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2-Chloro-5-thiophenecarboxaldehyde is remarkable for the fact that the electron delocalization system of the thiophene ring is jointly influenced by the electron-withdrawing effect of the chlorine atom and the electron-accepting property of the aldehyde group, resulting in a rigid planar structure with significant electron asymmetry.
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Chemical Formula |
C5H3ClOS |
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Exact Mass |
146 |
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Molecular Weight |
147 |
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m/z |
146 (100.0%), 148 (32.0%), 147 (5.4%), 148 (4.5%), 149 (1.7%), 150 (1.4%) |
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Elemental Analysis |
C, 40.97; H, 2.06; Cl, 24.18; O, 10.91; S, 21.87 |
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2-Chloro-5-thiophenecarboxaldehyde is a biochemical reagent that can be used as a biomaterial or organic compound for life science related research.
In the field of medicinal chemistry
1. Synthesis of anti-tumor drugsThis compound serves as a key intermediate for the preparation of various anti-tumor candidate drugs. It can undergo condensation reactions with amine compounds to efficiently construct thiophene-containing Schiff base derivatives. These derivatives show significant inhibitory effects against several common human cancer cell lines, including breast cancer MCF-7 and cervical cancer HeLa cells, and have good potential for further anti-tumor drug development.
Example:
Synthesis of compound A: It reacts with p-aminobenzenesulfonamide under reflux in ethanol to produce a Schiff base product, with an IC50 value of 2.1 μ M for HepG2 cells.Mechanism of action: The introduction of chlorine atoms enhances the lipophilicity of the molecule, promoting the penetration of drugs into the cell membrane; The imine bond formed by aldehyde and amino groups can bind to the active site of tumor associated kinases (such as EGFR), inhibiting signal transduction.
2. Development of antibacterial agents
It can also be used as an important precursor for the synthesis of thiophene-based antibacterial agents. By reducing the aldehyde group to a hydroxymethyl group and then performing a sulfonylation reaction, a series of thiophene sulfonate compounds can be obtained. These compounds usually exhibit broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria, providing a valuable structural platform for novel antibacterial agent research.
example:
Synthesis of compound B: 5-Chlorothiophene-2-aldehyde is reduced to an alcohol by NaBH ₄, and then reacted with benzenesulfonyl chloride. The MIC value of the product against Staphylococcus aureus is 4 μ g/mL.
Advantage: The presence of chlorine atoms enhances the accumulation efficiency of compounds in the cell walls of Gram positive bacteria.
3. Anti inflammatory drug design
By utilizing the oxidative properties of aldehyde groups, they can be converted into carboxylic acid derivatives as inhibitors of cyclooxygenase-2 (COX-2).
example:
Synthesis of compound C: This substance is oxidized by Jones to carboxylic acid, and then amidated with aminopyridine compounds. The inhibition rate of the product in the carrageenan induced mouse foot swelling model is 68%.
Materials Science Field
1. Conductive polymer monomer
2-Chloro-5-thiophenecarboxaldehyde can be used as a monomer for preparing functional conductive polymers through electrochemical polymerization, and the resulting polymers are applicable to organic field-effect transistors (OFETs) and various sensor devices.
Example: Synthesis of polymer D: Electrochemical polymerization is carried out in boron trifluoride ether solution to obtain poly (5-chlorothieno-2-formaldehyde). This polymer has a conductivity of 0.1 S/cm and is particularly suitable for the preparation of ammonia gas sensors, with a detection limit as low as 5 ppm.
Mechanism: The aldehyde groups in its structure act as electron acceptors, and they can form intramolecular charge transfer complexes with the conjugated system of thiophene rings, which effectively enhances the carrier mobility of the polymer and improves its conductive performance.
2. Photovoltaic material modification
This compound can serve as a sensitizer for dye-sensitized solar cells (DSSCs). The electron-withdrawing effect of the chlorine atom in its molecular structure can effectively regulate the energy level of the dye, thereby increasing the open circuit voltage of the solar cell and improving its photoelectric conversion performance.
Example: Synthesis of dye E: 2-Chloro-5-thiophenecarboxaldehyde is connected to the pyridine ruthenium complex through Sonogashira coupling reaction. The dye-sensitized solar cell prepared with this dye achieves a photoelectric conversion efficiency (PCE) of 8.2%.
Advantages: The chlorine substitution in the molecule reduces the HOMO energy level of the dye, which helps to reduce electron recombination in the solar cell system and significantly enhance the stability of the cell.
3. Functional polymer crosslinking agent
The aldehyde groups in 2-Chloro-5-thiophenecarboxaldehyde can undergo condensation reactions with functional groups such as amino and hydroxyl groups in other polymers, which is conducive to preparing cross-linked adsorbent materials with excellent performance.
Example: Synthesis of Resin F: 2-Chloro-5-thiophenecarboxaldehyde is crosslinked with chitosan under acidic conditions. The resulting cross-linked resin has a strong adsorption capacity for Cr (VI) ions, reaching 125 mg/g, which is significantly superior to that of traditional adsorbent materials.
Organic synthesis intermediates
1. Construction of heterocyclic compounds
Synthesis of thieno [3,2-b] thiophene compounds through Paal Knorr reaction for total synthesis of natural products.
example:
Synthesis of compound G: It reacts with thioacetamide in acetic acid to form a thienothiophene skeleton, which exists in certain marine natural products.
2. Alpha, β - unsaturated compound precursors
Participate in Wittig reaction or Knoevenagel condensation to generate conjugated aldehydes for the synthesis of prostaglandin analogues.
example:
Synthesis of compound H: After reacting with phosphothalide, the core skeleton of prostaglandin E ₁ is constructed through Diels Alder cycloaddition.
3. Chiral catalyst ligand
Aldehydes can condense with chiral amines to form ligands with a C ₂ symmetry axis, which are used for asymmetric catalysis.
example:
Synthesis of ligand I: Condensation with (1R, 2R) - cyclohexanediamine resulted in a copper complex with an ee value of 95% in the Henry reaction.
Pesticide chemistry field
1. Insecticide Synergists
It can act as an effective synergist for pyrethroid insecticides. Its main mechanism is to inhibit the metabolic activity of cytochrome P450 enzymes in insects, thereby slowing down the degradation of insecticides in the target organism and enhancing insecticidal efficacy.For example, in the synthesis process of synergist J, 2-chloro-5-thiophenecarboxaldehyde first undergoes a reaction with piperazine to form an intermediate structure. When this intermediate is compounded with cypermethrin, it can significantly improve the toxicity of the insecticide, reducing its LD₅₀ value by approximately 40%.
2. Structural modification of fungicides
By introducing thiophene rings and chlorine atoms into fungicide molecules, the lipophilicity and biological targeting of the compounds can be effectively improved, which helps the molecules penetrate cell membranes and act on pathogenic fungi more efficiently.For instance, in the synthesis of fungicide K, 2-chloro-5-thiophenecarboxaldehyde is spliced and modified with a triazole ring. The resulting compound shows excellent antifungal activity, with an EC₅₀ value of 0.3 μg/mL against Magnaporthe oryzae (rice blast fungus).
Analytical Chemistry Applications
1. Fluorescent probe labeling
Aldehyde groups can react with amino groups in biomolecules for fluorescent labeling of proteins or DNA.
example:
Synthesis of Probe L: Conjugated with Fluorescein isothiocyanate (FITC), successfully labeled with bovine serum albumin (BSA), resulting in a threefold increase in fluorescence quantum yield.
2. Electrochemical sensors
The polymerized thin film modified electrode exhibits high selectivity towards heavy metal ions such as Hg ² ⁺.
example:
Preparation of Sensor M: Electropolymerization of 5-Chlorothiophene-2-aldehyde on the surface of glassy carbon electrode, with a linear response range of 1-100 nM to Hg ² ⁺.
According to literature reports, the synthesis methods of thiophene formaldehyde mainly include the following routes:
(1) 5-chlorothiophene DMF, Phosphorus trichloride as raw material. The raw material price of this process is cheap, the process is mature, and the yield can reach over 70%. It is currently the main process route adopted in industrial production. However, the amount of wastewater caused by phosphorus oxychloride is large, the environmental pressure is high, and the treatment cost is high;
(2) Prepared from thienoformyl chloride. The raw material used for this route is specific sodium aluminum oxide, which is expensive and has a low product yield;
(3) Starting from thiophene methanol. This route uses the catalyst Ru, which is relatively expensive and has a low product yield;
(4) Using thiophene formic acid as raw material. The yield of this route is not high, and the catalyst used in the reaction is relatively expensive;
(5) Thiophene is synthesized in one step with solid phosgene. According to reports, this route has a high yield, but solid light requires the use of suitable solvents for dissolution, and post-treatment requires solvent treatment.
The author directly used 5-chlorothiophene, gas phosgene, and introduced a small amount of phase transfer catalyst to synthesize the target product in one step, and then obtained thiophene formaldehyde with a content greater than 99% through steam distillation and vacuum distillation in a distillation tower. This process is simple to operate, high in yield, low in production cost, solvent-free, and has less wastewater, making it suitable for industrial production. The synthesis reaction equation is shown in the following figure:
Experimental operation:
Method 1:
Add 1 mol/L 5-chlorothiophene, 1.2 mol/L LDMF, and 1 g of catalyst to a 250 mL reaction flask, stir and raise the temperature to 50-55 ℃. Evenly introduce 40 g/h of gas phosgene, and after 2.5 hours, take samples for central control analysis. Use the gas spectrum area normalization method to analyze the percentage content of thiophene and thiophene formaldehyde until the thiophene content is less than 1%. Stop introducing phosgene and switch to nitrogen gas to remove excess phosgene. After 2 hours, cool down to below 30 ℃, add 100 mL of cold water, stir for 0.5 hours, and switch to steam distillation to separate the organic phase. Use a distillation tower for vacuum distillation to obtain thiophene formaldehyde product with a content greater than 99% and a yield greater than 90%.
Method 2:
Firstly, thiophene is added from the top of the reaction vessel. 2-Chloro-5-thiophenecarboxaldehyde and DMF will enter from the bottom of the reaction vessel. The molar ratio of DMF: 5-chlorothiophene: phosgene is 2:3:1, and the molar ratio of 5-chlorothiophene: DMF is 1:2. In addition, phosgene should also enter the reaction vessel at the bottom. When the substance is used in the reaction vessel, attention should be paid to controlling the temperature, usually within 60 ℃. After the reaction, the tail gas will enter the condensation equipment from the top of the reaction vessel. The main function of the condensation equipment is to freeze and capture, and the product will overflow from the top side of the reaction vessel and continuously enter the enamel vessel. During operation, attention should be paid to maintaining the temperature of the enamel vessel. Generally, the standard requirements for enamel vessel temperature are within 40 ℃. Between~60 ℃.
Turn on the mixing equipment, and at the same time, nitrogen can be blown into the bottom of the enamel kettle to drive out the gas. After driving away the phosgene, it will come into contact with hydrogen chloride and be sent to the alkali washing process through a steel lined glass pipeline for absorption treatment. Transfer the products inside the enamel kettle to the interior of the distillation kettle according to production standards and specifications, and scientifically control the temperature inside the distillation kettle to collect the fractions. The temperature of distillation needs to be controlled at 198 ℃, and the fractions should be collected and cooled until the temperature is consistent with room temperature. After washing with water and drying, thiophene formaldehyde can be obtained.
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