4-(Carboxyvin-2-YL)phenylboronic acid

Base Information

• Chemical Name: 4-(Carboxyvin-2-YL)phenylboronic acid
• CAS No.: 159896-15-8
• Molecular Formula: C9H9BO4
• Molecular Weight: 191.979
• Hs Code.: 2931900090
• European Community (EC) Number: 687-142-2
• Wikidata: Q27093489
• Metabolomics Workbench ID: 147084
• ChEMBL ID: CHEMBL139928
• Mol file: 159896-15-8.mol

Synonyms:159896-15-8;(E)-3-(4-Boronophenyl)acrylic acid;151169-68-5;3-(4-Boronophenyl)Acrylic Acid;4-(2-Carboxyvinyl)phenylboronic acid;4-(E-2-Carboxyvinyl)phenylboronic acid;4-(CARBOXYVIN-2-YL)PHENYLBORONIC ACID;4-(2-CARBOXYVINYL)BENZENEBORONIC ACID;(E)-3-(4-boronophenyl)prop-2-enoic acid;CHEMBL139928;4-phenylpropylester boronic acid;4-(TRANS-2-CARBOXYVINYL)PHENYLBORONIC ACID;4-(E-2-Carboxyvinyl)benzeneboronic acid;2-Propenoic acid, 3-(4-boronophenyl)-;(2E)-3-[4-(DIHYDROXYBORANYL)PHENYL]PROP-2-ENOIC ACID;4-Boronocinnamic acid;D08LLS;3-(4-Boronophenyl)AcrylicAcid;IEMLKNHGGSYOMP-ZZXKWVIFSA-N;AMY33058;4-(2-Carboxyvinyl)phenylboronicacid;4-(2-Carboxyvinyl)benzeneboronicacid;BDBM50067886;MFCD01075704;AKOS004116400;DB02503;AS-55248;PD007916;[4-(e-2-carboxyvinyl)phenyl]boronic acid;4-[(E)-2-Carboxyvinyl]benzeneboronic acid;(2E)-3-(4-Boronophenyl)-2-propenoic acid;4-(trans-2-carboxyvinyl) phenylboronic acid;CS-0060215;W17849;2-Propenoic acid, 3-(4-boronophenyl)-, (2E)-;A809128;A883260;Q27093489

Chemical Property of 4-(Carboxyvin-2-YL)phenylboronic acid

Chemical Property:

• Melting Point: 222-224 °C
• Boiling Point: 439 °C at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 219.3 °C
• PSA: 77.76000
• Density: 1.33 g/cm³
• LogP: -0.53580
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 192.0593889
• Heavy Atom Count: 14
• Complexity: 219

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C=CC(=O)O)(O)O
• Isomeric SMILES: B(C1=CC=C(C=C1)/C=C/C(=O)O)(O)O
• Uses: Reactant for:Preparation of nickel thiocyanate pyridylphenylpropenate polymeric complex

Technology Process of 4-(Carboxyvin-2-YL)phenylboronic acid

There total 1 articles about 4-(Carboxyvin-2-YL)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: 92.0%

malonic acid (141-82-2) + 4-formylphenylboronic acid, (87199-17-5) → trans-4-(2-carboxyethenyl)benzeneboronic acid (159896-15-8)

Guidance literature:

With piperidine; In pyridine; malonic acid was added to soln. p-formylbenzeneboronic acid in pyridine at 25°C, piperidine was added and refluxed under N2 for 13 h; solvent was removed in vacuo, residue was taken up in water and acidified with concd. HCl, ppt. was collected, washed with water and dried in vacuo; elem. anal.;

DOI:10.1021/ic0605367

Reference yield: 90.0%

6-chloro-N-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine + trans-4-(2-carboxyethenyl)benzeneboronic acid (159896-15-8) → (E)-3-(4-(4-((4-fluorophenyl)amino)pyrido[3,2-d]pyrimidin-6-yl)phenyl)acrylic acid

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In 1,4-dioxane; water; for 2h; Reflux; Inert atmosphere;

DOI:10.3390/molecules25184318

Reference yield: 33.0%

bromobenzene (108-86-1,52753-63-6) + trans-4-(2-carboxyethenyl)benzeneboronic acid (159896-15-8) → (2E)-3-(1,1'-biphenyl-4-yl)acrylic acid (13026-23-8,88241-67-2,88241-65-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In ethanol; water; toluene; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c8md00432c

upstream raw materials:

malonic acid

4-formylphenylboronic acid,

Downstream raw materials:

(2E)-3-(1,1'-biphenyl-4-yl)acrylic acid

Refernces

• 1、 Sekiya, Ryo,Nishikiori, Shin-Ichi,Ogura, Katsuyuki. "Coordination framework hosts consisting of 4-pyridyl-substituted carboxylic acid (PCA) dimers and 1D chains of Ni2+ and SCN-: A rational structural extension toward coordination framework hosts with large rectangular cavities". . p. 9233 - 9244. Retrieved 2006.