5'-Fluoro-2'-hydroxyacetophenone supplier

Name
1-(5-Fluoro-2-hydroxyphenyl)-1-ethanone
EINECS 206-893-5
CAS No. 394-32-1
Article Data42
CAS DataBase
Density 1.247 g/cm³
Solubility 0.68 g/L in water
Melting Point 56-58 °C(lit.)
Formula C₈H₇FO₂
Boiling Point 182.2 °C at 760 mmHg
Molecular Weight 154.141
Flash Point 97.7 °C
Transport Information
Appearance light yellow to beige-brown crystals
Safety 26-37/39-36/37/39
Risk Codes 36/37/38-22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms Acetophenone,5'-fluoro-2'-hydroxy- (6CI,7CI,8CI);1-(5-fluoro-2-hydroxyphenyl)ethanone;2-Acetyl-4-fluorophenol;2'-Hydroxy-5'-fluoroacetophenone;3-Fluoro-6-hydroxyacetophenone;NSC 46624;
PSA 37.30000
LogP 1.73390

Synthetic route

: 405-51-6
4-fluorophenyl acetate

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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%

: 371-41-5
4-Fluorophenol

: 75-36-5
acetyl chloride

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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;

: 445-82-9
1-(5-fluoro-2-methoxyphenyl)ethanone

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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;

: 1799-18-4
1-(2-benzyloxy-5-fluorophenyl)-ethanone

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 4h; Inert atmosphere;	82%

: 371-41-5
4-Fluorophenol

: 64-19-7
acetic acid

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
With aluminum oxide; methanesulfonic acid at 120℃; for 2h;	60%
With boron trifluoride at 150℃; unter Druck;

: 459-60-9
1-fluoro-4-methoxybenzene

: 75-36-5
acetyl chloride

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
With aluminium trichloride In tetrachloromethane	44.1%

: 459-60-9
1-fluoro-4-methoxybenzene

: 75-36-5
acetyl chloride

A: 445-82-9
1-(5-fluoro-2-methoxyphenyl)ethanone

B: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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;

...Expand

: 7446-70-0
aluminium trichloride

: 405-51-6
4-fluorophenyl acetate

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
at 150℃;

: 371-41-5
4-Fluorophenol

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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

: 371-41-5
4-Fluorophenol

p-difluoro-benzene: p-difluoro-benzene

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / conc. H2SO4 2: 85 percent / AlCl3 / 2 h / 160 °C View Scheme

: 459-60-9
1-fluoro-4-methoxybenzene

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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

: 459-26-7
4-ethoxy-1-fluorobenzene

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: AlCl3; benzene 2: 100 °C 3: AlCl3 / 150 °C View Scheme

AlCl3 (for Friedel-Crafts reactions): AlCl3 (for Friedel-Crafts reactions)

: 405-51-6
4-fluorophenyl acetate

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 189628-38-4
3-fluoro-6-methoxybenzonitrile

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

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

: 358-23-6
trifluoromethylsulfonic anhydride

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 874388-48-4
2-acetyl-4-fluorophenyl triflate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃;	100%
With pyridine at 0 - 20℃; for 12h;	92%
With pyridine at 0 - 20℃;	68%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 105-39-5
chloroacetic acid ethyl ester

: 34849-57-5
(2-acetyl-4-fluorophenoxy)acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In acetone for 16h; Reflux; Inert atmosphere;	100%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 623-48-3
ethyl iodoacetae

: 34849-57-5
(2-acetyl-4-fluorophenoxy)acetic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In water; acetone	99%
With potassium carbonate In N,N-dimethyl-formamide at 90℃;

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 1-(5-fluoro-2-iodophenyl)ethan-1-ol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 1h; Cooling with ice;	99%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 70978-39-1
5'-fluoro-2'-hydroxy-3'-nitroacetophenone

Conditions

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%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 77-78-1
dimethyl sulfate

: 445-82-9
1-(5-fluoro-2-methoxyphenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 18h; Reflux;	98%

: 6165-76-0
propargyl p-toluenesulfonate

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 879216-16-7
1-(5-fluoro-2-(prop-2-yn-1-yloxy)phenyl)ethan-1-one

Conditions

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%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one oxime

Conditions

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;

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 95-92-1
oxalic acid diethyl ester

: ethyl 4-(5-fluoro-2-hydroxyphenyl)-2,4-dioxobutanoate

Conditions

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;

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 100-07-2
4-methoxy-benzoyl chloride

: 850799-88-1
1-(5-fluoro-2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione

Conditions

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%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 106-95-6
allyl bromide

: 1092306-36-9
1-[2-(allyloxy)-5-fluorophenyl]ethanone

Conditions

Conditions	Yield
With potassium carbonate In 4-methyl-2-pentanone for 8h; Reflux;	96%
With potassium carbonate In acetone Reflux;

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 4-Fluoro-2-((R)-1-hydroxy-ethyl)-phenol

Conditions

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;

: 2417-72-3
Methyl 4-(bromomethyl)benzoate

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: methyl 4-((2-acetyl-4-fluorophenoxy)methyl)benzoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	95%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 403-43-0
4-fluorobenzoyl chloride

: 1225785-23-8
1-(5-fluoro-2-hydroxyphenyl)-3-(4-fluorophenyl)propane-1,3-dione

Conditions

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%

: 74-96-4
ethyl bromide

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 1466-79-1
2'-ethoxy-5'-fluoroacetophenone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	94%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 37050-18-3
5-chloro-1-methyl-1H-imidazole-2-carbaldehyde

: (E)-3-(5-Chloro-1-methyl-1H-imidazol-2-yl)-1-(5-fluoro-2-hydroxy-phenyl)-propenone

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Ambient temperature;	93%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 446-52-6
2-Fluorobenzaldehyde

: 224294-29-5
3-(2-fluorophenyl)-1-(5-fluoro-2-hydroxyphenyl)-2-propen-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol	93%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 74-88-4
methyl iodide

: 445-82-9
1-(5-fluoro-2-methoxyphenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	93%
With potassium carbonate In acetone at 20℃;

: 437-81-0
2,6-difluorobenzaldehyde

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 224294-27-3
3-(2,6-difluorophenyl)-1-(5-fluoro-2-hydroxyphenyl)-2-propen-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol	92%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 120-92-3
cyclopentanone

: 111478-02-5
6-fluorospiro[chroman-2,1'-cyclopentan]-4-one

Conditions

Conditions	Yield
With pyrrole In toluene for 20h; Reflux;	92%
pyrrolidine In acetonitrile

: [Pd(CH2-C6H4-P(o-tolyl)2-κC,P)(μ-OOCCH3)]2

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 209810-53-7, 209743-84-0
2-acetyl-4-fluorophenolato-[o-(di-o-tolylphosphino)benzyl]palladium(II)

Conditions

Conditions	Yield
With potassium tert-butoxide In toluene Ar-atmosphere; stirring (12 h); filtering, evapn. (vac.), crystn. (toluene / pentane); elem. anal.;	92%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 372-09-8
cyanoacetic acid

: 288399-90-6
C11H6FNO2

Conditions

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%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 105-58-8
Diethyl carbonate

: 1994-13-4
6-fluoro-4-hydroxycoumarin

Conditions

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%

: 434-45-7
1,1,1-trifluoroacetophenone

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: (S)-4,4,4-trifluoro-1-(5-fluoro-2-hydroxyphenyl)-3-hydroxy-3-phenylbutan-1-one

Conditions

Conditions	Yield
With C19H25F6N3S In toluene at 0℃; for 96h; Aldol Addition; Inert atmosphere; enantioselective reaction;	91%

: 63944-31-0
6-chloro-8-formyl-1,3-benzodioxane

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 147722-92-7
(E)-3-(6-Chloro-4H-benzo[1,3]dioxin-8-yl)-1-(5-fluoro-2-hydroxy-phenyl)-propenone

Conditions

Conditions	Yield
With sodium hydroxide In ethanol Ambient temperature;	90%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 459-57-4
4-fluorobenzaldehyde

: 224294-26-2
(E)-1-(2-hydroxy-5-fluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

Conditions

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%

: 394-32-1
1-(5-fluoro-2-hydroxyphenyl)ethan-1-one

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 3-(dimethylamino)-1-(5-fluoro-2-hydroxyphenyl)prop-2-en-1-one

Conditions

Conditions	Yield
In toluene at 80℃; Sealed tube; Inert atmosphere;	90%
at 95℃; for 4h;	69%
at 100℃; for 2h;

5'-Fluoro-2'-hydroxyacetophenone Specification

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.

Product Name

1-(5-Fluoro-2-hydroxyphenyl)-1-ethanone

Synthetic route

5'-Fluoro-2'-hydroxyacetophenone Specification

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