This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
External Descriptors
Not available
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
149.190 g/mol
XLogP3
1.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
149.084 Da
Monoisotopic Mass
149.084 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
119.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calculadoras de soluciones
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Reseñas
Reseñas de cliente
Application Protocols
No standardized bioassay or immunoassay protocols apply to this small-molecule building block. Typical laboratory uses are synthetic transformations and method development. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for literature-based guidance. If employing this compound in an enzymatic assay (e.g., amidase activity studies), develop assay-specific conditions (substrate concentration, cosolvent percentage, buffer composition) empirically and validate with appropriate controls.
Research Use Note: For research use only.
Biological Roles
This product is supplied for research use only and is not intended for biological administration.
General biochemical context (literature): Simple N-formyl amides can serve as model compounds for studying amide hydrogen bonding, conformational preferences (cis/trans), and enzymatic hydrolysis (amidase/formamidase activity). The presence of an amide N–H enables both donor and acceptor interactions relevant to protein–ligand binding studies in vitro.
Metabolic relevance: Unlike naturally occurring N-formylated peptides (e.g., fMet in bacteria), N-(1-phenylethyl)formamide has no established endogenous biological role. If used in enzymology, it may act as a substrate or inhibitor mimic in assays exploring amide cleavage, but such uses depend on assay design and are not inherent properties.
Physicochemical traits of interest (literature):
Secondary amide functionality offers a well-defined H-bond topology useful for calibrating computational models (QSAR/QSPR) of amide-containing ligands.
The benzylic stereocenter can be leveraged in chiral recognition experiments; racemic mixtures may be resolved by chiral chromatography for such studies.
Any biological assay use should be performed under appropriate institutional approvals, acknowledging that the compound has no certified biological activity or therapeutic designation.
Buffer Applications
Not typically applicable. N-(1-Phenylethyl)formamide is not a buffering agent and does not form defined buffer systems in aqueous media. If used in biochemical assays, it is typically dissolved in compatible organic cosolvents (e.g., DMSO, acetonitrile) and then diluted into an assay buffer selected for the biology under study (e.g., phosphate, HEPES). Choose the buffer based on your assay requirements rather than the properties of this amide.
Green Alternatives
Although N-(1-phenylethyl)formamide is a reagent/intermediate rather than a solvent, its common manipulations can be designed with greener choices.
Greener solvents (literature): Prefer ethyl acetate, 2-MeTHF, or ethanol over dichloromethane or DMF where feasible. For hydrolysis/deprotection, aqueous ethanol or aqueous acetone frequently suffice.
Benign formylation strategies (literature): If preparing this amide in-house, consider formylation using formic acid or dimethyl carbonate under catalytic conditions instead of chlorinating agents (e.g., avoid oxalyl chloride/COCl2). CO2-derived carbonylation routes with hydrosilanes or catalytic systems are emerging.
Energy efficiency: Many N-formyl deprotections proceed at reflux in aqueous alcohols; using microwave heating or flow reactors can reduce time/energy.
Waste minimization:
Employ catalytic rather than stoichiometric activating agents when exchanging the N-formyl to other acyl groups.
Choose solvents amenable to recovery (EtOAc, MeCN) and design crystallization-driven purifications to limit silica use.
DCM workups vs. EtOAc: EtOAc offers lower toxicity and better biodegradability with similar extraction performance for amides.
DMF vs. MeCN/2-MeTHF: MeCN and 2-MeTHF are more volatile and easier to remove; 2-MeTHF is bio-based and water-separable.
Adopt PMI/E-factor tracking in route design to quantify the impact of solvent and reagent substitutions.
Pharmaceutical Uses
No therapeutic claims are made for this product. It is offered strictly for research and laboratory use.
Formulation/excipient status: Not a common pharmacopeial excipient. There is no item-specific pharmacopeia designation provided.
Role in process chemistry (literature):
N-Formyl derivatives are frequently used as protected-amine intermediates in API synthesis. The formyl group is compact, increases crystallinity in some series, and can be removed under relatively mild conditions compared with more robust protecting groups (e.g., Boc or Cbz), which may require stronger acids or hydrogenolysis.
The 1-phenylethyl scaffold serves as a benzylic handle; after deprotection, 1-phenylethylamine can be engaged in amide coupling, urea/carbamate formation, or reductive amination cascades common in medicinal chemistry.
Analytical considerations: Secondary aromatic amides show strong UV absorption at low wavelengths, which can aid in HPLC/UPLC method development for in-process controls (literature). Retention can be tuned via reversed-phase gradients with acetonitrile or methanol.
Item-specific regulatory status, residual solvent limits, and impurity controls are not provided here; consult the CoA/Spec Sheet for batch documentation if considering use in process development.
Physical Properties
Item-specific physical constants are not provided in the Product Data.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Density, BP/MP, refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Solubility (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Literature expectations (non-specification, for planning only):
Secondary aromatic amides such as N-(1-phenylethyl)formamide are typically low-melting solids or high-boiling liquids with moderate polarity.
Expected solubility: good in polar aprotic solvents (e.g., DMF, DMSO, acetonitrile, ethyl acetate) and chlorinated/aromatic solvents; limited in water due to the hydrophobic phenyl group (literature).
Hydrogen-bonding: one HBD (N–H) and one HBA (C=O), enabling strong intermolecular association; this can elevate boiling point and reduce volatility compared with analogous tertiary amides (literature).
LogP: Aromatic secondary amides with a single phenyl ring commonly show modest logP (≈1–2.5, literature range), reflecting amphiphilicity.
Note: Use the product CoA for authoritative, batch-specific values. Avoid relying on literature estimates for process-critical specifications.
Quality and Grades
Catalog grade/purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance):
Where indicated, “purity” typically reflects GC/HPLC area percent or NMR assay. For synthetic building blocks like N-(1-phenylethyl)formamide, low levels of residual solvents, starting amine, and formylating reagent/byproducts are typically controlled.
If an “anhydrous” or “dry” designation is offered in other lots, it denotes Karl Fischer–controlled moisture and packaging to minimize hydrolysis risks; no such designation is provided here unless stated on CoA.
Stabilizers: This compound usually requires no stabilizer. If any stabilizer is used in a specific lot, it will be disclosed on the CoA and may influence downstream reactions (e.g., catalytic hydrogenations).
Verification & documentation:
Request CoA for assay method, residual solvent profile, and impurity limits.
For enantiomeric applications, confirm racemic vs. enantioenriched status and any chiral assay (e.g., chiral HPLC).
Use in analytical workflows:
HPLC/GC suitability depends on UV profile and volatility; secondary aromatic amides often show strong UV absorption near 200–230 nm (literature). If “HPLC grade” is applicable to any solvent used with this product, it refers to solvent, not the amide itself.
If a specific specification (water, metals, UV cutoff) is required, please refer to the batch CoA—item-specific values are not provided here.
Reaction and Applications
As a secondary aromatic amide bearing an N-formyl group, N-(1-phenylethyl)formamide is useful in synthesis both as a building block and as a protected-amine equivalent.
N-Formyl as a protecting group (literature): The N-formyl group masks the amine, suppressing basicity and nucleophilicity. It is removed under acidic (e.g., HCl, H2SO4 in aqueous alcohol), basic (NaOH, K2CO3 in aqueous ethanol), or reductive conditions (e.g., hydride or hydrogenation when appropriate). Hydrolysis rates depend on temperature and solvent composition.
Directed transformations (literature):
Electrophilic aromatic substitution on the phenyl ring is feasible but the benzylic amide attenuates ring activation relative to benzylamine.
Benzylic functionalization: The 1-phenylethyl center can be oxidized, halogenated, or engaged in radical chemistry; conditions must avoid amide cleavage.
Formyl transfer/derivatization: The formyl moiety can be transformed to other N-acyl groups via exchange under activating conditions (e.g., via imidates or CDI-type reagents).
Coupling/derivative formation (literature): The amide N–H is a modestly acidic site; N-alkylation or sulfonylation is possible with strong base and suitable electrophiles. Careful control avoids over-alkylation or racemization at the benzylic center.
Applications:
Intermediate en route to 1-phenylethylamine via deprotection.
Model substrate for studying amidase or formamidase activity and hydrogen-bonding in amides.
Precursor to ureas, carbamates, or imidates through standard acyl/activation chemistry.
Practical tip: For hydrolytic deprotection, azeotropic removal of low-boiling solvents after reaction helps drive complete formyl removal and facilitates workup.
Reaction Conditions
The following are general, literature-informed conditions for common transformations of N-formyl secondary amides like N-(1-phenylethyl)formamide. They are guidance only and not item-specific specifications.
N-Formyl deprotection (hydrolysis):
Basic: K2CO3 (2–3 equiv) or NaOH (1–2 equiv) in EtOH/H2O (3:1 to 9:1), 50–80 °C, 1–6 h; workup by neutralization and extraction.
Acidic: 3–6 M HCl or H2SO4 in aqueous ethanol, 50–80 °C, 1–4 h; neutralize and isolate the amine (often as its salt).
Reductive methods:
BH3·THF or borane–dimethylsulfide can reduce amides; for N-formyl, milder conditions (e.g., NaBH4/MeOH with additives) are sometimes sufficient, but selectivity must be verified (literature). Catalytic hydrogenation is generally reserved for substrates bearing reducible groups.
N-Acyl exchange/activation:
CDI (1.2–1.5 equiv) in dry THF/DMF, 0–25 °C, 0.5–2 h to form an imidazolide, followed by nucleophile addition (amines, alcohols) at 0–25 °C.
N-Alkylation to tertiary amide:
NaH or KHMDS (1.1–1.5 equiv) in THF or DMF, 0–25 °C, then alkyl halide (1.1–1.5 equiv). Monitor for potential racemization at the benzylic stereocenter (literature).
Analytical monitoring:
TLC in 10–30% EtOAc/hexanes or DCM/MeOH systems; HPLC with C18 gradients (MeCN/H2O + 0.1% acid) is effective due to UV activity (literature).
Optimize equivalents and temperature for your substrate and scale; perform small-scale trials to confirm selectivity before scale-up.
Safety and Handling
GHS classification (item-specific): Not specified for this item; refer to the SDS.
Signal word / H-statements / pictograms (item-specific): Not specified for this item; refer to the SDS.
General hazards (literature): Aromatic amides may cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of vapors/aerosols and contact with skin/eyes.
PPE recommendations (good laboratory practice):
Wear lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when handling bulk quantities or heating.
Handling notes:
Prevent contact with strong oxidizers and strong acids/bases that can hydrolyze or degrade the amide (literature).
Avoid prolonged heating; secondary amides can undergo dehydration or formyl transfer under harsh conditions (literature).
If material is chiral/enantiopure, minimize racemization by avoiding strong base at elevated temperature.
First-aid overview (consult SDS for details):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Ingestion: Rinse mouth; obtain medical attention.
Fire safety: Combustible organic compound; use CO2, dry chemical, or foam extinguishers. Thermal decomposition may produce NOx/CO/CO2 (literature).
Always consult and follow the product SDS for authoritative hazard classifications and response measures.
Solvent Selection
N-(1-Phenylethyl)formamide is a moderately polar, hydrogen-bonding organic compound. Solvent choice is primarily driven by reaction type (protection/deprotection, coupling, or derivatization) and desired solubility.
Polarity class (literature): Polar protic donor (due to N–H) and polar aprotic acceptor (C=O); overall moderate polarity.
Limited: Water (hydrophobic phenyl ring reduces aqueous solubility).
Selection guidance:
For N-formyl deprotection (acidic or basic hydrolysis): aqueous alcohols or aqueous acetonitrile can balance solubility and phase behavior.
For coupling/activation at the formyl carbonyl or N-derivatization: dry polar aprotic media (DCM, THF, MeCN) facilitate control and minimize competing hydrolysis.
For catalytic hydrogenation (if used in sequences where benzylic manipulations occur): alcohols or ethyl acetate can be convenient; verify compatibility with catalyst.
Small comparison (literature):
DCM vs. EtOAc: DCM offers higher solubility and ease of removal; EtOAc is greener and often adequate for amide substrates.
DMF/DMSO vs. MeCN: DMF/DMSO maximize solubility for polar substrates but are harder to remove; MeCN offers volatility with sufficient solvating power for many amides.
Always verify solvent compatibility with reagents and catalysts used in your specific protocol.
Storage and Reconstitution
Storage (item-specific): Store at room temperature (Product Data). Protect from excessive heat and direct sunlight. Keep container tightly closed to avoid moisture ingress and contamination.
Shipping (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Stability (literature): Secondary aromatic amides are generally stable under ambient conditions. Avoid prolonged exposure to strong acids/bases or high temperatures that can promote hydrolysis or degradation. If chiral purity is critical, minimize storage at elevated temperature to avoid any potential racemization at the benzylic center under basic contamination.
Reconstitution/Handling:
If supplied as a solid or viscous oil, warm gently to ambient and dissolve in a suitable solvent (e.g., DCM, EtOAc, MeCN, DMF, or DMSO; literature guidance) to prepare stock solutions.
For aqueous work, use organic cosolvent to aid solubilization, then dilute into buffer as required. Filter through 0.2 µm if particle-free solutions are needed.
Store prepared solutions refrigerated and protected from light when practical; prepare fresh solutions for moisture- or base-sensitive reactions.
Always consult the product label and CoA/SDS for any lot-specific instructions.
Structure and Identity
N-(1-Phenylethyl)formamide is a secondary aromatic amide formed by N-formylation of 1-phenylethylamine. The molecule comprises a benzene ring linked via a chiral benzylic methine (–CH(CH3)–) to the amide nitrogen, which bears a single hydrogen and is attached to a formyl carbonyl (–C(=O)H).
Product identifiers (item-specific):
CAS: 6948-01-2 (Product Data)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Composition (item-specific):
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural information (for reference):
Typical formula for N-(1-phenylethyl)formamide (literature): C9H11NO.
Calculated average molecular weight (literature): ~149.19 g/mol.
Functional groups: secondary amide (hydrogen-bond donor/acceptor), benzylic stereocenter adjacent to an aromatic ring.
2D description: A benzene ring (C6) bonded to a benzylic carbon bearing a methyl substituent and attached to the amide nitrogen; the nitrogen connects to a formyl carbonyl (–CHO). The benzylic carbon is prochiral unless enantiomerically enriched material is specified.
Stereochemistry: Unless otherwise stated on the label/CoA, commercial material is typically racemic (literature). If a specific enantiomer is required, verify with the catalog title and CoA.
Synthetic Utility
N-(1-Phenylethyl)formamide is both a masked 1-phenylethylamine and a versatile amide substrate.
Protecting-group chemistry (literature): The N-formyl group suppresses basicity and nucleophilicity of the amine. It can be selectively removed post-transformation to unveil 1-phenylethylamine. Deprotection options include acidic or basic hydrolysis and certain reductive conditions. Compared to Boc/CBz, formyl is more atom-economical and avoids gaseous byproducts or hydrogenolysis.
Functional group interconversions:
N→N acyl exchange to access other amides under activation (e.g., CDI, acid chlorides with base).
Conversion to ureas/carbamates via activation followed by reaction with isocyanates/carbonates (or their surrogates).
N-alkylation at the amide nitrogen under strong base to generate tertiary amides (requires careful conditions to prevent racemization at the adjacent benzylic center).
Benzylic chemistry: The 1-phenylethyl motif enables:
Stereochemical studies; enantiomerically enriched variants can probe asymmetric induction in neighboring-group reactions.
Oxidation or halogenation at the benzylic position (conditions must avoid amide cleavage).
Downstream value: After deprotection, 1-phenylethylamine participates readily in amide couplings (EDC/HATU/DIC), sulfonamide formation, reductive aminations, and as a chiral resolving agent in salt formation (literature).
This substrate thus serves as a compact, manipulable node in routes where temporary amine masking and benzylic chemistry are advantageous.
Target Specificity
Not applicable. This product is a small-molecule amide building block, not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
Utilizamos cookies para garantizar el correcto funcionamiento del sitio web y, cuando esté permitido, para mejorar su experiencia. Puede gestionar sus preferencias en cualquier momento en Configuración. Más información en nuestra Política de Cookies.
¿Quieres que te enviemos un mensaje cuando tengamos descuentos disponibles?
Recordármelo más tarde
¡Gracias! Por favor, revisa tu bandeja de entrada de correo electrónico para confirmar.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
