123989-29-7

Usage

Uses

1. Used in Chemical Synthesis:
1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1 is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable building block for the creation of more complex molecules.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1 is utilized as a key component in the development of new drugs. Its specific chemical properties enable it to interact with biological targets, potentially leading to the discovery of novel therapeutic agents.
3. Used in Process for Preparation of Epoxides:
1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1 is used as a reagent in the process for the preparation of epoxides from aldehydes or ketones with sulfonium salts. This application is particularly relevant in the synthesis of various organic compounds, including those with potential pharmaceutical or industrial applications.
4. Used in Material Science:
In the field of material science, 1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1 may be employed in the development of new materials with specific properties. Its unique structure and reactivity could contribute to the creation of advanced materials with applications in various industries, such as electronics, aerospace, or automotive.
5. Used in Research and Development:
1-(4-Chlorophenyl)-2-Cyclopropylpropanon-1 is also used in research and development settings, where it can serve as a model compound for studying various chemical reactions and processes. Understanding its behavior in different reaction conditions can provide valuable insights into the development of new synthetic methods and the design of novel compounds.

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 
• 2403-61-4 p-chlorobenzaldehyde diethyl acetal 
• 765-43-5 Cyclopropyl methyl ketone 
• 92594-58-6 α-methoxy-p-chlorobenzylphosphonic acid diethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 140-53-4 p-chlorobenzyl cyanide 
• 10524-06-8 (±)-(1-chloroethyl)cyclopropane 
• 108054-54-2 diethyl (4-chlorophenyl)(hydroxy)methylphosphonate 
• 6329-48-2 dimethyl 1-hydroxy-1-(4-chlorophenyl)methylphosphonate 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

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

Relevant academic research and scientific papers

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.

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

The invention relates to a synthesis method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone, which comprises the following steps: 1) carrying out condensation on alpha-halogen substituted p-chlorobenzylphosphonate and cyclopropylmethyl ketone under alkaline conditions to obtain an alkenyl halide compound; and 2) hydrolyzing the alkenyl halide compound prepared in the step 1) to obtain the 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. According to the synthetic method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone, alpha-halogen substituted p-chlorobenzyl phosphonate and cyclopropylmethyl ketone are condensed under the alkaline condition to obtain the alkenyl halide compound, the obtained alkenyl halide compound is hydrolyzed to obtain 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone, the whole technological process is simple and smooth, reaction conditions are mild, and the method is suitable for industrial large-scale production; alpha-halogen substituted p-chlorobenzyl phosphonate and cyclopropylmethyl ketone are used as reaction substrates, so that the method is high in atom economy, green, environment-friendly and low in raw material cost.

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%.

Preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1-actone

The invention provides a preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1-actone. The 1-(4-chlorphenyl)-2-cyclopropyl-1-actone is prepared by reacting a compound of a structure in Formula (II)with p-chlorobenzaldehyde. The reaction raw material is low in price and easy to obtain, and the production cost is greatly reduced; the synthetic route is short and simple in technique; the raw material preparation and synthesis of the 1-(4-chlorphenyl)-2-cyclopropyl-1-actone are free from waste water, thus the risk to people and environment is reduced; and the green and environment-friendly chemical industry development requirement is met.

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.

One-pot synthesis of α,α-disubstituted Aryl-1-ethanones via the Wittig-Horner reaction

A one-pot methodology for the synthesis of α,α-disubstituted aryl-1-ethanones via the Wittig-Horner reaction has been developed and described in this manuscript. Both aryl/alkyl and dialkyl α-branched arylethanone were obtained in high yields (up to 96%) without the use of any metal catalysts. A total of 14 α,α-disubstituted arylethanone derivatives were synthesized based on this simple method that easily converts the carbonyl carbon (sp2) into the sp3 carbon. This versatile method is expected to further promote the use of substituted ketones as synthetic building blocks to construct a variety of α-branched aryl ketones.

Preparation method of cyproconazole intermediate 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone

The invention discloses a preparation method of cyproconazole intermediate1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. Compounds in a formula (I) and a formula (II) are taken as raw materials and are subjected to a weinreb ketone synthesis reaction, and 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone is prepared. The compounds in the formula (I) and the formula (II) are taken as raw materials for preparation of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. Compared with the prior art, the preparation method has the advantages that reaction raw materials are easy to obtain, no catalyst is used, the synthesis route is short, the process is simple and the production cost is low; 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone has high purity reaching 98.5% or above, higher yield being 80%-88% and higher conversion rate.

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

The invention discloses a preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The method comprises the steps of preparing acetal by adopting p-chlorobenzaldehyde and phenylcarbinol or a derivative thereof as raw materials under the action of a catalyst, reacting an acetal product with trimethyl phosphite or triethyl phosphite in an environment of a polar solvent under the catalysis of lewis acid to generate alpha-benzyloxy p-chlorobenzyl dimethyl phosphate, further reacting the alpha-benzyloxy p-chlorobenzyl dimethyl phosphate with cyclopropyl methyl ketone under the combined action of a base catalyst, a phase transfer catalyst and a cocatalyst to prepare a benzyloxy-propylene derivative; and then carrying out acidifying hydrolysis on the benzyloxy-propylene derivative to obtain the1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. Compared with the prior art, the method has the advantages of being safe in operation, controllable in process, low in toxicity in the process, mild in reaction condition, suitable for industrial production and high in product purity.

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

The invention relates to a preparation method of 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. A compound I and cyclopropyl methyl ketone react at 0-30 DEG C to obtain a compound II under the existence of alkali and organic solvent; the compound II is hydrolyzed under the existence of acid to obtain a compound III, namely 1-(4-chlorphenyl)-2-cyclopropyl-1-acetone. The structural formulas of the compound I, the compound II and the compound III are shown in the description, R1 is any one of trimethylsilyl, acetyl and methyl sulphonyl, and R2 is methyl or ethyl. The method is simple in process, low in cost, little in three wastes, high in target product content and yield and suitable for industrial production.

A 1 - (4 - chlorophenyl) - 2 - cyclopropyl - 1 - propanone preparation method

The invention relates to a 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone preparation method. The preparation method comprises that chlorobenzyl alcohol, sodium nitrite, acetic acid and concentrated hydrochloric acid undergo a reaction, the reaction product is treated to form a compound I, the compound I and cyclopropyl methyl ketone undergo a condensation reaction in the presence of an alkali and a solvent, the reaction product is treated to form a compound II, the compound II undergoes a reduction reaction in the presence of a reducer and a solvent, the reaction product is treated to form a compound III, the compound III undergoes a reduction reaction in the presence of a reducer and a solvent, and the reaction product is treated to form 1-(4-chlorophenyl)-2-cyclopropyl-1-propanone. The preparation method has the advantages of simple processes, use of cheap and easily available raw materials, low cost, less three wastes, industrial production feasibility and high product yield and content.