123989-29-7

Basic information

• Product Name: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1
• Synonyms: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1;1-Propanone, 1-(4-chlorophenyl)-2-cyclopropyl-;1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one;1-(4-chlorophenyl)-2-cyclopropyl-1-propanone
• CAS NO: 123989-29-7
• Molecular Formula: C₁₂H₁₃ClO
• Molecular Weight: 208.687
• Mol File: 123989-29-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 310.269 °C at 760 mmHg
• Flash Point: 166.719 °C
• Appearance: /
• Density: 1.180
• Vapor Pressure: 0.000607mmHg at 25°C
• Refractive Index: 1.565
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1(123989-29-7)
• EPA Substance Registry System: 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1(123989-29-7)

Safety Data

• Hazardous Substances Data: 123989-29-7(Hazardous Substances Data)

Usage

Uses

1-(4-Chlorophenyl)-2-cyclopropylpropan-1-one is used in process for preparation of epoxides from aldehydes or ketones with sulfonium salts.

InChI:InChI=1/C12H13ClO/c1-8(9-2-3-9)12(14)10-4-6-11(13)7-5-10/h4-9H,2-3H2,1H3

Synthetic route

C12H12Cl2 → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With sodium hydroxide In ethanol; water at 35 - 40℃; for 4h; Reagent/catalyst;	98%

C12H12BrCl → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20 - 30℃; for 2h; Reagent/catalyst;	98%

1-(4-chlorophenyl)-2-cyclopropyl-1-propanol (123989-28-6) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With aluminum isopropoxide; acetone In isopropyl alcohol for 5h; Reagent/catalyst; Solvent; Reflux;	94.5%

Cyclopropyl methyl ketone (765-43-5) + C14H22ClO5P → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With sodium methylate In methanol at 20 - 40℃; for 5h; Solvent; Temperature; Reagent/catalyst;	93%

1-chloro-4-(2-cyclopropyl-1-acetoxy-propen-1-yl)benzene → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃; for 8h;	93%

1-chloro-4-(2-cyclopropyl-1-trimethylsiloxypropen-1-yl)benzene → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With hydrogenchloride In water; toluene at 20℃; for 5h; Solvent; Reagent/catalyst;	92.5%

1-chloro-4-(2-cyclopropyl-1-methylsulfonylpropen-1-yl)benzene → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With phosphoric acid In toluene at 20℃; for 7h;	92.3%

C17H21ClO2 → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 40℃; for 1h; Reagent/catalyst; Temperature; Solvent;	92%

C5H9ClMg + 4-chloro-benzoyl chloride (122-01-0) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With iron(III)-acetylacetonate In tetrahydrofuran; tert-butyl methyl ether at 30℃; for 2h; Temperature; Solvent; Reagent/catalyst;	91%

4-chlorobenzoyl bromide (874-59-9) + C5H9ClMg → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With iron(III)-acetylacetonate In tetrahydrofuran at -30℃; for 2h; Temperature; Solvent;	90.1%

1-bromo-1-cyclopropylethane (80204-20-2) + 4-chloro-N-methoxy-N-methylbenzamide (122334-37-6) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Stage #1: 1-bromo-1-cyclopropylethane With magnesium In tetrahydrofuran at 20℃; for 3h; Stage #2: 4-chloro-N-methoxy-N-methylbenzamide In tetrahydrofuran at -20℃; for 3h;	88.2%

oxalyl dichloride (79-37-8) + SiO2, hexane-ethyl acetate + 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol (123989-28-6) + dimethyl sulfoxide (67-68-5) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With triethylamine In hexane; dichloromethane	86%

C6H11NO + p-chlorobenzenediazonium chloride (2028-74-2) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Stage #1: C6H11NO; p-chlorobenzenediazonium chloride With ammonium acetate; copper(II) sulfate at -10℃; for 0.5h; Stage #2: With sulfuric acid at 90℃; for 2h;	86%

cyclopropyl methyl ketone tosyl hydrazone (5508-41-8) + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With sodium hydrogencarbonate; lithium chloride In chloroform at 61℃; for 20h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	82%

C6H12N2O2S + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	82%

Cyclopropyl methyl ketone (765-43-5) + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Stage #1: 4-chlorobenzaldehyde With triethylamine; phosphonic acid diethyl ester In toluene at 20 - 25℃; for 6h; Stage #2: Cyclopropyl methyl ketone With sodium amide In toluene at 30 - 35℃; for 18h; Temperature; Solvent; Reagent/catalyst;	80.9%

C11H14N2O2S + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	78.5%

C9H12N2O2S2 + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	78%

C10H13N3O2S + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	77%

C10H14N2O2S2 + 4-chlorobenzaldehyde (104-88-1) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	77%

C13H14ClN → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; oxygen; potassium hydroxide In toluene at 80℃; for 6h; Reagent/catalyst; Temperature;	75%

4-chlorobenzaldehyde (104-88-1) + 5-cyclopropyl-2-methoxy-2,5-dimethyl-Δ3-1,3,4-oxadiazoline (119393-22-5, 119393-23-6) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
In dichloromethane at 20℃; under 5171.62 Torr; Inert atmosphere; UV-irradiation;	63%

hexane-washed sodium hydride + 4-chlorophenyl-(cyclopropylmethyl)-ketone (54839-12-2) + methyl iodide (74-88-4) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
In N-methyl-acetamide

4-chlorophenyl-(cyclopropylmethyl)-ketone (54839-12-2) + methyl iodide (74-88-4) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Stage #1: 4-chlorophenyl-(cyclopropylmethyl)-ketone With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at -20 - 20℃; for 12.5h;

p-chlorobenzaldehyde diethyl acetal (2403-61-4) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: zinc(II) chloride / dichloromethane / 60 h / -10 - 20 °C 2.1: sodium amide / dimethyl sulfoxide / 0.5 h / 20 °C 2.2: 4 h / 20 - 30 °C 3.1: hydrogenchloride; water / methanol / 4 h / 20 °C View Scheme

α-ethoxy-p-chlorobenzylphosphonic acid dimethyl ester → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium amide / dimethyl sulfoxide / 0.5 h / 20 °C 1.2: 4 h / 20 - 30 °C 2.1: hydrogenchloride; water / methanol / 4 h / 20 °C View Scheme

Cyclopropyl methyl ketone (765-43-5) + α-methoxy-p-chlorobenzylphosphonic acid diethyl ester (92594-58-6) → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / N,N-dimethyl-formamide / 7 h / 10 - 30 °C 2: hydrogenchloride; water / toluene / 10 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C 1.2: 3 h / -78 - 20 °C 2.1: trifluoroacetic acid / 12 h / 20 °C View Scheme

1-chloro-4-(2-cyclopropyl-1-methoxypropene-1-yl)benzene → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With hydrogenchloride; water In toluene at 20℃; for 10h; Solvent;	30.2 g
With trifluoroacetic acid at 20℃; for 12h;

1-chloro-4-(2-cyclopropyl-1-ethoxypropene-1-yl)benzene → 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7)

Conditions	Yield
With hydrogenchloride; water In methanol at 20℃; for 4h;	10.4 g

1,2,4-Triazole (288-88-0) + 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7) → cyproconazol (94361-06-5, 113096-99-4)

Conditions	Yield
Stage #1: 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one With dimethylsulfide; sodium methylate; dimethyl sulfate In acetonitrile at 20℃; for 10h; Stage #2: 1,2,4-Triazole With sodium hydride In N,N-dimethyl-formamide for 12h; Time; Reflux;	74.6%

1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7) + 1,1-Dibromoethane (557-91-5) → 2-(4-chlorophenyl)-2-(1-cyclopropylethyl)-3-methyloxirane (1615196-91-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	73%

1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one (123989-29-7) + dimethylsulfide (75-18-3) → 2-(4-chlorophenyl)-3-cyclopropyl-1,2-butylene oxide (94361-26-9)

Conditions	Yield
Stage #1: dimethylsulfide With dimethyl sulfate In acetonitrile at 0 - 20℃; for 16h; Stage #2: 1-(p-chlorophenyl)-2-cyclopropyl-2-methylethan-1-one With potassium hydroxide In dimethyl sulfoxide; acetonitrile at 20℃; for 16h;
With dimethyl sulfate; potassium hydroxide In 2-methyl-propan-1-ol

Upstream product

• 54839-12-2 4-chlorophenyl-(cyclopropylmethyl)-ketone 
• 74-88-4 methyl iodide 
• 79-37-8 oxalyl dichloride 
• 123989-28-6 1-(4-chlorophenyl)-2-cyclopropyl-1-propanol 
• 67-68-5 dimethyl sulfoxide 
• 765-43-5 Cyclopropyl methyl ketone 
• 104-88-1 4-chlorobenzaldehyde 
• 80204-20-2 1-bromo-1-cyclopropylethane 
• 122334-37-6 4-chloro-N-methoxy-N-methylbenzamide 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 874-59-9 4-chlorobenzoyl bromide 
• 119393-22-5 5-cyclopropyl-2-methoxy-2,5-dimethyl-Δ³-1,3,4-oxadiazoline 

Downstream Products

• 94361-26-9 2-(4-chlorophenyl)-3-cyclopropyl-1,2-butylene oxide 
• 94361-06-5 cyproconazol 
• 1615196-91-2 2-(4-chlorophenyl)-2-(1-cyclopropylethyl)-3-methyloxirane 

Relevant articles and documents

Synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

The invention provides a synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The method is shown in the following reaction process. The method comprises the following steps: 1) performing addition elimination on a p-chlorobenzyl halide metal reagent and cyclopropyl methyl ketone to obtain a compound as shown in a formula (II); and 2) oxidizing the compound as shown in the formula (II) to obtain a compound as shown in a formula (I), namely 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The method provided by the invention has the advantages of short synthetic route, high yield, low raw material cost, green and environment-friendly process, suitability for industrial large-scale production and the like.

A 1 - (4 - chlorophenyl) -2 - cyclopropyl -1 - acetone synthetic method

The invention discloses a 1 - (4 - chlorophenyl) - 2 - cyclopropyl - 1 - propanone synthetic method, in formula (I) of the formula (II) compound as a raw material, in the presence of a catalyst prepared by cross-coupling reaction of 1 - (4 - chlorophenyl) - 2 - cyclopropyl - 1 - propanone. The invention selective (I) of the formula (II) compound as the raw material for preparing 1 - (4 - chlorophenyl) - 2 - cyclopropyl - 1 - propanone, compared with the prior art, the reaction of the invention raw materials are easy, short synthetic route, the process is simple, after treatment is simple, the production cost is low, and the obtained 1 - (4 - chlorophenyl) - 2 - cyclopropyl - 1 - propanone high purity, in 98.5% or more, the yield and the reaction conversion is also high, the product yield is 80 - 92%.

C-H functionalisation of aldehydes using light generated, non-stabilised diazo compounds in flow

The difficulty in accessing and safely utilising non-stabilised diazo species has in the past limited the application of this class of compounds. Here we explore further the use of oxadiazolines, non-stabilised diazo precursors which are bench stable, in direct, non-catalytic, aldehyde C-H functionalisation reactions under UV photolysis in flow and free from additives. Commercially available aldehydes are coupled to afford unsymmetrical aryl-alkyl and alkyl-alkyl ketones while mild conditions and lack of transition metal catalysts allow for exceptional functional group tolerance. Examples are given on small scale and in a larger scale continuous production.