2-Methoxycarbonylphenylboronic acid

Base Information

• Chemical Name: 2-Methoxycarbonylphenylboronic acid
• CAS No.: 374538-03-1
• Molecular Formula: C8H9BO4
• Molecular Weight: 179.968
• Hs Code.: 29163990
• European Community (EC) Number: 640-205-8
• DSSTox Substance ID: DTXSID40378497
• Nikkaji Number: J2.042.078B
• Wikidata: Q70000029
• Mol file: 374538-03-1.mol

Synonyms:2-Methoxycarbonylphenylboronic acid;374538-03-1;2-(Methoxycarbonyl)benzeneboronic Acid;2-(Methoxycarbonyl)phenylboronic Acid;(2-methoxycarbonylphenyl)boronic Acid;(2-(methoxycarbonyl)phenyl)boronic acid;[2-(methoxycarbonyl)phenyl]boronic acid;2-Methoxycarbonylphenylboronicacid;MFCD02179452;Benzene acid 2-methyl ester;SCHEMBL129359;DTXSID40378497;ODAXNYMENLFYMY-UHFFFAOYSA-N;2-methoxycarbonyl-phenylboronic acid;2-methoxycarbonylphenyl boronic acid;BCP27576;2,6-DIPHENYL-4-PIPERIDONEHCL;AKOS015852309;AB11160;AC-2662;AM62768;CS-W002908;DS-1775;(2-(methoxycarbonyl)phenyl) boronic acid;SY002450;Benzoic acid, 2-borono-, 1-methyl ester;A6398;FT-0608833;M1905;2-Methoxycarbonylphenylboronic acid, >=95.0%;EN300-101521;J-509857;Z1255391218

Chemical Property of 2-Methoxycarbonylphenylboronic acid

Chemical Property:

• Vapor Pressure: 8.89E-06mmHg at 25°C
• Melting Point: 90-96°C
• Refractive Index: 1.532
• Boiling Point: 359 °C at 760 mmHg
• PKA: 8.19±0.58(Predicted)
• Flash Point: 170.9 °C
• PSA: 66.76000
• Density: 1.25 g/cm³
• LogP: -0.84700
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°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: 183

Purity/Quality:

2-Methoxycarbonylphenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C(=O)OC)(O)O

Technology Process of 2-Methoxycarbonylphenylboronic acid

There total 4 articles about 2-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: 75.0%

o-iodo-methyl-benzoic acid (610-97-9) → 2-methoxycarbonylphenylboronic acid (374538-03-1)

Guidance literature:

o-iodo-methyl-benzoic acid; With Bis<2-(N,N-dimethylamino)aethyl>aether; isopropylmagnesium chloride; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran;

DOI:10.1021/ol052704p

Reference yield: 72.5%

hydrogenchloride (7647-01-0,15364-23-5) + Triisopropyl borate (5419-55-6) + 2-bromobenzoic acid methyl ester (610-94-6) → 2-methoxycarbonylphenylboronic acid (374538-03-1)

Guidance literature:

Triisopropyl borate; 2-bromobenzoic acid methyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -85 - -75 ℃; for 2h; Inert atmosphere;

hydrogenchloride; In water; at -20 - 5 ℃; pH=4 - 5;

Reference yield:

methyl chlorobenzoate (610-96-8) → 2-methoxycarbonylphenylboronic acid (374538-03-1)

Guidance literature:

With tetrahydroxydiboron; (chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)); potassium acetate; XPhos; In ethanol; at 80 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja303181m

upstream raw materials:

o-iodo-methyl-benzoic acid

methyl chlorobenzoate

2-bromobenzoic acid methyl ester

hydrogenchloride

Downstream raw materials:

2,3-diphenyl-1H-inden-1-one

2,3-bis (4-methoxyphenyl)-1H-inden-1-one

2-methyl-3-phenylinden-1-one

3-methyl-2-phenyl-inden-1-one

Refernces

• 1、 Molander, Gary A.,Trice, Sarah L. J.,Kennedy, Steven M.,Dreher, Spencer D.,Tudge, Matthew T.. "Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid". supporting information; experimental part. p. 11667 - 11673. Retrieved 2012/09/05.