| Identification | More | [Name]
4-Bromo-2-fluorophenol | [CAS]
2105-94-4 | [Synonyms]
4-BROMO-2-FLUOROPHENOL
2-Fluoro-4-Bromophenol
4-Bromo-2-fluorophenol 98%
4-Bromo-2-fluorophenol98%
4-Bromo-2-fluorophenol, 97+% | [EINECS(EC#)]
218-284-1 | [Molecular Formula]
C6H4BrFO | [MDL Number]
MFCD00011722 | [Molecular Weight]
191 | [MOL File]
2105-94-4.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLORLESS TO BROWNISH LIQUID | [Boiling point ]
79 °C/7 mmHg (lit.) | [density ]
1.744 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.566(lit.)
| [Fp ]
210 °F
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
Liquid | [pka]
8.14±0.18(Predicted) | [color ]
Clear colorless to brown | [Specific Gravity]
1.744 | [BRN ]
1861281 | [InChI]
InChI=1S/C6H4BrFO/c7-4-1-2-6(9)5(8)3-4/h1-3,9H | [InChIKey]
RYVOZMPTISNBDB-UHFFFAOYSA-N | [SMILES]
C1(O)=CC=C(Br)C=C1F | [CAS DataBase Reference]
2105-94-4(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 .
S37/39:Wear suitable gloves and eye/face protection .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29081900 |
| Hazard Information | Back Directory | [Chemical Properties]
CLEAR COLORLESS TO BROWNISH LIQUID | [Uses]
4-Bromo-2-fluorophenol can be used as a starting material for the synthesis of:
- 4-Bromo-2-fluoro-6-iodoanisole via iodination and methylation.
- 2-Phenylpyran-4-ones for active cyclooxygenase-2 inhibitor evaluation.
- 1,4-Disubstituted 3-cyano-2-pyridones.
- Dicationic imidazolium-based compounds.
| [Synthesis]
Example 5: Preparation of methyl 2-[4-(4-bromo-2-fluorophenoxy)phenoxy]propionate (STR29)
1. 2-Fluorophenol (22.4 g, 0.2 mol) was dissolved in dichloromethane (250 mL) under ice bath conditions and cooled to about 3 °C. 2.
2. bromine (31.97 g, 0.2 mol) was added slowly, keeping the reaction temperature at ice bath conditions.
3. the reaction mixture was stirred at ice bath temperature for 2 hours, followed by continued stirring at room temperature for 1 hour.
4. the reaction mixture was quenched by pouring into water (600 mL) containing excess sodium bisulfite.
5. The organic phase was separated and the aqueous phase was washed with additional dichloromethane (200 mL).
6. The organic extracts were combined, washed with saturated sodium bicarbonate solution and subsequently dried over anhydrous magnesium sulfate.
7. The solvent was removed by evaporation to afford the target product 2-fluoro-4-bromophenol as a colorless oil (34.5 g, 90% yield).
8. The structure of the product was confirmed to be as expected by NMR hydrogen spectroscopy (CDCl3). | [References]
[1] Patent: US4642338, 1987, A
[2] Patent: US4725683, 1988, A
[3] Patent: US4808750, 1989, A
[4] Patent: US4550192, 1985, A
[5] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047 |
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