3'-(Difluoromethoxy)acetophenone

3'-(Difluoromethoxy)acetophenone Property

Boiling point:

223.8±30.0 °C(Predicted)

Density 

1.191±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Appearance

Colorless to light yellow Liquid

Safety

HazardClass 

IRRITANT

HS Code 

2914790090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H272May intensify fire; oxidizer

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P220Keep/Store away from clothing/…/combustible materials.

P221Take any precaution to avoid mixing with combustibles/…

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P370+P378In case of fire: Use … for extinction.

P391Collect spillage. Hazardous to the aquatic environment

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

3'-(Difluoromethoxy)acetophenone Chemical Properties,Usage,Production

Uses

3''-(Difluoromethoxy)acetophenone

Synthesis

General procedure for the synthesis of 1-[3-(difluoromethoxy)phenyl]ethanone from difluoromethyl trifluoromethanesulfonate and 3'-bromoacetophenone:[a] The reaction was carried out at 0.5 mmol, after which the yield was determined by 19F NMR spectroscopy, with the addition of PI1CF3 as an internal standard. Note: The reaction was hydroxylated under an inert atmosphere according to literature procedures. [Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc.] For oven-dried 4 mL vials, Pd2(dba)3 (9.2 mg, 0.010 mmol, 4.0 mol% Pd), 2-di-tert-butylphosphino-2',4',6' -triisopropylbiphenyl (tBu-XPhos, 17.0 mg, 0.040 mmol, 8.0 mol%), KOH (1.0-3.0 equiv), degassed H2O (150-300 μL), and dioxane (250-500 μL). Aryl halides (0.5 mmol, 1.0 eq.) were added (solid aryl halides were weighed into the vial prior to solvent addition and liquid aryl bromides were added via syringe after solvent addition). The vials were sealed with Teflon-lined caps and heated at 100°C for 1-18 hours. After completion of the reaction, the solution was allowed to cool and acetonitrile (500-750 μL, making a total volume of 1.0 mL of dioxane and acetonitrile) and 6 M KOH (700-850 μL, making a final volume of 1.0 mL of aqueous solvent) were added. The resulting mixture was stirred rapidly at room temperature and HCF2O2 (210 μL, 1.5 mmol, 3.0 eq.) was added immediately. Note: The reaction is exothermic. The mixture was stirred vigorously for 2 minutes. The reaction mixture was diluted with H2O (8 mL) and extracted with ether (2 x 8 mL). The combined organic layers were dried over MgSO4, concentrated, and purified by silica gel chromatography.

References

[1] Patent: WO2014/107380, 2014, A1. Location in patent: Paragraph 00166-00167