| Identification | More | [Name]
4-Trifluoromethoxyphenylboronic acid | [CAS]
139301-27-2 | [Synonyms]
4-(TRIFLUOROMETHOXY)BENZENEBORONIC ACID
4-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID
AKOS BRN-0136
P-TRIFLUOROMETHOXY BENZOBORIC ACID
P-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID
RARECHEM AH PB 0078
4-(Trifluoromethoxy)phenylboronicAcid(containsvaryingamountsofAnhydride)
4-(Trifluoromethoxy)phenylboronic aicd
44-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID
4-(TRIFLUOROMETHOXY)PJHENYLBORONICACID
4-(Trifluoromethoxy)-benzeneboronic acid ,98% | [EINECS(EC#)]
-0 | [Molecular Formula]
C7H6BF3O3 | [MDL Number]
MFCD01074648 | [Molecular Weight]
205.93 | [MOL File]
139301-27-2.mol |
| Chemical Properties | Back Directory | [Appearance]
white to beige crystalline powder | [Melting point ]
123-127 °C(lit.) | [Boiling point ]
256.6±50.0 °C(Predicted) | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
8.29±0.10(Predicted) | [color ]
White to beige | [Detection Methods]
HPLC,NMR | [BRN ]
8548201 | [InChI]
InChI=1S/C7H6BF3O3/c9-7(10,11)14-6-3-1-5(2-4-6)8(12)13/h1-4,12-13H | [InChIKey]
HUOFUOCSQCYFPW-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C(OC(F)(F)F)C=C1)(O)O | [CAS DataBase Reference]
139301-27-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29319099 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige crystalline powder | [Uses]
B-[4-(Trifluoromethoxy)phenyl]boronic Acid is a reagent used in the synthesis of orally bioavailable matrix metalloprotinase inhibitors. Also used in the preparation of chromen-4-one inhibitors used against DNA dependant protein kinases. | [Uses]
suzuki reaction | [Application]
4-Trifluoromethoxyphenylboronic acid can reactant involved in the synthesis of biologically active molecules including:
Lactate dehydrogenase inhibitors for use against cancer cell proliferation
Nitro-phenoxybenzoic acid derivatives for PAI-1 inhibition
PA-824 analogs for use as antituberculosis drugs
Modulators of survival motor neuron protein
Reactant involved in addition reactions and cross-coupling reactions including Suzuki-Miyaura cross-coupling | [Synthesis]
Example 1E Synthesis of 4-(trifluoromethoxy)phenylboronic acid: 1-bromo-4-(trifluoromethoxy)benzene (1.69 kg) and triisopropyl borate (1.46 kg) were dissolved in THF (6.75 L) at -70 °C. A hexane solution (3.27 L) of 2.25 M butyllithium was slowly added to this solution over a period of 2.3 hours, followed by stirring for 10 minutes. Next, the reaction was quenched with 6 M HCl (1.52 L) and stirred at room temperature for 18 hours. The reaction mixture was poured into a mixture of heptane (8.43 L) and 20% (w/w) aqueous sodium chloride solution (8.44 kg) and stirred for 10 min to separate the aqueous and organic phases. The organic phase was concentrated to give a white paste. The paste was dried in vacuum (100 mmHg) at ambient temperature while nitrogen was passed for 2 days. Subsequently, it was further dried at 40-50 °C for 18 h to give 1.306 kg (90.4% yield) of the target product 4-(trifluoromethoxy)phenylboronic acid as a solid. The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 7.24-7.19 (m, 2H), 8.14-8.10 (m, 2H) and additional absorption peaks were observed at δ 7.19-7.15 (m, 2H) and 8.04-8.00 (m, 2H), which corresponded to the cyclic boronic acid trimer. | [References]
[1] Patent: US2002/19539, 2002, A1
[2] Patent: US2002/19539, 2002, A1 |
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