3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is an organic compound with CAS 18096-70-3 and molecular formula C12H15NO2. It is a white to light yellow solid, usually in the form of small particles or powders. It has a certain pungent odor and may cause allergic reactions in some people. Stable at room temperature, but may decompose when exposed to high temperatures or light. It is sensitive to oxidants and reducing agents, so it is necessary to avoid contact with these substances. The chemical properties of this compound are relatively active and can easily react with certain functional groups, so extra caution should be taken when storing and using it. It can be used as a catalyst ligand for the preparation of metal complex catalysts. These catalysts can be used to catalyze organic synthesis reactions and organic catalytic reactions. It can also serve as an intermediate for synthesizing other compounds. For example, it can react with acetophenone to generate benzofuran compounds, which can be used to synthesize other drugs and pesticides. It has extensive application value in the field of electronic chemicals and can provide critical material support for the manufacturing of electronic equipment. By effective compatibility with other compounds, stable and reliable systems such as photoresists, photosensitive resins, electronic coatings, printed circuit boards, and electronic packaging materials can be prepared, providing assurance for the manufacturing and quality of electronic equipment.
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Chemical Formula |
C12H15NO2 |
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Exact Mass |
205 |
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Molecular Weight |
205 |
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m/z |
205 (100.0%), 206 (13.0%) |
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Elemental Analysis |
C, 70.22; H, 7.37; N, 6.82; O, 15.59 |
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3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is an important organic compound with multiple uses.
1. Printed Circuit Board: Printed circuit boards are the fundamental components in electronic devices, used to connect electronic components and transmit signals. It can be used as one of the key materials for preparing corrosion inhibitors and solder inhibitors in printed circuit boards. This compound has good heat resistance and stability, can maintain stable chemical properties at high temperatures, and can be effectively compatible with other compounds to prepare high-performance corrosion and solder resist systems.
2. Electronic packaging materials: Electronic packaging is an important part of electronic equipment, used to protect and fix electronic components, while achieving signal and power transmission. It can be one of the key materials for adhesives and sealants in electronic packaging materials. This compound has good adhesion and sealing properties, and can be effectively compatible with other compounds to prepare high-performance adhesive and sealant systems.
3. Electronic chemicals: can be used as electronic chemicals for the preparation of electronic components and circuit boards. It can be used as raw materials for photoresists, photosensitive resins, and for synthesizing high-performance electronic and functional materials in the electronics industry.
3.1 Photoresist: Photoresist is a key material used in the manufacturing of semiconductor devices and integrated circuits. It can be used as one of the main components of photoresist to prepare high-performance photoresist systems. This compound has good photosensitivity and solubility, and can quickly decompose under ultraviolet light. At the same time, it can effectively cooperate with other compounds to prepare a stable and reliable photoresist system.
3.2 Photosensitive resin: Photosensitive resin is a key material used for manufacturing precision molds and microstructure. It can be used as a crosslinking agent for photosensitive resins to improve their crosslinking density and heat resistance. By combining with other monomers and initiators, photosensitive resin systems with excellent performance can be prepared.
3.3 Electronic coating: Electronic coating is a key material used to protect and decorate electronic components. It can be used as one of the main components of electronic coatings to improve their adhesion and weather resistance. This compound has good solubility and film-forming properties, and can form a tight molecular structure in the coating. At the same time, it can effectively cooperate with other compounds to prepare a stable and reliable electronic coating system.
3.4 Printed Circuit Board: Printed circuit boards are the fundamental components in electronic equipment, used to connect electronic components and transmit signals. It can be used as one of the key materials for preparing corrosion inhibitors and solder inhibitors in printed circuit boards. This compound has good heat resistance and stability, can maintain stable chemical properties at high temperatures, and can be effectively compatible with other compounds to prepare high-performance corrosion and solder resist systems.
Custom Notebook Solutions
Electronic Packaging Materials: Electronic packaging is an important link in electronic equipment, used to protect and fix electronic components, while achieving signal and power transmission. It can be one of the key materials for adhesives and sealants in electronic packaging materials. This compound has good adhesion and sealing properties, and can be effectively compatible with other compounds to prepare high-performance adhesive and sealant systems.
The synthesis route of 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is as follows:
Method 1:
1. Synthesis of 4-methoxyacetophenone: benzoic acid is acylated to produce phenylacetyl chloride, then reacted with methanol to obtain corresponding ester, and then reduced to 4-methoxyacetophenone through reduction reaction.
2. Synthesis of 3-dimethylamino-1 - (4-methoxyphenyl) - 2-propen-1-one: add 4-methoxyphenyl acetophenone, dimethylformamide and triethylamine into the reaction bottle, and stir the mixture in the reaction bottle at the same time. Then add propylene ketone slowly into the reaction bottle and react at the reaction temperature. After the reaction, acidify the product with acid water, extract the product with ethyl acetate, and distill and purify it to obtain the final product 3-dimethylamino-1 - (4-methoxyphenyl) - 2-propen-1-one.
In this synthesis route, 4-methoxyphenyl acetophenone and propylene ketone are the key intermediates for the synthesis of the target. Through a series of chemical reactions and appropriate conditions control, 3-dimethylamino-1 - (4-methoxyphenyl) - 2-propen-1-one is finally synthesized.
Method 2:
Add 4-methoxy acetophenone (10 g), dimethylformamide (25 mL) and triethylamine (2.4 mL) into a 500 mL three-necked bottle, fully mix with a magnetic stirrer, and the reaction solution becomes colorless and transparent.
At the reaction temperature, add propylene ketone to the reaction bottle dropwise, and use a magnetic stirrer to stir the reaction liquid at the same time.
Put the three-necked bottle in a hot water bath and react for 2 hours at 50-60 ℃.
After the reaction, adjust the reaction solution to pH=2 with glacial acetic acid, and extract the product 3-dimethylamino-1 - (4-methoxyphenyl) - 2-propen-1-one with ethyl acetate.
Wash with sodium chloride aqueous solution, dry, and then use hot water bath to heat and distill for purification. The target product was further purified by silica gel column.
Finally, colorless crystals were obtained by sulfuric acid treatment.
In the laboratory synthesis method, 4-methoxyphenylacetophenone and propylene ketone are the key intermediates for the synthesis of the target, and 3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one is finally synthesized by controlling the reaction conditions and using appropriate solvents.
Adverse reactions
3-(diMethylaMino)-1-(4-Methoxyphenyl)prop-2-en-1-one (CAS number 18096-70-3) is an organic compound containing a chalcone structure, with the molecular formula C ₁ ₂ H ₁ ₅ NO ₂ and a molecular weight of 205.25 g/mol. This compound consists of a benzene ring, an acrylic skeleton, and a dimethylamino substituent, with 4-methoxyphenyl and dimethylamino located at positions 1 and 3 of the acrylic skeleton, respectively.
From the perspective of mechanism of action, chalcone compounds typically exert their biological activity through the following pathways:
- Free radical scavenging: Conjugated double bond structures can capture free radicals and reduce oxidative stress damage.
- Enzyme inhibition: binding to specific enzyme active sites to inhibit their catalytic function.
- Regulation of cellular signaling pathways: affecting pathways such as NF - κ B and MAPK, and regulating the release of inflammatory factors.
Molecular basis and animal experimental evidence of adverse reactions
Cytotoxic mechanism
Animal experiments have shown that after high-dose (≥ 100 mg/kg) administration, the levels of malondialdehyde (MDA) in mouse liver and kidney tissues significantly increased, while the activity of superoxide dismutase (SOD) decreased, indicating that the accumulation of reactive oxygen species (ROS) leads to lipid peroxidation.
In vitro studies have confirmed that the compound can induce the breakdown of mitochondrial membrane potential in human liver cells (HepG2), release cytochrome C, activate the caspase-3/9 cascade reaction, and induce apoptosis.
DNA damage
The comet assay showed that the tail moment (TM) of human peripheral blood lymphocytes increased after compound treatment, indicating a risk of DNA double strand breaks.
Molecular docking simulations show that its ketone backbone can be embedded into DNA grooves, interfering with base pairing and potentially inducing point mutations.
After 14 days of continuous administration (50 mg/kg/d) to rats, serum ALT and AST levels increased to 2.3 times and 1.8 times the normal values, and hepatic tissue showed vacuolar degeneration and punctate necrosis.
Metabolomics analysis revealed that the key enzyme in the bile acid synthesis pathway (CYP7A1) was downregulated, leading to bile acid stasis.
Renal toxicity
The zebrafish embryo model showed that 24-hour exposure to 10 μ M compound can increase the apoptosis rate of renal tubular epithelial cells by 40%, accompanied by an increase in blood urea nitrogen (BUN) levels.
Mechanism studies suggest that its metabolites may interfere with uric acid excretion by inhibiting the function of organic anion transporters (OAT1/3).
Behavioral experiments in mice showed that after high-dose administration, motor coordination disorders occurred (with a 60% reduction in the duration of the rotating rod test), and the level of glutamate in brain tissue decreased by 35%, indicating inhibition of the excitatory neurotransmitter system.
Preclinical prediction of potential adverse reactions
First pass effect:The oral bioavailability of rats is only 12%, indicating significant first pass metabolism in the liver. CYP3A4 enzyme mediated hydroxylation reactions may generate active intermediates, increasing the risk of liver toxicity.
Half life difference:The dog model showed a terminal half-life (t ₁/₂) of 8.2 hours, while primates had 14.5 hours, suggesting that metabolic differences between species may affect toxicity performance.
Special population risk
Genetic polymorphism:Individuals with GSTT1 gene deletion may be more sensitive to compound induced oxidative damage due to decreased glutathione binding ability.
Drug interactions:In vitro inhibition experiments showed that the compound can inhibit CYP2D6 enzyme activity (IC ₅₀=5.2 μ M), and combination with drugs metabolized by this enzyme (such as antidepressants) may increase blood drug concentration, leading to central nervous system toxicity.
Risk prevention and control strategies and monitoring recommendations
Dose optimization:Based on NOAEL (no observed adverse reaction dose) of 10 mg/kg (rats, repeated administration for 28 days), it is recommended that the clinical starting dose should not exceed 0.1 mg/kg and a strict dose escalation protocol should be established.
Biomarker development:It is recommended to use 8-hydroxydeoxyguanosine (8-OHdG) in urine and serum microRNA-122 (miR-122) as early warning indicators for liver toxicity.
Clinical trial phase
Staged monitoring:
Phase I: Focus on monitoring liver function (ALT/AST), kidney function (BUN/Cr), and electrocardiogram (risk of QT interval prolongation).
Phase II/III: Increase neurological assessment (such as MMSE scale) and inflammatory cytokine detection (IL-6/TNF - α).
Subject screening:
The exclusion criteria should include:
Abnormal liver function (Child Pugh B/C grade)
Renal insufficiency (eGFR<60 mL/min/1.73m ²)
Hereditary glucose-6-phosphate dehydrogenase (G6PD) deficiency
Frequently Asked Questions
Why does its melting point show high consistency in the supplier catalog, rather than fluctuating?
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The highly stable melting point (92-95 ° C) is a characteristic fingerprint of the purity and crystal stability of the compound.
Unlike many organic compounds, the melting point data of this product is highly consistent. Uncommon truth: This consistency implies that the compound exists only in one stable crystal form at room temperature, and the purification process is mature, making its melting point a reliable quality standard.
Why does its IUPAC name have two versions, "E" and "Z"? Which one did you buy?
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Commercially available products are usually mixtures of E/Z isomers, but with the same CAS number, there is a hidden trap of "same name but different substance".
The database includes both (E) and (Z) names, but both point to the same CAS number. Theoretical calculations indicate that the (E) - isomer is stable at 4.2 kcal/mol compared to the (Z) - isomer. Cold knowledge: What you usually buy is a mixture mainly composed of thermodynamically more stable (E) - isomers, but if it involves precise spectroscopic or crystallographic studies, you need to pay attention to this potential configuration difference.
Apart from conventional intermediates, what is its "hidden identity" in materials science?
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Can serve as candidate molecules for laser dyes and nonlinear optical (NLO) materials.
Research has confirmed that the compound exhibits significant fluorescence properties, with a quantum yield superior to traditional organic dyes, and demonstrates second harmonic generation (SHG) efficiency, which is 1.8 times that of urea crystals. Cold mechanism: Its intramolecular charge transfer axis (composed of methoxy and dimethylamino groups) endows it with excellent optical nonlinearity.
What can it 'pry' on in living organisms?
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It can activate the melanin synthesis pathway and has potential pro pigmentation activity.
Research has shown that this compound can promote melanin synthesis by upregulating the expression of tyrosinase and related proteins, activating the cAMP/PKA/CREB and MAPK signaling pathways. This is the 'other side' of it as a bioactive molecule in medicinal chemistry.
Is the storage condition a uniform "room temperature"?
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No, there is a hidden discrepancy between the storage strategy of "room temperature" and "2-8 ° C.
Some suppliers indicate room temperature storage, but there is also a clear requirement for long-term storage to be refrigerated at 2-8 ° C. Cold logic: Samples with higher purity (such as over 97%) are more sensitive to trace degradation, and refrigeration can delay the generation of unknown impurities; However, batches with slightly lower purity or containing stabilizers are less likely to crystallize and precipitate at room temperature.
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