Ethyl 4-boronocinnamate

Base Information

• Chemical Name: Ethyl 4-boronocinnamate
• CAS No.: 850568-49-9
• Molecular Formula: C11H13BO4
• Molecular Weight: 220.033
• Hs Code.: 2931900090
• European Community (EC) Number: 690-442-6
• Wikidata: Q76313466
• Mol file: 850568-49-9.mol

Synonyms:Ethyl 4-boronocinnamate;850568-49-9;(E)-(4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid;4-(E-3-Ethoxy-3-oxo-1-propen-1-yl)phenylboronic acid;[4-[(E)-3-ethoxy-3-oxoprop-1-enyl]phenyl]boronic acid;945837-75-2;4-(TRANS-3-ETHOXY-3-OXO-1-PROPEN-1-YL)BENZENEBORONIC ACID;4-(3-ETHOXY-3-OXOPROP-1-ENYL)PHENYLBORONIC ACID;(4-(3-Ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid;[4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl]boronic acid;SCHEMBL767758;SCHEMBL767759;[4-(E-3-Ethoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid;OVNZUEJWYIMMSW-VMPITWQZSA-N;MFCD04115651;AKOS015838770;AM87250;AS-58052;CS-0174621;I12499;4-(AMINOMETHYL)-CYCLOHEXANECARBOXYLICACID;A863744;(E)-4-(3-ethoxy-3-oxoprop-1-enyl)phenylboronic acid;4-(E-3-Ethoxy-3-oxo-1-propen-1-yl)benzeneboronic acid;{4-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]phenyl}boronic acid

Chemical Property of Ethyl 4-boronocinnamate

Chemical Property:

• Vapor Pressure: 3.27E-07mmHg at 25°C
• Melting Point: 130-134 °C
• Refractive Index: 1.539
• Boiling Point: 402.8 °C at 760 mmHg
• Flash Point: 197.4 °C
• PSA: 66.76000
• Density: 1.18 g/cm³
• LogP: -0.05730
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 220.0906891
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

98%Min ^*data from raw suppliers

4-(E-3-Ethoxy-3-oxo-1-propen-1-yl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C=CC(=O)OCC)(O)O
• Isomeric SMILES: B(C1=CC=C(C=C1)/C=C/C(=O)OCC)(O)O

Technology Process of Ethyl 4-boronocinnamate

There total 2 articles about Ethyl 4-boronocinnamate 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: 80.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 4-formylphenylboronic acid, (87199-17-5) → (E)-(4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid (850568-49-9)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at 0 - 20 ℃; for 0.666667h; Inert atmosphere;

4-formylphenylboronic acid,; In acetonitrile; at 20 ℃; for 3h; Time; Inert atmosphere;

Reference yield: 80.0%

4-formylphenylboronic acid, (87199-17-5) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → (E)-(4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid (850568-49-9)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1002/jccs.200500150

Reference yield: 49.0%

(E)-(4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)boronic acid (850568-49-9) + benzyl (2E,4E)-octa-2,4-dienoate + m-Chlorobenzaldehyde (587-04-2) → C33H35ClO5 + C33H35ClO5

Guidance literature:

With lithium hydroxide monohydrate; [RhCl((R,R)-Ph-tfb(*))]2; In water; N,N-dimethyl-formamide; at 0 ℃; Overall yield = 65 percentSpectr.; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c05427

upstream raw materials:

4-formylphenylboronic acid,

ethyl (triphenylphosphoranylidene)acetate

diethoxyphosphoryl-acetic acid ethyl ester

Downstream raw materials:

(E/Z)-ethyl 2-azido-3-(4-boronophenyl)acrylate

C₁₁H₁₆BNO₄

(E)-ethyl 3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate

(E)-ethyl 3-(4-iodophenyl)prop-2-enoate

Refernces

• 1、 Chang, Meng-Yang,Lin, Chun-Yu,Sun, Pei-Pei. "Synthesis of phenylalanine analogs". . p. 1061 - 1067. Retrieved 2007/10/03.