[4-(trifluoromethyl)phenyl]boronic acid

• ChemBase ID: 9265
• Molecular Formular: C7H6BF3O2
• Molecular Mass: 189.9275496
• Monoisotopic Mass: 190.04129449
• SMILES: c1(ccc(cc1)C(F)(F)F)B(O)O
• Canonical SMILES: OB(c1ccc(cc1)C(F)(F)F)O
• InChI: InChI=1S/C7H6BF3O2/c9-7(10,11)5-1-3-6(4-2-5)8(12)13/h1-4,12-13H
• InChIKey: ALMFIOZYDASRRC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(trifluoromethyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(trifluoromethyl)phenylboronic acid
• Synonyms: 4-(Trifluoromethyl)phenylboronic acid; [p-(Trifluoromethyl)phenyl]boronic acid; α,α,α-Trifluoro-p-tolylboronic acid; 4-(Trifluoromethyl)benzeneboronic acid; 4-(Trifluoromethyl)phenylboronic acid; [4-(trifluoromethyl)phenyl]boranediol; 4-(Trifluoromethyl)phenylboronic acid; 4-(Trifluoromethyl)benzeneboronic acid; 4-Boronobenzotrifluoride; 4-(Trifluoromethyl)benzeneboronic acid 98%; α,α,α-三氟对甲苯基硼酸; 对三氟甲基苯硼酸; 4-(三氟甲基)苯硼酸

Database IDs

• CAS Number: 128796-39-4
• EC Number: 000-000-0
• MDL Number: MFCD00151855
• Beilstein Number: 3544189
• PubChem SID: 160972572; 24867498
• PubChem CID: 2734389

CALCULATED PROPERTIES

• Acid pKa: 8.728637
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.5223448
• LogD (pH = 7.4): 2.5027926
• Log P: 2.5226
• Molar Refractivity: 36.5772 cm^3
• Polarizability: 14.783645 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 235-238°C; 237 - 238°C; 238-242°C; 245-250 °C(lit.); 245-250°C
• Hydrophobicity(logP): 2.478

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H315-H319-H335
• GHS Precautionary statements: 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%; 97%; 98%
• Linear Formula: CF3C6H4B(OH)2

DETAILS

Apollo Scientific Ltd - PC1111

J. Org. Chem., 59, 5304 (1994): phosphine-freeSuzuki coupling with aryl halides, catalysed with Pd

Sigma Aldrich - 439320

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Site-selective Suzuki-Miyaura cross-coupling reactions1
• Palladium-catalyzed direct arylation reactions2
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence3
• Ruthenium catalyzed direct arylation4
• Ligand-free copper-catalyzed coupling reactions5
• Amination and conjugate addition reactions6
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions7
• Rhodium-catalyzed asymmetric 1,4-addition reactions8
• Copper-catalyzed nitration reactions9
• Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation10Reagent used in Preparation of
• Thiazole derivatives for printable electronics11
• Terphenyl benzimidazoles as tubulin polymerization inhibitors12

REFERENCES

• For phosphine-free palladium-catalyzed Suzuki coupling with aryl halides, see: J. Org. Chem., 59, 5034 (1994).