4-Carboxyphenylboronic acid

Base Information

• Chemical Name: 4-Carboxyphenylboronic acid
• CAS No.: 14047-29-1
• Molecular Formula: C7H7BO4
• Molecular Weight: 165.941
• Hs Code.: 29319090
• NSC Number: 221170
• UNII: XQQ1T11DYK
• DSSTox Substance ID: DTXSID20930850
• Nikkaji Number: J54.862F
• Wikipedia: 4-carboxyphenylboronic acid
• Wikidata: Q27094084
• Metabolomics Workbench ID: 147673
• ChEMBL ID: CHEMBL82324
• Mol file: 14047-29-1.mol

Synonyms:4-Carboxyphenylboronic acid;14047-29-1;4-Boronobenzoic acid;4-Carboxybenzeneboronic Acid;Benzoic acid, 4-borono-;4-(Dihydroxyboryl)benzoic acid;4-(dihydroxyboranyl)benzoic acid;MFCD00151801;C7H7BO4;Benzeneboronic acid, p-carboxy-;Benzoic acid, p-borono-;4-Carboxyphenylboronicacid;4-phenylester boronic acid;CHEMBL82324;NSC-221170;Aurora 14935;4-Boronobenzoicacid;WLN: VHOR DBQQ;4-carboxyphenyboronic acid;4-Carboxypenylboronic Acid;4-carboxy-phenylboronic acid;4-carboxyphenyl boronic acid;4-carboxy-benzeneboronic acid;4-carboxybenzene boronic acid;4-carboxybenzene-boronic acid;(4-carboxyphenyl)boronic acid;4-carboxy phenyl boronic acid;4-carboxy-phenyl boronic acid;SCHEMBL128618;4-(Dihydroxyboryl) benzoic acid;DTXSID20930850;HMS3604I11;4-CARBOXYLPHENYLBORONIC ACID;BCP03528;4-Carboxyphenylboronic acid (contains varying amounts of Anhydride);4-hydroxycarbonyl-phenyl boronic acid;AC-981;BDBM50067885;NSC221170;STK499958;4-dihydroxyBoranyl-benzoic acid anion;AKOS000264728;AB03988;AS-2261;CS-W019665;DB03140;NCGC00092012-01;NCGC00092012-02;SY001195;AM20020472;BB 0323402;FT-0600906;EN300-29555;4-boronobenzoic acid;AF-399/25108028;Q-102227;Q27094084;F1371-0202;Z285136920

Chemical Property of 4-Carboxyphenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white to light beige powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 220 °C (dec.)(lit.)
• Refractive Index: 1.585
• Boiling Point: 406.383 °C at 760 mmHg
• PKA: 4.08±0.10(Predicted)
• Flash Point: 199.574 °C
• PSA: 77.76000
• Density: 1.406 g/cm³
• LogP: -0.93540
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 166.0437389
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

4-Carboxyphenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(C1=CC=C(C=C1)C(=O)O)(O)O
• Description: 4-Carboxyphenylboronic acid is a highly versatile reagent. It is a reagent used in various reactions including condensation reactions with stabilizer chains at the surface of polystyrene latex, Suzuki coupling reactions, esterification, derivatization of polyvinylamine, synthesis of isotopically labeled mercury and functionalization of poly-SiNW for detection of dopamine. It is reagents used for Suzuki-Miyaura cross-coupling, induction of pH sensitivity on fluorescence lifetime of quantum dots by NIR fluorescent dyes, bio-supported palladium nanoparticles as phosphine-free catalyst for Suzuki reaction in water and Chan-Lam-type Copper (Cu)-catalyzed S-arylation with aryl boronic acids at room temperature. It is reagents used for the preparation of isoquinolones via regioselective Suzuki-Miyaura cross-coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation, amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors, phenols via visible-light initiated aerobic oxidative hydroxylation of arylboronic acids using air as oxidant catalyzed by Ruthenium (Ru)-complex, glucose sensitive boronic acid-bearing block copolymers, trisulfonated calixarene upper-rim sulfonamido derivatives and their complexation with the trimethyllysine epigenetic mark. It can also be used as a corrosion inhibitor for steel.
• Uses: suzuki reaction 4-Carboxyphenylboronic acid is a reagent used in suzuki coupling reactions. Intermediates of Liquid Crystals

Technology Process of 4-Carboxyphenylboronic acid

There total 30 articles about 4-Carboxyphenylboronic 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: 96.5%

4-methoxycarbonylphenylboronic acid (99768-12-4) → 4-carboxyphenylboronic acid (14047-29-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 3h; Concentration; Reagent/catalyst; Reflux;

Reference yield: 95.8%

(4-(diisopropylcarbamoyl)phenyl)boronic acid (850568-33-1) → 4-carboxyphenylboronic acid (14047-29-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 2h; Time;

Reference yield: 95.2%

p-ethoxycarbonylphenylboronic acid (4334-88-7) → 4-carboxyphenylboronic acid (14047-29-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; for 3h; Concentration; Reagent/catalyst; Reflux;

upstream raw materials:

4-methylphenylboronic acid

3-Formylphenylboronic acid

4-Bromobenzoic acid

4-formylphenylboronic acid,

Downstream raw materials:

4-dihydroxyboranyl-mandelonitrile

(4-carboxy-2-nitro phenyl)dihydroxy borane

benzoic acid

4-n-butylaminocarbonylphenylboronic acid

Refernces

• 1、 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". . p. 9765 - 9771. Retrieved 2017.
• 2、 Li, Chong,Hu, Zhe,Aldred, Matthew P.,Zhao, Ling-Xi,Yan, Hui,Zhang, Guo-Feng,Huang, Zhen-Li,Li, Alexander D. Q.,Zhu, Ming-Qiang. "Water-soluble polymeric photoswitching dyads impart super-resolution lysosome highlighters". . p. 8594 - 8601. Retrieved 2014.
• 3、 -. "Preparation method of anti-tumor drug Acalabrutinib key intermediate". . . Retrieved 2019/01/14.
• 4、 -. "A N, 6 diphenyl pyrimidine -4 - amine Bcr - Abl inhibitor and its preparation method and application (by machine translation)". . . Retrieved 2017/04/28.