2,4-Bis(methylthio)pyrimidine (CAS No.: 5909-26-2) – Comprehensive Analysis of a Multifunctional Pyrimidine Compound

I. Basic Information and Physicochemical Properties

(1) Core Chemical Parameters

• Chinese Name:
  

• English Name: 2,4-Bis(methylthio)pyrimidine

• CAS No.: 5909-26-2

• Molecular Formula: $C_6{H}_8{N}_2{S}_2$

• Molecular Weight: 172.27 g/mol

• Appearance: White to light-yellow crystalline powder

(2) Physicochemical Properties

• Melting Point: 72–74°C

• Boiling Point: 275–277°C (atmospheric pressure)

• Density: 1.28 g/cm3

• Solubility: Insoluble in water; soluble in organic solvents (e.g., acetone, chloroform, ethyl acetate, toluene).

• Chemical Characteristics:

• The methylthio ($?SC{H}_3$) group exhibits nucleophilicity and reducibility, enabling participation in oxidation, substitution, and other reactions.

• The pyrimidine ring is aromatic and stable but can undergo electrophilic substitution under specific conditions.

II. Upstream and Downstream Industry Chain Analysis

(1) Upstream Raw Materials and Synthesis Process

• Key Raw Materials: 2,4-Dichloropyrimidine, sodium methanethiolate.

• Main Synthesis Route:

• Starting from 2,4-dichloropyrimidine, substitution with sodium methanethiolate in ethanol solvent.

• Chlorine atoms are replaced by methylthio groups at controlled temperature and time.

• Purification via filtration, washing, and recrystallization yields high-purity product (75%–85% yield).

(2) Downstream Products and Derivatives

• Pharmaceuticals:

• Key intermediate for antimalarial and antineoplastic drugs. Derivatives target pathogen/tumor-specific pathways.

• Used in antiarrhythmic drugs to regulate cardiac ion channels.

• Agrochemicals:

• Synthesizes low-toxicity insecticides/fungicides. Derivatives disrupt pest nervous systems or fungal metabolism.

• Herbicide precursor with crop selectivity.

• Materials Science:

• Precursor for organic semiconductors with optoelectronic applications (OLEDs, OFETs).

• Functional polymers with adsorption properties (e.g., metal ion removal in wastewater).

III. Key Application Areas

(1) Pharmaceutical R&D and Innovative Drugs

• Antimalarials: Derivatives inhibit Plasmodium growth by disrupting nucleic acid/protein synthesis. Animal studies show promising antimalarial activity.

• Oncology: Induces tumor apoptosis or inhibits angiogenesis. Demonstrates cytotoxicity in vitro against multiple cancer cell lines.

(2) Agrochemical Innovation and Green Pest Control

• Insecticides: Targets pest nervous systems (e.g., acetylcholinesterase inhibition). Environmentally friendly with low non-target toxicity.

• Fungicides: Inhibits fungal cell wall synthesis or respiration. Effective against crop diseases (e.g., cucumber downy mildew, tomato early blight).

(3) Materials Science and Advanced Technologies

• Organic Semiconductors: Conjugated polymers with high charge carrier mobility and optoelectronic efficiency. Used in OLED emissive/charge transport layers.

• Polymers: Introduction of 2,4-bis(methylthio)pyrimidine units imparts metal ion adsorption for applications like wastewater treatment.

IV. Technical Advantages and Market Dynamics

(1) Technical Strengths

• Mature synthesis process with mild, controllable conditions. Optimized solvents/catalysts enhance yield/purity.

• Reactive methylthio and pyrimidine sites enable diverse functional derivatizations.

(2) Market Trends

• Growing demand in pharmaceuticals, agrochemicals, and materials. Global market size ~$18 million in 2024, projected CAGR 11%–14%.

• Leading producers in China, USA, and Europe. Chinese firms gain market share via cost advantage and technical innovation.

V. Safety and Storage Recommendations

(1) Hazards

• Irritating to eyes, skin, and respiratory tract. Avoid inhalation, ingestion, or skin contact. Wear protective gear (goggles, gloves, respirator).

(2) Storage Conditions

• Store in cool, dry, ventilated areas away from heat/ignition sources. Keep containers sealed, separated from oxidizers/acids.

VI. SEO Optimization Strategy

(1) Keyword Layout

• Core Keywords: 2,4-bis(methylthio)pyrimidine, 5909-26-2, pyrimidine intermediate.

• Long-tail Keywords: 2,4-bis(methylthio)pyrimidine synthesis, pharmaceutical applications, market prospects.

Translation formatted for technical clarity and SEO optimization, retaining chemical nomenclature and industrial context.