1081-09-0

Basic information

• Product Name: 3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR&
• Synonyms: 3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR&;1,1'-(1,4-dihydro-2,4,6-trimethylpyridine-3,5-diyl)bisethan-1-one;3,5-Diacetyl-1,4-dihydro-2,4,6-trimethylpyridine;1-(5-acetyl-2,4,6-trimethyl-1,4-dihydropyridin-3-yl)ethanone;1-(5-ethanoyl-2,4,6-trimethyl-1,4-dihydropyridin-3-yl)ethanone;1-(5-acetyl-2,4,6-trimethyl-1,4-dihydro-3-pyridinyl)ethanone
• CAS NO: 1081-09-0
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.26888
• EINECS: 214-099-5
• Product Categories: C9 to C46;Heterocyclic Building Blocks;Pyridines;Building Blocks;C12;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1081-09-0.mol

Chemical Properties

• Melting Point: 154-159 °C(lit.)
• Boiling Point: 344.6oC at 760 mmHg
• Flash Point: 135oC
• Appearance: /
• Density: 1.018g/cm3
• PKA: 3.53±0.70(Predicted)
• CAS DataBase Reference: 3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR&(CAS DataBase Reference)
• NIST Chemistry Reference: 3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR&(1081-09-0)
• EPA Substance Registry System: 3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR&(1081-09-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1081-09-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Diacetyl-2,4,6-trimethyl-1,4-dihydropyridine is used as an intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and properties, contributing to the development of new drugs and medicinal compounds.
Used in Food Industry:
In the food industry, 3,5-Diacetyl-2,4,6-trimethyl-1,4-dihydropyridine is used as a flavoring agent, enhancing the taste and aroma of food products, leveraging its distinct odor to create desirable flavor profiles.
Used in Organic Chemistry:
3,5-Diacetyl-2,4,6-trimethyl-1,4-dihydropyridine serves as a reagent in organic chemistry reactions, facilitating specific transformations and syntheses that are essential for the creation of a range of organic compounds.
Used as a Precursor in Chemical Production:
3 5-DIACETYL-2 4 6-TRIMETHYL-1 4-DIHYDR& is also utilized as a precursor in the production of other important chemicals, indicating its versatility and significance in the broader chemical industry.

Upstream product

• 75-07-0 acetaldehyde 
• 123-54-6 acetylacetone 
• 58052-80-5 2,4,6-Trimethyl-[1,3,5]triazinane; hydrate 
• 15181-39-2 3-ethylidene-pentane-2,4-dione 
• 108-05-4 vinyl acetate 

Downstream Products

• 1123-09-7 3,5-dimethyl-2-cyclohexen-1-one 
• 1447968-00-4 (2E,2'E)-1,1'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(3-(4-bromophenyl)prop-2-en-1-one) 
• 1447967-99-8 (2E,2'E)-1,1'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(3-(4-chlorophenyl)prop-2-en-1-one) 
• 1447967-98-7 (2E,2'E)-1,1'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(3-(3-chlorophenyl)prop-2-en-1-one) 
• 1447967-97-6 (2E,2'E)-1,1'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(3-(4-nitrophenyl)prop-2-en-1-one) 
• 1447968-17-3 5,5-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(4'-chloro-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one) 
• 1447968-15-1 2,2'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(2-methyl-3-(p-tolyl)-1,3-oxazinane-4,6-dione) 
• 1447968-14-0 (N,N'E,N,N'E)-N,N'-((2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(ethan-1-yl-1-ylidene))bis(4-methylaniline) 
• 1447968-12-8 diethyl 5,5'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(2-acetyl-3-(4-chlorophenyl)-5-oxopentanoate) 
• 1447968-16-2 diethyl 5,5-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(4'-chloro-4-oxo-1,2,3,4-tetrahydro-[1,1'-biphenyl]-3-carboxylate) 
• 1447968-13-9 2,2'-(2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(4-(4-chlorophenyl)decahydroquinoline) 
• 1447968-11-7 2,2'-((2,4,6-trimethyl-1,4-dihydropyridine-3,5-diyl)bis(1-(4-chlorophenyl)-3-oxopropane-3,1-diyl))dicyclohexanone 
• 1447968-10-6 3,5-bis(5-(4-bromophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2,4,6-trimethyl-1,4-dihydropyridine 
• 1447968-09-3 3,5-bis(5-(4-chlorophenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-2,4,6-trimethyl-1,4-dihydropyridine 

Relevant articles and documents

Synthetic Regulation of 1,4-Dihydropyridines for the AIE or AIEE Effect: From Rational Design to Mechanistic Views

Aggregation-induced emission/aggregation-induced emission enhancement (AIE/AIEE) has recently attracted intense research, and a large number of AIE/AIEE luminogens (AIE/AIEEgens) have been constructed for application in diverse scientific fields. The AIE and AIEE effects have similar, but not identical, photophysical behaviors, which are closely related to molecular architectures. However, the current understanding of the inherent differences between AIE and AIEE is still obscure. Herein, a rational design strategy is reported for achieving AIE and AIEE effects by simply incorporating different substituents at the periphery of the same core skeleton. Experimental and theoretical studies on the series of compounds indicated that the restriction of intramolecular twisting motions or/and rotations plays an important role in regard to the corresponding AIE or AIEE behaviors. Moreover, compound 1 a (FW=203, ΦF=80.9 %) was discovered as the lowest molecular weight AIEEgen with a high quantum yield in the solid state despite having no rotatable units. Compound 2 a also exhibited an AIEE effect with the minimum necessary structure (a single ring).

Synthesis and photochemistry of novel 3,5-diacetyl-1,4-dihydropyridines. II [1]

In continuation of previous work some novel 3,5-diacetyl-1,4- dihydropyridine derivatives were synthesized and their photochemical behavior was studied under oxygen and argon atmosphere. Oxidation of the dihydropyridine ring and formation of pyridine derivatives was the result of the reaction. The presence of oxygen affects not only on the rate of oxidation, but also the formation of some unidentified by-products was observed on irradiation under this atmosphere. Springer-Verlag 2004.

1,4-Dihydropyridines: discovery of minimal AIEEgens and their mitochondrial imaging applications

Typical aggregation-induced emission enhancement fluorogens (AIEEgens) generally are designed as propeller-shaped molecules with multiple aromatic rotors. Described herein are 1,4-dihydropyridines, which have the minimum size necessary for AIEE, containing only a single ring, synthesized through a facile biocatalysis procedure. Owing to the AIEE property, intramolecular motion can be restrained by the surrounding environment, causing the radiative channel to open up. Both the fluorescence intensities and the lifetimes of the 1,4-dihydropyridine representatives increased with increasing viscosity, and high sensitivities were observed. On the basis of the single crystal X-ray structures, density functional theory (DFT) calculations were performed to explain the mechanism of the single-ring AIEE behaviour. Moreover, a few of the neutral AIEEgens were found to possess a high specificity towards mitochondria. As an example, one of the AIEEgens exhibited superior photostability and excellent storage tolerance, allowing for real-time imaging, viscosity mapping, and long-term tracking of the dynamics of the mitochondrial morphology.

Ultrasound-mediated, uranyl nitrate hexahydrate-catalyzed synthesis of 1,4-dihydropyridines under mild conditions

Abstract Synthesis of 1,4-dihydropyridines by three-component condensation reaction of aldehyde, 1,3-dicarbonyl compounds, and ammonium acetate have been found to be efficiently catalyzed by uranyl nitrate hexahydrate [UO2(NO3)2 ·6H2O] at room temperature under ultrasound irradiation. This novel synthetic method offers the advantages of high yields, short reaction times, simplicity, and easy workup compared to the conventional methods reported in the literature.

Etidronic acid catalyzed synthesis of 1,4-dihydropyridines

One pot, three components cyclaconctensation reaction of various arylaldehydes. ethyl acetoacetate/acetyl acetone and ammonium acetate with etidronic acid as catalyst afforded the corresponding 1,4 -dihydropyridines in better yields under solvent free conditions.

Etidronic acid catalyzed synthesis of 1,4-dihydropyridines

One pot, three components cyclocondensation reaction of various arylaldehydes, ethyl acetoacetate/acetyl acetone and ammonium acetate with etidronic acid as catalyst afforded the corresponding 1,4-dihydropyridines in better yields under solvent free conditions.

PREPARATION OF NEW ORGANIC LUMINOPHORES BASED ON 3,5-DIACETYLPYRIDINES

The reaction of acetylacetone or sodium salt of oxymethyleneacetone with corresponding aldehydes has been used to prepare 3,5-diacetyl-1,4-dihydropyridines III which have been oxidized to diacetylpyridines VII.These compounds have been transformed by an acid-catalyzed reaction with benzaldehyde into the chalcones VIII which have been utilized for the Kroehnke synthesis of luminophoric terpyridines I and II.