4-(2-Ethoxycarbonylethyl)phenylboronic acid

Base Information

• Chemical Name: 4-(2-Ethoxycarbonylethyl)phenylboronic acid
• CAS No.: 660440-57-3
• Molecular Formula: C11H15BO4
• Molecular Weight: 222.049
• Hs Code.: 2931900090
• European Community (EC) Number: 691-017-8
• DSSTox Substance ID: DTXSID60397322
• Wikidata: Q82198573
• Mol file: 660440-57-3.mol

Synonyms:660440-57-3;4-(2-Ethoxycarbonylethyl)phenylboronic acid;[4-(2-ethoxycarbonylethyl)phenyl]boronic Acid;[4-(3-ethoxy-3-oxopropyl)phenyl]boronic acid;4-(3-ethoxy-3-oxopropyl)phenylboronic acid;(4-(3-Ethoxy-3-oxopropyl)phenyl)boronic acid;4-[2-ethoxycarbonylethyl]phenylboronic acid;(4-(2-ethoxycarbonylethyl)phenyl)boronic acid;Ethyl 3-(4-boronophenyl)propionate;4-(2-Ethoxycarbonylethyl)benzeneboronic acid;4-(3-Ethoxy-3-oxopropyl)benzeneboronic acid;SCHEMBL4630;DTXSID60397322;PRCOGZNDLWXGHB-UHFFFAOYSA-N;MFCD04115652;AKOS015838767;(2-HYDROXYPHENYL)PHOSPHONICACID;AB20332;AM87128;AS-66505;4-(2-carbethoxyethyl)benzene-boronic acid;[4(2-ethoxycarbonylethyl)phenyl]boronic acid;4-(2-ethoxycarbonylethyl)phenyl boronic acid;CS-0174556;FT-0687775;4-(2-ethoxycarbonyl-ethyl)-phenylboronic acid;4-(2-ethoxycarbonyl-ethyl)phenyl boronic acid;I12500;EN300-7390273

Chemical Property of 4-(2-Ethoxycarbonylethyl)phenylboronic acid

Chemical Property:

• Vapor Pressure: 3.76E-06mmHg at 25°C
• Melting Point: 80-84°C
• Refractive Index: 1.518
• Boiling Point: 370.7°C at 760 mmHg
• PKA: 8.66±0.16(Predicted)
• Flash Point: 178°C
• PSA: 66.76000
• Density: 1.15g/cm³
• LogP: -0.13790
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 222.1063391
• Heavy Atom Count: 16
• Complexity: 212

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(2-Ethoxycarbonylethyl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• 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=C(C=C1)CCC(=O)OCC)(O)O
• Uses: 4-(2-Ethoxycarbonylethyl)phenylboronic acid

Technology Process of 4-(2-Ethoxycarbonylethyl)phenylboronic acid

There total 3 articles about 4-(2-Ethoxycarbonylethyl)phenylboronic 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: 76.0%

ethyl 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]propanoate (490035-79-5) → (4-(3-ethoxy-3-oxopropyl)phenyl)boronic acid (660440-57-3)

Guidance literature:

ethyl 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]propanoate; With 2,2'-iminobis[ethanol]; In isopropyl alcohol; at 0 ℃; for 3h;

With sulfuric acid; In diethyl ether;

DOI:10.1016/S0022-328X(02)01383-9

Reference yield:

ethanol (64-17-5) + 4-(2-carboxyethyl)benzeneboronic acid (166316-48-9) → (4-(3-ethoxy-3-oxopropyl)phenyl)boronic acid (660440-57-3)

Guidance literature:

With hydrogenchloride; for 24h; Heating / reflux;

Reference yield:

3-(4-bromo-phenyl)-propionic acid ethyl ester (40640-98-0) → (4-(3-ethoxy-3-oxopropyl)phenyl)boronic acid (660440-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / PdCl₂(dppf); potassium acetate / dimethylsulfoxide / 27 h / 80 °C

2.1: diethanolamine / propan-2-ol / 3 h / 0 °C

2.2: 76 percent / aq. sulfuric acid / diethyl ether

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; 2,2'-iminobis[ethanol]; In dimethyl sulfoxide; isopropyl alcohol;

DOI:10.1016/S0022-328X(02)01383-9

upstream raw materials:

ethyl 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]propanoate

3-(4-bromo-phenyl)-propionic acid ethyl ester

ethanol

4-(2-carboxyethyl)benzeneboronic acid

Downstream raw materials:

methyl 3-(4-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}phenyl)propanoate

3-[4-((1S)-3-oxo-cydopentyl)-phenyl]-propionic acid ethyl ester

C₂₄H₂₆N₂O₄

4-{3-[4-(4-methoxyphenyl)phenyl]propanoyl}amino-1-methylpyrrole-3-carboxylic acid

Refernces

• 1、 Zaidlewicz, Marek,Wolan, Andrzej. "Syntheses with organoboranes. XIII. Synthesis of ω-(4-bromophenyl)alkanoic acids and their borylation". . p. 129 - 135. Retrieved 2007/10/03.