[3,5-bis(trifluoromethyl)phenyl]boronic acid

• ChemBase ID: 9526
• Molecular Formular: C8H5BF6O2
• Molecular Mass: 257.9255192
• Monoisotopic Mass: 258.02867912
• SMILES: c1(cc(cc(c1)B(O)O)C(F)(F)F)C(F)(F)F
• Canonical SMILES: OB(c1cc(cc(c1)C(F)(F)F)C(F)(F)F)O
• InChI: InChI=1S/C8H5BF6O2/c10-7(11,12)4-1-5(8(13,14)15)3-6(2-4)9(16)17/h1-3,16-17H
• InChIKey: BPTABBGLHGBJQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3,5-bis(trifluoromethyl)phenyl]boronic acid
• IUPAC Traditional name: 3,5-bis(trifluoromethyl)phenylboronic acid
• Synonyms: 3,5-Bis(trifluoromethyl)phenylboronic acid; 3,5-Bis(trifluoromethyl)benzeneboronic acid; (3,5-Bis(trifluoromethyl)phenyl)boronic acid; 3,5-Bis(trifluoromethyl)benzeneboronic acid 98%; 3,5-Bis(trifluoromethyl)benzeneboronic acid; 3,5-Di(trifluoromethyl)benzeneboronic acid; 3,5-Bis(trifluoromethyl)phenylboronic acid; 3,5-BIS(TRIFLUOROMETHYL)PHENYLBORONIC ACID; 3,5-双(三氟甲基)苯硼酸

Database IDs

• CAS Number: 73852-19-4
• EC Number: 000-000-0
• MDL Number: MFCD00051850
• Beilstein Number: 7379990
• PubChem SID: 24870695; 160972833
• PubChem CID: 156265

CALCULATED PROPERTIES

• Acid pKa: 8.570875
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 3.4050333
• LogD (pH = 7.4): 3.3771927
• Log P: 3.4054
• Molar Refractivity: 42.5509 cm^3
• Polarizability: 16.471169 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 217-220 °C(lit.); 219-221°C; 219-224°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• 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: 97+%; 98%
• Linear Formula: (CF3)2C6H3B(OH)2

DETAILS

Apollo Scientific Ltd - PC0540

GC reagent for diols: J. Chromat., 158,33 (1978), can also be used to form chiral catalysts for enantioselective Diels-Alder reactions: J. Org. Chem., 62, 3206 (1997).

Sigma Aldrich - 471070

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant involved in the synthesis of:
• Methylene-arylbutenones via carbonylative arylation of allenols1
• 4-aminoquinoline analogs via Ullman / Suzuki / Negishi coupling2
• Primary amino acid derivatives with anticonvulsant activity3
• Alkyl arylcarbamates via Cu-catalyzed coupling with potassium cyanate4
• Aryl-substituted succinimides and cyclic ketones by asymmetric conjugate addition5
• Axially chiral dicarboxylic acids for asymmetric Mannich-type reactions6

REFERENCES

• Has been used to form chiral catalysts for use in enantioselective Diels-Alder reactions; see, for example: J. Org. Chem., 62, 3026 (1997) and references therein. See Appendix 5.
• GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979).
• Has been used to protect a 1,3-diamine as the 2-aryl-1,3,2-diazaborinane, permitting selective reaction at a remote amine function: J. Am. Chem. Soc., 118, 1569 (1996).