1823-63-8

Basic information

• Product Name: 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE
• Synonyms: 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE;Ethanone, 2,2,2-trifluoro-1-(4-hydroxyphenyl)-;3-(1-amino-2,2,2-trifluoroethyl)phenol;4'-Hydroxy-2,2,2-trifluoroacetophenone;4-(Trifluoroacetyl)phenol;2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one;2,2,2-Trifluoro-4'-hydroxyacetophenone
• CAS NO: 1823-63-8
• Molecular Formula: C₈H₅F₃O₂
• Molecular Weight: 190.12
• Mol File: 1823-63-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 114 °C
• Boiling Point: 261.911 °C at 760 mmHg
• Flash Point: 112.2 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.481
• Storage Temp.: 2-8°C
• PKA: 7.60±0.13(Predicted)
• CAS DataBase Reference: 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE(1823-63-8)
• EPA Substance Registry System: 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE(1823-63-8)

Safety Data

• Hazardous Substances Data: 1823-63-8(Hazardous Substances Data)

Usage

General Description

2,2,2-Trifluoro-1-(4-hydroxy-phenyl)-ethanone is a chemical compound with the molecular formula C8H7F3O2. It is a ketone derivative with a trifluoromethyl group and a hydroxyphenyl group attached to the carbonyl carbon. 2,2,2-TRIFLUORO-1-(4-HYDROXY-PHENYL)-ETHANONE is commonly used in organic synthesis as a building block for pharmaceuticals, agrochemicals, and materials science. It is also used as a synthetic intermediate in the production of various pharmaceuticals and agrochemicals. 2,2,2-Trifluoro-1-(4-hydroxy-phenyl)-ethanone is known for its versatility and is often used in the development of new chemical compounds with useful properties.

InChI:InChI=1/C8H5F3O2/c9-8(10,11)7(13)5-1-3-6(12)4-2-5/h1-4,12H

Synthetic route

4'-methoxy-2,2,2-trifluoroacetophenone (711-38-6) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 16h;	96%
With lithium chloride In N,N-dimethyl-formamide for 2h; Heating;	88%
With boron tribromide In dichloromethane at -78 - 20℃;	88%

1-[4-[{(1,1-dimethylethyl)dimethylsilyl}oxy]phenyl]-2,2,2-trifluoroethan-1-one (760969-01-5) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;	90%

(4-bromophenoxy)trimethylsilane (17878-44-3) + ethyl trifluoroacetate, (383-63-1) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran	68%

4-bromo-phenol (106-41-2) + concentrated aqueous KOH-solution → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / imidazole / dimethylformamide / 0 - 20 °C 2: 56 percent / Mg / tetrahydrofuran / 20 °C 3: 90 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

t-butyldimethylsilyl-4-bromophenol (67963-68-2) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / Mg / tetrahydrofuran / 20 °C 2: 90 percent / TBAF / tetrahydrofuran / 20 °C View Scheme

trifluoracetyl chloride (354-32-5) + phenol (108-95-2) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethyl alcohol (246245-20-5) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 12h; Reflux;

4-hydroxy-benzaldehyde (123-08-0) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 1.2: 4 h / Acidic conditions 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 12 h / Reflux View Scheme

bromoacetic acid tert-butyl ester (5292-43-3) + 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → C14H15F3O4 (1351283-01-6)

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 120℃; for 0.666667h; Microwave irradiation;	95%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + poly(ethylene glycol) monomethyl ether, mesylate → poly(ethylene glycol) methyl 4-(α,α,α-trifluoroacetyl)phenyl ether

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 65℃;	90%

4-chloromethyl-3,5-dimethylisoxazole (19788-37-5) + 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → 1-[4-(3,5-dimethylisoxazol-4-ylmethoxy)phenyl]-2,2,2-trifluoroethanone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	90%

(S)-Methyl lactate (27871-49-4) + 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → methyl (S)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate

Conditions	Yield
Stage #1: (S)-Methyl lactate; 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Mitsunobu Displacement; Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Mitsunobu Displacement;	78%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + ethylene dibromide (106-93-4) → C10H8BrF3O2

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In ethyl acetate Reflux;	76.8%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-(4E)-tetradecene-1,3,14-triol (608880-37-1) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol (608880-41-7)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; Mitsunobu reaction;	74%

(R)-Methyl lactate (17392-83-5) + 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → methyl (R)-2-(4-(2,2,2-trifluoroacetyl)phenoxy)propanoate

Conditions	Yield
Stage #1: (R)-Methyl lactate; 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With triphenylphosphine In dichloromethane at 0℃; for 0.166667h; Mitsunobu Displacement; Stage #2: With diethylazodicarboxylate In dichloromethane at 0 - 20℃; for 8h; Mitsunobu Displacement;	74%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → 1-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)phenyl)-2,2,2-trifluoroethan-1-one (271252-24-5)

Conditions	Yield
With 18-crown-6 ether; potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere; Schlenk technique;	70%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + ethyl bromoacetate (105-36-2) → C12H11F3O4 (1453102-20-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 60℃; for 4h; Inert atmosphere;	33%

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + 2-(diethylamino)ethyl chloride (100-35-6) → 2,2,2-Trifluor-4'-(2-diethylamino-ethoxy)-acetophenon (3705-09-7)

Conditions	Yield
(i) Na, (ii) /BRN= 605300/; Multistep reaction;

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + 4-pentylbenzoic acid (26311-45-5) → 4-Pentyl-benzoic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester (136101-39-8)

Conditions	Yield
With dicyclohexyl-carbodiimide

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + 4-trans-pentyl-cyclohexane-1-carboxylic acid (38792-89-1) → 4-Pentyl-cyclohexanecarboxylic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester (136101-38-7)

Conditions	Yield
With dicyclohexyl-carbodiimide

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + trans-trans-4-n-pentylcyclohexyl-cyclohexane-4'-carboxylic acid (82372-79-0) → 4'-Pentyl-bicyclohexyl-4-carboxylic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester (136101-40-1)

Conditions	Yield
With dicyclohexyl-carbodiimide

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) + p-(4-trans-n-Pentylcyclohexyl)benzoic acid (66227-33-6) → 4-(4-Pentyl-cyclohexyl)-benzoic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester (136101-41-2)

Conditions	Yield
With dicyclohexyl-carbodiimide

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethyl alcohol (246245-20-5)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane; isopropyl alcohol at 20℃; Rate constant;
With sodium cyanoborohydride; zinc(II) iodide In 1,1-dichloroethane at 20℃; for 18h;

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-2-amino-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol (608880-47-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C 6: 82 percent / I2; Et3N / methanol / 1 h / 20 °C 7: 80 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diazirin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol (727975-09-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C 6: 82 percent / I2; Et3N / methanol / 1 h / 20 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diaziridin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol (608880-45-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C 5: 97 percent / NaOH; MeOH / 20 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-[4'-[3-(trifluoromethyl)diaziridin-3-yl]phenyl]-(4E)-tetradecene-1,3,14-triol (608880-44-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C 4: 80 percent / ammonia / CH2Cl2 / -78 - 20 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol oxime (608880-42-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol O-tosyl oxime (608880-43-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / DIAD; Ph3P / CH2Cl2 / 0 - 20 °C 2: 99 percent / hydroxylamine hydrochloride; pyridine / ethanol / 12 h / 50 - 60 °C 3: 99 percent / triethylamine; DMAP / CH2Cl2 / 0 - 20 °C View Scheme

2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → 1-(4-Chlor-phenyl)-2-<4-(2-diethylamino-ethoxy)-phenyl>-3,3,3-trifluor-propan-2-ol (4048-18-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Na, (ii) /BRN= 605300/ View Scheme

dibromodifluoromethane (75-61-6) + 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one (1823-63-8) → 4'-bromodifluoromethoxy-2,2,2-trifluoroacetophenone (849370-45-2)

Conditions	Yield
Stage #1: 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethan-1-one With sodium hydride In 1,3-dimethyl-2-imidazolidinone at 20℃; for 0.5h; Stage #2: dibromodifluoromethane In 1,3-dimethyl-2-imidazolidinone at 0 - 10℃; Stage #3: With potassium tert-butylate In 1,3-dimethyl-2-imidazolidinone at 20℃; for 1h;

Upstream product

• 354-32-5 trifluoracetyl chloride 
• 108-95-2 phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 123-08-0 4-hydroxy-benzaldehyde 
• 246245-20-5 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethyl alcohol 
• 17878-44-3 (4-bromophenoxy)trimethylsilane 
• 383-63-1 ethyl trifluoroacetate, 
• 67963-68-2 t-butyldimethylsilyl-4-bromophenol 
• 106-41-2 4-bromo-phenol 
• 760969-01-5 1-[4-[{(1,1-dimethylethyl)dimethylsilyl}oxy]phenyl]-2,2,2-trifluoroethan-1-one 
• 711-38-6 4'-methoxy-2,2,2-trifluoroacetophenone 

Downstream Products

• 3705-09-7 2,2,2-Trifluor-4'-(2-diethylamino-ethoxy)-acetophenon 
• 136101-39-8 4-Pentyl-benzoic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester 
• 136101-38-7 4-Pentyl-cyclohexanecarboxylic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester 
• 136101-40-1 4'-Pentyl-bicyclohexyl-4-carboxylic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester 
• 136101-41-2 4-(4-Pentyl-cyclohexyl)-benzoic acid 4-(2,2,2-trifluoro-acetyl)-phenyl ester 
• 246245-20-5 2,2,2-trifluoro-1-(4-hydroxyphenyl)ethyl alcohol 
• 849370-45-2 4'-bromodifluoromethoxy-2,2,2-trifluoroacetophenone 
• 1453102-19-6 N-(4-methoxyphenyl)-2,2,2-trifluoro-1-(4-ethylphenoxyacetate)ethan-1-amine 
• 1453102-20-9 C₁₂H₁₁F₃O₄ 

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