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4,5-Dicyanoimidazole
1. Basic Information
Name: 4,5-Dicyanoimidazole
Alias: DCI, 1H-Imidazole-4,5-dicarbonitrile
CAS No.: 1122-28-7
Molecular Formula: C5H2N4
Molecular Weight: 118.09
Category: Nucleic acid synthesis activator, heterocyclic pharmaceutical intermediate, organic synthetic catalyst, electronic chemical reagent
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline powder
- Odor: Odorless
- Solubility: Soluble in DMF, DMSO, acetonitrile, hot methanol; slightly soluble in ethanol; almost insoluble in cold water, ethers and aliphatic hydrocarbons
- Melting Point: 168–172 °C (decomposes)
- Predicted Density: 1.38 g/cm3
- Hygroscopy: Moderately hygroscopic, easy to agglomerate under high humidity
- Aqueous property: Weakly acidic nitrogen heterocycle; stable in neutral cold water; cyano groups hydrolyze under strong acid/alkali heating
Chemical Properties
- Molecular structure: Imidazole ring disubstituted with cyano groups at C4 and C5 positions, contains active NH proton and two electrophilic cyano functional groups
- Catalytic activity: Powerful activator for phosphoramidite coupling in oligonucleotide DNA/RNA synthesis, accelerates phosphite triester formation
- Functional group reactivity: Cyano groups can be hydrolyzed to carboxylic acids, reduced to amines, or cyclized to construct fused nitrogen heterocycles; ring NH undergoes alkylation and acylation
- Photostability: Slightly light-sensitive; long-term UV exposure generates minor oxidative impurities
- Thermal stability: Stable below 150 °C; above melting point, thermal decomposition releases toxic cyanide fumes
- Compatibility: Compatible with anhydrous polar aprotic solvents used in nucleic acid synthesis; incompatible with strong oxidants, concentrated strong acid and alkaline solutions under heating
3. Main Application Fields
1. Oligonucleotide Synthesis Activator (Core Application)
Industry-standard coupling catalyst for solid-phase synthesis of DNA, RNA and modified nucleic acid raw materials
2. Pharmaceutical Heterocyclic Intermediate
Precursor for synthesizing imidazole-based anti-viral, anti-inflammatory and anti-tumor small-molecule APIs
3. Organic Synthetic Base Catalyst
Mild nitrogen heterocyclic catalyst for esterification, condensation and cyclization reactions
4. Electronic Chemical Additive
Component for semiconductor photoresist and high-purity electronic grade reagent formulations
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 1122-28-7 |
| Molecular Formula | C5H2N4 |
| Appearance | Uniform white crystalline powder without discoloration |
| HPLC Purity | Nucleic Acid Grade ≥99.5%, Synthetic Grade ≥99.0% |
| Melting Point | 168–172 °C (decomposed) |
| Water Content (KF) | ≤0.30% |
| Residue on Ignition | ≤0.05% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤5 ppm |
| Packaging | Light-proof nitrogen-filled aluminum foil vacuum bag; bulk 25kg PE lined fiber drum |
| Storage Condition | Hermetically sealed cool dry warehouse at 2–25 °C, full light shielding, isolated from humid air and oxidants |
| Transportation Requirement | Hygroscopic light-sensitive heterocyclic powder, moisture-proof sealed packaging, separated from corrosive hazardous goods |
| Shelf Life | 24 months under nitrogen vacuum sealed storage |
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