| Identification | More | [Name]
2,6-Difluorophenylboronic acid | [CAS]
162101-25-9 | [Synonyms]
2,6-DIFLUOROBENZENEBORONIC ACID
2,6-DIFLUORO PHENYLBORIC ACID
2,6-DIFLUOROPHENYLBORONIC ACID
2,6-DIMETHOXYBENZENEBORONIC ACID
2,6-DIMETHOXYPHENYLBORONIC ACID
AKOS BRN-0146
AKOS BRN-0261
CHEMBRDG-BB 3200972
RARECHEM AH PB 0108
RARECHEM AH PB 0164
TIMTEC-BB SBB003736
Boronic acid, (2,6-difluorophenyl)-(9CI)
2,6-Difluorophenylboronic
2,6-Difluorobenzeneboronic acid 98%
2,6-Difluorobenzeneboronicacid98%
2,6-Difluoropenylboronic acid
2,6-Difluorophenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
627-874-1 | [Molecular Formula]
C6H5BF2O2 | [MDL Number]
MFCD01318987 | [Molecular Weight]
157.91 | [MOL File]
162101-25-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white crystalline powder | [Melting point ]
147-149 °C (lit.) | [Boiling point ]
260.1±50.0 °C(Predicted) | [density ]
1.35±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
Soluble in methanol. | [form ]
solid | [pka]
8.12±0.58(Predicted) | [color ]
White to Almost white | [Usage]
Intermediates of Liquid Crystals | [BRN ]
8545931 | [InChI]
InChI=1S/C6H5BF2O2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,10-11H | [InChIKey]
DBZAICSEFBVFHL-UHFFFAOYSA-N | [SMILES]
B(C1=C(F)C=CC=C1F)(O)O | [CAS DataBase Reference]
162101-25-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319099 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white crystalline powder | [Uses]
2,6-Difluorophenylboronic acid can be used:
- As a substrate in the model reaction of Suzuki–Miyaura coupling with?4-chloro-3-methylanisole.
- To prepare 4-bromo-2,3′,5′,6-tetrafluorobiphenyl, a key intermediate for the synthesis of 2,6-difluorinated oligophenyls applicable in organic semiconductors.
- To prepare ethyl 4-(2,6-difluorophenyl)nicotinate, a key intermediate for the synthesis of 4-phenyl pyridine based potent TGR5 agonists.
| [Uses]
Intermediates of Liquid Crystals | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 2,6-difluorophenylboronic acid from trimethyl borate and 1,3-difluorobenzene was as follows: 22.8 g of 1,3-difluorobenzene (Compound I) and 150 mL of anhydrous ethyl ether were added to a 500 mL dry reaction flask under nitrogen protection and the system was cooled to -78 °C. Slowly 187 mL of 1.6 M n-butyllithium hexane solution was added dropwise to the mixture. After the dropwise addition was completed, the reaction was stirred at -60 to -70 °C for 2 hours. The system was again cooled to -78°C and 60 g of trimethyl borate was slowly added dropwise, and after the dropwise addition was completed, the reaction was stirred at a controlled temperature of -50 to -60°C for 2 hours. The reaction mixture was slowly warmed to room temperature, the reaction was quenched by the addition of 200 mL of water and acidified with 36% hydrochloric acid. After recovering the organic solvent by ascending distillation, the reaction mixture was stirred at 70 to 80 °C for 6 hours. Finally, the system was cooled to crystallization, filtered and washed with cold water to afford 27.0 g of 2,6-difluorophenylboronic acid (Compound II). | [References]
[1] Patent: CN103819401, 2016, B. Location in patent: Paragraph 0023; 0066; 0067 |
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