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L-4-Iodophenylalanine
1. Basic Information
Name: L-4-Iodophenylalanine
Alias: 4-Iodo-L-phenylalanine, p-Iodo-L-phenylalanine
CAS No.: 24250-85-9
Molecular Formula: C9H10INO2
Molecular Weight: 291.09
Category: Iodinated chiral aromatic amino acid, peptide & biochemistry research intermediate
2. Physical and Chemical Properties
Physical Properties
- Appearance: White to off-white crystalline powder
- Odor: Odorless
- Solubility: Slightly soluble in water; soluble in dilute acid, dilute alkali, DMSO; hardly soluble in methanol, ethanol, acetone, ethyl acetate
- Melting Range: 262–266 °C (decomposes upon melting)
- Hygroscopy: Slightly hygroscopic under high humidity
- Aqueous Property: Amphoteric compound, isoelectric point near pH 5.5, low aqueous solubility
Chemical Properties
- Molecular Structure: L-phenylalanine skeleton with iodine substitution at para-position of benzene ring, fixed L chiral configuration at α-carbon
- Amino & Carboxyl Amphoterism: Can form salts with acid/base; capable of Boc/Fmoc protection, peptide condensation, esterification for peptide synthesis
- Aryl Iodide Reactivity: Para C–I bond participates in Suzuki, Heck, Sonogashira cross-coupling to introduce fluorescent groups, isotopic markers
- Thermal Stability: Stable below 220 °C; high temperature decomposes, releases iodine vapor
- Photostability: Highly sensitive to UV light; long-term illumination causes deiodination and yellow discoloration
- Compatibility: Compatible with peptide synthesis anhydrous solvents; incompatible with strong reducing agents, concentrated strong alkali, heavy metal salts
3. Main Application Fields
1. Peptide & Protein Labeling Research (Core Application)
Non-natural amino acid for site-specific protein modification; iodine atom serves as heavy atom marker for X-ray crystallography protein structure analysis
2. Chiral Pharmaceutical Intermediate
Building block for iodinated polypeptide drugs, enzyme inhibitors, targeted small molecule therapeutics
3. Biochemical NMR/Mass Spec Standard
Isotope precursor and chromatographic reference standard for amino acid derivative detection
4. Organic Cross-Coupling Substrate
Aryl iodide monomer for synthesizing fluorescent biological probes
4. Quality Specification Table
| Test Item | Standard Specification |
| CAS Number | 24250-85-9 |
| Molecular Formula | C9H10INO2 |
| Appearance | Uniform white crystalline powder without brown deiodination impurities |
| HPLC Purity | Biochemical Grade ≥99.0%; Reference Standard ≥99.5% |
| Optical Rotation [α]D20 | -16.0 ~ -19.0 (c=2, 1M HCl) |
| Water Content (KF) | ≤0.30% |
| Residue on Ignition | ≤0.10% |
| Single Unknown Impurity | ≤0.10% |
| Heavy Metals (Pb) | ≤10 ppm |
| Packaging | Nitrogen-purged amber glass vials / vacuum aluminum foil bags |
| Storage Condition | Hermetically sealed cool dark warehouse below 25 °C; strictly shielded from light, isolate from reducing substances |
| Transportation Requirement | Light-sensitive iodinated amino acid solid, moisture-proof light-proof sealed packaging |
| Shelf Life | 24 months under nitrogen-filled vacuum sealed storage |
Safety Warning
Mild irritant iodinated amino acid powder. Dust irritates eyes, respiratory tract and skin; long-term contact may cause mild skin allergy. All operations must be performed in ventilated fume hoods with dust respirators and chemical-resistant gloves. Avoid contact with strong reducing agents to prevent toxic iodine release. Waste liquid neutralized before solvent recovery; solid waste classified as organic hazardous waste and handled by licensed professional disposal institutions.
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