| Identification | More | [Name]
4-Fluoro-2-methylphenylboronic acid | [CAS]
139911-29-8 | [Synonyms]
2-METHYL-4-FLUOROPHENYLBORONIC ACID
4-FLUORO-2-METHYLBENZENEBORONIC ACID
4-FLUORO-2-METHYLPHENYLBORONIC ACID
4-FLUORO-O-TOLYLBORONIC ACID
AKOS BRN-0102
4-Fluoro-2-methylphenylboronic acid~4-Fluoro-o-tolylboronic acid
Boronic acid, (4-fluoro-2-methylphenyl)-(9CI)
4-Fluoro-2-Methylphenylboronic
4-Fluoro-2-methylbenzeneboronic acid 98%
4-Fluoro-2-methylbenzeneboronicacid98%
4-Fluoro-2-methylphenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
642-527-4 | [Molecular Formula]
C7H8BFO2 | [MDL Number]
MFCD02093072 | [Molecular Weight]
153.95 | [MOL File]
139911-29-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [Melting point ]
191-196 °C(lit.) | [Boiling point ]
277.4±50.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
8.75±0.58(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C7H8BFO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4,10-11H,1H3 | [InChIKey]
IQMLIVUHMSIOQP-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C(F)C=C1C)(O)O | [CAS DataBase Reference]
139911-29-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white powder | [Uses]
suzuki reaction | [Synthesis]
The general procedure for the synthesis of 4-fluoro-2-methylphenylboronic acid from triisopropyl borate and 2-bromo-5-fluorotoluene was carried out as follows: 2-bromo-5-fluorotoluene (250 g) was dissolved in a solvent mixture of tetrahydrofuran (250 ml) and n-hexane (250 ml) under dry conditions, and cooled to -78 °C. At this temperature, n-butyllithium (991.5 ml) was slowly added dropwise and the reaction temperature was maintained in an ice bath. After the dropwise addition, the reaction mixture was stirred for 1 hour. Subsequently, triisopropyl borate (373.11 g) was added dropwise and stirring was continued at -78°C for 1 hour. After completion of the reaction, the reaction mixture was diluted with aqueous sodium hydroxide solution and then washed with n-heptane. The pH of the aqueous layer was adjusted to 2-3 with hydrochloric acid followed by extraction with ethyl acetate. The organic layers were combined and concentrated under vacuum. The concentrated product was dissolved in ethyl acetate at about 40 °C and n-heptane was added to promote crystallization, resulting in 4-fluoro-2-methylphenylboronic acid. The yield was 61.5% and the HPLC purity was 99.00%. | [References]
[1] Patent: WO2017/125835, 2017, A1. Location in patent: Paragraph 00117 |
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