Phenethyl anthranilate - FCC, ≥98% , CAS No.133-18-6

CAS: 133-18-6 Cat. No.: P1068061 Formule: C₁₅H₁₅NO₂ Poids moléculaire: 241.280 Numéro CE: 205-098-0

GRADE & PURITY FCC, ≥98%

Storage

Room temperature

Specifications

Spécifications et pureté

FCC, ≥98%

Conditions de stockage de stockage

Room temperature

Grade

FCC

Pureté

≥98%

Noms et identifiants

Sourires canoniques

C1=CC=C(C=C1)CCOC(=O)C2=CC=CC=C2N

IUPAC Name

2-phenylethyl 2-aminobenzoate

InChIKey

PXWNBAGCFUDYBE-UHFFFAOYSA-N

INCHI

1S/C15H15NO2/c16-14-9-5-4-8-13(14)15(17)18-11-10-12-6-2-1-3-7-12/h1-9H,10-11,16H2

Poids moléculaire

241.280

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acid esters
• Alternative Parents: Aminobenzoic acids and derivatives Benzoyl derivatives Aniline and substituted anilines Vinylogous amides Carboxylic acid esters Amino acids and derivatives Monocarboxylic acids and derivatives Primary amines Organopnictogen compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminobenzoic acid or derivatives - Benzoate ester - Benzoyl - Aniline or substituted anilines - Vinylogous amide - Amino acid or derivatives - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Organopnictogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Poids moléculaire: 241.280 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 241.11 Da
• Monoisotopic Mass: 241.11 Da
• Topological Polar Surface Area: 52.300 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 261.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No assay/application protocols are provided for this item. It is a general research chemical (small molecule). For synthetic or analytical use, refer to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for practical guidance, and consult primary literature for detailed procedures using anthranilate esters.

Biological Roles

Item-specific biological/biochemical activity data are not provided for this product; it is supplied for research use only.

General context (literature):

• Anthranilate motif in metabolism: Anthranilic acid (2‑aminobenzoic acid) is a key intermediate in tryptophan biosynthesis and degradation (kynurenine pathway) in various organisms. While phenethyl anthranilate is an esterified, non-physiological derivative, it can serve as a stable, lipophilic anthranilate surrogate in model systems.
• Physicochemical effects: The aniline and benzoate chromophores confer UV absorption in the near‑UV, which can be useful for analytical detection (HPLC/UV) in biochemical assays.
• Enzymatic susceptibility: In biological matrices, general (non-specific) esterases may hydrolyze aromatic esters to release anthranilic acid and 2‑phenethyl alcohol; the rate depends on lipophilicity, steric hindrance, and binding in protein environments (literature principle). No item-specific kinetic data are provided.

Important note: No claims are made regarding physiological effects, safety, or efficacy. Any use should be confined to controlled laboratory research with appropriate approvals.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare aqueous buffer systems. It lacks acid–base pairs in the physiological pH range suitable for buffering (the aniline is weakly basic and the carboxyl group is esterified).

For experiments requiring buffered conditions with this compound present, select a compatible buffer (e.g., phosphate, HEPES) and ensure sufficient organic co‑solvent (EtOH, DMSO, or MeCN at minimal percentages) to maintain solubility, then validate that the buffer does not induce ester hydrolysis or amine protonation that interferes with your assay.

Green Alternatives

Phenethyl anthranilate is a functionalized aromatic building block, not a process solvent. Greener considerations apply to the choice of media and reagents used with it.

Greener solvent options (relative to common chlorinated/aromatic solvents):

• Replace dichloromethane/chloroform with:
  • Ethyl acetate (readily biodegradable, low toxicity) for extractions and many reactions where moderate polarity suffices.
  • 2‑MeTHF or CPME as ether alternatives to THF/Et2O, offering improved safety (lower peroxide formation than THF; higher boiling points) and better renewability (2‑MeTHF from hemicellulose).
  • Alcohols (EtOH, i‑PrOH) from bio-based sources for transesterification or as co‑solvents, with attention to ester interchange.
• Minimize toluene/xylene by using greener high‑boiling esters (e.g., propylene carbonate) when compatible, though basicity/viscosity may limit applicability.

Reagent and process choices:

• Catalysis: Employ catalytic acid (Amberlyst, tosylic acid) or organocatalysts for transesterification instead of stoichiometric mineral acids where feasible.
• Energy: Favor microwave or flow conditions to reduce reaction times and energy input for hydrolysis or substitution steps.
• Workup: Use brine-sparing phase separation and recover/recycle EtOAc or alcohols via simple distillation to lower solvent footprint.

Trade-offs to consider:

• Efficacy: Chlorinated solvents often dissolve aromatic amines exceptionally well; greener replacements may require higher temperatures or longer times.
• Selectivity: Protic green solvents (EtOH, water) may accelerate undesired ester hydrolysis/transesterification; validate on small scale first.

Pharmaceutical Uses

Item-specific pharmacopeial listings and excipient roles are not provided for this product. The grade is FCC, but this catalog item is designated for research use only and is not for use in humans or animals.

General R&D context (literature/industry practice):

• Intermediate building block: Anthranilate esters are common intermediates in the synthesis of benzoxazinones, quinazolinones, and other heterocycles that appear in drug discovery libraries. Phenethyl anthranilate provides an aniline handle and a modifiable ester for divergent synthesis.
• Formulation studies: Its aromatic chromophore allows straightforward HPLC/UV tracking in preformulation or stability model studies. Its hydrophobicity can be leveraged in lipid or polymer matrices for material‑science interfaces.
• Excipient relevance: No specific excipient function is attributed to phenethyl anthranilate. Where fragrance/flavor functionality is studied in formulation science, related anthranilates are sometimes used as model compounds; such uses remain strictly non-clinical in the research setting.

Regulatory note: Any application beyond bench research would require verification of applicable monographs/specifications and regulatory compliance; none are claimed here for this item.

Physical Properties

Item-specific specifications such as exact bp/mp, density, refractive index, water/peroxide/metal content are not specified for this item; refer to CoA/Spec Sheet.

Literature/estimated properties (for general reference only; not item specifications):

• Physical state/appearance: typically a low-melting solid or high-boiling liquid for analogous anthranilate esters; exact appearance for this SKU is not specified.
• Solubility: expected to be sparingly soluble in water and freely soluble in common organic solvents (EtOAc, DCM, toluene, alcohols) due to dual aryl rings and ester functionality (literature, qualitative).
• Lipophilicity: moderate-to-high logP anticipated for anilide/benzoate esters with phenethyl moieties (literature expectation).
• UV absorption: aniline/benzoate chromophores generally display strong π–π* absorption in the near‑UV; specific λmax for this item is not specified; consult literature UV spectra if needed for analytical work.
• Acidity/basicity: the aniline –NH2 is weakly basic (typical aniline pKaH ~4.6–5.5, literature), and the benzoate ester is non-ionizable under neutral conditions.

Practical notes for handling and characterization (general):

• NMR: diagnostic signals include an aniline NH2 (often broad, D2O‑exchangeable), benzoate carbonyl at ~165–170 ppm (13C), and benzylic CH2 groups at ~2.8–4.5 ppm (1H) depending on solvent and temperature (literature ranges).
• Chromatography: nonpolar to moderately polar on silica; elutes with hexanes/EtOAc mixtures; addition of a base modifier (e.g., 0.1% NEt3) can sharpen bands if amine–silica interactions are observed (general practice).

Quality and Grades

• Item-specific grade
  • FCC grade: Indicates compliance with Food Chemicals Codex monograph requirements for identity and purity parameters appropriate to that compendium. Note: This catalog item is provided for research use only (per Product Data); not for human or animal consumption or therapeutic use.

What FCC grade generally implies (context; not item-specific specifications):

• Identity tests, assay, and limits on typical impurities as defined by the FCC monograph (if available for this substance or for the relevant class). Low levels of residual solvents, heavy metals, and related substances are typically controlled.
• Consistency suitable for formulation/process development studies where compendial conformance is important.

Analytical considerations (general guidance):

• For QC in research settings, typical assessments include 1H/13C NMR for identity, HPLC/GC for purity/assay, and water content by Karl Fischer where applicable. UV–Vis may be used for screening given the aromatic chromophore.

Item-specific notes not provided:

• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• Detailed impurity limits (metals, peroxides, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

Research-use reactions leveraging the aniline and benzoate ester functional groups (literature/general guidance):

• Chemoselective transformations
  • Aniline functionalization: Acylation to give anthranilide derivatives (e.g., with acyl chlorides/anhydrides); sulfonylation (e.g., tosylation) to tune basicity and reactivity.
  • Electrophilic aromatic substitution on the aniline ring (nitration, halogenation) is ortho/para‑directed by –NH2, but the adjacent ester and existing ortho‑substituent bias substitution patterns; protective strategies may be required.
  • Diazotization of the aniline (NaNO2/HCl, 0–5 °C) followed by Sandmeyer-type substitutions to install halides, CN, or to effect Schiemann/Meerwein transformations (literature), enabling diversification of the benzoate ring.
• Ester bond chemistry
  • Hydrolysis to regenerate anthranilic acid and 2‑phenethyl alcohol under acidic (refluxing mineral acid in alcohol/water) or basic (aqueous NaOH/MeOH) conditions; neutral workup affords the acid.
  • Transesterification with other alcohols (Fischer or base-catalyzed) to access a library of anthranilate esters.
• Intramolecular/cyclization strategies (anthranilate motif)
  • Construction of benzoxazinones/quinazolinones often uses anthranilic derivatives via activation (e.g., carbamoylation or acylation followed by cyclization). While the carboxyl is esterified here, the aniline may be elaborated toward such heterocycles.
• Cross-coupling handles via prefunctionalization
  • Conversion of the aniline to aryl halides (through diazonium intermediates) or to boronates enables Suzuki/Negishi couplings on the benzoate ring (literature approach).

Practical tips

• Protecting groups: Boc or Cbz protection of the aniline can improve selectivity in ester manipulations. Deprotection conditions should be chosen to avoid ester cleavage.
• Base sensitivity: Prolonged strong basic conditions promote ester saponification; monitor by TLC/HPLC.
• Workup: Aromatic amines can emulsify; salt formation (e.g., HCl or p‑TsOH) during extraction can aid phase separation.

Reaction Conditions

General literature-type conditions for common transformations of anthranilate esters; these are guidance only and not specifications for this item:

• Acidic hydrolysis (ester → anthranilic acid + alcohol):
  • Conditions: 1–3 M HCl or H2SO4 in aqueous ethanol or dioxane/water, 60–100 °C; time 2–16 h. Monitor by TLC/HPLC.
  • Workup: Neutralize, extract the alcohol-rich phase, isolate the acid by basification/acIDification sequence as needed.
• Basic saponification:
  • Conditions: 1–2 equiv NaOH or KOH in MeOH/H2O (9:1 to 1:1), 20–60 °C; 1–6 h. Quench with acid to pH ~2 to precipitate the acid.
• Transesterification (Fischer):
  • Conditions: Excess ROH (e.g., MeOH, EtOH) with catalytic H2SO4 or p‑TsOH, reflux; Dean–Stark if water is present and higher alcohols are used.
• Aniline acylation (to anthranilide):
  • Conditions: Acyl chloride (1.1–1.5 equiv), base (Et3N or DIPEA, 2–3 equiv), DCM or THF, 0 °C to rt, 1–3 h. Protect ester as needed if acylation triggers transacylation.
• Diazotization and substitution:
  • Conditions: NaNO2 (1.1 equiv) in 2–6 M HCl, 0–5 °C, then add appropriate copper(I/II) salts or nucleophiles for Sandmeyer-type substitutions. Maintain low temperature to control side reactions.
• Protection (Boc):
  • Conditions: Boc2O (1.1–1.5 equiv), base (Na2CO3 or Et3N), acetonitrile/THF, 0 °C to rt, 1–4 h.

Analytical/monitoring:

• Use HPLC/UV (254–280 nm) for convenient monitoring due to aromatic chromophores. Confirm identity by 1H/13C NMR and HRMS as needed.

Note: Exact conditions vary with scale, solvent, and desired selectivity. Conduct small-scale trials and consult primary literature for closely related anthranilate substrates.

Safety and Handling

• Item-specific hazard information (from Product Data)
  • Signal word: Not specified for this item; refer to SDS.
  • H‑Statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

General safety considerations for aromatic amines/benzoate esters (literature/practice; not a substitute for the SDS):

• Likely hazards: May cause eye/skin irritation and respiratory tract irritation on dust/vapor exposure. Avoid ingestion and inhalation. Treat as a combustible organic compound.
• PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to minimize vapor/aerosol exposure.
• Incompatibilities: Strong oxidizers; strong acids/bases (can hydrolyze ester under forcing conditions); acylation reagents may react with the aniline –NH2.
• First aid (overview):
  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire safety: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen-containing fumes; firefighters should wear SCBA.
• Spill response: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains. Decontaminate area with suitable solvent/detergent per institutional procedures.

Always consult the product’s SDS for authoritative hazard classification, exposure limits, and emergency procedures.

Solvent Selection

This product is a hydrophobic aromatic ester bearing an aniline –NH2. It is not used as a solvent itself; solvent selection here refers to dissolving/processing it for reactions, purification, or analysis.

• Polarity/miscibility (literature, qualitative):
  • Sparingly soluble in water; freely soluble in moderately polar to nonpolar organic solvents (e.g., dichloromethane, chloroform, toluene, ethyl acetate, THF, acetone, alcohols).
• Recommended solvent choices by task (general lab guidance):
  • Reaction medium for acylation/alkylation of the aniline: DCM, THF, or acetonitrile with a non-nucleophilic base (e.g., DIPEA). Alcoholic media may compete in transesterification under strong conditions.
  • Hydrolysis/transesterification studies: Alcohols (MeOH, EtOH) with catalytic acid/base; toluene or xylene for higher‑temperature stability tests.
  • Purification by flash chromatography: Hexanes/EtOAc gradient; add 0.1–1% Et3N to suppress amine–silica tailing if observed.
  • Analytical HPLC: Reverse-phase (C18) with MeCN/H2O + 0.1% formic acid or MeOH/H2O; expect late retention due to hydrophobicity.
• Comparison to alternatives:
  • If protic conditions are undesirable (to avoid ester exchange), use aprotic solvents (DCM, toluene, acetonitrile). For greener profiles, consider EtOAc or 2-MeTHF where compatible (see Green Alternatives).

Drying: If water-sensitive transformations are planned (e.g., acyl chloride formation on the aniline), dry solvents (3 Å MS, solvent stills, or commercial anhydrous grades) are recommended.

Storage and Reconstitution

• Item-specific storage (from Product Data): Store at room temperature.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling recommendations for aromatic amine esters:

• Protect from prolonged exposure to light and air to minimize slow oxidation/discoloration sometimes observed with anilines. Keep container tightly closed.
• If solidification or crystallization occurs at lower temperatures, warm gently (e.g., to 30–40 °C) to liquefy before dispensing; avoid overheating.
• If preparing stock solutions: Use dry, oxygen-stable solvents (e.g., DMSO, MeCN, EtOAc). For biological assays, prepare concentrated stocks in DMSO or EtOH and dilute into buffered media immediately before use; verify that ester stability is adequate under assay conditions.
• Freeze–thaw: Not typically required. If solutions must be stored, aliquot and freeze at ≤−20 °C to limit hydrolysis; bring to room temperature before opening to avoid moisture ingress.

Disposal: Dispose of contents/container in accordance with local/regional regulations for organic chemical waste. Always consult the product’s SDS for detailed storage incompatibilities and stability information.

Structure and Identity

Phenethyl anthranilate is an ortho‑aminobenzoate ester derived from anthranilic acid and 2‑phenethyl alcohol; it combines an aniline functionality (–NH2) with an aromatic benzoate ester.

• Item-specific (from Product Data)
  • SKU: P1068061
  • Product name: Phenethyl anthranilate
  • CAS: 133-18-6
  • Grade/Purity: FCC
  • Storage conditions: Room temperature
  • InChIKey: 289865 (as provided; not in standard 27-character InChIKey format; consult CoA/SDS for authoritative identifier)
• Computed/literature identifiers and composition (for reference; not item-specific specifications)
  • Synonym (literature): 2-aminobenzoic acid 2-phenylethyl ester; phenethyl 2‑aminobenzoate
  • Molecular formula (literature, based on structure): C15H15NO2
  • Molecular weight (literature): ~241.29 g/mol
  • SMILES (literature): NC1=CC=CC=C1C(=O)OCCc2ccccc2
  • Structural features: one aniline ring bearing an ortho‑amino group relative to the benzoate carbonyl; benzoate ester linked to a phenethyl group (–CH2–CH2–Ph). No stereocenters.
• 2D description in words
  • A benzene ring carrying adjacent (ortho) –NH2 and –C(=O)O– substituents; the ester oxygen is connected to an ethylene spacer terminating in a second phenyl ring (phenethyl moiety).

Synthetic Utility

Phenethyl anthranilate provides two orthogonal reactive elements: a free aniline and an aryl ester.

• Aniline locus (nucleophilic, weak base):
  • Protection: Boc, Cbz, or acyl protection to control reactivity during ester transformations.
  • Electrophile capture: Acyl/sulfonyl/alkyl carbamate formation; urea/thiourea assembly via isocyanates/isothiocyanates, enabling subsequent intramolecular cyclizations to benzoxazinones/quinazolinones (literature routes).
  • Diazotization: Access to diazonium chemistry for ring functionalization (installation of halogen, CN, or coupling to generate biaryl frameworks after converting the aniline to a transient diazonium salt).
• Benzoate ester (leaving‑group manifold):
  • Hydrolysis to anthranilic acid for late-stage diversification; re‑esterification with alternative alcohols (e.g., chiral alcohols) to tune properties.
  • Aminolysis under forcing conditions to give anthranilamides (though direct amidation of aryl esters may require activation or catalysts).
• Phenethyl side chain:
  • Benzylic oxidation (literature) to aldehyde/acid derivatives post‑hydrolysis or via selective C–H oxidation strategies.

Strategic value in synthesis:

• Orthogonal reactivity permits sequential modifications (e.g., protect aniline → functionalize ring via EAS/diazotization → deprotect → manipulate ester), enabling convergent routes to nitrogen-containing heterocycles and substituted anthranilate libraries used in SAR campaigns.

Target Specificity

Not applicable. This product is a small-molecule chemical and not an affinity reagent or biologic. No antigen/epitope, species reactivity, clone, or isotype information applies.