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[(2-Chlorophenyl)methylene]malononitrile
1. Basic Information
Name: [(2-Chlorophenyl)methylene]malononitrile
Alias: 2-Chlorobenzylidene malononitrile, CS tear gas
CAS No.: 2698-41-1
Molecular Formula: C10H5ClN2
Molecular Weight: 188.61
Category: Chlorinated aromatic α,β-unsaturated dicyano compound, riot control agent & fine chemical intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Pale yellow crystalline solid
- Odor: Powerful irritating lacrimatory odor, stimulates eyes and respiratory tract intensely
- Solubility: Soluble in acetone, chloroform, toluene, dichloromethane; slightly soluble in hot alcohol; insoluble in cold water and aliphatic alkanes
- Melting Range: 92–96 °C
- Hygroscopy: Non-hygroscopic under normal ambient humidity
- Aqueous Property: Neutral lipophilic conjugated nitrile compound, barely soluble in water
Chemical Properties
- Molecular Structure: Ortho-chlorobenzene conjugated with malononitrile via carbon-carbon double bond, two cyano groups on terminal carbon
- Conjugated Double Bond Reactivity: The electrophilic C=C bond undergoes Michael addition with amines, alcohols, thiols for organic derivatization
- Cyano Group Characteristics: Two cyano groups can be hydrolyzed to amides/carboxylic acids or cyclized to construct nitrogen heterocycles
- Thermal Stability: Stable below 80 °C; above melting point easy to volatilize to form irritating vapor; high temperature decomposition releases toxic cyanide fumes
- Photostability: Sensitive to UV light; long-term illumination causes discoloration and partial decomposition
- Compatibility: Compatible with aprotic organic solvents; incompatible with strong alkalis, strong oxidants, ammonia and primary amines
3. Main Application Fields
1. Riot Control & Self-Defense Agent (Core Application)
Primary component of tear gas, riot control sprays; vapor induces intense lacrimation, nasal irritation and skin stinging to restrict target mobility
2. Organic Synthetic Intermediate
Building block for synthesizing dyes, fluorescent materials, pharmaceutical heterocyclic derivatives and agrochemical intermediates via Michael addition
3. HPLC Reference Standard
Reference substance for detection of benzylidene malononitrile derivatives in chemical production
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 2698-41-1 |
| Molecular Formula | C10H5ClN2 |
| Appearance | Uniform pale yellow crystalline powder without dark impurities |
| HPLC Purity | Synthetic Grade ≥99.0% |
| Water Content (KF) | ≤0.20% |
| Melting Range | 92–96 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Fully sealed nitrogen-filled amber aluminum foil bags / PE lined sealed metal drums |
| Storage Condition | Hermetically sealed cool dark warehouse below 25 °C; strictly isolated from air, alkaline substances, oxidants and food materials |
| Transportation Requirement | Highly irritating toxic solid, airtight sealed packaging, separated from food, daily chemicals and acidic cargo |
| Shelf Life | 24 months under nitrogen-filled vacuum sealed storage |
Safety Warning
Highly irritating toxic crystalline solid, lacrimatory hazard. Dust and volatile vapor cause severe eye pain, tearing, cough, dyspnea and skin burning; high concentration inhalation may trigger respiratory injury. All operations must be performed in fully enclosed ventilated fume hoods with full-face gas respirator, acid-resistant gloves and protective chemical suit. Strictly avoid heating to prevent toxic vapor leakage. Waste liquid needs anhydrous solvent recovery and detoxification treatment; solid waste belongs to highly toxic hazardous waste and must be disposed by licensed professional hazardous waste treatment facilities with special poison handling procedures.
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