N-(3-hydroxypropyl)prop-2-enamide , CAS No.44817-99-4

CAS: 44817-99-4 Cat. No.: N1016432 Formula: C₆H₁₁NO₂ Peso molecolare: 129.160 Numero EC: 624-753-5

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

C=CC(=O)NCCCO

IUPAC Name

N-(3-hydroxypropyl)prop-2-enamide

InChIKey

ZEMHQYNMVKDBFJ-UHFFFAOYSA-N

INCHI

1S/C6H11NO2/c1-2-6(9)7-4-3-5-8/h2,8H,1,3-5H2,(H,7,9)

Peso molecolare

129.160

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Acrylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Acrylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acrylic acids and derivatives
• Alternative Parents: Secondary carboxylic acid amides Alkanolamines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acrylic acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Alkanolamine - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Organonitrogen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
• 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: 129.160 g/mol
• XLogP3: -0.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 129.079 Da
• Monoisotopic Mass: 129.079 Da
• Topological Polar Surface Area: 49.300 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 101.000
• 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 antibody/assay application protocols apply to this small-molecule monomer. For synthetic and polymerization uses, see the Reaction Conditions and Reaction & Applications sections for general procedural guidance.

Biological Roles

This compound is a synthetic small-molecule monomer, not a natural metabolite.

• General biochemical context (literature/general)

  • Functional resemblance: The pendant primary alcohol can engage in hydrogen bonding with biomacromolecules, mimicking aspects of serine/hydroxypropyl motifs in polymers and surfaces.
  • Biomaterials research: Polymers incorporating N-(3-hydroxypropyl)acrylamide are studied for hydrophilic, low-fouling coatings and hydrogel networks that interact favorably with aqueous biological environments. Such uses focus on physicochemical properties (hydration layer formation, reduced protein adsorption) rather than any intrinsic biological activity of the monomer itself.

• Enzymatic/biological reactivity

  • The monomer’s α,β-unsaturated carbonyl is a Michael acceptor in chemical terms; however, biological nucleophiles (e.g., thiols) could, in principle, react under certain conditions. No specific metabolic pathways are established for this synthetic compound in vivo.

• Important restriction

  • This product is provided strictly for laboratory research use only. It is not intended for use in humans or animals, and no clinical or therapeutic claims are made.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare pH buffer systems.

• Practical note: If used in aqueous reactions or polymerizations, choose an appropriate external buffer (e.g., phosphate, bicarbonate, or Tris) compatible with Michael reactions and radical initiators. Avoid amine buffers for aza–Michael studies unless intended, and avoid strong bases that could promote undesired side reactions or polymerization.

Green Alternatives

• Solvent and process choices (general, not item-specific)

  • Aqueous media: Many polymerizations and Michael additions of acrylamides proceed efficiently in water or water/ethanol, eliminating chlorinated or high-VOC solvents.
  • Photoinitiation: Light-driven thiol–ene or radical polymerizations reduce thermal energy input; pair with water-soluble photoinitiators for greener processing.

• Alternative monomers and trade-offs (literature/general)

  • 2-Hydroxyethyl acrylate (HEA): Lower molecular weight, similar reactivity; typically derived from petro feedstocks; can be more volatile/odorous compared to hydroxypropyl acrylamide.
  • N-(2-hydroxyethyl)acrylamide (HEAm): Similar functionality with two-carbon spacer; high water solubility; selection depends on mechanical and hydration properties of resulting polymers.

• Comparison highlights (general)

  • Metric | Water-soluble processing | Hazard profile | Functionality
    • N-(3-hydroxypropyl)acrylamide | Excellent | Typical acrylamide-type irritant risks | Amide + primary alcohol
    • HEA | Good to excellent | Acrylic ester irritant; often inhibitor-stabilized | Ester + primary alcohol
    • HEAm | Excellent | Similar to other acrylamides | Amide + primary alcohol

• Greener workup/purification

  • Favor aqueous crystallization or antisolvent precipitation over chromatography when feasible.
  • Use reusable inhibitor-removal cartridges (alumina) rather than solvent-intensive distillations.

• Waste minimization

  • Quench residual radicals with oxygen or radical scavengers; polymerize leftover monomer to solid for easier disposal per local regulations.

Pharmaceutical Uses

• Item-specific regulatory status: Not specified for this item; refer to CoA/Spec Sheet for any compendial references if applicable.

• General formulation/manufacturing context (literature/general)

  • As a monomer: Used in research to prepare hydrophilic polymers and hydrogels that can serve as excipient matrices, coatings on devices, or as components of controlled-release systems after appropriate polymerization and purification.
  • Processing considerations: Residual monomer content in polymeric materials is typically minimized via exhaustive extraction or dialysis to meet biocompatibility targets in research prototypes. Polymerization initiator and inhibitor residues should be qualified.
  • Surface modification: Copolymers containing hydroxypropyl acrylamide units are explored for improving wettability and lubricity of polymeric or metallic substrates in device R&D.

• Compliance and documentation

  • Any pharmaceutical or biomedical deployment would require separate sourcing to the relevant pharmacopeial standards and full toxicological qualification. This catalog item is for research use only and not supplied to any pharmacopeial grade.

Physical Properties

• Item-specific specifications

  • Boiling point, melting point, density, refractive index, water/peroxide content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties (typical for N-(3-hydroxypropyl)acrylamide; not item-specific)

  • Physical state: often reported as a low-melting solid or viscous liquid depending on purity and temperature.
  • Polarity: highly polar due to amide and alcohol; strong hydrogen-bonding capacity.
  • Solubility: expected to be miscible with water; readily soluble in alcohols (MeOH, EtOH) and polar aprotic solvents (DMSO, DMF).
  • Acid–base: neutral under physiological pH; amide non-basic; primary alcohol pKa ~16–17 (literature, for aliphatic alcohols). Amide N pKa (conjugate acid) ~–1 to 0 (literature, very weak base).
  • LogP: anticipated low/negative (literature expectation for hydroxyalkyl acrylamides), indicative of hydrophilicity.

• Practical handling implications (general)

  • Hygroscopicity: hydrophilic monomers can absorb moisture; consider minimizing headspace and resealing promptly.
  • Thermal behavior: α,β-unsaturated amides may polymerize upon heating; avoid unnecessary heat exposure.
  • Spectroscopy: strong IR bands near ~1650–1680 cm⁻¹ (amide C=O) and ~3200–3500 cm⁻¹ (O–H/N–H stretching) are typical (literature).

Quality and Grades

• Item-specific details

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizer/inhibitor content: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance)

  • Research/Biochemical grade: Typically suitable for most laboratory syntheses and polymerizations; may have higher limits on residual solvents or UV-absorbing impurities than HPLC grade materials.
  • Inhibitor-stabilized monomers: Many acrylic monomers are supplied with trace inhibitors (e.g., MEHQ) to suppress polymerization; such stabilizers can affect polymerization kinetics and may require removal (e.g., inhibitor scavengers, alumina) for sensitive applications. Confirm presence/absence on the CoA for this item.
  • Low metal/ionic content: For radical polymerizations in water or for biomedical materials research, low transition-metal content minimizes unwanted redox initiation; verify specifications if critical.

• Documentation and verification

  • CoA/Spec Sheet will provide batch-specific assay, residual solvents, moisture, and inhibitor content (if applicable). Request and review these documents for process-critical work, particularly where polymer molecular weight control or biocompatibility testing is planned.

Reaction and Applications

• Polymerization (literature/general)

  • Free-radical homopolymerization/copolymerization: The acrylamide double bond undergoes rapid radical polymerization (AIBN, peroxide, or APS/TEMED). Copolymerizes with acrylamide, acrylic acid, DMAA, PEG acrylates to introduce pendant primary alcohols for post-polymer modification and enhanced hydrophilicity.
  • Controlled radical methods: RAFT and ATRP-compatible (with appropriate chain transfer agents/initiators), enabling block and gradient copolymers incorporating hydroxypropyl acrylamide units.

• Click and conjugation chemistry

  • Thiol–Michael addition: Base- or nucleophile-catalyzed addition of thiols to the activated double bond at room temperature to install thioether linkages.
  • Aza–Michael addition: Secondary amines add under mild base; primary amines possible but may require more forcing conditions.
  • Radical thiol–ene: Photoinitiated reactions allow spatial/temporal control on surfaces or in bulk formulations.

• Alcohol handle transformations (post-functionalization)

  • Esterification and carbonate formation: Couple the primary alcohol with acyl chlorides, activated esters, or carbonates to introduce functionality (e.g., cross-linkable groups, dyes).
  • Sulfonate activation: Convert –OH to tosylate/mesylate, enabling SN2 substitution (e.g., with azide, halide, or amine nucleophiles).
  • Oxidation: TEMPO/bleach or Dess–Martin to aldehyde; further to carboxylic acid, enabling bifunctional linker chemistry.

• Materials applications (research)

  • Hydrogels and coatings: Provides hydrophilic, H-bonding side chains; useful in anti-fouling coatings, hydrogel networks (via copolymerization and cross-linking), and responsive materials design.

• Practical tips

  • Drying: If moisture-sensitive steps are planned (e.g., acylation with acid chlorides), dry over molecular sieves and work under inert atmosphere.
  • Inhibitors: If present, remove prior to polymerization for maximum activity; confirm by CoA/SDS for this item.

Reaction Conditions

All conditions below are literature/general guidance for N-(hydroxyalkyl)acrylamides and are not item-specific. Optimize for your system.

• Free-radical polymerization

  • Solvents: Water, water/EtOH, or DMF/DMSO for hydrophobic comonomers.
  • Initiators: AIBN (0.5–1.0 mol% at 60–70 °C in organic media); APS/TEMED or APS/sodium metabisulfite (0.1–1 wt% each) in water at 20–50 °C for redox initiation.
  • Atmosphere: Degas (N2/Ar) to remove O2; typical conversions >80% in 2–12 h depending on temperature and composition (literature reports).

• Thiol–Michael addition

  • Base catalysts: Triethylamine (1–10 mol%), DBU (1–5 mol%), or bicarbonate in water/MeOH; 20–25 °C, 0.5–4 h to completion with slight thiol excess (1.05–1.2 equiv).
  • Photobase/photoinitiated variants: Use UV/visible photobases or radicals with Type I photoinitiators; rapid curing within minutes under irradiation.

• Alcohol functionalization

  • Esterification: DIC/DMAP, RT to 40 °C, 2–16 h in DCM/DMF; or acid chloride/pyridine at 0–25 °C. Protect or avoid conditions that trigger conjugate addition.
  • Tosylation: TsCl, pyridine or NEt3, 0–25 °C; follow by SN2 in DMF with nucleophiles at 25–60 °C.
  • Oxidation: TEMPO (5–10 mol%), NaOCl (pH ~9), 0–5 °C to aldehyde; Pinnick to acid as needed.

• Purification tips

  • Due to hydrophilicity, prefer aqueous workups with salting-out or precipitation into acetone/IPA/EtOAc. For monomer purification, inhibitor removal (if present) by basic alumina is common in literature.

Safety and Handling

• Authoritative source: Always consult the SDS for definitive hazard, PPE, and first-aid information for this specific catalog item.

• Item-specific hazard data

  • GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
  • Research Use: For research use only.

• General safety considerations for acrylamide-type monomers (literature/general guidance)

  • Irritation/sensitization: α,β-Unsaturated amides can be skin/eye irritants and may cause sensitization. Avoid skin contact and inhalation of vapors/aerosols.
  • Polymerization risk: Unsaturated monomers may undergo exothermic polymerization, especially when heated or contaminated with radicals. Keep away from heat, peroxides, and radical initiators unless intentionally polymerizing. Do not distill to dryness.
  • Incompatibilities: Strong oxidizers, strong acids/bases (may accelerate polymerization or cause degradation), and reactive acylating/alkylating agents.

• Recommended PPE and handling (general best practice)

  • Wear lab coat, chemical-resistant gloves (e.g., nitrile), and eye protection. Use in a fume hood when handling bulk quantities or generating aerosols.
  • Storage: Keep container tightly closed at room temperature as specified; protect from light and heat. Use inert gas blanket for long-term storage if feasible.

• First-aid overview (general)

  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Solvent Selection

• Polarity and miscibility (literature/general)

  • Class: Polar protic/amide-alcohol functionality; strong hydrogen bonding.
  • Water: Expected to be fully miscible; suitable for aqueous polymerizations (redox-initiated) and Michael additions.
  • Organic solvents: Highly soluble in MeOH, EtOH, i-PrOH, DMSO, DMF; moderate in acetonitrile; limited in nonpolar solvents (hexanes, toluene).

• Practical guidance

  • Aqueous processes: For free-radical copolymerization with hydrophilic comonomers (e.g., acrylamide, N,N-dimethylacrylamide), water is typically the solvent of choice; ionic strength and pH can tune kinetics and solubility of initiators.
  • Organic processes: Use polar aprotic solvents (DMF/DMSO) for nucleophilic substitutions after converting the alcohol (e.g., to sulfonate); alcohol/amide hydrogen bonding can retard some reactions—catalysts or dehydrating agents may be beneficial.
  • Extractive workups: Due to hydrophilicity, partitioning into organic phases can be poor; consider salting out or using butanol/EtOAc mixtures to recover product.

• Comparison (general)

  • Versus N-isopropylacrylamide (NIPAM): More hydrophilic; better water miscibility but less propensity for LCST-type phase behavior.
  • Versus hydroxyethyl methacrylate (HEMA): Similar hydrophilicity; acrylamide moiety is typically more reactive in radical polymerization than methacrylate under comparable conditions.

Storage and Reconstitution

• Item-specific storage

  • Store at room temperature (as provided in Product Data).

• General storage guidance for acrylamide-type monomers (literature/general)

  • Keep tightly closed in a dry, well-ventilated place. Minimize exposure to heat and light. If long-term storage is planned, consider inert gas blanketing to limit oxidative polymerization.
  • If an inhibitor is present (not specified for this item), maintain recommended storage conditions to preserve stabilizer efficacy.

• Reconstitution and handling

  • Dissolution: Readily dissolves in water, alcohols, and polar aprotic solvents; prepare fresh solutions before use to minimize unintended polymerization.
  • Filtration: Pass through 0.2 µm PTFE/nylon filters to remove particulates prior to sensitive reactions or polymerizations.
  • Aliquoting: For moisture/oxygen-sensitive applications, aliquot under inert atmosphere to avoid repeated headspace exchange.

• Shipping

  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Stability notes

  • Avoid prolonged heating. Do not distill to dryness. Monitor for viscosity increase or discoloration as signs of polymerization; if observed, evaluate before use.

Structure and Identity

Brief overview: N-(3-hydroxypropyl)prop-2-enamide is the N-(3-hydroxypropyl) derivative of acrylamide, featuring a polymerizable acrylamide double bond and a terminal primary alcohol.

• Item-specific (from Product Data)

  • SKU: N1016432
  • Product name: N-(3-hydroxypropyl)prop-2-enamide
  • CAS: 44817-99-4
  • PubChem CID: 10396866
  • InChIKey: 454780 (as provided; not the standard-length InChIKey)
  • Storage: Room temperature

• Literature/computed identifiers and descriptors (not item-specific)

  • Synonym: N-(3-hydroxypropyl)acrylamide; 3-hydroxypropyl acrylamide
  • Molecular formula (literature): C6H11NO2
  • Molecular weight (literature): ~129.16 g/mol
  • SMILES (literature): C=CC(=O)NCCCO
  • Structural features: acrylamide moiety (electron-poor C=C conjugated to amide C=O); secondary amide (N-substituted); terminal primary alcohol (–CH2–CH2–CH2–OH). No stereocenters.
  • 2D structure in words: A trans-substitutable vinyl group (CH2=CH–) attached to a carbonyl (–C(=O)–), which is bound to an N atom; the nitrogen bears a 3-carbon tether terminating in a primary hydroxyl group (–NH–CH2–CH2–CH2–OH). Conjugation runs from the C=C through the carbonyl into the amide.

• General chemistry notes

  • Functional groups: Michael acceptor (α,β-unsaturated amide), secondary amide H-bond donor/acceptor, primary alcohol (H-bond donor/acceptor).

Synthetic Utility

• Functional group leverage (literature/general)

  • Michael acceptor: The conjugated C=C of the acrylamide enables nucleophilic conjugate additions (thiols, amines, phosphines), expanding structural diversity rapidly under mild conditions.
  • Primary alcohol: Amenable to esterification, carbonate/carbamate formation, sulfonate activation, oxidation to aldehyde/acid—providing a modular handle orthogonal to the Michael acceptor.
  • Amide: Offers hydrogen bonding and polarity; largely inert to many bases/nucleophiles, providing chemoselectivity.

• Retrosynthetic/value considerations

  • As a bifunctional monomer, it enables “polymer-analogous” synthesis after incorporation into a polymer backbone, facilitating post-polymer modification without losing hydrophilicity.
  • Useful as a hydrophilic spacer in small-molecule conjugates: the –(CH2)3–OH chain separates the amide from appended motifs, reducing steric congestion during downstream coupling.

• Named/typical transformations

  • Thiol–Michael and aza–Michael additions; radical polymerization (AIBN, peroxides), RAFT/ATRP; Mitsunobu inversion on the alcohol where retention/inversion control is desired; TEMPO-mediated oxidations to aldehyde followed by reductive amination to introduce amine handles.

• Selectivity tips

  • Perform alcohol derivatizations under conditions that do not engage the Michael acceptor (e.g., avoid strong bases/nucleophiles or protect the double bond via prior conjugate addition/polymerization when necessary). Employ mild acylation (DMAP, DIC) to minimize side reactions.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent/monomer, not a biological targeting reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.