(4-bromophenyl)boronic acid

• ChemBase ID: 7926
• Molecular Formular: C6H6BBrO2
• Molecular Mass: 200.82564
• Monoisotopic Mass: 199.96442183
• SMILES: c1(ccc(cc1)Br)B(O)O
• Canonical SMILES: OB(c1ccc(cc1)Br)O
• InChI: InChI=1S/C6H6BBrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChIKey: QBLFZIBJXUQVRF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-bromophenyl)boronic acid
• IUPAC Traditional name: 4-bromophenylboric acid
• Synonyms: B-(4-Bromophenyl)boronic Acid; (4-Bromophenyl)boronic Acid; 4-Bromophenylboronic Acid (contains varying amounts of Anhydride); 4-Bromo-phenylboronic acid; (p-Bromophenyl)boronic acid; 4-Bromophenylboric acid; p-Bromobenzeneboronic acid; p-Bromophenylboric acid; NSC 25407; 4-Bromobenzeneboronic acid; 4-Bromophenylboronic acid; 4-Bromobenzeneboronic acid; 4-Bromophenylboronic acid; p-BROMOPHENYLBORONIC ACID; (4-bromophenyl)boranediol; 4-Bromophenylboronic acid; 4-Bromobenzeneboronic acid; 4-溴苯基硼酸; 4-溴苯硼酸

Database IDs

• CAS Number: 5467-74-3
• EC Number: 226-779-9
• MDL Number: MFCD00002104
• Beilstein Number: 2936347
• PubChem SID: 24892010; 24850877; 160971233
• PubChem CID: 79599

CALCULATED PROPERTIES

• Acid pKa: 8.7287245
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.431345
• LogD (pH = 7.4): 2.4117966
• Log P: 2.4316
• Molar Refractivity: 38.2263 cm^3
• Polarizability: 16.381119 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 282-286°C; 282-286°C; 284-288 °C(lit.); 284-288°C; 291 - 292°C
• Hydrophobicity(logP): 2.458

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon/Keep Cold
• RTECS: CY8650000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: true; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; ≥95.0% (HPLC); 95%; 97+%; 98%
• Grade: purum
• Quality: variable mixture of acid and anhydride
• Linear Formula: BrC6H4B(OH)2

DETAILS

MP Biomedicals - 05215741

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B75956

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Palladium catalyzed Suzuki-Miyaura cross-couplings1
• Pd(II)-catalyzed diastereoselective conjugate additions2
• Palladium-catalyzed stereoselective Heck-type reaction of allylic esters with arylboronic acids3
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence4
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides5
• Pd-catalyzed arylative cyclization of alkyne-tethered enals or enones via carbopalladation of alkynes6
• Copper-catalyzed cross-couplings7,8Reagent used in Preparation of
• Gallate-based obovatol analogs with potential anti-tumor activity9
• Protein modulators and enzymatic and kinase inhibitors10,11

Sigma Aldrich - 18057

Other Notes
Contains varying amounts of anhydride

Toronto Research Chemicals - B686545

4-Bromophenylboric acid is used in the preparation of arylboronates as inhibitors of fatty acid amide hydrolase.

REFERENCES

• Weston, G.S., et al.: J. Med. Chem., 41, 4577 (1998)
• GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979).
• Carbonylative cross-coupling with iodobenzenes and CO, catalyzed by trans-Dichlorobis(triphenylphosphine)palladium(II), 10491, gives unsymmetrical diaryl ketones: Tetrahedron Lett., 34, 7595 (1993); J. Org. Chem., 63, 4726 (1998). For reactions of boronic acids, see Appendix 5.