14123-60-5

Basic information

• Product Name: 3-CHLOROPHENYLACETONE
• Synonyms: 3-CHLOROPHENYLACETONE;1-(3-CHLOROPHENYL)PROPAN-2-ONE;(M-CHLOROPHENYL)ACETONE;TIMTEC-BB SBB005838;3-CHLOROPHENYLACETONE 94%;3-Chlorophenylacetone,94%;M-chlorophenylpropan-2-one;2-Propanone,1-(3-chlorophenyl)-
• CAS NO: 14123-60-5
• Molecular Formula: C₉H₉ClO
• Molecular Weight: 168.62
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 14123-60-5.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 99°C/5mmHg(lit.)
• Flash Point: 116.3 °C
• Appearance: Clear yellow/Liquid
• Density: 1.1115 (rough estimate)
• Vapor Pressure: 0.047mmHg at 25°C
• Refractive Index: 1.532-1.536
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-CHLOROPHENYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLOROPHENYLACETONE(14123-60-5)
• EPA Substance Registry System: 3-CHLOROPHENYLACETONE(14123-60-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-52
• Safety Statements: 24/25
• Hazardous Substances Data: 14123-60-5(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C9H9ClO/c1-7(11)5-8-3-2-4-9(10)6-8/h2-4,6H,5H2,1H3

Synthetic route

Isopropenyl acetate (108-22-5) + 3-chloro-aniline (108-42-9) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
Stage #1: 3-chloro-aniline With tetrafluoroboric acid; cis-nitrous acid Stage #2: Isopropenyl acetate With copper(I) oxide; sodium acetate Meerwein arylation;	85%
With tert.-butylnitrite; water; salicylic acid In acetonitrile at 20℃; for 3h; Inert atmosphere; Schlenk technique;	61%
Stage #1: 3-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With tetrafluoroboric acid In water for 3h; Stage #3: Isopropenyl acetate With copper(I) oxide; sodium acetate In water at 35 - 40℃; for 8h;

(E)-2-methyl-3-(3-chlorophenyl)acrylic acid (109619-78-5) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene at 25 - 110℃; for 1.5h;	81%
Multi-step reaction with 2 steps 1: thionyl chloride / tetrachloromethane / 0.5 h / 35 °C 2: sodium azide; tetrabutylammomium bromide; water / tetrachloromethane / 1.5 h / Reflux View Scheme

C9H7ClN2O3S (1401722-60-8) + acetone (67-64-1) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 60℃; for 24h; Inert atmosphere; chemoselective reaction;	80%

C6H4ClCH2COCH3FeC5H5(1+)*PF6(1-) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
Sample heated for 1.0 h at 200-220°C and 1 torr.; Sublimation; chromy. (F-20 alumina, CCl4/CHCl3).;	75%

5-Chloro-7-methyl-bicyclo[4.2.0]octa-1(6),2,4-trien-7-ol → 3-chlorophenylacetone (14123-60-5) + 1-(2-Chloro-6-methyl-phenyl)-ethanone

Conditions	Yield
With sodium methylate In methanol at 65℃; for 0.25h; Product distribution; variation of base;	A 31% B 69%
With sodium tert-pentoxide In tetrahydrofuran at -40℃; for 0.25h; Yield given. Yields of byproduct given;
With sodium methylate In methanol Heating; Yield given. Yields of byproduct given;

2-(3'-chlorophenyl)-3-methyloxirane (954262-36-3) → 3-chlorophenylacetone (14123-60-5) + (RS,RS)-1-fluoro-1-(3'-chlorophenyl)propan-2-ol

Conditions	Yield
Stage #1: 2-(3'-chlorophenyl)-3-methyloxirane With boron trifluoride diethyl etherate In dichloromethane at -20℃; for 0.166667h; Stage #2: With water; sodium hydrogencarbonate In dichloromethane optical yield given as %de; stereoselective reaction;	A 74 mg B 64%

2-(3'-chlorophenyl)-3-methyloxirane (954262-36-3) + 2-fluoro-4,4,5,5-tetramethyl-1,3-dioxa-2-boracyclopentane → 3-chlorophenylacetone (14123-60-5) + (RS,RS)-1-fluoro-1-(3'-chlorophenyl)propan-2-ol + C9H10ClFO

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	A 23% B 56% C n/a

Isopropenyl acetate (108-22-5) + 3-chlorobenzenediazonium tetrafluoroborate (456-39-3) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With 1-aminomorpholine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 3h;	45%

(E)-1-(3'-chlorophenyl)-2-nitropropene (19394-34-4) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With hydrogenchloride; water; iron
With hydrogenchloride; iron(III) chloride; iron for 1h; Heating;
With hydrogenchloride; iron

3-chlorophenylacetic acid (1878-65-5) + acetic anhydride (108-24-7) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With pyridine modified Dakin West reaction;
With 1-methyl-1H-imidazole at 20℃; for 12h; Dakin-West Ketone Synthesis; Inert atmosphere;

(Z)-1-(3-Chloro-phenyl)-propen-2-ol (144380-79-0) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
In benzene-d6 at 25℃; Equilibrium constant; other solvent;

chlorobenzene (108-90-7) + acetone (67-64-1) → 2-chlorophenylacetone (6305-95-9) + 3-chlorophenylacetone (14123-60-5) + 1-(4-chlorophenyl)propan-2-one (5586-88-9)

Conditions	Yield
With manganese triacetate; acetic acid Heating; Yield given. Yields of byproduct given;
With manganese triacetate In acetic acid Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With manganese triacetate In various solvent(s) for 1.5h; ultrasonic irradiation;

chlorobenzene (108-90-7) + acetone (67-64-1) → 3-chlorophenylacetone (14123-60-5) + 1-(4-chlorophenyl)propan-2-one (5586-88-9)

Conditions	Yield
With manganese triacetate In acetic acid at 60℃; Rate constant; also in the presence of benzene at 70 deg C (relative reactivity);

C11H12ClNO (69390-31-4) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With phosphorus pentachloride In 1,4-dioxane; diethyl ether
With phosphorus pentachloride In diethyl ether

2-(3-chloro-phenyl)-acetoacetonitrile (14123-79-6) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With hydrogenchloride; acetic acid

acetone (67-64-1) + cyclopentadienyliron complexes → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With potassium carbonate 1.) THF, DMSO, r.t., 5 h, 2.) 200-220 deg C, 1 torr; Yield given. Multistep reaction;

3-Chlorobenzaldehyde (587-04-2) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4OAc / acetic acid / 3 h / Heating 2: Fe, FeCl3, aq. HCl / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: NH4OAc, AcOH 2: Fe, aq. HCl View Scheme

3-chloro-benzeneacetonitrile (1529-41-5) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOEt / ethanol 2: aq. HCl, AcOH View Scheme

3-chloro-aniline (108-42-9) → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite / water / 0.67 h / 0 °C 2: 1-aminomorpholine / dimethyl sulfoxide; N,N-dimethyl-formamide / 3 h / 20 °C View Scheme

C10H8Cl2O → 3-chlorophenylacetone (14123-60-5)

Conditions	Yield
With sodium azide; tetrabutylammomium bromide; water In tetrachloromethane for 1.5h; Reflux;	4.3 g

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-chlorophenylacetone (14123-60-5) → ethyl 4-(3-chlorophenyl)-3-methylbut-2-enoate

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 2h; Horner-Wadsworth-Emmons Olefination; Reflux; Inert atmosphere;	97%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 3-chlorophenylacetone In tetrahydrofuran; mineral oil at 0 - 23℃;

3-chlorophenylacetone (14123-60-5) + 1,1'-((4-chlorophenyl)methylene)diurea (55718-52-0) → 5-(3-chlorophenyl)-4-(4-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions	Yield
With caesium carbonate In ethanol at 70℃; for 24h;	94%

3-chlorophenylacetone (14123-60-5) → 1-(m-chlorophenyl)-2-propanone oxime (319474-76-5)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 1h; Reflux;	93%

3-chlorophenylacetone (14123-60-5) + 2-Mercaptobenzothiazole (149-30-4) → 1-(benzo[d]thiazol-2-ylthio)-3-(3-chlorophenyl)propan-2-one

Conditions	Yield
With dipotassium peroxodisulfate; potassium iodide In dimethyl sulfoxide at 20℃; for 24h; Schlenk technique;	89%

3-chlorophenylacetone (14123-60-5) + Benzhydrylamine (91-00-9) → N-benzhydryl-1-(3-chlorophenyl)propan-2-amine

Conditions	Yield
With titanium(IV) isopropylate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; C27H34NO2P; hydrogen; trifluoroacetic acid In dichloromethane at 20℃; under 45603.1 Torr; Autoclave; Molecular sieve; enantioselective reaction;	87%

3-chlorophenylacetone (14123-60-5) + N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester → methyl 2-(tert-butoxycarbonylamino)-4-(3-chlorophenyl)-5-oxo-hexanoate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3.25h; Inert atmosphere;	80%
With caesium carbonate In N,N-dimethyl-formamide for 2.5h;
Stage #1: N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester With caesium carbonate In N,N-dimethyl-formamide at 23℃; for 0.75h; Stage #2: 3-chlorophenylacetone With caesium carbonate In N,N-dimethyl-formamide for 2.5h;
Stage #1: N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester With caesium carbonate In N,N-dimethyl-formamide at 23℃; for 0.75h; Stage #2: 3-chlorophenylacetone With caesium carbonate In N,N-dimethyl-formamide for 2.5h;
Stage #1: N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester With caesium carbonate In N,N-dimethyl-formamide at 23℃; for 0.75h; Stage #2: 3-chlorophenylacetone With caesium carbonate In N,N-dimethyl-formamide for 2.5h;

3-chlorophenylacetone (14123-60-5) + Benzimidazol-2-thiol (134469-07-1) → 2-(3-chlorophenyl)-3-methylbenzo[4,5]imidazo[2,1-b]thiazole

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; dimethyl sulfoxide In water at 135℃; for 0.5h; Sealed tube; Green chemistry; regioselective reaction;	78%

3-chlorophenylacetone (14123-60-5) + sodium nitromalonaldehyde (34461-00-2) → 3'-Chloro-5-nitro-biphenyl-2-ol (79287-43-7)

Conditions	Yield
With sodium hydroxide In ethanol for 20h;	65%

3-chlorophenylacetone (14123-60-5) + prenyl bromide (870-63-3) → 3-(3-chlorophenyl)-6-methylhept-5-en-2-one (1344666-75-6)

Conditions	Yield
Stage #1: 3-chlorophenylacetone With sodium hydride In N,N-dimethyl-formamide at -20℃; for 0.333333h; Stage #2: prenyl bromide In N,N-dimethyl-formamide at -20 - 20℃; for 1.33333h;	63%

(3-methylbut-3-en-1-oxy)trimethylsilane (25195-89-5) + 3-chlorophenylacetone (14123-60-5) → 5-chloro-1,9-dimethyl-10-oxatricyclo[7.3.1.02,7]-trideca-2,4,6-triene

Conditions	Yield
Stage #1: (3-methylbut-3-en-1-oxy)trimethylsilane; 3-chlorophenylacetone In chloroform for 0.0833333h; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In chloroform for 4h; Inert atmosphere; Reflux;	41%

3-chlorophenylacetone (14123-60-5) → 1-bromo-1-(3-chlorophenyl)propan-2-one (91391-56-9)

Conditions	Yield
With bromine; acetic acid

3-chlorophenylacetone (14123-60-5) + methyl iodide (74-88-4) → 3-(3-chlorophenyl)butan-2-one (21905-97-5)

Conditions	Yield
(i) NaOiPr, iPrOH, (ii) /BRN= 969135/; Multistep reaction;
With sodium hydroxide In dichloromethane; water

3-chlorophenylacetone (14123-60-5) → (Z)-1-(3-Chloro-phenyl)-propen-2-ol (144380-79-0)

Conditions	Yield
In benzene-d6 at 25℃; Equilibrium constant; other solvent;

3-chlorophenylacetone (14123-60-5) → 2-(3-Chloro-phenyl)-1-methyl-ethylideneamine (144380-85-8)

Conditions	Yield
With ammonia In benzene Heating;

3-chlorophenylacetone (14123-60-5) + NCNMe2 (1467-79-4) → C12H14Cl2N2*Cl2HO2P

Conditions	Yield
With trichlorophosphate 1.) benzene, reflux, 15 min, 2.) benzene, ether, RT, 1 h; Multistep reaction;

3-chlorophenylacetone (14123-60-5) + acetonitrile (75-05-8) → C11H11Cl3NO2P

Conditions	Yield
With trichlorophosphate Heating;

Upstream product

• 19394-34-4 (E)-1-(3'-chlorophenyl)-2-nitropropene 
• 1878-65-5 3-chlorophenylacetic acid 
• 108-24-7 acetic anhydride 
• 144380-79-0 (Z)-1-(3-Chloro-phenyl)-propen-2-ol 
• 108-90-7 chlorobenzene 
• 67-64-1 acetone 
• 69390-31-4 C₁₁H₁₂ClNO 
• 14123-79-6 2-(3-chloro-phenyl)-acetoacetonitrile 
• 108-22-5 Isopropenyl acetate 
• 108-42-9 3-chloro-aniline 
• 587-04-2 m-Chlorobenzaldehyde 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 954262-36-3 2-(3'-chlorophenyl)-3-methyloxirane 
• 1401722-60-8 C₉H₇ClN₂O₃S 

Downstream Products

• 91391-56-9 1-bromo-1-(3-chlorophenyl)propan-2-one 
• 21905-97-5 3-(3-chlorophenyl)butan-2-one 
• 144380-85-8 2-(3-Chloro-phenyl)-1-methyl-ethylideneamine 
• 65738-63-8 2-(3'-Chlorbenzyl)-2-methylbernsteinsaeure 
• 595610-33-6 ethyl 5-(3-chlorophenyl)-2,4-dioxopentanoate 
• 595610-43-8 5-(3-chlorobenzyl)-1H-pyrazole-3-carboxylic acid ethyl ester 
• 79305-46-7 3'-Chloro-5-(7-chloro-quinolin-4-ylamino)-3-diethylaminomethyl-biphenyl-2-ol 
• 79286-97-8 3'-Chloro-5-(7-chloro-1-oxy-quinolin-4-ylamino)-3-diethylaminomethyl-biphenyl-2-ol 
• 20110-25-2 2-(m-Chlorphenyl)-3-butylamin 
• 94026-06-9 1-<3-Chlor-anilino>-1-<3-chlor-phenyl>-propanon-(2) 
• 319474-76-5 1-(m-chlorophenyl)-2-propanone oxime 
• 1262155-47-4 C₁₉H₁₆ClNO₃S 
• 1344666-75-6 3-(3-chlorophenyl)-6-methylhept-5-en-2-one 
• 1375470-88-4 (3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride 

Relevant articles and documents

1-aryl-2-acetone compound preparation method

The invention discloses a 1-aryl-2-acetone compound preparation method, which comprises: (1) carrying out a reaction on (E)-2-methyl-3-aryl acrylic acid (I) as a starting raw material and diphenyl azidophosphate (DPPPA) in the presence of an organic alkali; (2) carrying out a heating reaction; and (3) adding an acidic aqueous solution into the reaction solution, and carrying out a reaction to obtain the 1-aryl-2-acetone compound with a structural formula (IV). According to the present invention, the method can solve the technical problems of difficultly available, highly-corrosive, highly toxic and highly explosive reagents, long steps, low yield, tedious operation and the like in the 1-aryl-2-acetone synthesis in the prior art, has characteristics of easily available raw materials, safe and simple operation, mild condition and high yield, and is suitable for industrial production.

Application of piperidine-containing thiazole compound and preparation method thereof

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Direct Asymmetric Reductive Amination for the Synthesis of Chiral β-Arylamines

The highly efficient and direct asymmetric reductive amination of arylacetones catalyzed by an iridium complex for the preparation of enantiomerically pure β-arylamines is described. The monodentate phosphoramidite ligand exhibits superb reactivity (TONs of up to 20 000) and enantioselectivity (up to 99 % ee). Additives played important roles in this reductive coupling reaction. Asymmetric reductive coupling of a ketone and an amine is a straightforward and atom-economic approach for preparing optically enriched amines. The highly efficient and direct asymmetric reductive amination of arylacetones, catalyzed by an iridium complex, supplies enantiomerically pure β-arylamines. The new phosphoramidite ligands reported show superb reactivity and enantioselectivity in this reductive coupling. M.S.=molecular sieves, TFA=trifluoroacetic acid.