704-10-9

Basic information

• Product Name: 2,4-Dichloro-5-fluoroacetophenone
• Synonyms: 2,4-DICHLORO-5-FLUOROACETOPHENONE;1-(2,4-DICHLORO-5-FLUOROPHENYL)ETHAN-1-ONE;1-(2,4-DICHLORO-5-FLUORO-PHENYL)-ETHANONE;2',4'-Dichloro-5'-Fluoroacetophenone 2,4-Dichloro-5-Fluoroacetophenone;2',4'-DICHLORO-5'-FLUOROACETOPHENONE, 90;2',4'-Dichloro-5'-fluoroacetophenone 98%;2',4'-Dichloro-5'-fluoroacetophenone98%;2,4- Dichloro -5-fluorohypnone
• CAS NO: 704-10-9
• Molecular Formula: C₈H₅Cl₂FO
• Molecular Weight: 207.03
• EINECS: -0
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Acetophenones & Derivatives (substituted);ketone;C7 to C8;Carbonyl Compounds;Ketones;Ciprofloxacin intermediate
• Mol File: 704-10-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 33-36 °C
• Boiling Point: 167 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow cryst. low melting solid
• Density: 1.425 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.275mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 3090042
• CAS DataBase Reference: 2,4-Dichloro-5-fluoroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-5-fluoroacetophenone(704-10-9)
• EPA Substance Registry System: 2,4-Dichloro-5-fluoroacetophenone(704-10-9)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 704-10-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H7BrF6O/c1-18-7-5-3-2-4-6(7)8(11,9(12,13)14)10(15,16)17/h2-5H,1H3

Synthetic route

1,3-dichloro-4-fluorobenzene (1435-48-9) + acetyl chloride (75-36-5) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
With aluminum (III) chloride at 110℃; Reagent/catalyst; Temperature;	89.3%
With aluminum (III) chloride Friedel Crafts acylation;	52%
With aluminum (III) chloride at 30 - 120℃; Product distribution / selectivity;
aluminum (III) chloride

1,3-dichloro-4-fluorobenzene (1435-48-9) + acetic anhydride (108-24-7) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
With aluminium trichloride
With aluminum (III) chloride at 70 - 120℃; for 25h;	165 g

1-(1-butoxy-vinyl)-2,4-dichloro-5-fluoro-benzene → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
With hydrogenchloride for 0.5h;

1-bromo-2,4-dichloro-5-fluorobenzene (1481-63-6) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-butyl-3-methylimidazolium*BF4; 1,3-bis(diphenylphosphino)propane; Et3N / Ni(OAc)2 / 30 h / 130 °C 2: aq. HCl / 0.5 h View Scheme

1,3-dichloro-4-fluorobenzene (1435-48-9) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
With hydrogenchloride; acetic anhydride; aluminium trichloride

1,2-dichloro-benzene (95-50-1) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: nitric acid; sulfuric acid / 2 h / 95 - 100 °C 2.1: potassium fluoride / 3 h / 140 - 150 °C 2.2: 7 h / 165 - 170 °C 3.1: chlorine / 8 h / 170 - 180 °C 4.1: aluminum (III) chloride / 110 °C View Scheme

3,4-dichloronitrobenzene (99-54-7) → 2,4-dichloro-5-fluoroacetophenone (704-10-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium fluoride / 3 h / 140 - 150 °C 1.2: 7 h / 165 - 170 °C 2.1: chlorine / 8 h / 170 - 180 °C 3.1: aluminum (III) chloride / 110 °C View Scheme

2,4-dichloro-5-fluoroacetophenone (704-10-9) → 2,4-dichloro-5-fluoro-benzoic acid (86522-89-6)

Conditions	Yield
With oxygen; nitric acid In water; acetic acid at 70℃; under 1500.15 Torr; for 0.15h; Catalytic behavior; Temperature; Time; Pressure; Flow reactor; Industrial scale; Green chemistry;	99.9%
With sodium hypochlorite In 1,4-dioxane	98%
With sodium hydroxide; chlorine In ethanol pH=10;	90%
With sodium percarbonate; potassium tert-butylate; sphingosylphosphorylcholine; meta-dinitrobenzene In tert-butyl alcohol at 80℃; for 5h;	35%
With sodium hydroxide; chlorine In ethanol for 6h; pH=8 - 10;

2,4-dichloro-5-fluoroacetophenone (704-10-9) → α,α,α,2,4-pentachloro-5-fluoroacetophenone

Conditions	Yield
With chlorine In water	96%

2,4-dichloro-5-fluoroacetophenone (704-10-9) → 2,4-dichloro-5-fluoro-3-nitro-benzoic acid (106809-14-7)

Conditions	Yield
With sulfuric acid; nitric acid at 103 - 110℃; for 3h; Temperature;	91%
With sulfuric acid; nitric acid 1.) 55 deg C; 2.) 75 deg C, 3 h;	82%

5-(4-chlorophenyl)-2-furaldehyde (34035-03-5) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → (E)-3-[5-(4-Chloro-phenyl)-furan-2-yl]-1-(2,4-dichloro-5-fluoro-phenyl)-propenone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	90%

5-(2-chlorophenyl)furan-2-carbaldehyde (34035-04-6) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → (E)-3-[5-(2-Chloro-phenyl)-furan-2-yl]-1-(2,4-dichloro-5-fluoro-phenyl)-propenone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	89%

2,4-dichloro-5-fluoroacetophenone (704-10-9) → C8H8Cl2FN (855715-32-1)

Conditions	Yield
With N,N'-bis(salicylidene)-1,2-phenylene-diaminocobalt(II); ammonia; hydrogen In water at 130℃; for 24h; Autoclave;	89%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + oxalic acid diethyl ester (95-92-1) → ethyl (Z)-4-(2,4-dichloro-5-fluorophenyl)-2-hydroxy-4-oxobut-2-enoate

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; Claisen Condensation;	88%

2,4-dichloro-5-fluoroacetophenone (704-10-9) → α-bromo-(2,4-dichloro-5-fluoro)acetophenone (357915-19-6)

Conditions	Yield
With 1-butyl-3-methylimidazolium tribromide In neat (no solvent) for 0.266667h;	83.2%
With bromine In chloroform Photolysis;
With bromine In tetrachloromethane at 0 - 20℃;

2,4-dichloro-5-fluoroacetophenone (704-10-9) + Diethyl carbonate (105-58-8) → ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate (86483-51-4)

Conditions	Yield
With sodium hydride at 80℃; for 1.5h;	80%
	47%
With sodium hydride In tetrahydrofuran at 45 - 55℃; for 5h; Inert atmosphere;	215 g
With sodium hydride

2,4-dichloro-5-fluoroacetophenone (704-10-9) + benzonitrile (100-47-0) → 3-(2,4-dichloro-5-fluorobenzoyl)-5-phenyl-1,2,4-oxadiazole

Conditions	Yield
With nitric acid at 80℃; for 4h;	80%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + carbonic acid dimethyl ester (616-38-6) → methyl 2,4-dichloro-5-fluoro-benzoylacetate (103319-17-1)

Conditions	Yield
Stage #1: carbonic acid dimethyl ester With sodium methylate at 75℃; for 0.25h; Stage #2: 2,4-dichloro-5-fluoroacetophenone at 85℃; for 3h;	80%

(3,4-Dimethoxyphenyl)acetic acid (93-40-3) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → 1-(2,4-dichloro-5-fluorophenyl)-6,7-dimethoxy-1-methylisochroman-3-one

Conditions	Yield
Stage #1: (3,4-Dimethoxyphenyl)acetic acid With trifluoroacetic anhydride In acetonitrile at 25℃; for 0.166667h; Green chemistry; Stage #2: 2,4-dichloro-5-fluoroacetophenone In acetonitrile at 25℃; for 10h; Green chemistry;	80%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + phenyl isothiocyanate (103-72-0) → (2,4-dichloro-5-fluorophenyl)((3Z)-5-(phenylamino)-3-(phenylimino)-3H-1,2-dithiol-4-yl)methanone (1181767-93-0)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 20℃; for 9h;	78.5%

5-(4-nitrophenyl)-2-furaldehyde (7147-77-5) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → (E)-1-(2,4-Dichloro-5-fluoro-phenyl)-3-[5-(4-nitro-phenyl)-furan-2-yl]-propenone (395060-33-0)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	78%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + indole-2,3-dione (91-56-5) → 2-(2,4-dichloro-5-fluorophenyl)quinoline-4-carboxylic acid (903596-57-6)

Conditions	Yield
With sodium hydroxide In water for 2h; Heating;	78%
With sodium hydroxide Pfitzinger reaction; Heating;

2,4-dichloro-5-fluoroacetophenone (704-10-9) + 5-Bromo-1H-indole-2,3-dione (87-48-9) → 6-bromo-2-(2,4-dichloro-5-fluorophenyl)quinoline-4-carboxylic acid (903596-58-7)

Conditions	Yield
With sodium hydroxide In water for 2h; Heating;	76%

2,4-dichloro-5-fluoroacetophenone (704-10-9) → 2,4-dihloro-5-fluorophenylglyoxal (875119-43-0)

Conditions	Yield
With selenium(IV) oxide; silica gel for 0.133333h; microwave irradiation;	75%
With selenium(IV) oxide In 1,4-dioxane; water for 4h; Reflux;

2,4-dichloro-5-fluoroacetophenone (704-10-9) + 5-(4-bromophenyl)-2-furancarboxyaldehyde (20005-42-9) → (E)-3-[5-(4-Bromo-phenyl)-furan-2-yl]-1-(2,4-dichloro-5-fluoro-phenyl)-propenone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	73%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + phenyl isothiocyanate (103-72-0) → (3Z)-7-chloro-6-fluoro-9-phenyl-3-(phenylimino)-3H-[1,2]dithiolo[3,4-b]quinolin-4(9H)-one (1181768-07-9)

Conditions	Yield
Stage #1: 2,4-dichloro-5-fluoroacetophenone With potassium; potassium hydroxide In 1,4-dioxane for 0.166667h; Reflux; Stage #2: phenyl isothiocyanate In 1,4-dioxane for 9h; Reflux; Stage #3: With cerous nitrate In water	70.5%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + acetonitrile (75-05-8) → 3-(2,4-dichloro-5-fluorobenzoyl)-5-methyl-1,2,4-oxadiazole

Conditions	Yield
With nitric acid at 80℃; for 30h;	68%

5-(3-nitrophenyl)furfural (13148-43-1) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → (E)-1-(2,4-Dichloro-5-fluoro-phenyl)-3-[5-(3-nitro-phenyl)-furan-2-yl]-propenone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	61%

5-(2-nitrophenyl)-2-furaldehyde (20000-96-8) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → (E)-1-(2,4-Dichloro-5-fluoro-phenyl)-3-[5-(2-nitro-phenyl)-furan-2-yl]-propenone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 4h; Claisen-Schmidt condensation;	60%

2-aminopyridine (504-29-0) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → 2,4-dichloro-5-fluoro-N-(pyridin-2-yl)benzamide

Conditions	Yield
With tert.-butylhydroperoxide; trifluorormethanesulfonic acid; tetra-(n-butyl)ammonium iodide In water at 80℃; Sealed tube;	59%

1-Iodonaphthalene (90-14-2) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → 9-chloro-8-fluorochrysen-6-ol (1149756-67-1)

Conditions	Yield
With norborn-2-ene; palladium diacetate; caesium carbonate; triphenylphosphine In acetonitrile at 90℃; for 24h; Inert atmosphere; regioselective reaction;	52%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + 1H-indazol-5-ylamine (19335-11-6) → 1-[5-(5-amino-1H-indazol-1-yl)-2,4-dichlorophenyl]ethan-1-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 20h;	6%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 20h;	6%

2,4-dichloro-5-fluoroacetophenone (704-10-9) + methyl magnesium carbonate → 2,4-dichloro-5-fluorobenzoylacetic acid (111760-50-0)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 1h; Yield given;

2,4-dichloro-5-fluoroacetophenone (704-10-9) → Methyl-<2,4-dichlor-5-fluor-phenyl>-carbinol (704-09-6)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate

ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate (17823-58-4) + 2,4-dichloro-5-fluoroacetophenone (704-10-9) → 6-(2,4-Dichloro-5-fluoro-phenyl)-4-methylsulfanyl-2-oxo-2H-pyran-3-carbonitrile

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide

Upstream product

• 1435-48-9 1,3-dichloro-4-fluorobenzene 
• 95-50-1 1,2-dichloro-benzene 
• 99-54-7 3,4-dichloronitrobenzene 
• 1481-63-6 1-bromo-2,4-dichloro-5-fluorobenzene 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 903596-58-7 6-bromo-2-(2,4-dichloro-5-fluorophenyl)quinoline-4-carboxylic acid 
• 903596-57-6 2-(2,4-dichloro-5-fluorophenyl)quinoline-4-carboxylic acid 
• 875119-43-0 2,4-dihloro-5-fluorophenylglyoxal 
• 618098-87-6 3-(2,4-dichloro-5-fluoro-phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 86522-89-6 2,4-dichloro-5-fluoro-benzoic acid 
• 357915-19-6 α-bromo-(2,4-dichloro-5-fluoro)acetophenone 
• 107611-42-7 2-chloro-1-(2,4-dichloro-5-fluoro-phenyl)-ethanone 
• 395060-33-0 (E)-1-(2,4-Dichloro-5-fluoro-phenyl)-3-[5-(4-nitro-phenyl)-furan-2-yl]-propenone 
• 86483-51-4 ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate 
• 106809-14-7 2,4-dichloro-5-fluoro-3-nitro-benzoic acid 
• 111760-50-0 2,4-dichloro-5-fluorobenzoylacetic acid 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 
• 86393-33-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid 

Relevant articles and documents

Preparation method of 2, 4-dichloro-5-fluoroacetophenone

The invention provides a preparation method of 2, 4-dichloro-5-fluoroacetophenone. The method comprises the following steps: by taking 2, 4-dichlorofluorobenzene as a raw material, carrying out Friedel-Crafts reaction on 2, 4-dichlorofluorobenzene and vinylidene chloride in the presence of anhydrous aluminum chloride and protonic acid at the same time to generate 1-(1, 1-dichloroethyl)-2, 4-dichloro-5-fluoroacetophenone benzene, carrying out hydrolysis reaction on the intermediate product under the catalysis of Lewis acid to generate 2, 4-dichloro-5-fluoroacetophenone and hydrogen chloride, adding a proper amount of water for layering after the reaction is finished, and rectifying an organic layer to obtain the product. According to the method, the cost of raw materials and auxiliary materials is greatly reduced, the post-treatment pressure is relieved, the yield can reach 85% or above, and the method belongs to the technical field of organic chemical industry.

ANTIVIRAL AND ANTIMICROBIAL COMPOUNDS

Disclosed are guanidine and biguanidine derivatives which have anti-viral and antibacterial activity. Also disclosed are pharmaceutical compositions containing such compounds as an active ingredient, and anti-viral and anti-bacterial methods utilizing such compounds. Methods of treating infections using the guanidine and biguanidine derivatives are also disclosed.

A novel approach to Finafloxacin hydrochloride (BAY35-3377)

Finafloxacin hydrochloride, an important clinical compound was synthesized by a novel synthetic approach. An active intermediate ethyl 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 19 was prepared by a new route. The chiral (S,S′)-N-Boc 10 was derived from protected pyrrolidine and the absolute stereochemistry was established by X-ray analysis.