66346-01-8

Basic information

• Product Name: 1-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone
• Synonyms: 1-(4-chlorophenyl)-4,4-dimethyl-3-pentanon;hwg1608-alkylketon;1-(4-CHLOROPHENYL)-4,4-DIMETHYL-3-PENTANONE;1-(4-CHLORO-PHENYL)-4,4-DIMETHYL-PENTAN-3-ONE;(4-CHLOROPHENYLETHYL)-(1,1-DIMETHYLETHYL)-KETONE;1-(4-Chlorophenyl)-4,4-Dimethylpentane-3-One;4,4-Dimethyl-1-(p-chlorophenyl)-3-pentanone;1-(4-Chlorophenyl)-4,4-dimethy
• CAS NO: 66346-01-8
• Molecular Formula: C₁₃H₁₇ClO
• Molecular Weight: 224.73
• Product Categories: (intermediate of tebuconazole)
• Mol File: 66346-01-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 297.4 °C at 760 mmHg
• Flash Point: 178.9 °C
• Appearance: /
• Density: 1.05 g/cm³
• Vapor Pressure: 0.00136mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 1-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone(66346-01-8)
• EPA Substance Registry System: 1-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone(66346-01-8)

Safety Data

• Hazardous Substances Data: 66346-01-8(Hazardous Substances Data)

Usage

General Description

1-(4-Chlorophenyl)-4,4-dimethyl-3-pentanone, also known as PDCPD, is a chemical compound with the molecular formula C13H17ClO. It is a colorless liquid with a strong, sweet odor. PDCPD is commonly used as a solvent in various industrial applications, such as in the production of adhesives, coatings, and pharmaceuticals. It is also used as an intermediate in the synthesis of other organic compounds. PDCPD is considered to be a flammable liquid and should be handled with care, as exposure to high concentrations can cause irritation to the skin, eyes, and respiratory tract. Additionally, it may have harmful effects if ingested or inhaled and should be stored and used in a well-ventilated area.

InChI:InChI=1/C13H17ClO/c1-13(2,3)12(15)9-6-10-4-7-11(14)8-5-10/h4-5,7-8H,6,9H2,1-3H3

Synthetic route

1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one (1577-03-3) → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
With sulfolane; hydrogen In methanol at 50 - 60℃; under 750.075 Torr; Temperature; Pressure; Reagent/catalyst; Autoclave;	99%
With sodium phosphite; hydrogen; ethanolamine In methanol at 70℃; under 6750.68 Torr; Reagent/catalyst; Temperature; Pressure; Autoclave;	97.8%
With hydrogen In ethanol at 80℃; under 22502.3 Torr; for 2h;

1,3-diphenyl-propen-3-one (614-47-1) → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
With hydrogen; aluminum nickel In ethyl acetate

2,2'-thiobis-ethanol (111-48-8) + (E)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one (41564-62-9) → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
aluminum nickel In methanol

4-chlorobenzaldehyde (104-88-1) → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 2.5 h / 60 °C / Cooling with ice 2: hydrogen / ethanol / 2 h / 80 °C / 22502.3 Torr View Scheme

3,3-dimethyl-butan-2-one (75-97-8) → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol / 2.5 h / 60 °C / Cooling with ice 2: hydrogen / ethanol / 2 h / 80 °C / 22502.3 Torr View Scheme

2-(4-chlorobenzyl)-4,4-dimethyl-3-carbonylvaleric acid methyl ester → 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8)

Conditions	Yield
With isopropyl alcohol; sodium hydroxide at 85℃; for 1h; Reagent/catalyst; Temperature;	38 g

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) + dimethyl sulfate (77-78-1) → 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide (80443-63-6)

Conditions	Yield
Stage #1: dimethyl sulfate With p-propoxybenzyl sulfide at 90℃; for 2h; Stage #2: 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one With potassium hydroxide In toluene at 50℃; for 4h; Reagent/catalyst; Concentration; Temperature;	99.6%
With dimethylsulfide; potassium hydroxide In toluene at 25 - 50℃; for 5h; Reagent/catalyst; Temperature; Solvent;	98.8%

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) + methyl iodide (74-88-4) → 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide (80443-63-6)

Conditions	Yield
Stage #1: methyl iodide With p-propoxybenzyl sulfide at 90℃; for 2h; Stage #2: 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one With potassium hydroxide In toluene at 0℃; for 4h;	99.2%

trimethylsulfonium chloride (3086-29-1) + 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide (80443-63-6)

Conditions	Yield
Stage #1: trimethylsulfonium chloride; 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one In toluene at 80℃; for 10h; Solvent; Temperature;	95%

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 1-(4'-chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one (66346-02-9)

Conditions	Yield
With 1-butyl-3-methylpyridinium tribromide for 0.2h; Inert atmosphere; Cooling; regioselective reaction;	94.2%
With 1-butyl-3-methylimidazolium tribromide for 0.166667h; Ionic liquid;	92.7%
With copper(ll) bromide In ethanol for 4h; Reflux;

trimethylsulphonium bromide (3084-53-5) + 1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide (80443-63-6)

Conditions	Yield
With potassium hydroxide In toluene at 40 - 45℃; for 5h;	92%

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → (R)-2-[2-(4-Chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyraldehyde (120687-96-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 15 h / 40 - 50 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (80443-41-0, 107534-96-3, 119364-85-1, 120786-56-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 15 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C 5: dimethylformamide / 6 h / 120 °C View Scheme
Multi-step reaction with 5 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 0.25 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C 5: dimethylformamide / 6 h / 120 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → (S)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (119364-85-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 15 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C 5: dimethylformamide / 6 h / 120 °C View Scheme
Multi-step reaction with 5 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 0.25 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C 5: 49 percent / dimethylformamide / 6 h / 120 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → Methanesulfonic acid (R)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester (120687-98-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 15 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → Methanesulfonic acid (S)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester (119298-84-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1) 1.98 M BuLi / 1) n-hexane, THF, -78 to 0 deg C, 2) THF, 30 min, 25 deg C 2: NCS, AgNO3 / acetonitrile / 0.25 h / 40 - 50 °C 3: LiAlH4 / diethyl ether / 3 h / 35 °C 4: NEt3 / CH2Cl2 / 4 h / 25 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 1-(4'-chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one (66346-02-9) + paclobutrazol (66345-53-7, 66346-05-2, 76738-62-0, 76738-64-2, 82336-55-8, 98169-53-0, 102735-64-8, 115509-55-2, 66346-04-1)

Conditions	Yield
With bromine In tetrachloromethane

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-aminenitrate (1239339-35-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1-butyl-3-methylimidazolium tribromide / 0.17 h / Ionic liquid 2: ethanol / 3 h / Reflux 3: silver nitrate / ethanol / 0.5 h / 35 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 2-amino-4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-3-ium bromide (1068658-48-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-butyl-3-methylimidazolium tribromide / 0.17 h / Ionic liquid 2: ethanol / 3 h / Reflux View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → 4-tert-butyl-5-[4-chlorobenzyl]-1,3-thiazol-2-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(ll) bromide / ethanol / 4 h / Reflux 2: ethanol / 7.5 h / Reflux View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → N-(4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-yl)-2-methoxybenzamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper(ll) bromide / ethanol / 4 h / Reflux 2.1: ethanol / 7.5 h / Reflux 3.1: dmap / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → N-(4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-yl)-2-chlorobenzamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper(ll) bromide / ethanol / 4 h / Reflux 2.1: ethanol / 7.5 h / Reflux 3.1: dmap / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C View Scheme

1-(4-chlorophenyl)-4,4-dimethyl-pentan-3-one (66346-01-8) → N-(4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-yl)-4-chlorobenzamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: copper(ll) bromide / ethanol / 4 h / Reflux 2.1: ethanol / 7.5 h / Reflux 3.1: dmap / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C View Scheme

Upstream product

• 614-47-1 1,3-diphenyl-propen-3-one 
• 111-48-8 2,2'-thiobis-ethanol 
• 41564-62-9 (E)-1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one 
• 104-88-1 4-chlorobenzaldehyde 
• 1577-03-3 1-(4-chlorophenyl)-4,4-dimethylpent-1-en-3-one 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

• 119364-84-0 (R)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 119298-82-7 (S)-1-(4-Chloro-phenyl)-4,4-dimethyl-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-pentan-3-ol 
• 107534-96-3 tebuconazole 
• 80443-63-6 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)ethylene oxide 
• 1350799-71-1 C₁₆H₂₀ClNOS 
• 66346-02-9 1-(4'-chlorophenyl)-2-bromo-4,4-dimethylpentan-3-one 
• 1068658-48-9 2-amino-4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-3-ium bromide 
• 1239339-35-5 4-(tert-butyl)-5-(4-chlorobenzyl)thiazol-2-aminenitrate 
• 66345-53-7 paclobutrazol 
• 119298-84-9 Methanesulfonic acid (S)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester 
• 120687-98-1 Methanesulfonic acid (R)-2-[2-(4-chloro-phenyl)-ethyl]-2-hydroxy-3,3-dimethyl-butyl ester 
• 119364-85-1 (S)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol 
• 80443-41-0 (R)-1-p-chlorophenyl-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol 

Relevant articles and documents

Synthesis method of 1-(4-chlorphenyl)-4,4-dimethyl-3-pentanone

The invention discloses a synthetic method of 1-(4-chlorphenyl)-4,4-dimethyl-3-pentanone. The target compound is prepared through condensation, hydrolysis and decarboxylation, the middle-high pressurehydrogenation step of a traditional process is omitted, and safety is remarkably improved. The method is mild in reaction condition, simple in process and suitable for industrial production.

Design, synthesis and neuraminidase inhibitory activity of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides

A series of N-(5-benzyl-4-(tert-butyl)thiazol-2-yl)benzamides were synthesized and the structures were characterized by 1H NMR, MS and elemental analyses. The crystal structures of compounds F5 and F16 were determined by single-crystal X-ray diffraction. The neuraminidase inhibitory activities of compounds F1-F32 were evaluated in vitro at the concentration of 40 μg/mL. The results indicated that compounds F8, F26 and F32 exhibited most potent inhibitory activity against NA. Molecular docking was performed by LeDock to further explain the structure-activity relationship of compound F26. The docking modeling showed that compound F26 was in good combination with oseltamivir binding sites of NA and could be a potential NA inhibitor agent.

Process for the hydrogenation of α,β-unsaturated ketones

The catalytic hydrogenation of α,β-unsaturated ketones of the formula in which R1 and R2 independently of one another represent straight-chain or branched alkyl, hydroxy-alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl or aryl, where at least one of the radicals R1 and R2 is monosubstituted to trisubstituted by halogen, can be carried out on a Ni-containing catalyst and in the presence of an organic sulphur compound of the formula in which R3 and R4 independently of one another denote straight-chain or branched alkyl, hydroxy-alkyl, carboxyalkyl or phenyl, and furthermore R3 and R4 may together represent --CH=CH--CH=CH--, --(CH2)4 --, --(CH2)5 --, --(CH2)2 --S--(CH2)2 -- or --(CH2)2 --O--(CH2)2 --, R4 may additionally denote hydrogen or CO--C1 -C12 -alkyl and n assumes the value 0 or 1.