(4-formylphenyl)boronic acid

• ChemBase ID: 8355
• Molecular Formular: C7H7BO3
• Molecular Mass: 149.93968
• Monoisotopic Mass: 150.04882448
• SMILES: c1c(ccc(c1)B(O)O)C=O
• Canonical SMILES: O=Cc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
• InChIKey: VXWBQOJISHAKKM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-formylphenyl)boronic acid
• IUPAC Traditional name: 4-formylphenylboronic acid
• Synonyms: 4-Boronobenzaldehyde; 4-Formylbenzeneboronic acid; 4-Formylbenzeneboronic acid; p-Formylbenzeneboronic acid; p-Formylphenylboronic acid; 4-(Dihydroxyboryl)benzaldehyde; 4-Formylphenylboronic acid; 4-Formylphenylboronic acid; 4-Formylbenzeneboronic acid; 4-(dihydroxyboranyl)benzaldehyde; (4-ForMylphenyl)boronic acid; 4-Formylphenylboronic acid; 4-醛基苯硼酸; 对甲酰苯硼酸; 4-甲酰基苯硼酸

Database IDs

• CAS Number: 87199-17-5
• EC Number: 438-670-5
• MDL Number: MFCD00151823
• Beilstein Number: 3030770
• PubChem SID: 24867058; 160971662
• PubChem CID: 591073

CALCULATED PROPERTIES

• Acid pKa: 8.585433
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3149453
• LogD (pH = 7.4): 1.2879936
• Log P: 1.3153
• Molar Refractivity: 37.1875 cm^3
• Polarizability: 15.43236 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 237-242 °C(lit.); 237-242°C; 241 - 242°C; 260-266°C; 265-268°C
• Hydrophobicity(logP): 0.948

Safety Information

• Storage Warning: Air Sensitive; Corrosive; IRRITANT, AIR SENSITIVE
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 1759
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 34; 43
• Safety Statements: 22-26-36/37/39-45; 24-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314-H317; H317
• GHS Precautionary statements: P280G-P262; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1759 8/PG 3

Product Information

• Purity: ≥95.0%; 95%; 97%; 98%
• Linear Formula: HCOC6H4B(OH)2

DETAILS

Sigma Aldrich - 431966

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water1
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2
• Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids3
• Triethylamine-catalyzed three-component Hantzsch condensations4
• Copper-catalyzed nitrations5
• Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta6
• Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides7
• Palladium-catalyzed aerobic oxidative cross-coupling reactions8 Reagent used in Preparation of
• Sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells9
• A novel protein synthesis inhibitor active against Gram-positive bacteria10