N-((S)-1-phenylethyl)acrylamide - ≥98% , CAS No.19035-71-3

CAS: 19035-71-3 Cat. No.: N997563 Formula: C₁₁H₁₃NO Peso molecolare: 175.230

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

C[C@@H](C1=CC=CC=C1)NC(=O)C=C

IUPAC Name

N-[(1S)-1-phenylethyl]prop-2-enamide

InChIKey

RBVOJZBQNQTPRA-VIFPVBQESA-N

INCHI

1S/C11H13NO/c1-3-11(13)12-9(2)10-7-5-4-6-8-10/h3-9H,1H2,2H3,(H,12,13)/t9-/m0/s1

Peso molecolare

175.230

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Acrylic acids and derivatives Secondary carboxylic acid amides Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Monocyclic benzene moiety - Acrylic acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aromatic homomonocyclic compound
• Descrizione: 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

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

Proprietà chimiche e fisiche

• Peso molecolare: 175.230 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 175.1 Da
• Monoisotopic Mass: 175.1 Da
• Topological Polar Surface Area: 29.100 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 183.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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 standardized bioassay or immunoassay protocols apply to this small-molecule acrylamide. For synthetic applications, consider the Reaction Conditions and Synthetic Utility tabs for general procedural guidance, and consult primary literature for specific catalysts, stoichiometries, and workups matching your transformation.

Biological Roles

This compound is a synthetic, chiral acrylamide designed for chemical synthesis and materials applications. It does not have established endogenous biological roles.

• General chemical biology considerations (literature/generic):

  • As an α,β-unsaturated amide (Michael acceptor), it can react covalently with thiols and amines in biomolecules under suitable conditions. Such reactivity is exploited in bioconjugation chemistry but also underlies potential nonspecific reactivity; handle accordingly.
  • The N-(1-phenylethyl) group increases hydrophobicity, which can influence membrane association in model systems or polymer–biomolecule interactions when incorporated into materials.

• No clinical or therapeutic claims are made. For research use only (as per Product Data).

Buffer Applications

This is not a buffering reagent. It lacks acid/base pairs with suitable aqueous pKa values for practical buffer preparation. If aqueous handling is required (e.g., for extractions or bioconjugation), select a compatible buffer (phosphate, HEPES, MOPS) based on your reaction pH, and confirm the compound’s low water solubility and potential Michael reactivity toward nucleophiles.

Green Alternatives

• Greener solvent choices (general guidance):

  • Replace DMF/DMSO where feasible with MeCN, 2-MeTHF, ethyl acetate, or propylene carbonate, balancing solubility and reaction rates.
  • For radical/polymer work, consider anisole or CPME instead of chlorinated solvents.

• Comparison (literature/generic):

  | Use case | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | Michael addition | DMF, THF | 2-MeTHF, EtOAc | Slightly reduced solubility; easier workup and lower toxicity | | Hydrogenation | DCM, THF | EtOH, iPrOH | Protic solvents may affect catalyst choice/rate | | Photoredox additions | MeCN, DCM | MeCN, EtOAc, anisole | Quantum yield/catalyst solubility may vary | | Polymerization | Toluene, bulk | Anisole, CPME | Tg and Mw control may differ; verify inhibitor profile |

• Process intensification:

  • Flow chemistry for exothermic additions to the α,β-unsaturated system reduces solvent volume and improves heat removal.
  • Use of solid-supported bases/nucleophiles can simplify workup and reduce aqueous waste.

• Waste minimization:

  • Favor catalytic over stoichiometric reagents; recover palladium/rhodium catalysts when used.
  • Implement solvent recovery (MeCN, EtOAc) by fractional distillation.

Pharmaceutical Uses

• This product is offered for research use only. No therapeutic or clinical use is claimed or supported.

• Formulation/manufacturing context (general):

  • Acrylamide monomers can be employed to prepare functional polymers and resins used in pharmaceutical process aids (e.g., chiral stationary phases, affinity media). N-((S)-1-phenylethyl)acrylamide may serve as a chiral monomer in custom polymer matrices that impart chiral recognition.
  • The amide itself is not a common excipient. If used in process development, ensure extractables/leachables and residual monomer specifications are defined and validated.

• Regulatory note: No pharmacopeial monograph is known for this specific compound; suitability is determined by internal specifications and risk assessment.

Physical Properties

• Item-specific specifications (this lot):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, refractive index, UV cutoff, residual water/peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for the neat compound (for reference only; not product specifications):

  • Phase at ambient conditions: typically a low-melting solid or viscous oil among N-arylalkyl acrylamides; exact MP/BP vary by stereopurity and sample history.
  • Solubility: expected to be soluble in polar aprotic organic solvents (DMF, DMSO, acetonitrile, THF, ethyl acetate) and moderately soluble in alcohols; low solubility in water due to hydrophobic phenyl group.
  • pKa (amide N–H): very weakly acidic (amide N–H pKa typically ~16–18 in DMSO, literature); not appreciably basic at neutral pH.
  • LogP: aromatic, neutral amide likely exhibits moderate hydrophobicity (qualitative); specific value not established here.

• Notes for practitioners:

  • The α,β-unsaturated system may slowly polymerize under light/heat; stabilize and store accordingly (see Safety & Handling / Storage tabs).
  • Drying prior to moisture-sensitive transformations can be accomplished by azeotropic removal (toluene) or high-vacuum at mild temperature, verifying integrity by NMR/LC.

Quality and Grades

• Grade/Purity for this SKU: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades (general):

  • Research grade: Suitable for most synthesis and method development; verify impurity profile when stereochemical fidelity is critical.
  • Chiral purity: For enantioenriched N-((S)-1-phenylethyl)acrylamide, enantiomeric excess (ee) and optical rotation often govern selectivity as a chiral auxiliary; request CoA data if not listed.
  • Stabilization: Acrylamide monomers may include polymerization inhibitors (e.g., MEHQ, BHT) in some commercial grades; none is specified for this item. Confirm presence/absence of stabilizers in the CoA if your application is inhibitor-sensitive (e.g., controlled radical polymerization).

• What to verify on receipt:

  • Identity by 1H/13C NMR (vinylic protons ~5.5–6.5 ppm; amide NH ~6–8 ppm; benzylic chiral CH ~4–5 ppm), IR (amide C=O ~1650–1680 cm−1), and LC/MS (M+H+ ~176, literature).
  • Water content and polymer content when relevant to your process; Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

This chiral acrylamide is a versatile electrophile and a useful monomeric handle for introducing chiral, benzylic auxiliaries or pendants.

• Conjugate (Michael) additions (literature):

  • Soft nucleophiles (thiols, malonates, enolates, sulfinates) add to the β-carbon under base or organocatalysis, giving β-substituted amides. The (S)-1-phenylethyl N-substituent can induce diastereoselectivity via steric and H-bonding interactions.
  • Secondary amine catalysis (e.g., enamine/iminium activation) and phase-transfer catalysis are commonly applied; solvents include MeCN, THF, or toluene.

• Radical and photochemical additions:

  • Acrylamides engage in atom-transfer radical addition (ATRA), thiol–ene coupling, and photoredox-mediated hydro/aryl additions. Control inhibitors and oxygen rigorously for reproducibility.

• Polymer and materials uses:

  • Functions as a specialty acrylamide monomer to install chiral benzylic side chains into (co)polymers, enabling chiroptical properties, chiral recognition, or asymmetric environments in catalysts/sorbents.

• Hydrogenation and hydrofunctionalization:

  • Catalytic hydrogenation of the C=C provides the saturated N-((S)-1-phenylethyl)propionamide.
  • Hydroboration–oxidation and hydroamination deliver β-functionalized amides.

• Auxiliary strategy:

  • The N-(1-phenylethyl) group is a classical removable chiral auxiliary on nitrogen; post-transformation, acid/base hydrolysis can release (S)-1-phenylethylamine (and the transformed acid/amide), enabling stereochemical relay. Optimize conditions to limit racemization.

• Analysis and control:

  • Monitor conversions by 1H NMR (disappearance of vinylic signals ~5.5–6.5 ppm) and LC/MS. Assess diastereomeric ratios by chiral HPLC when auxiliary control is exploited.

Reaction Conditions

General literature guidance (not product specifications):

• Michael additions:

  • Typical solvents: MeCN, THF, toluene, EtOAc; for more polar nucleophiles, DMF/DMSO.
  • Bases/catalysts: Tertiary amines (Et3N, DIPEA), K2CO3, DBU; organocatalysts (secondary amines), or phase-transfer catalysts.
  • Temperature/time: 0–25 °C for thiol/amine additions (0.5–6 h); 25–60 °C for carbon nucleophiles (4–24 h). Monitor by TLC/LC-MS.

• Hydrogenation of C=C:

  • Catalyst: 5–10% Pd/C (0.5–5 mol% metal), H2 1–3 bar.
  • Solvent: EtOH, iPrOH, or EtOAc; 20–40 °C; 2–8 h. Work up by filtration over celite; check for N-debenzylation-like side reactions (rare under mild conditions).

• Hydroboration–oxidation:

  • Reagents: 9-BBN or BH3·THF (1.1–1.5 eq), THF, 0–25 °C; oxidative workup with H2O2/NaOH at 0–25 °C.

• Thiol–ene coupling:

  • Initiation: AIBN (0.1–2 mol%) at 60–80 °C or photoinitiation (365–405 nm) with type I photoinitiator.
  • Solvents: Toluene, MeCN, or bulk; inert atmosphere recommended.

• Polymerization (radical):

  • Initiators: AIBN, ACVA (0.1–1 wt%).
  • Solvent: anisole, toluene, or bulk; 60–80 °C; rigorously deoxygenate.

• Notes:

  • Protect from light/oxygen to reduce premature polymerization.
  • If auxiliary control is desired, evaluate temperature and solvent to maximize diastereodifferentiation; analyze by chiral HPLC/NMR.

Safety and Handling

• Product Data (this item):

  • GHS Classification, Signal Word, Pictograms, H-Statements: Not specified for this item; refer to SDS.

• General safety expectations for α,β-unsaturated amides (literature/generic; not product-specific):

  • Hazards: May act as a Michael acceptor toward nucleophiles (skin/eye sensitization potential in general class). Acrylamide derivatives can undergo radical polymerization; exothermic runaway is possible if heated in bulk without inhibitor.
  • PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of aerosols or vapors.
  • Incompatibilities: Strong bases and nucleophiles may add across the double bond; strong oxidizers; radical initiators and UV/light that can promote polymerization.
  • Handling tips:
    • Minimize exposure to strong nucleophiles unless intended for conjugate addition.
    • Use amber glassware or foil wrap to limit photoinitiated polymerization.
    • Consider adding a trace radical inhibitor in reaction solvents if long-term storage in solution is required (verify compatibility with your chemistry).
  • First aid (generic): If on skin/eyes, rinse with water for ≥15 min and remove contaminated clothing; if inhaled, move to fresh air; if ingested, seek medical attention. Always follow institutional protocols.

• Always consult the product SDS for authoritative hazard, exposure limits, and emergency procedures.

Solvent Selection

• Polarity and miscibility (general guidance):

  • The molecule is a neutral, moderately polar amide with an aromatic substituent. It dissolves well in polar aprotic solvents (DMF, DMSO, NMP, MeCN) and is typically soluble in THF, dioxane, ethyl acetate, and dichloromethane; limited aqueous solubility is expected.

• Choosing a solvent by transformation:

  • Conjugate (Michael) additions: MeCN, THF, or alcohols for soft nucleophiles (thiols, amines); DMF/DMSO for less soluble nucleophiles or catalytic enantioselective variants.
  • Radical or photoinitiated additions/polymerizations: Toluene, dioxane, or bulk; degas and control temperature. Use inhibitor-free conditions when required and handle with care.
  • Hydrogenation (C=C reduction): Alcohols (EtOH, iPrOH) or ethyl acetate under Pd/C or Rh catalysts.
  • Hydroboration–oxidation across the double bond: THF or THF/H2O mixtures with BH3·THF or 9-BBN; quench/oxidize under standard conditions.

• Practical notes:

  • Avoid strongly basic aqueous media that can lead to amide hydrolysis and racemization at elevated temperature.
  • For analytical work (HPLC/UPLC), MeCN/H2O with 0.1% acid modifier typically resolves the parent and any oligomers; ensure stabilizer status is known if UV background matters.

• Quick comparison (general):

  • MeCN: good for kinetics/clean NMR; THF: versatile, easy removal; DMF/DMSO: maximal solubility; EtOAc/DCM: convenient workup and chromatography.

Storage and Reconstitution

• Storage (Product Data): Room temperature.

• General storage guidance for acrylamides (literature/generic):

  • Store tightly sealed under inert gas (nitrogen/argon) if possible, in amber glass, away from heat and light to minimize spontaneous polymerization.
  • If long-term storage is anticipated, refrigeration (2–8 °C) can further reduce polymerization risk; allow to warm to room temperature before opening to prevent condensation.

• Inhibitors/stabilizers:

  • None are specified for this item; refer to CoA/Spec Sheet. If present, document type and concentration for sensitive applications.

• Reconstitution and solution handling:

  • Prepare stock solutions in dry solvents such as MeCN, THF, DCM, DMF, or DMSO. Typical stock concentrations: 10–500 mM depending on solubility and intended use.
  • Degas solutions for radical or photochemical reactions; store solutions at low temperature and protected from light. Avoid prolonged storage in basic media to prevent hydrolysis.

• Freeze–thaw guidance:

  • Solid material tolerates ambient storage; solutions in DMSO/DMF can be aliquoted and frozen (−20 °C) to limit repeated thaw cycles. Verify integrity by NMR/LC before critical experiments.

• Research Use: For research use only (per Product Data).

Structure and Identity

N-((S)-1-phenylethyl)acrylamide is a chiral, conjugated amide bearing an activated α,β-unsaturated carbonyl (acrylamide) and an N-substituted (S)-1-phenylethyl group.

• Product Data (as provided):

  • CAS: 19035-71-3
  • CID: 11480756
  • InChIKey: 312319 (as provided; note this is not the standard 27-character InChIKey format)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity details (for reference; not item-specific specifications):

  • Common structural formula: CH2=CH–C(=O)–NH–CH(CH3)–C6H5
  • Functional groups: α,β-unsaturated amide (Michael acceptor), secondary amide, aromatic ring; one stereogenic center at the benzylic carbon (S configuration)
  • Molecular formula (computed from structure): C11H13NO
  • Molecular weight (calculated): ~175.23 g/mol
  • Example SMILES (literature): C=CC(=O)NC@Hc1ccccc1

• 2D structure description (verbal):

  • An acrylamide fragment (terminal CH2=CH–) conjugated to a carbonyl, followed by an –NH– linker to a chiral benzylic center bearing a methyl substituent and a phenyl ring. The S-configuration at the benzylic carbon orients the phenyl and methyl substituents stereodefined relative to the amide N–H.

Synthetic Utility

• Electrophilic handle:

  • The conjugated C=C–C=O system makes the β-carbon a soft electrophile for Michael additions. This enables rapid assembly of β-functionalized amides from diverse carbon and heteroatom nucleophiles.

• Chiral information carrier:

  • The (S)-1-phenylethyl substituent serves as an N-centered chiral auxiliary. Through steric and H-bonding interactions, it can bias facial selectivity in additions to the acrylamide or subsequent transformations at the amide α/β positions. After elaboration, the auxiliary can be removed (typically hydrolysis or transamidation) to reveal the target motif and recover (S)-1-phenylethylamine.

• Downstream transformations (literature examples):

  • Hydrogenation to saturated amides; halofunctionalization across the double bond; thiol–ene coupling; conjugate cyanation; conjugate addition of stabilized carbanions (malonates, nitroalkanes) followed by oxidation/reduction sequences.
  • Amide activation (e.g., via CDI, Ghosez reagent) can enable further N-derivatization or intramolecular cyclizations.

• Retrosynthetic value:

  • View it as an acrylamide linchpin that can diversify at the β-position under mild, chemoselective conditions while temporarily encoding chirality on nitrogen.

Target Specificity

Not applicable. This product is a small-molecule acrylamide, not a biological targeting reagent or antibody. No antigen/epitope or species reactivity is relevant.