4-Ethoxycarbonylphenylboronic acid

Base Information

• Chemical Name: 4-Ethoxycarbonylphenylboronic acid
• CAS No.: 4334-88-7
• Molecular Formula: C9H11BO4
• Molecular Weight: 193.995
• Hs Code.: 29163990
• European Community (EC) Number: 670-243-0
• UNII: LA4EMV9J6S
• DSSTox Substance ID: DTXSID10370241
• Nikkaji Number: J1.787.871I
• Wikidata: Q72471414
• Mol file: 4334-88-7.mol

Synonyms:4-Ethoxycarbonylphenylboronic acid;4334-88-7;(4-Ethoxycarbonylphenyl)Boronic Acid;4-(ethoxycarbonyl)phenylboronic acid;(4-(ethoxycarbonyl)phenyl)boronic acid;4-(ethoxycarbonyl)benzeneboronic acid;MFCD02179441;Benzoic acid, 4-borono-, 1-ethyl ester;4-Ethoxycarbonylbenzeneboronic acid;[4-(ethoxycarbonyl)phenyl]boronic acid;Ethyl 4-boronobenzoate;p-ethoxycarbonylphenylboronic acid;4-Ethoxy carbonyl phenylboronic acid;LA4EMV9J6S;SCHEMBL5122;4-Athyloxycarbonylphenylboronsaure;DTXSID10370241;4-Ethoxycarbonylphenylboronoc acid;ZLNFACCFYUFTLD-UHFFFAOYSA-N;4-ethoxycarbonyl phenylboronic acid;4-ethoxycarbonyl-phenylboronic acid;4-ethoxycarbonylphenyl boronic acid;(4-Ethoxycarbonylphenyl)BoronicAcid;4-ethoxycarbonyl phenyl boronic acid;4-ethoxycarbonyl-phenyl boronic acid;(4-ethoxycarbonylphenyl) boronic acid;AKOS004119211;Benzoic acid, p-borono-, ethyl ester;4-(2-ethoxycarbonyl)phenylboronic acid;4-(ethoxycarbonyl)-phenyl boronic acid;AB11136;AS-2307;CS-W000930;Benzoic acid, p-borono-, 1-ethyl ester;NCGC00249522-01;SY012740;4-(Dihydroxyboryl)benzoic acid ethyl ester;{4-[(ethyloxy)carbonyl]phenyl}boronic acid;AM20060342;E0868;FT-0601788;A826253;J-515276

Chemical Property of 4-Ethoxycarbonylphenylboronic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.14E-05mmHg at 25°C
• Melting Point: 184-189 °C
• Refractive Index: 1.526
• Boiling Point: 355.5 °C at 760 mmHg
• PKA: 7.69±0.10(Predicted)
• Flash Point: 168.8 °C
• PSA: 66.76000
• Density: 1.21 g/cm³
• LogP: -0.45690
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• 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: 187

Purity/Quality:

99% ^*data from raw suppliers

4-Ethoxycarbonylphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 36/37/38-26-22
• Safety Statements: 37/39-26-45-36/37-28

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C(=O)OCC)(O)O
• Uses: Reactant involved in:? ;Oxidative hydroxylation for the preparation of phenols1? ;Homolytic aromatic substitution2? ;Cross-coupling with α-bromocarbonyl compounds3? ;Suzuki-coupling reaction with quinoline carboxylates4? ;Trifluoromethylation5? ;Carbometalation of ynamides6 suzuki reaction 4-(Ethoxycarbonyl)benzeneboronic acid is used as a reactant involved in oxidative hydroxylation for the preparation of phenols, homolytic aromatic substitution, cross-coupling with α-bromocarbonyl compounds, Suzuki-coupling reaction with quinoline carboxylates, trifluoromethylation and carbometalation of ynamides.

Technology Process of 4-Ethoxycarbonylphenylboronic acid

There total 12 articles about 4-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: 95.2%

ethanol (64-17-5) + 4-carboxyphenylboronic acid (14047-29-1) → p-ethoxycarbonylphenylboronic acid (4334-88-7)

Guidance literature:

With thionyl chloride; at 50 - 65 ℃; Autoclave; Industrial scale;

Reference yield: 94.4%

boric acid tributyl ester (688-74-4) + 4-iodobenzoic acid ethyl ester (51934-41-9) → p-ethoxycarbonylphenylboronic acid (4334-88-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Concentration;

Reference yield: 92.0%

Triisopropyl borate (5419-55-6) + 4-iodobenzoic acid ethyl ester (51934-41-9) → p-ethoxycarbonylphenylboronic acid (4334-88-7)

Guidance literature:

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

upstream raw materials:

4-iodobenzoic acid ethyl ester

4-carboxyphenylboronic acid

sulfuric acid

ethanol

Downstream raw materials:

1-(4-ethoxylcarbonylphenyl)-1-octyne

diethyl biphenyl-4,4'-dicarboxylate

ethyl 4'-acetyl-1,1'-biphenyl-4-carboxylate

ethyl 4'-nitro-(1,1'-biphenyl)-4-carboxylate

Refernces

• 1、 Arman, Hadi D.,Dang, Hang. T.,Haug, Graham C.,He, Ru,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Schanze, Kirk S.. "Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds". supporting information. . Retrieved 2020/02/04.
• 2、 Verma, Ashish,De, Dinesh,Tomar, Kapil,Bharadwaj, Parimal K.. "An Amine Functionalized Metal-Organic Framework as an Effective Catalyst for Conversion of CO2 and Biginelli Reactions". supporting information. p. 9765 - 9771. Retrieved 2017/08/26.