Dibenzofuran-4-boronic acid

• CAS: 100124-06-9
• Catalog Number: ACM100124069
• Category: Boronic Acids
• Molecular Weight: 212.01g/mol
• Molecular Formula: C12H9BO3
• Synonyms: RARECHEM AH PB 0052;TIMTEC-BB SBB003426;DIBENZO[B,D]FURAN-4-YLBORONIC ACID;DIBENZOFURAN-4-BORONIC ACID;4-DIBENZOFURANBORONIC ACID;AKOS BRN-0085;Dibenzofuran-4-boronic acid, 98+%;dibenzofuran-4-ylboronic acid
• IUPAC Name: dibenzofuran-4-ylboronic acid
• Canonical SMILES: B(C1=C2C(=CC=C1)C3=CC=CC=C3O2)(O)O
• InChI: InChI=1S/C12H9BO3/c14-13(15)10-6-3-5-9-8-4-1-2-7-11(8)16-12(9)10/h1-7,14-15H
• InChI Key: ZXHUJRZYLRVVNP-UHFFFAOYSA-N
• Application: Dibenzofuran-4-boronic acid, an off-white to beige powder, serves a critical role in various chemical applications due to its unique properties as a water-soluble boronic acid. Its primary purpose is as a functional group in the development of glycosensors, owing to its ability to alter fluorescence properties upon interacting with sugars. This makes it particularly valuable for designing carbohydrate fluorescence sensors, as it can display distinct fluorescence changes at three wavelengths in near-physiological conditions. Additionally, Dibenzofuran-4-boronic acid is utilized as a cross-coupling agent in the Suzuki coupling reaction. Although its initial efficiency was low, improvements have been achieved by leveraging methanol extraction and exploiting its photophysical properties. Furthermore, when coupled with imidazole derivatives, it aids in the synthesis of anti-inflammatory compounds, and its bond cleavage and hydrogen bonding characteristics make it an attractive candidate for drug synthesis.
• Complexity: 259
• Covalently-Bonded Unit Count: 1
• Exact Mass: 212.064474g/mol
• Formal Charge: 0
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Heavy Atom Count: 16
• Monoisotopic Mass: 212.064474g/mol
• Rotatable Bond Count: 1

Custom Q&A

What is the molecular formula of Dibenzofuran-4-boronic acid?

The molecular formula of Dibenzofuran-4-boronic acid is C12H9BO3.

What is the molecular weight of Dibenzofuran-4-boronic acid?

The molecular weight of Dibenzofuran-4-boronic acid is 212.01 g/mol.

What is the IUPAC name of Dibenzofuran-4-boronic acid?

The IUPAC name of Dibenzofuran-4-boronic acid is dibenzofuran-4-ylboronic acid.

What is the InChI of Dibenzofuran-4-boronic acid?

The InChI of Dibenzofuran-4-boronic acid is InChI=1S/C12H9BO3/c14-13(15)10-6-3-5-9-8-4-1-2-7-11(8)16-12(9)10/h1-7,14-15H.

What is the InChIKey of Dibenzofuran-4-boronic acid?

The InChIKey of Dibenzofuran-4-boronic acid is ZXHUJRZYLRVVNP-UHFFFAOYSA-N.

What is the canonical SMILES of Dibenzofuran-4-boronic acid?

The canonical SMILES of Dibenzofuran-4-boronic acid is B(C1=C2C(=CC=C1)C3=CC=CC=C3O2)(O)O.

What is the CAS number of Dibenzofuran-4-boronic acid?

The CAS number of Dibenzofuran-4-boronic acid is 100124-06-9.

What is the European Community (EC) number of Dibenzofuran-4-boronic acid?

The European Community (EC) number of Dibenzofuran-4-boronic acid is 672-293-9.

What is the DSSTox Substance ID of Dibenzofuran-4-boronic acid?

The DSSTox Substance ID of Dibenzofuran-4-boronic acid is DTXSID40370219.

Is Dibenzofuran-4-boronic acid considered a covalently-bonded unit?

Yes, Dibenzofuran-4-boronic acid is considered a covalently-bonded unit.

Synthetic Use

Upstream Synthesis Route 1

• 89827-45-2
• 121-43-7

• 100124-06-9

Reference: [1] Patent: US9172047, 2015, B2, . Location in patent: Page/Page column 17

Downstream Synthesis Route 1

• 100124-06-9

• 65344-26-5

Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660

Downstream Synthesis Route 2

• 100124-06-9

• 50548-43-1

Reference: [1] Angewandte Chemie - International Edition, 2009, vol. 48, # 6, p. 1114 - 1116
[2] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18253 - 18256

Downstream Synthesis Route 3

• 100124-06-9
• 608-72-0

• 109392-74-7

Reference: [1]Journal of Organic Chemistry,1987,vol. 52,p. 3932 - 3934

Downstream Synthesis Route 4

• 100124-06-9
• 88275-87-0

• 1027019-64-2

Reference: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3573 - 3575

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