2-FLUORO-4-METHYLPHENOL

2-FLUORO-4-METHYLPHENOL Property

Boiling point:

173.0±20.0 °C(Predicted)

Density 

1.164±0.06 g/cm3(Predicted)

refractive index 

1.513

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

9.01±0.18(Predicted)

form 

liquid

color 

Clear, colourless

InChI

InChI=1S/C7H7FO/c1-5-2-3-7(9)6(8)4-5/h2-4,9H,1H3

InChIKey

WJKISRFVKIOBCQ-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(C)C=C1F

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-34-22

Safety Statements 

26-36/37/39

RIDADR 

2922

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2908990000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

H312Harmful in contact with skin

H314Causes severe skin burns and eye damage

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P309IF exposed or if you feel unwell:

P310Immediately call a POISON CENTER or doctor/physician.

2-FLUORO-4-METHYLPHENOL Chemical Properties,Usage,Production

Synthesis

GENERAL METHOD: To a solution of the substrate 4-methylphenol (1 mmol) in 10 mL of solvent (acetonitrile or methanol) was added Fluoride Reagent 1, 2 or 3 (1.1 mmol). The reaction mixture was stirred under reflux conditions for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was dissolved in 50 mL of dichloromethane and filtered to remove insoluble material. The filtrate was washed with 30 mL of water and the organic layer was dried with anhydrous sodium sulfate followed by evaporation of the solvent. The crude product was analyzed by 1H NMR and 19F NMR spectroscopy. The relative distribution and total yield of the fluorinated products were determined by 19F NMR using octafluoronaphthalene (OFN) as an internal standard. The identification of the products was accomplished by comparing their NMR spectral data with those reported in the literature, independently prepared samples, or their conversion to known compounds. In the presence of excess reagents, 2-fluoro-4-alkyl-substituted phenols or alkoxybenzenes (5, see Scheme 1) can be converted to 2,2-difluoro-4-alkyl-3,5-cyclohexadienones (unknown compounds 8b or 8c) or hydrolyzed to 2-fluoro-4-methylphenols (4aa). 4-fluoro-4-alkyl-2,5-cyclohexadienones (6a, 6b, and 6c) were determined by preparative thin layer chromatography (silica gel , dichloromethane/petroleum ether, 4:1) from the crude mixture and identified on the basis of their spectral data. Also, 4-fluoroalkoxybenzene derivatives could be identified by hydrolytic conversion to 4-fluorophenol or by comparison with independently prepared compounds.

References

[1] Journal of Fluorine Chemistry, 1981, vol. 17, p. 159 - 172
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 17, p. 2469 - 2474
[3] Journal of Fluorine Chemistry, 1981, vol. 17, p. 159 - 172
[4] Journal of Fluorine Chemistry, 2013, vol. 156, p. 276 - 282
[5] Tetrahedron, 2006, vol. 62, # 18, p. 4474 - 4481