4-Carboxyphenylboronic acid

4-Carboxyphenylboronic acid Basic information
Description Reference
Product Name:4-Carboxyphenylboronic acid
Synonyms:4-borono-benzoicaci;AKOS BRN-0008;RARECHEM AH PB 0147;TIMTEC-BB SBB003899;OTAVA-BB BB7110951390;P-CARBOXYPHENYLBORONIC ACID;ZERENEX ZX001647;4-(Dihydroxyboronyl)benzoic acid, 4-Boronobenzoic acid
CAS:14047-29-1
MF:C7H7BO4
MW:165.94
EINECS:604-189-6
Product Categories:Boric Acid| Boric Acid Ester| Potassium Trifluoroborate| carboxylic acid;Boronate Ester;B (Classes of Boron Compounds);organic or inorganic borate;Plant extract;Potassium Trifluoroborate;Substituted Boronic Acids;Heterocyclic Compounds;Boronic Acid;Aryl;Organoborons;CHIRAL CHEMICALS;Boronic Acids & Esters;Phenyls & Phenyl-Het;blocks;BoronicAcids;Carboxes;Boronic Acid series;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids
Mol File:14047-29-1.mol
4-Carboxyphenylboronic acid Structure
4-Carboxyphenylboronic acid Chemical Properties
Melting point 220 °C (dec.) (lit.)
Boiling point 406.4±47.0 °C(Predicted)
density 1.40±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form Powder
pka4.08±0.10(Predicted)
color Off-white to light beige
BRN 3031088
InChIInChI=1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)
InChIKeySIAVMDKGVRXFAX-UHFFFAOYSA-N
SMILESC(O)(=O)C1=CC=C(B(O)O)C=C1
CAS DataBase Reference14047-29-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-20/21/22
Safety Statements 37/39-26-36
WGK Germany 2
RTECS CY8925000
TSCA No
HazardClass IRRITANT
HS Code 29319090
MSDS Information
ProviderLanguage
4-Boronobenzoic acid English
SigmaAldrich English
ACROS English
ALFA English
4-Carboxyphenylboronic acid Usage And Synthesis
Description4-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.
Reference
  1. Nam, N. D., et al. "A study of 4-carboxyphenylboronic acid as a corrosion inhibitor for steel in carbon dioxide containing environments." Corrosion Science 76.10(2013):257-266.
  2. Vollmueller, Frank, et al. "Cyclization of 4-carboxyphenylboronic acid with hydrazide derivative; hydrolysis; catalytic esterification." US, US 6197967 B1. 2001.
Chemical PropertiesOff-white to light beige powder
Usessuzuki reaction
Uses4-Carboxyphenylboronic acid is a reagent used in suzuki coupling reactions.
UsesIntermediates of Liquid Crystals
4-Carboxyphenylboronic acid Preparation Products And Raw materials
Preparation Products4-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->4-(PIPERIDINE-1-CARBONYL)PHENYLBORONIC ACID-->4-Carbamoylphenylboronic acid-->4-AZIDOBENZOIC ACID-->4-(1H-PYRAZOL-4-YL)BENZOIC ACID-->4-Carboxylphenylboronic acid pinacol ester-->4'-METHYLSULFANYL-BIPHENYL-4-CARBOXYLIC ACID-->2'-ACETYL[1,1'-BIPHENYL]-4-CARBOXYLIC ACID-->4-(8-Bromo-[1,7]naphthyridin-6-yl)-benzoic acid-->2',3',5',6'-tetramethylterphenyl-4,4"-dicarboxylic acid-->4-(1-Methyl-1H-pyrazol-3-yl)benzoic acid-->4-(6-METHOXYPYRIDAZIN-3-YL)BENZOIC ACID
Carboxy styrene-butadiene latex 4-Carboxynaphthalene-1-boronic acid 4-Carboxyphenylboronic acid METHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE (2-AMINO-4-CARBOXYPHENYL)BORONIC ACID ETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE 4-Carboxylphenylboronic acid pinacol ester AQUANTRAAL 3-Carboxyphenylboronic acid Homophthalic acid 4-(TERT-BUTOXYCARBONYL)PHENYLBORONIC ACID Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate Phenylboronic acid 4-Hydroxyphenylboronic acid 4-METHOXYCARBONYL-2,6-DIFLUOROPHENYLBORONIC ACID 4-ISOPROPOXYCARBONYLPHENYLBORONIC ACID 2-Carboxybenzaldehyde BENZOICACID

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