(3,4,5-trifluorophenyl)boronic acid

• ChemBase ID: 12425
• Molecular Formular: C6H4BF3O2
• Molecular Mass: 175.9009696
• Monoisotopic Mass: 176.02564443
• SMILES: c1(c(c(cc(c1)B(O)O)F)F)F
• Canonical SMILES: OB(c1cc(F)c(c(c1)F)F)O
• InChI: InChI=1S/C6H4BF3O2/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,11-12H
• InChIKey: UHDDEIOYXFXNNJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3,4,5-trifluorophenyl)boronic acid
• IUPAC Traditional name: 3,4,5-trifluorophenylboronic acid
• Synonyms: 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid; 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid 97%; (3,4,5-Trifluorophenyl)boronic acid; 3,4,5-Trifluorophenylboronic acid; 3,4,5-Trifluorobenzeneboronic acid; (3,4,5-trifluorophenyl)boranediol; 3,4,5-三氟苯硼酸

Database IDs

• CAS Number: 143418-49-9
• EC Number: 000-000-0
• MDL Number: MFCD02093069
• Beilstein Number: 7371914
• PubChem SID: 24874437; 160975732
• PubChem CID: 2734671

CALCULATED PROPERTIES

• Acid pKa: 8.491755
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.05786
• LogD (pH = 7.4): 2.0246685
• Log P: 2.0583
• Molar Refractivity: 31.2527 cm^3
• Polarizability: 12.921739 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 275-279°C; 275-279°C; 290-295 °C(lit.); 295 - 297°C
• Hydrophobicity(logP): 1.884

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%; 98%
• Linear Formula: F3C6H2B(OH)2

DETAILS

Apollo Scientific Ltd - PC4336

Very reactive catalyst to produce amides in high yieldsfrom carboxylic acids and primary or secondary aminesJ. Org. Chem., 61, 4196 (1996)

Sigma Aldrich - 524700

Other Notes
Contains varying amounts of anhydride.
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Preparation of phenylboronic catechol esters and determination of Lewis acidity1
• Synthesis of benzopyranone derivatives as GABAA receptor modulators2
• Synthesis of multisubstituted olefins and conjugate dienes3
• Suzuki cross-coupling reactions4,5
• Preparation of fluorinated aromatic poly(ether-amide)s6

REFERENCES

• Extremely active catalyst for the reaction of carboxylic acids with primary and secondary amines to give the corresponding amides in very high yields: J. Org. Chem., 61, 4196 (1996). Also useful in the one-pot synthesis of acyl azides from carboxylic acids and NaN₃: Tetrahedron Lett.,43, 9715 (2002). Mediates the mild, one-pot reduction of carboxylic acids to alcohols with NaBH₄: Tetrahedron Lett., 44, 3427 (2003).
• For other boronic acid chemistry, see Appendix 5.