Comprehensive Analysis of 1,6-Dihydro-2-methyl-6-oxo-5-pyrimidine carbonitrile (CAS No.: 27058-54-4) – A Key Pyrimidine Compound

I. Basic Information and Physicochemical Properties
(1) Core Chemical Parameters

• Chinese Name: 1,6-Dihydro-2-methyl-6-oxo-5-pyrimidine carbonitrile

• English Name: 2-Methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

• CAS No.: 27058-54-4

• Molecular Formula: $C_6{H}_5{N}_{3}O$

• Molecular Weight: 135.12

• Appearance: White to light-yellow crystalline powder

(2) Physicochemical Properties

• Melting Point: 240–242°C

• Boiling Point: 405°C (atmospheric pressure)

• Density: 1.33 g/cm3

• Solubility: Slightly soluble in water; highly soluble in polar organic solvents (e.g., DMSO, DMF), with moderate solubility in ethanol and methanol.

• Chemical Characteristics:

• The cyano group ($?CN$) exhibits high reactivity, enabling hydrolysis, addition reactions, etc.

• The carbonyl group at position 6 and 1,6-dihydro structure create unique electron cloud distribution, allowing diverse acid/base-catalyzed reactions.

• The methyl group at position 2 is relatively stable but may participate in specific reactions.

II. Upstream and Downstream Industry Chain Analysis
(1) Upstream Raw Materials and Synthesis Process

• Key Raw Materials: Malononitrile, ethyl acetoacetate, formamide.

• Main Synthesis Route:

• Condensation of malononitrile and ethyl acetoacetate under alkaline conditions to form an intermediate.

• Subsequent reaction with formamide at high temperatures, followed by cyclization, yielding 1,6-dihydro-2-methyl-6-oxo-5-pyrimidine carbonitrile.

• Purification via recrystallization achieves 60%–70% yield.

(2) Downstream Products and Derivatives

• Pharmaceuticals: A critical intermediate for antiarrhythmic drugs, antibiotics, and anticancer compounds (inhibiting tumor cell proliferation/apoptosis).

• Agrochemicals: Used in novel insecticides/fungicides (disrupting pest neural systems or fungal metabolism) and plant growth regulators.

• Materials Science: Precursor for organic semiconductors with photoelectrical properties, applicable in OLEDs and OFETs.

III. Key Application Areas
(1) Pharmaceutical R&D and Innovative Drugs

• Antiarrhythmics: Derivatives modulate cardiac ion channels, stabilizing electrical activity.

• Antibiotics: Inhibit bacterial cell wall synthesis or nucleic acid metabolism, showing in vitro activity against Gram-positive/negative bacteria.

(2) Agrochemical Innovation and Green Pest Control

• Insecticides: Target pest neural systems (e.g., acetylcholinesterase inhibition) with low environmental toxicity.

• Fungicides: Disrupt fungal respiration/cell wall synthesis, effective against crop diseases like wheat rust and cucumber powdery mildew.

(3) Materials Science and Advanced Technologies

• Organic Semiconductors: Conjugated polymers synthesized from this compound exhibit high carrier mobility and photoelectrical conversion efficiency, enhancing OLED/OFET performance.

IV. Technological Advantages and Market Dynamics
(1) Technological Strengths

• Stable synthesis process with optimized conditions/catalysts improving yield/purity.

• Cyano, carbonyl, and dihydro groups enable versatile derivatization for functional compounds.

(2) Market Trends

• Growing demand in pharmaceuticals, agrochemicals, and materials science.

• 2024 Global Market: ~$10 million, projected to grow at 10%–13% annually.

• Key Producers: China, India, and Europe. Chinese firms gain global share via cost efficiency and technological advancements.

V. Safety and Storage Recommendations
(1) Hazards

• Irritating to eyes, skin, and respiratory tract. Ingestion/inhalation/skin contact may cause harm. Use protective equipment (goggles, gloves, respirator). Avoid contact with food/beverages due to cyano toxicity.

(2) Storage Conditions

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

VI. SEO Optimization Strategy
(1) Keyword Layout

• Core Keywords: 1,6-dihydro-2-methyl-6-oxo-5-pyrimidine carbonitrile, 27058-54-4, pyrimidine carbonitrile intermediate.

• Long-Tail Keywords: Synthesis process of 1,6-dihydro-2-methyl-6-oxo-5-pyrimidine carbonitrile, applications in pharmaceuticals, market prospects.

Formatted for clarity and SEO optimization, emphasizing technical accuracy and industrial relevance.