94-38-2

Basic information

• Product Name: 3-(diethylamino)propiophenone
• Synonyms: 3-(diethylamino)propiophenone;3-(diethylamino)-1-phenylpropan-1-one;1-Phenyl-3-(diethylamino)-1-propanone;3-(Diethylamino)-1-phenyl-1-propanone;3-(diethylamino)-1-phenylpropan-1-one HCl
• CAS NO: 94-38-2
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.29606
• EINECS: 202-329-7
• Mol File: 94-38-2.mol

Chemical Properties

• Boiling Point: 301.7°C at 760 mmHg
• Flash Point: 101.4°C
• Appearance: /
• Density: 0.974g/cm³
• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: 3-(diethylamino)propiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(diethylamino)propiophenone(94-38-2)
• EPA Substance Registry System: 3-(diethylamino)propiophenone(94-38-2)

Safety Data

• Hazardous Substances Data: 94-38-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(diethylamino)propiophenone is used as an intermediate for the production of various pharmaceuticals, contributing to the synthesis of different medicinal compounds.
Used in Organic Synthesis:
DEP is used as a reagent in organic synthesis, facilitating the creation of a range of chemical products through its reactive properties.
Used in Dye and Pigment Manufacturing:
3-(diethylamino)propiophenone is used as a precursor in the manufacture of dyes and pigments, playing a role in the coloration processes of various materials.
Used in Fine Chemical Production:
DEP is utilized in the production of other fine chemicals, indicating its versatility in the chemical industry for creating specialty products.
Used in Synthesis of Biologically Active Compounds:
3-(diethylamino)propiophenone is used as a reagent in the synthesis of biologically active compounds, highlighting its potential in developing new pharmaceuticals and bioactive substances.
Used in Material Development:
DEP serves as a building block in the development of new materials, showcasing its application in the innovation of novel substances with specific properties.

InChI:InChI=1/C13H19NO/c1-3-14(4-2)11-10-13(15)12-8-6-5-7-9-12/h5-9H,3-4,10-11H2,1-2H3

Upstream product

• 660-68-4 diethyl amine hydrochloride 
• 98-86-2 acetophenone 
• 50-00-0 formaldehyd 
• 109-89-7 diethylamine 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 52853-18-6 N,N-diethyl(methylene)ammonium chloride 
• 29636-75-7 3-bromo-1-phenylpropan-1-one 
• 936-59-4 3-chloropropiophenone 
• 24070-51-7 β-iodopropiophenone 
• 91935-86-3 1-Phenyl-3-p-tolylsulfonyl-2-propen-1-ol 
• 768-03-6 Phenyl vinyl ketone 
• 7664-93-9 sulfuric acid 
• 3204-31-7 1,3-Dimethyl-2,3-dihydro-1H-benzoimidazole 
• 21440-46-0 1-Phenyl-3-p-toluolsulfonyl-propen-⁽²⁾-on-⁽¹⁾ 

Downstream Products

• 3506-43-2 4-(3-oxo-3-phenylpropylamino)benzoic acid 
• 62365-91-7 3-(N-3'-Oxo-3'-phenylpropyl)-aminochinolin 
• 92515-07-6 (2S,3R)-3-Hydroxy-2-(3-oxo-3-phenyl-propylamino)-butyric acid 
• 92515-09-8 [2-(3-Oxo-3-phenyl-propylamino)-acetylamino]-acetic acid 
• 91958-55-3 ethyl 2-nitro-5-oxo-5-phenylpentanoate 
• 16324-15-5 diethyl (3-oxo-3-phenylpropyl)phosphonate 
• 768-03-6 Phenyl vinyl ketone 
• 28312-41-6 diethyl-methyl-(3-oxo-3-phenyl-propyl)-ammonium; iodide 
• 102012-76-0 4-methyl-4-nitro-1,7-diphenyl-heptane-1,7-dione 
• 4369-48-6 3-diethylamino-1,1-diphenyl-propan-1-ol 
• 5806-14-4 3-diethylamino-1-phenyl-1-pyridin-2-yl-propan-1-ol 
• 14398-97-1 (1-methylpyrrolidin-3-yl)(phenyl)methanone 
• 5409-66-5 3-benzoyl-4-hydroxy-1-methyl-4-phenylpiperidine 
• 745826-58-8 9-(3-oxo-3-phenyl-propyl)-fluorene-9-carboxylic acid 

Relevant articles and documents

Metal-free synthesis of β-aminoketones by the reductive hydroamination of ynones

This study describes a cascade method for the synthesis of β-aminoketones through the reductive hydroamination of alkynes under very mild metal-free conditions. It allows for the rapid conversion of ynones and amines into corresponding β-aminoketones with a broad substrate scope and diverse functionalities. This straightforward and easy-to-handle reaction process can be successfully applied for the synthesis of Proroxan and Propipocaine, offering a potential option for the synthesis of drug molecules with the β-aminoketone skeleton.

SMALL MOLECULE CMKLR1 ANTAGONISTS IN INFLAMMATORY DISEASE

α-NETA analogs are provided for the treatment of inflammatory disease.

Mechanistic studies on counter-ionic effects of camphorsulfonate-based ionic liquids on kinetics, thermodynamics and stereoselectivity of β-amino carbonyl compounds

Catalysis is important in various applications of organic chemistry and its output product control for stereoselective compounds is outrageous. Establishment of experimental facts of stereoselective compounds from catalysis and their validation using theoretical evidences is the key to understand various mechanisms of optically active compounds. A family of new ionic liquids (ILs) with various imidazolium cations and camphorsulfonate anion as environmentally benign liquid salts have been synthesized and deployed for catalysis of β-amino carbonyl compounds. The products were formed using ILs as a homogeneous catalyst with excellent product yield and diastereoselectivity. The effect of counter ions, Hammett acidity and viscosity of ILs along with solvent and temperature are explored in terms of reaction kinetics and product yields. Density functional theory (DFT) was used to investigate thermodynamical study of mechanistic pathway of the reaction. The DFT calculations predicted that the catalysis mechanism involved both counterions of the IL. Moreover, it is evidenced that the syn-pathway required lower activation energy while anti-pathway led to thermodynamically stable product. This study explores new avenues for using ILs as potential homogeneous catalysts for the production of stereoselective species.

Aza-Michael reaction promoted by aqueous sodium carbonate solution

A general and efficient aza-Michael reaction promoted by aqueous sodium carbonate solution has been developed. The reaction has complete mono-alkylation selectivity and proceeds with complete chirality retention for chiral amino esters. With a broad substrate scope, a well-common catalyst and simple operation, the catalytic approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of β-amino carbonyl compounds.

A novel method for biomimetic synthesis of Mannich bases

Since the early studies of Mannich, Mannich reaction has become an important tool for the synthesis of new compounds. Mannich bases can be either directly employed or used as intermediates. In this work, the one-carbon unit transfer reaction of tetrahydrofolate coenzyme was initiated. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. 1,3-Dimethylimidazolidine as a new tetrahydrofolate coenzyme model at formaldehyde oxidation level was used to react with ketone having active hydrogen atoms and amine to give the corresponding Mannich base in good yield by a covert Mannich reaction. A novel method for biomimetic synthesis of various Mannich bases is provided. Copyright

Covert Mannich reaction via carbon transfer

1,3-Dimethylbenzimidazolidine reacts with ketones, which can provide activating α hydrogens and primary or secondary amines under acidic conditions, to yield aminomethylation derivatives by a covert Mannich reaction. Copyright Taylor & Francis Group, LLC.

Anticonvulsant activity of semicarbazone derivatives of Mannich bases

A series of semicarbazones of semicarbazide/p-chlorophenyl semicarbazide and Mannich bases of acetophenone/p-chloroacetophenone has been synthesized and their anticonvulsant activity screened against MES and scPTZ test. p-Chlorophenyl semi-carbazone of N,N-dimethylaminopropiophenone has been found to be the most active in all these tests.

Microwave-assisted regioselective synthesis of β-aminoketones via the Mannich reaction

A new and efficient method for the regioselective synthesis of β- aminoketones has been achieved by a simple reaction of formaldehyde, a secondary amine and a ketone under microwave irradiation.

Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents

A number of N-substituted β-alkylaminophenone derivatives including two (α- and two γ-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 μM.

A Convenient Regioselective Synthesis of Mannich Bases

A new, convenient regioselective process for aminomethylation of ketones is reported, involving the in situ formation of silyl enol ethers and iminium salts.