Comprehensive Analysis of 5-Bromo-2-chloro-4,6-dimethylpyrimidine (CAS No.: 4786-72-5) – A Key Heterocyclic Intermediate

I. Basic Information and Physicochemical Properties

(1) Core Chemical Parameters

• Chinese Name:
  

• English Name: 5-Bromo-2-chloro-4,6-dimethylpyrimidine

• CAS No.: 4786-72-5

• Molecular Formula: $C_6{H}_{6}BrCl{N}_2$

• Molecular Weight: 221.48 g/mol

• Appearance: White to light-yellow crystalline powder

(2) Physicochemical Properties

• Melting Point: 115–117℃

• Boiling Point: 285–287℃ (at atmospheric pressure)

• Density: 1.64 g/cm3

• Solubility: Slightly soluble in water, highly soluble in organic solvents (e.g., acetone, chloroform, ethyl acetate).

• Chemical Characteristics:

• Bromine and chlorine atoms in the molecule exhibit high reactivity, enabling nucleophilic substitution reactions with nucleophiles (e.g., amines, hydroxyl groups, thiols), yielding compounds with diverse functionalities.

• Methyl groups at positions 4 and 6 enhance molecular stability and influence electron cloud distribution, affecting reaction activity.

II. Upstream and Downstream Industrial Chain Analysis

(1) Upstream Raw Materials and Synthesis Process

• Key Raw Materials:

• Brominating agents (e.g., liquid bromine, N-bromosuccinimide [NBS]).

• Chlorinating agents (e.g., phosphorus oxychloride, chlorine gas).

• Mainstream Synthesis Route:

• Starting with 4,6-dimethylpyrimidine, bromination at position 5 is achieved using brominating agents in solvents (e.g., dichloromethane).

• Subsequent chlorination at position 2 using chlorinating agents yields 5-bromo-2-chloro-4,6-dimethylpyrimidine after purification.

• Total Yield: ~60%–70%.

(2) Downstream Products and Derivatives

• Pharmaceuticals:

• Key intermediate for novel antidepressants and antiepileptic drugs. Structural modifications enable compounds with specific pharmacological activities.

• Potential anticancer applications via disrupting tumor cell metabolism or signaling pathways.

• Agrochemicals:

• Precursor for low-toxicity insecticides and fungicides. Derivatives target pest nervous systems or fungal cell wall synthesis.

• Critical for novel herbicides with selective weed control and minimal crop impact.

• Materials Science:

• Precursor for organic semiconductor materials with high optoelectronic performance, applicable in OLEDs and OFETs.

III. Core Application Fields

(1) Pharmaceutical R&D and Innovative Drugs

• Antidepressants: Derivatives regulate neurotransmitters (e.g., serotonin, dopamine) to alleviate depressive symptoms. Clinical trials show efficacy with low side effects.

• Antiepileptics: Derivatives stabilize neuronal membrane potentials and inhibit abnormal discharges, demonstrating anticonvulsant effects in animal models.

(2) Agrochemical Innovation and Green Pest Control

• Insecticides: Derivatives disrupt pest neural systems (e.g., inhibiting acetylcholinesterase) with low environmental toxicity.

• Fungicides: Inhibit fungal growth by interfering with cell wall synthesis or respiration, effective against crop diseases (e.g., wheat rust, cucumber powdery mildew).

(3) Materials Science and Advanced Technologies

• Organic Semiconductors: Conjugated polymers synthesized from this intermediate exhibit high carrier mobility and optoelectronic conversion efficiency. Applications include OLED emissive layers and charge transport layers.

IV. Technical Advantages and Market Dynamics

(1) Technical Advantages

• Mature synthesis processes with optimized conditions for high yield and purity.

• Bromine and chlorine atoms enable versatile derivatization for functional compound development.

(2) Market Trends

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

• 2024 Global Market Size: ~$15 million, projected to grow at 12%–15% annually.

• Major producers in China, USA, and Europe. Chinese firms gain market share via cost advantages and technological progress.

V. Safety and Storage Recommendations

(1) Hazards

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

• Toxic; avoid contact with food or beverages.

(2) Storage Conditions

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

VI. SEO Optimization Strategy

(1) Keyword Layout

• Core Keywords: 5-Bromo-2-chloro-4,6-dimethylpyrimidine, 4786-72-5, pyrimidine intermediate.

• Long-Tail Keywords:

• 5-Bromo-2-chloro-4,6-dimethylpyrimidine synthesis process.

• Applications of 5-Bromo-2-chloro-4,6-dimethylpyrimidine in pharmaceuticals.

• Market prospects of 5-Bromo-2-chloro-4,6-dimethylpyrimidine.

Formatted for clarity and SEO optimization while maintaining technical accuracy.