
• DSSTox Substance ID: DTXSID40370259
• Nikkaji Number: J806.560H
• Wikidata: Q72488374
• ChEMBL ID: CHEMBL1824169
• Mol file: 99768-12-4.mol

Synonyms:99768-12-4;4-Methoxycarbonylphenylboronic acid;4-(Methoxycarbonyl)phenylboronic acid;Methyl 4-boronobenzoate;(4-(Methoxycarbonyl)phenyl)boronic acid;(4-Methoxycarbonylphenyl)boronic acid;4-(Methoxycarbonyl)benzeneboronic Acid;[4-(methoxycarbonyl)phenyl]boronic acid;4-Methoxycarbonylbenzeneboronic acid;4-(methoxycabonyl)phenylboronic acid;p-(methoxycarbonyl)phenylboronic acid;4-carbomethoxyphenylboronic acid;4-methoxycarbonyl phenyl boronic acid;MFCD01632203;Methyl4-boronobenzoate;Methyl 4-(Dihydroxyboranyl)Benzoate;SCHEMBL140644;CHEMBL1824169;p-carbomethoxyphenyl boronic acid;DTXSID40370259;Methyl 4-(dihydroxyboryl)benzoate;p-methoxycarbonylphenylboronic acid;PQCXFUXRTRESBD-UHFFFAOYSA-N;4-(carbomethoxy)phenylboronic acid;4-methoxycarbonyl phenylboronic acid;4-methoxycarbonyl-phenylboronic acid;4-methoxycarbonylphenyl boronic acid;4-methoxycarbonylphenyl-boronic acid;BCP03529;4-methoxycarbonyl-phenyl boronic acid;4-methoxycarbonyl-phenyl-boronic acid;STK503726;(4-methoxycarbonylphenyl)-boronic acid;4-(methoxycarbonyl) phenylboronic acid;4-(methoxycarbonyl)-phenylboronic acid;4-(methoxycarbonyl)phenyl-boronic acid;AKOS000264853;(4-(Methoxycarbonyl)phenyl)boronicacid;4-(Methoxycarbonyl)phenyl boronic acid;AB09470;AC-2895;AM62784;AS-2263;CS-W003977;(4-methoxycarbonyl-phenyl) boronic acid;4-(methoxycarbonyl) phenyl boronic acid;NCGC00249475-01;(4-(methoxycarbonyl)phenyl) boronic acid;[4-(methoxy carbonyl)phenyl]boronic acid;[4-(methoxycarbonyl)-phenyl]boronic acid;BP-11412;SY003283;Benzoic acid, 4-borono-, 1-methyl ester;{4-[(methyloxy)carbonyl]phenyl}boronic acid;A6989;FT-0601787;M1907;EN300-68541;J-515664;Z1095162714;4-(methoxycarbonyl)phenylboronic acid;4-Methoxycarbonylphenylboronic Acid

Chemical Property of 4-Methoxycarbonylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.29E-05mmHg at 25°C
• Melting Point: 197-200 °C(lit.)
• Refractive Index: 1.532
• Boiling Point: 345.8 °C at 760 mmHg
• PKA: 7.69±0.10(Predicted)
• Flash Point: 162.9 °C
• PSA: 66.76000
• Density: 1.25 g/cm³
• LogP: -0.84700
• Storage Temp.: 0-6°C
• Solubility.: Soluble in methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.0593889
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

98% ^*data from raw suppliers

4-Methoxycarbonylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C(=O)OC)(O)O
• Uses: 4-(Methoxycarbonyl)phenylboronic Acid is a reagent used for? ;Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence1 ? ;Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2 ? ;One-pot ipso-nitration of arylboronic acids3 ? ;Copper-catalyzed nitration4 ? ;Cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling5 ? ;Reagent used in Preparation of? ;Biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6? ? ;Chromenones and their suzuki reaction 4-(Methoxycarbonyl)phenylboronic Acid is used in the synthesis and evaluation of several organic compounds including that of 4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate which is a potent inhibitor of intracellular NAAA activity. Also used in the design and synthesis of BMS-955176 which is a potent, orally active second generation HIV-1 maturation inhibitor.

Technology Process of 4-Methoxycarbonylphenylboronic acid

There total 25 articles about 4-Methoxycarbonylphenylboronic 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: 99.0%

methanol (67-56-1) + 4-carboxyphenylboronic acid (14047-29-1) → 4-methoxycarbonylphenylboronic acid (99768-12-4)

Guidance literature:

With sulfuric acid; for 30h; Reflux;

DOI:10.1021/jacs.6b08176

Reference yield: 95.5%

Triisopropyl borate (5419-55-6) + 4-methoxycarbonylphenyl bromide (619-42-1) → 4-methoxycarbonylphenylboronic acid (99768-12-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

Reference yield: 94.8%

Triisopropyl borate (5419-55-6) + methyl 4-iodobenzoate (619-44-3) → 4-methoxycarbonylphenylboronic acid (99768-12-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Concentration; Reagent/catalyst;

upstream raw materials:

methanol

4-carboxyphenylboronic acid

methyl 4-iodobenzoate

diazomethyl-trimethyl-silane

Downstream raw materials:

dimethyl 4,4'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)dibenzoate

Refernces

• 1、 Kühl, Nikos,Leuthold, Mila M.,Behnam, Mira A. M.,Klein, Christian D.. "Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture". . p. 4567 - 4587. Retrieved 2021/05/06.
• 2、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.