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4-Chloromandelic Acid
1. Basic Information
Name: 4-Chloromandelic Acid
Alias: 2-(4-Chlorophenyl)-2-hydroxyacetic acid
CAS No.: 492-86-4
Molecular Formula: C8H7ClO3
Molecular Weight: 186.59
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline powder
- Odor: Faint mild aromatic odor
- Solubility: Soluble in CH3OH, C2H5OH, acetone, ethyl acetate; slightly soluble in hot H2O; insoluble in aliphatic hydrocarbons
- Melting Point: 118–122 °C
- Hygroscopicity: Slightly hygroscopic under high humidity
- Aqueous Characteristic: Weakly acidic aqueous solution with phenolic hydroxyl and carboxylic acid groups
Chemical Properties
- Molecular Structure: Benzene ring substituted with chlorine at para-position, attached to a mandelic acid skeleton containing hydroxyl and carboxyl groups
- Acid-base Reaction: Reacts with alkalis and carbonates to form corresponding carboxylate salts
- Esterification: Carboxyl group undergoes esterification with alcohols under acid catalysis
- Thermal Stability: Stable below 80 °C; dehydration and slight decomposition occur at temperatures above melting point
- Photostability: Sensitive to ultraviolet light, long-term illumination causes yellowing
- Compatibility: Compatible with common polar organic solvents; incompatible with strong oxidants and concentrated alkaline solutions
3. Main Application Fields
1. Chiral Pharmaceutical Synthetic Intermediate (Core Application)
Key raw material for synthesizing anti-allergy, anti-inflammatory and cardiovascular chiral pharmaceutical APIs, widely used for asymmetric resolution and chiral skeleton construction
2. Fine Organic Synthesis Building Block
Precursor for halogenated aromatic ester, ketone and heterocyclic fine chemicals
3. HPLC Reference Standard
Reference substance for detection of chlorinated mandelic acid intermediates in pharmaceutical production
4. Quality Specification Table
| Test Item | Standard Index |
| CAS Number | 492-86-4 |
| Molecular Formula | C8H7ClO3 |
| Appearance | White crystalline powder |
| HPLC Purity | Pharma Intermediate Grade ≥99.0% |
| Water Content (KF) | ≤0.30% |
| Melting Range | 118–122 °C |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb1) | ≤10 ppm |
| Packaging | Nitrogen-purged amber aluminum foil vacuum bag / 25kg PE-lined fiber drum |
| Storage Condition | Hermetically sealed in cool dark warehouse below 25 °C; isolate from light, oxidants and alkaline chemicals |
| Transportation Requirement | Light-sensitive halogenated aromatic acid solid, light-proof fully sealed packaging |
| Shelf Life | 24 months under nitrogen-sealed vacuum packaging |
Safety Warning
Irritant halogenated aromatic carboxylic acid solid. Dust severely irritates eyes, respiratory tract and skin; long-term skin contact may cause redness and allergic inflammation. Operate in ventilated fume hood with dust mask, acid-resistant gloves and full-face sealed goggles. Keep airtight storage to avoid photooxidation discoloration. Waste liquid requires neutralization and solvent recovery treatment; solid waste belongs to organic hazardous waste and must be disposed by professional hazardous waste institutions.
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