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N-Allylthiourea, chemical formula C4H8N2S, CAS 109-57-9, is a sulfur-containing organic compound with white crystals. There is a slight garlic odor. Taste bitter. The solubility in water is 6.7g/mL, soluble in ethanol, slightly soluble in ether, and insoluble in benzene. Melting point 78 ℃; The relative density is 1.22. Toxic, LD50 (rat, subcutaneous) 850mg/kg. It is stimulating. Used as a preservative; Topical medication used in plastic surgery to eliminate scars; Cosmetics to eliminate skin scars; Cyanide free copper plating additive; Organic synthetic raw materials. Used in wastewater testing to suppress nitrification reactions.
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Chemical Formula |
C4H8N2S |
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Exact Mass |
116 |
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Molecular Weight |
116 |
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m/z |
116 (100.0%), 118 (4.5%), 117 (4.3%) |
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Elemental Analysis |
C, 41.35; H, 6.94; N, 24.11; S, 27.59 |
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Allylthiourea, as a multifunctional organic compound, has demonstrated extensive application value in industries such as medicine, agriculture, and materials science due to its unique chemical structure and biological activity.
1. Industrial anti-corrosion system
Cement and coating industry: As an efficient mold inhibitor, allyl thiourea can inhibit microbial growth in cement mortar, prevent frosting and deterioration, and significantly extend the storage period of building materials. Adding 0.5% -2% mass fraction to the coating formula can improve the water resistance of the coating by more than 30% and reduce the problem of detachment caused by microbial corrosion. The second-generation products require sealed storage due to volatility, while the fourth generation products achieve zero volatility through molecular design and have been replaced in high-end coatings.
Metal protection: Adding 0.1% -0.3% allyl thiourea to the pickling solution can reduce the corrosion rate of steel by more than 85%. Its mechanism of action includes the formation of a dense adsorption film on the metal surface (adsorption free energy -28.6 kJ/mol), and the inhibition of anodic dissolution through the complexation of thiourea groups with Fe ² ⁺ (complexation constant K=10 ⁵ L/mol).
2. Daily chemical and food contact materials
Cosmetics anti-corrosion: As a preservative allowed by the "Technical Specification for Safety of Cosmetics", N-Allylthiourea maximum allowable concentration is 0.5%. In cream products, a 0.3% addition can inhibit Aspergillus niger and Pseudomonas aeruginosa for 28 days while maintaining a stable pH value (5.5-7.0).
Food packaging: Although not directly used as a food preservative, its derivatives (such as N-allyl-N '- phenylthiourea) can be used for antibacterial modification of polyethylene film, increasing the antibacterial rate of packaging materials against Escherichia coli to 99.2%.
1. Cyanide free copper plating process
As a key brightener, allyl thiourea can significantly improve the quality of the coating in the sulfate copper plating system:
Bright current density range: extended from 2-4 A/dm ² in traditional processes to 0.5-6 A/dm ²
Coating characteristics: Thickness uniformity increased by 40%, microhardness reached HV180-220, salt spray resistance test time extended to 500 hours (traditional process only 200 hours)
Application case: In PCB electroplating, an addition of 0.2 g/L can reduce the thickness difference of copper plating on the hole wall from 15 μ m to 5 μ m, meeting the requirements of HDI board processing.
2. Removal of magnesium alloy coating
In the repair process of electroless nickel phosphorus alloy plating on magnesium alloys, allyl thiourea can be used as a corrosion inhibitor to achieve selective stripping:
Withdrawal solution formula: 68% nitric acid 200-400 mL/L+40% hydrofluoric acid 200-420 mL/L+allyl thiourea 5-15 mg/L
Technical advantages: The plating rate can reach 10-15 μ m/min, the substrate corrosion rate is less than 0.5 μ m/h, and the environmental friendliness is improved by 70% compared to traditional chromic anhydride systems
Economic benefits: The cost of single plating removal has been reduced to 0.3 yuan/dm ², and the solution can be recycled for more than 10 times.
3. Acid pickling corrosion inhibitor
In the hydrochloric acid pickling process, the complex system of allyl thiourea and bamboo leaf extract exhibits a synergistic effect:
Corrosion inhibition efficiency: In a 10% HCl solution, a 0.5% compound agent can reduce the corrosion rate of carbon steel from 12.8 g/(m ² · h) to 0.3 g/(m ² · h)
Environmental characteristics: Compared to traditional chromium containing corrosion inhibitors, COD emissions are reduced by 85%, and there is no risk of residual hexavalent chromium
Scope of application: Successfully applied to acid pickling and descaling of petrochemical equipment, boilers, and pipelines, with a temperature range expanded to 40-80 ℃
1. Drug molecule construction
Allyl thiourea, as a pharmacophore, plays a crucial role in the synthesis of various drugs:
Anticancer drug: a derivative prepared by condensation with benzimidazole ring, with an IC50 value of 0.8 μ M for A549 lung cancer cells, which is three times lower than cisplatin
Antibacterial drugs: Triazolothiazole compounds prepared by click chemistry have a MIC value of 2 μ g/mL against Staphylococcus aureus
Synthesis process: Adopting a "one pot method" series reaction, the total yield is increased to 65%, which shortens the working hours by 30% compared to the traditional stepwise method
2. Pesticide active ingredients
In the field of pesticides, allyl thiourea derivatives exhibit excellent biological activity:
Insecticides: N-allyl-N '- arylthiourea compounds have an LC ₅₀ value of 1.2 ppm against diamondback moth, which is 40% higher than imidacloprid
Fungicide: a derivative containing fluorine substituents, with an EC ₅₀ value of 0.5 μ g/mL against rice blast fungus, and a 90% reduction in toxicity to aquatic organisms
Synthesis pathway: Through N-alkylation reaction of allyl bromide and thiourea, combined with Suzuki coupling to achieve aromatic ring modification, the total yield is stable at 55% -60%
3. Functional material monomers
In materials science, allyl thiourea is involved in the preparation of various functional materials:
Metal organic frameworks (MOFs): Zn ATU MOFs coordinated with Zn ² ⁺, with a CO ₂ adsorption capacity of up to 120 mg/g (298K, 1 bar)
Ionic liquid: N-Allylthiourea based ionic liquid, with a catalytic efficiency twice that of traditional NaOH system in biodiesel ester exchange reaction
Polymer modification: Grafted onto the polyacrylate chain, the material's adsorption capacity for Cu ² ⁺ was increased to 280 mg/g, and the adsorption rate remained at 85% after 10 cycles of use
1. Scar repair
In the field of plastic surgery, allyl thiourea for external use (0.5% gel) showed significant efficacy:
Clinical data: After an 8-week treatment period, the scar volume reduction rate reached 68%, an increase of 22% compared to the silicone dressing group
Mechanism of action: By inhibiting the expression of TGF - β 1 (reducing it by 45%) and regulating the balance of MMP-2/TIMP-1, it promotes the orderly arrangement of collagen fibers
Safety: The transdermal toxicity test showed that LD ₅₀>5000 mg/kg, and the skin irritation index was 0 (evaluated according to the Draize method)
2. Development of antibacterial agents
Its derivatives have made breakthrough progress in the field of antibacterial:
Broad spectrum antibacterial activity: The MIC value of the quaternary ammonium salt modified product against MRSA is 4 μ g/mL, and there is no induction of drug resistance
Anti biofilm activity: At a concentration of 0.5%, it can destroy 80% of the biofilm of Pseudomonas aeruginosa, which is three times higher than traditional antibiotics
Preparation form: various dosage forms such as nano emulsion (particle size 80nm), hydrogel (swelling degree 1200%) have been developed
3. Antioxidants
In the field of free radical scavenging, allyl thiourea exhibits SOD like activity:
In vitro experiment: The IC ₅₀ value of · OH is 12 μ M, which is 60% lower than that of mannitol
In vivo experiment: In the D-galactose-induced aging model, it can reduce the serum MDA level by 35% and increase the SOD activity by 40% in mice
Structure activity relationship: By introducing a benzene ring at position C-2, its antioxidant activity can be further increased by 2 times
1. Sewage treatment
In the field of nitrification inhibition, allyl thiourea exhibits high selectivity:
Inhibition effect: At a concentration of 0.1 mg/L, the activity of ammonia oxidizing bacteria (AOB) can be reduced by 90%, while the inhibition rate of nitrite oxidizing bacteria (NOB) is less than 10%
Application scenario: In the treatment of leachate from garbage, the total nitrogen removal rate can be increased from 65% to 85% without affecting the denitrification process
Economy: Processing costs are reduced by 40% compared to traditional methanol addition methods
2. Heavy metal remediation
As a chelating agent, it exhibits excellent performance in soil remediation:
Cd ² ⁺ remediation: Under pH=6 conditions, the extraction rate of Cd from contaminated soil reached 85%, which is 20% higher than EDTA
Hg ² ⁺ fixation: The formed Hg ATU complex has a Ksp value of 10 ⁻³ ⁸ and is more stable than mercury sulfide
Ecological risk: Residue half-life in soil<30 days, acute toxicity to earthworms LC ₅₀>1000 mg/kg
Material modification technology
1. Rubber additives
In the tire industry, as an anti scorching agent, it can achieve:
Process improvement: The burning time (t ₅) of the rubber material has been extended from 8 minutes to 15 minutes, and the processing safety has been improved by 87.5%
Performance improvement: Vulcanized rubber hardness reduced by 5 Shore A, wear resistance increased by 20%, and dynamic heat generation reduced by 15%
Economic benefits: The cost of a single tire has been reduced by 0.8 yuan, resulting in an annual cost savings of over 10 million yuan (based on a production capacity of 10 million yuan)
2. Plastic additives
In PVC processing, as a stabilizer, it has unique advantages:
Thermal stability: Extend PVC degradation time from 30 minutes to 90 minutes at 180 ℃
Light stability: After 1000 hours of xenon lamp aging, the color difference Δ E is less than 3, which is 100% more environmentally friendly than the lead salt system
Synergistic effect: When used in combination with calcium zinc composite stabilizers, it can reduce processing torque by 15% and increase extrusion rate by 25%
1. New energy materials
In lithium sulfur batteries, as a positive electrode binder, N-Allylthiourea can achieve:
Electrochemical performance: Increases the initial efficiency of the battery from 75% to 88%, with a capacity retention rate of>80% after 500 cycles
Interface stability: During SEI film formation, the shuttle effect of polysulfides can be suppressed by up to 90%
Cost advantage: Compared to PVDF binder, the cost is reduced by 60%, and the solvent recovery rate is>95%
2. Biosensors
Based on its electrochemical activity, a high-sensitivity detection platform has been developed:
Detection limit: The detection limit for Hg ² ⁺ reaches 0.1 ppt, which is 3 orders of magnitude higher than traditional methods
Selectivity: In the presence of 1000 times interference ions, the signal-to-noise ratio is still>10
Application scenario: Rapid on-site detection of heavy metals in water and food has been achieved, with a detection time of less than 5 minutes
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