Conditions | Yield |
---|---|
With aluminum (III) chloride at 140℃; for 3h; Fries Phenol Ester Rearrangement; | 100% |
With trifluorormethanesulfonic acid at 0 - 20℃; for 16h; Fries rearrangement; regiospecific reaction; | 92% |
With hydrogenchloride; aluminum (III) chloride In water at 140 - 145℃; Fries Phenol Ester Rearrangement; | 92% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 130℃; for 2h; | 98.4% |
With aluminium trichloride at 130℃; for 2h; | 89% |
With aluminium trichloride at 180℃; for 0.5h; | 65% |
Stage #1: 4-Fluorophenol; acetyl chloride In toluene at 40℃; Stage #2: With aluminium trichloride In toluene at 80℃; Further stages.; | |
Stage #1: 4-Fluorophenol; acetyl chloride In neat (no solvent) at 0 - 20℃; for 2h; Stage #2: With aluminum (III) chloride In neat (no solvent) at 130℃; for 2h; |
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at -5 - 25℃; | 90% |
With pyridine hydrochloride | |
With boron tribromide In dichloromethane at -78 - 23℃; for 1h; |
Conditions | Yield |
---|---|
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 4h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With aluminum oxide; methanesulfonic acid at 120℃; for 2h; | 60% |
With boron trifluoride at 150℃; unter Druck; |
1-fluoro-4-methoxybenzene
acetyl chloride
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
With aluminium trichloride In tetrachloromethane | 44.1% |
1-fluoro-4-methoxybenzene
acetyl chloride
A
1-(5-fluoro-2-methoxyphenyl)ethanone
B
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
With carbon disulfide; aluminium trichloride | |
Stage #1: 1-fluoro-4-methoxybenzene; acetyl chloride With aluminum (III) chloride In dichloromethane Friedel-Crafts Acylation; Inert atmosphere; Stage #2: With water; acetic acid; sodium hydroxide at 0 - 8℃; Cooling with ice; Overall yield = 97%; Overall yield = 13.0g; |
aluminium trichloride
4-fluorophenyl acetate
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
at 150℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlCl3 / 130 °C View Scheme | |
Multi-step reaction with 2 steps 1: H2SO4 / 120 °C 2: AlCl3 / 160 °C View Scheme | |
Multi-step reaction with 2 steps 1: 84.55 percent / pyridine / CH2Cl2 / 5 °C 2: 44 percent / aluminium chloride / 2 h / 140 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 80 percent / conc. H2SO4 2: 85 percent / AlCl3 / 2 h / 160 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: AlCl3; benzene 2: 100 °C 3: AlCl3 / 150 °C View Scheme | |
Multi-step reaction with 2 steps 1: AlCl3; CS2 2: pyridine hydrochloride View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: AlCl3; benzene 2: 100 °C 3: AlCl3 / 150 °C View Scheme |
3-fluoro-6-methoxybenzonitrile
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 6 h / Reflux 1.2: 20 h / 75 °C 2.1: boron tribromide / dichloromethane / 1 h / -78 - 23 °C View Scheme |
trifluoromethylsulfonic anhydride
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
2-acetyl-4-fluorophenyl triflate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; | 100% |
With pyridine at 0 - 20℃; for 12h; | 92% |
With pyridine at 0 - 20℃; | 68% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
chloroacetic acid ethyl ester
(2-acetyl-4-fluorophenoxy)acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 16h; Reflux; Inert atmosphere; | 100% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
ethyl iodoacetae
(2-acetyl-4-fluorophenoxy)acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 90℃; |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 1h; Cooling with ice; | 99% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
5'-fluoro-2'-hydroxy-3'-nitroacetophenone
Conditions | Yield |
---|---|
With nitric acid; acetic acid In acetic acid at 0 - 20℃; for 3h; | 98.48% |
With nitric acid In tetrachloromethane at 20℃; Reflux; | 97% |
With nitric acid; acetic acid at 0 - 20℃; for 16h; | 89% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
dimethyl sulfate
1-(5-fluoro-2-methoxyphenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 18h; Reflux; | 98% |
propargyl p-toluenesulfonate
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
1-(5-fluoro-2-(prop-2-yn-1-yloxy)phenyl)ethan-1-one
Conditions | Yield |
---|---|
With 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin; potassium carbonate In acetonitrile Heating; | 98% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In pyridine; methanol at 20℃; for 14h; | 98% |
With hydroxylamine hydrochloride; sodium acetate In methanol at 78℃; for 4h; | 88% |
With hydroxylamine hydrochloride; sodium acetate In methanol at 70℃; for 4h; |
Conditions | Yield |
---|---|
With sodium methylate In methanol at 65 - 70℃; Claisen Condensation; | 97% |
With sodium ethanolate In ethanol at 80℃; for 1.33333h; Cooling with ice; |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
4-methoxy-benzoyl chloride
1-(5-fluoro-2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: 4-methoxy-benzoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 96.31% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
allyl bromide
1-[2-(allyloxy)-5-fluorophenyl]ethanone
Conditions | Yield |
---|---|
With potassium carbonate In 4-methyl-2-pentanone for 8h; Reflux; | 96% |
With potassium carbonate In acetone Reflux; |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Conditions | Yield |
---|---|
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With borane-THF In tetrahydrofuran for 0.5h; Inert atmosphere; Heating; | 95% |
With (-)-diisopinocamphenylborane chloride In tetrahydrofuran for 12h; Ambient temperature; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | 95% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
4-fluorobenzoyl chloride
1-(5-fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)propane-1,3-dione
Conditions | Yield |
---|---|
Stage #1: 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one With lithium hexamethyldisilazane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: 4-fluorobenzoyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 94.5% |
ethyl bromide
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
2'-ethoxy-5'-fluoroacetophenone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 94% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
5-chloro-1-methyl-1H-imidazole-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Ambient temperature; | 93% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
2-Fluorobenzaldehyde
3-(2-fluorophenyl)-1-(5-fluoro-2-hydroxyphenyl)-2-propen-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol | 93% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
methyl iodide
1-(5-fluoro-2-methoxyphenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 93% |
With potassium carbonate In acetone at 20℃; |
2,6-difluorobenzaldehyde
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
3-(2,6-difluorophenyl)-1-(5-fluoro-2-hydroxyphenyl)-2-propen-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol | 92% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
cyclopentanone
6-fluorospiro[chroman-2,1'-cyclopentan]-4-one
Conditions | Yield |
---|---|
With pyrrole In toluene for 20h; Reflux; | 92% |
pyrrolidine In acetonitrile |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
2-acetyl-4-fluorophenolato-[o-(di-o-tolylphosphino)benzyl]palladium(II)
Conditions | Yield |
---|---|
With potassium tert-butoxide In toluene Ar-atmosphere; stirring (12 h); filtering, evapn. (vac.), crystn. (toluene / pentane); elem. anal.; | 92% |
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In acetic acid butyl ester; ethyl acetate at 120℃; Perkin condensation; | 92% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
Diethyl carbonate
6-fluoro-4-hydroxycoumarin
Conditions | Yield |
---|---|
With sodium hydride In mineral oil at 0 - 100℃; | 91% |
With potassium tert-butylate In tetrahydrofuran at 20℃; for 10h; Inert atmosphere; | 78% |
With sodium hydride In dimethyl sulfoxide at 0 - 100℃; for 2h; | 29% |
Conditions | Yield |
---|---|
With C19H25F6N3S In toluene at 0℃; for 96h; Aldol Addition; Inert atmosphere; enantioselective reaction; | 91% |
6-chloro-8-formyl-1,3-benzodioxane
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
(E)-3-(6-Chloro-4H-benzo[1,3]dioxin-8-yl)-1-(5-fluoro-2-hydroxy-phenyl)-propenone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Ambient temperature; | 90% |
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one
4-fluorobenzaldehyde
(E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol | 90% |
With potassium hydroxide In ethanol; water at 20℃; Claisen-Schmidt Condensation; | 80% |
With sodium hydroxide In ethanol; water at 30℃; for 24h; | 19% |
Conditions | Yield |
---|---|
In toluene at 80℃; Sealed tube; Inert atmosphere; | 90% |
at 95℃; for 4h; | 69% |
at 100℃; for 2h; |
The IUPAC name of Ethanone,1-(5-fluoro-2-hydroxyphenyl)- is 1-(5-fluoro-2-hydroxyphenyl)ethanone. With the CAS registry number 394-32-1, it is also named as 5'-Fluoro-2'-hydroxyacetophenone. The product's categories are Alcohols and Derivatives; Carbonyl Compounds; Aromatic Acetophenones & Derivatives (substituted); ketone; (intermediate of nebivolol); Benzenes; Adehydes, Acetals & Ketones; Fluorine Compounds; Phenols; C7 to C8; Carbonyl Compounds; Ketones; Acetophenone Series. Besides, it is light yellow to beige-brown crystals, which is soluble in water. In addition, its molecular formula is C8H7FO2 and molecular weight is 154.14.
The other characteristics of this product can be summarized as: (1)EINECS: 206-893-5; (2)ACD/LogP: 2.30; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.3; (5)ACD/LogD (pH 7.4): 2.3; (6)ACD/BCF (pH 5.5): 33.1; (7)ACD/BCF (pH 7.4): 33.04; (8)ACD/KOC (pH 5.5): 426.07; (9)ACD/KOC (pH 7.4): 425.36; (10)H bond acceptors: 2; (11)H bond donors: 1; (12)Freely Rotating Bonds: 2; (13)Index of Refraction: 1.529; (14)Molar Refractivity: 38.15 cm3; (15)Molar Volume: 123.6 cm3; (16)Surface Tension: 41.9 dyne/cm; (17)Density: 1.247 g/cm3; (18)Flash Point: 97.7 °C; (19)Melting point: 54-59 °C; (20)Water solubility: soluble 0.68 g/L; (21)Enthalpy of Vaporization: 43.56 kJ/mol; (22)Boiling Point: 182.2 °C at 760 mmHg; (23)Vapour Pressure: 0.603 mmHg at 25 °C.
Preparation of Ethanone,1-(5-fluoro-2-hydroxyphenyl)-: this chemical can be prepared by Acetic acid-(4-fluoro-phenyl ester).
This reaction needs AlCl3 at temperature of 160 °C. The reaction time is 2 hours. The yield is 85 %.
Uses of Ethanone,1-(5-fluoro-2-hydroxyphenyl)-: it can react with 6-Chloro-4H-benzo[1,3]dioxin-8-carbaldehyde to get 3-(6-Chloro-4H-benzo[1,3]dioxin-8-yl)-1-(5-fluoro-2-hydroxy-phenyl)-propenone.
This reaction needs 50percent aq. NaOH and Ethanol at ambient temperature. The yield is 90 %.
When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. It is also irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye / face protection when use it. Moreover, in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
People can use the following data to convert to the molecule structure.
(1)SMILES:O=C(c1cc(F)ccc1O)C
(2)InChI:InChI=1/C8H7FO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3
(3)InChIKey:KOFFXZYMDLWRHX-UHFFFAOYAY
(4)Std. InChI:InChI=1S/C8H7FO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3
(5)Std. InChIKey:KOFFXZYMDLWRHX-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 1gm/kg (1000mg/kg) | Medicina Experimentalis. Vol. 11, Pg. 137, 1964. |
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