1. Product Overview
N-(4-Chlorobenzoyl)-2-phenylglycine (CAS 69605-02-3) is an N-acyl amino acid derivative featuring a 4-chlorobenzoyl group linked to the nitrogen of 2-phenylglycine (a non-proteinogenic α-amino acid with a phenyl substituent at the α-carbon). The molecule combines the structural features of a protected amino acid (carboxylic acid + secondary amide) with a chlorinated aromatic system, making it a versatile intermediate for peptide coupling, amide bond formation, and the construction of bioactive molecules containing the phenylglycine scaffold. It is widely used in pharmaceutical synthesis and medicinal chemistry as a building block for drug candidates targeting neurological disorders, antimicrobial agents, and enzyme inhibitors.
2. Key Features and Benefits
• Dual Functional Groups: The free carboxylic acid (–COOH) and the secondary amide (–NH–C=O) provide two distinct sites for further chemical modification—amide coupling at the carboxyl and N-alkylation/acylation at the amide nitrogen under forcing conditions.
• Chiral Center: The α-carbon bearing the phenyl group is a stereogenic center (typically supplied as racemate or single enantiomer depending on batch), enabling asymmetric synthesis and SAR studies in drug discovery.
• Electron-Deficient Aromatic Ring: The 4-chlorobenzoyl moiety introduces an electron-withdrawing halogen substituent, influencing the compound's reactivity in electrophilic aromatic substitution and providing a handle for cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig after activation).
• High Purity: Supplied at ≥98% (HPLC), ensuring minimal interference from deacylated byproducts or residual solvents in multi-step synthesis.
• Stable Crystalline Form: White to off-white solid with good shelf stability under recommended storage conditions.
3. Major Applications
• Peptide & Peptidomimetic Synthesis: Used as a non-natural amino acid building block in solid-phase peptide synthesis (SPPS) or solution-phase peptide coupling to introduce phenylglycine residues into bioactive peptides.
• Pharmaceutical Intermediate: Key scaffold for synthesizing drugs targeting GABA transporters, NMDA receptors, and other neurological targets where phenylglycine derivatives are known to play a role.
• Antibacterial Agent Precursors: Phenylglycine derivatives are structural components of several β-lactam antibiotics (e.g., ampicillin analogs); this compound serves as a precursor for semi-synthetic antibiotic research.
• Enzyme Inhibitor Development: Employed in the design of protease inhibitors, aminopeptidase modulators, and other enzyme-targeted small molecules.
• Asymmetric Catalysis: The chiral phenylglycine backbone can be incorporated into ligand frameworks for asymmetric hydrogenation, aldol reactions, or organocatalysis.
4. Technical Specifications
Item Description
Product Name N-(4-Chlorobenzoyl)-2-phenylglycine
Synonyms N-(4-Chlorobenzoyl)phenylglycine; 2-(Benzoylamino)-2-phenylacetic acid, 4-chloro derivative; N-(p-Chlorobenzoyl)-2-phenylglycine
CAS Number 69605-02-3
Molecular Formula C₁₅H₁₂ClNO₃
Molecular Weight 289.71 g/mol
MDL Number —
Assay (Purity) ≥95% / ≥98% (HPLC)
Appearance White to off-white crystalline solid or powder
Melting Point ~180–210 °C (decomposes, typical for N-acyl amino acids)
Boiling Point ~523.5 °C (Predicted)
Density ~1.35 g/cm³ (Predicted)
pKa (Predicted) ~3.5 ± 0.3 (Carboxylic acid); ~11.5 ± 0.3 (Amide N-H)
Calculated LogP ~2.8
Polar Surface Area (PSA) ~66.4 Ų
Solubility Soluble: DMSO (>50 mg/mL), DMF, Methanol (slightly), Ethanol (slightly), Acetone.
Slightly Soluble:Water (free acid, pH-dependent; more soluble as sodium/potassium salt).
Insoluble:Hexane, Ether.
Spectral Data (Predicted) ¹H NMR (DMSO‑d₆, 400 MHz): δ 5.20 (d, J≈8.0 Hz, 1H, CHPh), 7.10–7.55 (m, 9H, ArH), 8.55 (d, J≈8.0 Hz, 1H, NH), 12.8 (br s, 1H, COOH).
¹³C NMR (DMSO‑d₆):δ 55.5 (CHPh), 126–138 (aromatic Cs), 165.5 (CONH), 172.0 (COOH).
SMILES ClC1=CC=C(C=C1)C(=O)NC(C2=CC=CC=C2)C(=O)O
InChI Key BZUERJQYKMOJCD-UHFFFAOYSA-N
Storage (Powder) 2–8 °C, sealed, protected from light and moisture; stable ≥18–24 months
HS Code 2924.29.90 / 2933.99.90
5. Storage and Handling
• Storage: Store in a tightly sealed container at 2–8 °C, protected from light and moisture. For long-term storage (>12 months), keep in a desiccator. The compound is stable as a solid under these conditions but may slowly hydrolyze under prolonged exposure to high humidity or strong acid/base.
• Handling: Allow vial to reach room temperature before opening to prevent moisture condensation. Dissolve in anhydrous DMSO, DMF, or MeOH as required. For aqueous work, the carboxylic acid can be neutralized with dilute NaOH or KHCO₃ to form a water-soluble salt.
• Amide Bond Stability: The N-benzoyl amide is generally stable to mild acid/base but can be hydrolyzed under strongly acidic (6 M HCl, reflux) or strongly basic (2 M NaOH, heat) conditions—useful for deprotection if needed.
• Solution Stability: Prepare fresh for critical couplings; DMSO stocks may degrade over time. Avoid heating above 60 °C in protic solvents.
6. Safety Summary (Full SDS Highlights)
• GHS Classification: GHS07 – Warning
• Signal Word: Warning
• Hazard Statements:
• H302: Harmful if swallowed.
• H315: Causes skin irritation.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.
• Precautionary Statements:
• P261: Avoid breathing dust/mist/vapors. Use only in a well-ventilated area or fume hood.
• P264: Wash hands, forearms, and face thoroughly after handling.
• P270: Do not eat, drink, or smoke in areas where this material is used.
• P271: Use only outdoors or in a well-ventilated area.
• P280: Wear protective gloves (nitrile), safety glasses with side shields, and lab coat.
• P301+P312: IF SWALLOWED: Call a POISON CENTER or physician if you feel unwell.
• P302+P352: IF ON SKIN: Wash with plenty of soap and water.
• P304+P340: IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
• P330: Rinse mouth if swallowed.
• P337+P313: If eye irritation persists: Get medical advice/attention.
• P403+P233: Store in a well-ventilated place. Keep container tightly closed.
• P501: Dispose of contents/container in accordance with local, regional, and national regulations.
• First Aid Measures:
• Inhalation: Remove to fresh air. If breathing difficult, administer oxygen and seek medical attention.
• Skin Contact: Immediately wash with plenty of soap and water. Remove contaminated clothing. Seek medical advice if irritation or rash develops.
• Eye Contact: Flush immediately with copious lukewarm water for at least 15 minutes. Remove contact lenses if possible. Seek medical attention.
• Ingestion: Rinse mouth. Do NOT induce vomiting. Give water to drink if conscious. Seek medical advice.
• Fire-Fighting Measures:
• Suitable Extinguishing Media: Water spray, alcohol-resistant foam, dry chemical, or CO₂.
• Special Hazards: Combustion may produce irritating/acrid smoke (HCl, CO, NOₓ).
• Protective Equipment: Wear self-contained breathing apparatus (SCBA) and full protective clothing.
• Spill Response:
• Avoid dust generation. Sweep up and place in a suitable closed container for disposal. Do not allow entry to drains or waterways. Ventilate area after cleanup.
• Handling & Storage:
• Handle in fume hood. Keep container closed when not in use. Store cool (2–8 °C), dry, and away from strong oxidizers and strong acids/bases.
• Intended Use: For laboratory research and development ONLY. Not for human or veterinary therapeutic, diagnostic, or food use.
