2-Ethoxycarbonylphenylboronic acid

Base Information

• Chemical Name: 2-Ethoxycarbonylphenylboronic acid
• CAS No.: 380430-53-5
• Molecular Formula: C9H11BO4
• Molecular Weight: 193.995
• Hs Code.: 29319090
• European Community (EC) Number: 670-416-0
• UNII: B5E3T39L3Q
• DSSTox Substance ID: DTXSID70378440
• Nikkaji Number: J3.454.232E
• Wikidata: Q72471346
• ChEMBL ID: CHEMBL3236886
• Mol file: 380430-53-5.mol

Synonyms:380430-53-5;2-Ethoxycarbonylphenylboronic acid;(2-(Ethoxycarbonyl)phenyl)boronic acid;2-Ethoxycarbonylbenzeneboronic acid;(2-ethoxycarbonylphenyl)boronic Acid;2-(ethoxycarbonyl)phenylboronic acid;Benzoic acid, 2-borono-, 1-ethyl ester;MFCD02179453;[2-(ethoxycarbonyl)phenyl]boronic acid;2-(ethoxycarbonyl)phenylboronicacid;1-Ethyl 2-boronobenzoate;SCHEMBL519974;B5E3T39L3Q;2-Ethoxycarbonylphenylboronicacid;CHEMBL3236886;AMY1600;DTXSID70378440;QZKVVOXAEBCLPZ-UHFFFAOYSA-N;2-ethoxycarbonyl-phenylboronic acid;2-ethoxycarbonylphenyl boronic acid;2-ethoxycarbonyl-benzeneboronic acid;2-(ethoxycarbonyl)benzeneboronic acid;2- ethoxycarbonyl-phenyl boronic acid;AKOS006220725;GS-6809;2-ETHOXYCARBOXYPHENYLBORONIC ACID;NCGC00249524-01;SY002451;2-(Dihydroxyboryl)benzoic acid ethyl ester;A6457;CS-0042759;E0877;FT-0678854;Q-102211

Chemical Property of 2-Ethoxycarbonylphenylboronic acid

Chemical Property:

• Vapor Pressure: 4.75E-06mmHg at 25°C
• Melting Point: 137 °C
• Refractive Index: 1.526
• Boiling Point: 367.5 °C at 760 mmHg
• PKA: 8.18±0.53(Predicted)
• Flash Point: 176.1 °C
• PSA: 66.76000
• Density: 1.21 g/cm³
• LogP: -0.45690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.0750390
• Heavy Atom Count: 14
• Complexity: 195

Purity/Quality:

98% ^*data from raw suppliers

2-Ethoxycarbonylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1C(=O)OCC)(O)O
• Uses: suzuki reaction Reactant for:Synthesis of embelin derivatives via Suzuki-Miyaura reaction, cross metathesis and Wittig olefinationAsymmetric cyclopropanation of alkenes with di-Me diazomalonate catalyzed by chiral diene-rhodium complexesPreparation of phenylalanines as selective AMPA- and kainate receptor ligandsPreparation of aryl pyrazinones via microwave-assisted palladium-catalyzed arylation of resin supported pyrazinones under simultaneous cooling conditionRegioselective preparation of (aryl)hydroxyquinolines via Suzuki-Miyaura cross-coupling with chloro(tosyloxy)quinoline under anhydrous conditions followed by nucleophilic deprotection of the tosyl group

Technology Process of 2-Ethoxycarbonylphenylboronic acid

There total 2 articles about 2-Ethoxycarbonylphenylboronic 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%

Trimethyl borate (121-43-7,63156-11-6) + ethyl 2-iodobenzoate (1829-28-3) + water (7732-18-5) → 2-(ethoxycarbonyl)phenylboronic acid (380430-53-5)

Guidance literature:

ethyl 2-iodobenzoate; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 1h;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

water; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/anie.201903561

Reference yield:

Triisopropyl borate (5419-55-6) + benzoic acid ethyl ester (93-89-0,99341-95-4) → 2-(ethoxycarbonyl)phenylboronic acid (380430-53-5)

Guidance literature:

Triisopropyl borate; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; hexane; at -73 ℃; for 0.333333h; Inert atmosphere;

benzoic acid ethyl ester; In tetrahydrofuran; hexane; at -73 ℃; for 3.66667h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; hexane; at -30 - -10 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.15227/orgsyn.081.0134

Reference yield: 100.0%

2-(ethoxycarbonyl)phenylboronic acid (380430-53-5) + 3,4-dibromothiophene (3141-26-2) → diethyl 2,2'-(thiophene-3,4-diyl)dibenzoate

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 100 ℃; for 16h; Inert atmosphere; Sealed tube;

upstream raw materials:

Triisopropyl borate

benzoic acid ethyl ester

Trimethyl borate

ethyl 2-iodobenzoate

Downstream raw materials:

2-[9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl]-benzoic acid ethyl ester

[CpFe(CO)2C₆H₄-2-C(O)OEt]

4-o-(ethoxycarbonyl)phenyl-8-tosyloxyquinoline

C₃₀H₂₂F₄O₄

Refernces

• 1、 Kristensen, Jesper Langgaard,Lysén, Morten,Veds?, Per,Begtrup, Mikael,Seidel, Günter,Fürstner, Alois. "Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates: 2-(5,5-Dimethyl-1,3,2-dioxaborinan-2-YL)Benzoic acid ethyl ester: [Benzoic acid, 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-, ethyl ester]". . p. 134 - 139. Retrieved 2017/09/16.