4-Carboxyphenylboronic acid

• CAS: 14047-29-1
• Catalog Number: ACM14047291
• Category: Boronic Acids
• Molecular Weight: 165.94
• Molecular Formula: C7H7BO4
• Synonyms: Benzeneboronic acid, p-carboxy-
• IUPAC Name: 4-boronobenzoic acid
• SMILES: B(C1=CC=C(C=C1)C(=O)O)(O)O
• InChI: InChI=1S/C7H7BO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,11-12H,(H,9,10)
• InChI Key: SIAVMDKGVRXFAX-UHFFFAOYSA-N
• Boiling Point: 406.4±47.0 °C
• Melting Point: 220 °C (dec.)(lit.)
• Density: 1.40±0.1 g/ml
• Application: 4-Carboxyphenylboronic acid serves as a versatile reagent with a broad range of applications, particularly in the synthesis and functionalization of various chemical compounds. It plays a key role in condensation reactions with stabilizer chains on polystyrene latex surfaces and is essential in Suzuki-Miyaura cross-coupling reactions, which are crucial for forming carbon-carbon bonds. This reagent is also employed in esterification processes, the derivatization of polyvinylamine, and the synthesis of isotopically labeled mercury. Additionally, it facilitates the functionalization of poly-SiNW for dopamine detection and plays a part in inducing pH sensitivity on the fluorescence lifetime of quantum dots with NIR fluorescent dyes. The application of 4-Carboxyphenylboronic acid extends to bio-supported palladium nanoparticles acting as a phosphine-free catalyst for Suzuki reactions in aqueous environments and enabling Chan-Lam-type Copper-catalyzed S-arylation at room temperature. It aids in preparing isoquinolones through regioselective Suzuki-Miyaura cross-coupling, followed by tandem palladium-catalyzed aminocarbonylation and annulation, as well as developing ultra-potent HIV-1 protease inhibitors based on amprenavir. Furthermore, it is involved in the visible-light initiated aerobic oxidative hydroxylation of arylboronic acids, the creation of glucose-sensitive boronic acid-bearing block copolymers, and forming trisulfonated calixarene derivatives for complexation with the trimethyllysine epigenetic mark. In addition to these applications, 4-Carboxyphenylboronic acid can function as a corrosion inhibitor for steel.
• Complexity: 163
• Covalently-Bonded Unit Count: 1
• Exact Mass: 166.043739g/mol
• Formal Charge: 0
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Heavy Atom Count: 12
• Monoisotopic Mass: 166.043739g/mol
• NSC Number: 221170
• Rotatable Bond Count: 2

Custom Q&A

What is the molecular formula of 4-Carboxyphenylboronic acid?

The molecular formula is C7H7BO4.

What is the molecular weight of 4-Carboxyphenylboronic acid?

The molecular weight is 165.94 g/mol.

What is another name or synonym for 4-Carboxyphenylboronic acid?

Some synonyms include 4-Boronobenzoic acid and 4-Carboxybenzeneboronic Acid.

When was 4-Carboxyphenylboronic acid created and last modified?

It was created on 2005-03-26 and last modified on 2023-12-02.

What is the IUPAC name for 4-Carboxyphenylboronic acid?

The IUPAC name is 4-boronobenzoic acid.

What is the InChI key for 4-Carboxyphenylboronic acid?

The InChI key is SIAVMDKGVRXFAX-UHFFFAOYSA-N.

How many hydrogen bond donor counts does 4-Carboxyphenylboronic acid have?

It has 3 hydrogen bond donor counts.

What is the exact mass and monoisotopic mass of 4-Carboxyphenylboronic acid?

The exact mass and monoisotopic mass are both 166.0437389 g/mol.

What is the topological polar surface area of 4-Carboxyphenylboronic acid?

The topological polar surface area is 77.8Ų.

Is the compound canonicalized for 4-Carboxyphenylboronic acid?

Yes, the compound is canonicalized.

Synthetic Use

Downstream Synthesis Route 1

• 14047-29-1

• 85107-54-6

Reference: [1]Journal of the American Chemical Society,1959,vol. 81,p. 3017

Downstream Synthesis Route 2

• 1003-09-4
• 14047-29-1

• 29886-62-2

Reference: [1]Synlett,2000,p. 829 - 831

Downstream Synthesis Route 3

• 109-04-6
• 14047-29-1

• 4385-62-0

Reference: [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 73

Downstream Synthesis Route 4

• 1120-87-2
• 14047-29-1

• 4385-76-6

Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 8, p. 478 - 484

Downstream Synthesis Route 5

• 14047-29-1
• 19524-06-2

• 4385-76-6

Reference: [1] Synlett, 2000, # 6, p. 829 - 831

* For details of the synthesis route, please refer to the original source to ensure accuracy.