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N-(3-Chloro-ortho-tolyl)anthranilic acid
1. Basic Information
Name: N-(3-Chloro-ortho-tolyl)anthranilic acid
Alias: 2-[(3-Chloro-2-methylphenyl)amino]benzoic acid
CAS No.: 13710-19-5
Molecular Formula: C14H12ClNO2
Molecular Weight: 261.70
Category: Chlorinated diphenylamine carboxylic acid, pharmaceutical NSAID intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: Off-white to pale beige crystalline powder
- Odor: Faint aromatic odor
- Solubility: Soluble in ethanol, methanol, acetone, DMSO, dilute alkaline aqueous solution; slightly soluble in hot water; insoluble in cold water and aliphatic hydrocarbons
- Melting Range: 208–213 °C (partial decomposition)
- Hygroscopy: Non-hygroscopic under normal storage conditions
- Aqueous Property: Weakly acidic organic acid, dissolves in alkali to form soluble carboxylate salt
Chemical Properties
- Molecular Structure: Benzoic acid core with secondary amine linkage to 3-chloro-2-methylphenyl group; contains aryl chlorine, carboxyl and secondary aromatic amine functional groups
- Carboxyl reactivity: Esterification, amidation, salt formation, acyl chloride preparation for drug side chain derivation
- Secondary Aromatic Amine: Capable of acylation, diazotization, cross-coupling reactions; prone to slow oxidation in air
- Aryl Chloride: Stable under neutral/mild acidic conditions; undergoes nucleophilic substitution under high temperature alkaline conditions
- Thermal Stability: Stable below 190 °C; long-time heating above melting point leads to decarboxylation and darkening
- Photostability: Moderately UV-sensitive; long-term illumination generates faint yellow oxidation impurities
- Compatibility: Compatible with polar organic solvents; incompatible with strong oxidants, concentrated strong alkali
3. Main Application Fields
1. Non-Steroidal Anti-Inflammatory Drug Intermediate (Core Application)
Key precursor for meclofenamic acid, a fenamate-class NSAID used for analgesia, anti-inflammatory and antipyretic treatment; undergoes salt formation or ester modification to prepare finished drugs
2. Organic Dye Intermediate
Raw material for azo acid dyes and metal complex dyes with diphenylamine parent skeleton
3. HPLC Reference Standard
Chromatographic standard for purity detection of fenamic acid drug intermediates in pharmaceutical production QC
4. Metal Chelating Reagent Precursor
Synthesis of aromatic carboxylic acid chelators for trace metal analysis
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 13710-19-5 |
| Molecular Formula | C14H12ClNO2 |
| Appearance | Uniform pale beige crystalline powder without dark oxidation impurities |
| HPLC Purity | Pharma Grade ≥99.0% |
| Water Content (KF) | ≤0.20% |
| Melting Range | 208–213 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber vacuum aluminum foil bags / PE-lined fiber drums |
| Storage Condition | Hermetically sealed cool dry warehouse below 25 °C; shield from light, separate from strong oxidants |
| Transportation Requirement | Light-sensitive chlorinated aromatic acid solid, light-proof sealed packaging |
| Shelf Life | 24 months under nitrogen-filled vacuum sealed storage |
Safety Warning
Mild irritant chlorinated aromatic carboxylic acid powder. Dust irritates eyes, respiratory tract and skin; prolonged skin contact may cause dryness and mild allergic redness for sensitive populations. All operations shall be performed in ventilated fume hoods with dust respirators and chemical-resistant gloves. Avoid mixing with strong oxidants to prevent oxidative degradation. Waste liquid recovered by solvent distillation and neutralized before discharge; solid waste classified as halogen-containing organic hazardous waste and disposed by licensed professional hazardous waste treatment institutions.
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