2-Chloro-4,6-diphenyl-1,3,5-triazine CAS 3842-55-5 98% Off White Solid OLED Intermediate Fine Chemical Intermediate

1. Product Overview

2-Chloro-4,6-diphenyl-1,3,5-triazine (CAS 3842-55-5) is a key electron-deficient heterocyclic compound with the molecular formula C₁₅H₁₀ClN₃ and a molecular weight of 267.71. It features a central 1,3,5-triazine core where the 2-position is substituted with a reactive chlorine atom, while the 4- and 6-positions are occupied by phenyl groups. This structure combines a strong electron-withdrawing triazine ring with sterically hindered, moderately electron-donating diphenyl substituents, resulting in a rigid, planar-to-slightly-twisted conjugated system. The compound typically appears as an off-white to pale yellow crystalline solid or powder with a melting point of 138–142 °C. Supplied at ≥98% HPLC purity, it is widely used as an OLED intermediate for synthesizing electron-transporting materials (ETMs) and host emitters via nucleophilic substitution or cross-coupling at the chloro site, and also serves as a fine chemical intermediate in pharmaceutical and heterocyclic synthesis.

2. Key Features and Advantages

• High Purity Standard: Minimum 98% by HPLC ensures clean reactivity and reproducible device performance in OLED material fabrication.

• Reactive Chlorine Handle: The 2-chloro substituent is susceptible to nucleophilic aromatic substitution (SNAr) by amines, phenols, and thiols, and can participate in Pd-catalyzed cross-couplings (e.g., Suzuki with boronic acids), enabling versatile functionalization.

• Electron-Transporting Core: The electron-deficient triazine ring promotes electron affinity and balanced charge transport, making it ideal for ETL, EBM, and TADF host design.

• Steric and Thermal Stability: The 4,6-diphenyl groups provide steric hindrance that suppresses concentration quenching and aggregation, while the high melting point supports vacuum thermal evaporation.

• Off-White Solid Morphology: Free-flowing powder facilitates accurate weighing for lab-scale synthesis and pilot-scale OLED material preparation.

• Dual Application: Bridges OLED optoelectronics (ETM/host precursors) and fine chemical/pharmaceutical intermediate uses (triazine scaffold for bioactive heterocycles).

3. Main Applications

• OLED Intermediates: A fundamental building block for electron-transporting layers (ETL) and electron-blocking/hole-transport layers. The chloro group is displaced by carbazole, triphenylamine, or phenothiazine to yield materials like Cl-TPTA derivatives; also used to construct TADF emitters and deep-blue phosphorescent hosts with tuned LUMO levels.

• Pharmaceutical Fine Chemical: Serves as a triazine-based electrophile for introducing the 2-chloro-4,6-diphenyltriazinyl moiety into drug candidates; used in synthesizing benzimidazole derivatives and kinase-inhibitor scaffolds.

• Organic Synthesis: Acts as a versatile synthon for SNAr with N/O/S nucleophiles, and as a precursor for 2-substituted-4,6-diphenyltriazines via Suzuki or Buchwald–Hartwig amination.

• Advanced Materials R&D: Employed in designing conjugated small molecules, dendrimers, and polymers for organic photovoltaics (OPVs) and thin-film transistors where electron acceptance is required.

• Custom Ligand Synthesis: Used to prepare triazine-based ligands for transition-metal catalysis and as a core for covalent organic frameworks (COFs) with electron-poor linkages.

4. Technical Specifications

5. Storage and Handling

Store in a tightly sealed container in a cool, dry, and well-ventilated area protected from light. Stable at room temperature (15–25 °C); for long-term storage, keep in a desiccator or refrigerate at 2–8 °C to prevent slow discoloration or hydrolysis of the chloro group under humid conditions. Avoid exposure to moisture and strong nucleophiles (amines, alcohols) at elevated temperatures which could trigger premature SNAr. Handle in a fume hood; wear nitrile gloves, safety goggles, and a lab coat. Minimize dust generation. Keep away from strong oxidizers and incompatible nucleophiles. Reseal immediately after use; consider inert gas purge for opened packages if storing >3 months. Dispose as halogenated nitrogen heterocycle waste per local regulations. Always refer to the latest SDS.

6. Safety Overview

This substance may cause irritation to skin, eyes, and respiratory tract. Signal Word: Warning. Hazard Statements: H302—Harmful if swallowed; H315—Causes skin irritation; H319—Causes serious eye irritation; H335—May cause respiratory irritation. Precautionary Statements: P261—Avoid breathing dust/fume/mist; P264—Wash thoroughly after handling; P270—Do not eat/drink/smoke when using; P271—Use only outdoors or in well-ventilated area; P280—Wear protective gloves/eye protection/face protection; P301+P312—IF SWALLOWED: Call a poison center/doctor if unwell; P302+P352—IF ON SKIN: Wash with plenty of soap and water; P305+P351+P338—IF IN EYES: Rinse cautiously with water for several minutes, remove contacts if present, continue rinsing; P330—Rinse mouth; P332+P313—If skin irritation occurs: Get medical advice/attention; P337+P313—If eye irritation persists: Get medical advice/attention; P362—Take off contaminated clothing and wash before reuse; P403+P233—Store in well-ventilated place, keep container tightly closed; P501—Dispose of contents/container per local regulations for halogenated heterocycles. In case of contact, rinse affected area with copious water; for eye contact flush ≥15 min and seek care if irritation persists. Always use latest SDS.