4-Carboxyphenylboronic Acid

HCID 312183

Basic information

CAS
14047-29-1
Standard SMILES
O=C(O)c1ccc(B(O)O)cc1
InChIKey
SIAVMDKGVRXFAX-UHFFFAOYSA-N
Molecular formula
C7H7BO4
Average molar mass
165.94 g/mol
Monoisotopic mass
166.0437391

Names & identifiers

Preferred name
4-Carboxyphenylboronic Acid
IUPAC
4-boronobenzoic acid
English name
4-Carboxyphenylboronic acid
Molecular formula
C7H7BO4
Molecular weight
165.94

Names & synonyms

4-Carboxyphenylboronic acid14047-29-14-Boronobenzoic acidBenzoic acid, 4-borono-4-(dihydroxyboranyl)benzoic acid4-(Dihydroxyboryl)benzoic acidp-Carboxyphenylboronic acidBenzeneboronic acid, p-carboxy-XQQ1T11DYKNSC-221170DTXSID20930850pBoronobenzoic acid
Show more names
4-CarboxyphenyL4-borono-benzoicaci4-Carboxyphenylboronic4-CARBOXYBENZENEBORONIC ACID4-Carboxyphenylboronic acid, 97% 5GRNSC 221170AURORA 14935AKOS BRN-0008WLN: VHOR DBQQ
4Boronobenzoic acidBenzoic acid, 4boronoRefChem:98281pCarboxyphenylboronic acidpCarboxybenzeneboronic acid4carboxybenzeneboronic acidBenzeneboronic acid, pcarboxyBenzoic acid, 4borono (9CI)

Database identifiers

CAS
14047-29-1
PubChem CID
312183
DTXSID
DTXSID20930850
ChEMBL
CHEMBL82324
UNII
XQQ1T11DYK
EC Number
604-189-6
Nikkaji
J54.862F

Properties

Computed structural properties

Topological polar surface area
77.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesMetals -> Metalloid Compounds (Boron)
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionPowder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
220 °C · 220 °C (dec.) (lit.)
Boiling point
406.4 · 406.4±47.0 °C(Predicted)
Density
1.4 · 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)
pka
4.08 · 4.08±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (23.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 17 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 30-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/30475
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Benzeneboronic acid.
Hazard Classes and CategoriesAcute Tox. 4 (23.5%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
No
rtecs
CY8925000
hs_code
29319090
risk_code
36/37/38-20/21/22

Chemistry & industry

Applications · 4 items

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.

Usessuzuki reaction

Uses4-Carboxyphenylboronic acid is a reagent used in suzuki coupling reactions.

UsesIntermediates of Liquid Crystals

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Related reactions

384 records

Compound notes

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