700-35-6

Basic information

• Product Name: 2'-CHLORO-4'-FLUOROACETOPHENONE
• Synonyms: 2'-Chloro-4'-fluoroacetophenone99%;2'-Chloro-4'-fluoroacetophenone, 98+%;1-(2-Chloro-4-fluorophenyl)ethan-1-one;2-Chloro-4-fluorophenyl methyl ketone;Ethanone,1-(2-chloro-4-fluorophenyl)-
• CAS NO: 700-35-6
• Molecular Formula: C₈H₆ClFO
• Molecular Weight: 172.58
• EINECS: -0
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Adehydes, Acetals & Ketones;Chlorine Compounds;Fluorine Compounds
• Mol File: 700-35-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 110°C 19mm
• Flash Point: 110°C/19mm
• Appearance: Clear colourless to light yellow liquid
• Density: 1.258±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.278mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2249796
• CAS DataBase Reference: 2'-CHLORO-4'-FLUOROACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-CHLORO-4'-FLUOROACETOPHENONE(700-35-6)
• EPA Substance Registry System: 2'-CHLORO-4'-FLUOROACETOPHENONE(700-35-6)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• Hazardous Substances Data: 700-35-6(Hazardous Substances Data)

Usage

Uses

2''-Chloro-4''-fluoroacetophenone

InChI:InChI=1/C8H6ClFO/c1-5(11)7-3-2-6(10)4-8(7)9/h2-4H,1H3

Synthetic route

2-chloro-4-fluoro-N-methoxy-N-methylbenzamide + methylmagnesium bromide (75-16-1) → 2'-chloro-4'-fluoroacetophenone (700-35-6)

Conditions	Yield
In tetrahydrofuran at -78 - 0℃; for 5.5h;	98.42%

1-(2-chloro-4-fluorophenyl)ethan-1-ol (112108-68-6) → 2'-chloro-4'-fluoroacetophenone (700-35-6)

Conditions	Yield
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;	26%

3-chlorofluorobenzene (625-98-9) + acetyl chloride (75-36-5) → 2'-chloro-4'-fluoroacetophenone (700-35-6)

Conditions	Yield
With aluminium trichloride In carbon disulfide Heating;

3-chlorofluorobenzene (625-98-9) + acetic anhydride (108-24-7) → 2'-chloro-4'-fluoroacetophenone (700-35-6)

Conditions	Yield
With aluminium trichloride In carbon disulfide Heating;

2-choro-4-fluorobenzoic acid (2252-51-9) → 2'-chloro-4'-fluoroacetophenone (700-35-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 15 °C 2: tetrahydrofuran / 5.5 h / -78 - 0 °C View Scheme

4-n-butylphenol (1638-22-8) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 4-(4-butylphenoxy)-2-chloroacetophenone

Conditions	Yield
Stage #1: 4-n-butylphenol With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #2: 2'-chloro-4'-fluoroacetophenone In N,N-dimethyl-formamide at 115℃; Inert atmosphere;	100%

2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-fluorophenyl)ethan-1-ol (112108-68-6)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 15℃; for 3h;	97.81%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 1.16667h;	0.4 g

4-Trifluoromethoxyphenol (828-27-3) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-(4-(trifluoromethoxy)phenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2.5h;	91.3%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 4-chloro-phenol (106-48-9) → 1-(2-chloro-4-(4-chlorophenoxy)phenyl)-ethan-1-one (119851-28-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 115℃; for 8h;	90%
With potassium carbonate In N,N-dimethyl-formamide for 48h; Reflux;

2'-chloro-4'-fluoroacetophenone (700-35-6) + 4-chloro-3-fluorophenol (348-60-7) → 1-(2-chloro-4-(4-chloro-3-fluorophenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	89.4%

2'-chloro-4'-fluoroacetophenone (700-35-6) + ethyl 2-cyanoacetate (105-56-6) → Ethyl 2-cyano-4-(4-fluorophenyl)-4-oxobutanoate (131952-81-3)

Conditions	Yield
With sodium In ethanol; water	88%

4-bromo-phenol (106-41-2) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(4-(4-bromophenoxy)-2-chlorophenyl)ethan-1-one

Conditions	Yield
Stage #1: 4-bromo-phenol With potassium carbonate In N,N-dimethyl-formamide at 21℃; for 0.166667h; Stage #2: 2'-chloro-4'-fluoroacetophenone In N,N-dimethyl-formamide at 120℃; for 3h;	87%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 1.5h;

2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(4-fluorophenyl)ethanone (403-42-9)

Conditions	Yield
With isopropyl alcohol for 15h; Schlenk technique; Inert atmosphere; Irradiation; Heating;	87%

4-butylthiophenol (4946-15-0) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 4-(4-butylphenylthio)-2-chloroacetophenone

Conditions	Yield
Stage #1: 4-butylthiophenol With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 0.5h; Stage #2: 2'-chloro-4'-fluoroacetophenone In N,N-dimethyl-formamide at 115℃; Inert atmosphere;	85%

3-Bromopyridine (626-55-1) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(4-fluoro-2-(pyridin-3-yl)phenyl)ethanone

Conditions	Yield
Stage #1: 3-Bromopyridine With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane; water at 80℃; Inert atmosphere; Stage #2: 2'-chloro-4'-fluoroacetophenone With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Inert atmosphere; Sealed tube;	84%

2'-chloro-4'-fluoroacetophenone (700-35-6) + allyl bromide (106-95-6) → 2-(2-chloro-4-fluorophenyl)pent-4-en-2-ol

Conditions	Yield
With zinc In dimethyl sulfoxide for 2h; Barbier Coupling Reaction; Milling;	79%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 4-bromo-3-fluorophenol (121219-03-2) → 1-(4-(4-bromo-3-fluorophenoxy)-2-chlorophenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	78.3%

2,4-difluorophenol (367-27-1) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-(2,4-difluorophenoxy)phenyl)ethan-1-one (1044060-07-2)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 5.5h;	77.3%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h;	100 g

2'-chloro-4'-fluoroacetophenone (700-35-6) → (2-Chloro-4-fluoro-phenyl)-oxo-acetaldehyde (81593-25-1)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water for 4h;	76%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 4-cyanophenol (767-00-0) → 1-(2-chloro-4-(4-cyanophenoxy) phenyl)ethan-1-one (1246382-67-1)

Conditions	Yield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 1h;	73.9%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 4-methoxy-phenol (150-76-5) → 1-(2-chloro-4-(4-methoxyphenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	73.3%

3-mercaptophenol (40248-84-8) + 2'-chloro-4'-fluoroacetophenone (700-35-6) + benzyl bromide (100-39-0) → 1-(4-(3-(benzyloxy)phenylthio)-2-chlorophenyl)ethanone (1007165-40-3)

Conditions	Yield
Stage #1: 3-mercaptophenol; 2'-chloro-4'-fluoroacetophenone With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3 - 18h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 60℃; for 3h;	70%

3,4-difluorophenol (2713-33-9) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-(3,4-difluorophenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h;	69%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 2,4-dichlorophenol (120-83-2) → 1-(2-chloro-4-(2,4-dichlorophenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 120℃; for 4.75h;	68.3%

6-hydroxyquinoline (580-16-5) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-(quinolin-6-yloxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 3.5h;	68.1%

(3-((tert-butyldimethylsilyl)oxy)phenyl)zinc chloride + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(3'-((tert-butyldimethylsilyl)oxy)-5-fluoro-[1,1'-biphenyl]-2-yl)ethan-1-one

Conditions	Yield
With Li2CoCl4; sodium formate In tetrahydrofuran at 25℃; Negishi Coupling; Inert atmosphere; Schlenk technique;	68%

2'-chloro-4'-fluoroacetophenone (700-35-6) + 2-chloro-5-trifluoromethylpyridine (52334-81-3) → 1-(2-Chloro-4-Fluorophenyl)-2-(5-Trifluoromethyl-2-Pyridinyl)Ethanone (372122-68-4)

Conditions	Yield
Stage #1: 2'-chloro-4'-fluoroacetophenone; 2-chloro-5-trifluoromethylpyridine With sodium hydride In 1,2-dimethoxyethane at 20 - 45℃; for 1h; Stage #2: With water In 1,2-dimethoxyethane at 5℃;	67%

2'-chloro-4'-fluoroacetophenone (700-35-6) + (1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (113451-59-5) → tert-butyl(1S,4S)-5-(4-acetyl-3-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1186334-88-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h;	66%
With potassium carbonate In N,N,N,N,N,N-hexamethylphosphoric triamide Inert atmosphere;

formaldehyd (50-00-0) + 2'-chloro-4'-fluoroacetophenone (700-35-6) + N,N-dimethylammonium chloride (506-59-2) + oxalic acid (144-62-7) → 1-(2-Chloro-4-fluoro-phenyl)-3-dimethylamino-propan-1-one; compound with oxalic acid (76475-98-4)

Conditions	Yield
With hydrogenchloride In ethanol for 8h; Heating;	65.4%

formaldehyd (50-00-0) + 2'-chloro-4'-fluoroacetophenone (700-35-6) + piperazine hydrochloride (7542-23-6) → 1-(2-Chloro-4-fluoro-phenyl)-3-{4-[3-(2-chloro-4-fluoro-phenyl)-3-oxo-propyl]-piperazin-1-yl}-propan-1-one; hydrochloride (76476-01-2)

Conditions	Yield
With hydrogenchloride In ethanol for 8h; Heating;	63%

formaldehyd (50-00-0) + 2'-chloro-4'-fluoroacetophenone (700-35-6) + piperidine hydrochloride (6091-44-7) → 1-(2-Chloro-4-fluoro-phenyl)-3-piperidin-1-yl-propan-1-one; hydrochloride (76476-00-1)

Conditions	Yield
With hydrogenchloride In ethanol for 8h; Heating;	62.7%

3,4-dichlorophenol (95-77-2) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 1-(2-chloro-4-(3,4-dichlorophenoxy)phenyl)ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 6h;	62.1%

ethyl trifluoroacetate, (383-63-1) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → 2-chloro-4-fluorobenzoyltrifluoroacetone (38440-20-9)

Conditions	Yield
With sodium amide In diethyl ether 0 deg C, 1 h, r.t., overnight then reflux, 4 h;	62%

ethyl 5-bromo-3-pyridinecarboxylate (20986-40-7) + 2'-chloro-4'-fluoroacetophenone (700-35-6) → ethyl 5-(2-acetyl-5-fluorophenyl)nicotinate

Conditions

Yield

Stage #1: ethyl 5-bromo-3-pyridinecarboxylate With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane; water at 80℃; Inert atmosphere; Stage #2: 2'-chloro-4'-fluoroacetophenone With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; XPhos In 1,4-dioxane; water at 100℃; for 24h; Inert atmosphere; Sealed tube;

62%

Upstream product

• 112108-68-6 1-(2-chloro-4-fluorophenyl)ethan-1-ol 
• 75-16-1 methylmagnesium bromide 
• 2252-51-9 2-choro-4-fluorobenzoic acid 
• 625-98-9 3-chlorofluorobenzene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 

Downstream Products

• 112108-68-6 1-(2-chloro-4-fluorophenyl)ethan-1-ol 
• 2252-51-9 2-choro-4-fluorobenzoic acid 
• 38440-20-9 2-chloro-4-fluorobenzoyltrifluoroacetone 
• 78864-22-9 [5-(2-chloro-4-fluoro-phenyl)-thiazol-2-yl]-(4-chloro-phenyl)-amine 
• 76475-98-4 1-(2-Chloro-4-fluoro-phenyl)-3-dimethylamino-propan-1-one; compound with oxalic acid 
• 76475-99-5 1-(2-Chloro-4-fluoro-phenyl)-3-diethylamino-propan-1-one; hydrochloride 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1021187-74-5 1-(4-(4-fluorophenoxy)-2-chlorophenyl)ethanone 
• 1246382-67-1 1-(2-chloro-4-(4-cyanophenoxy) phenyl)ethan-1-one 

Relevant articles and documents

Transfer-dehydrogenation of secondary alcohols catalyzed by manganese NNN-pincer complexes

Novel catalytic systems based on pentacarbonylmanganese bromide and stable NNN-pincer ligands are presented for the transfer-dehydrogenation of secondary alcohols to give the corresponding ketones in good to excellent isolated yields. Best results are obtained using di-picolylamine derivatives as ligands and acetone as an inexpensive hydrogen acceptor. Besides high activity for benzylic substrates, aliphatic alcohols, as well as steroid derivatives, are readily oxidized in the presence of the optimal phosphorus-free catalyst.