N-Hydroxyethyl-N-methylstearamide - ≥97% , CAS No.35699-24-2

CAS: 35699-24-2 Cat. No.: N970453 Formula: C₂₁H₄₃NO₂ Molecular Weight: 341.600 EC Number: 864-424-5

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifications & Purity

≥97%

Storage

Room temperature

Purity

≥97%

Names and Identifiers

Canonical Smiles

CCCCCCCCCCCCCCCCCC(=O)N(C)CCO

IUPAC Name

N-(2-hydroxyethyl)-N-methyloctadecanamide

InChIKey

UOFPCDKBJJVSSD-UHFFFAOYSA-N

INCHI

1S/C21H43NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(24)22(2)19-20-23/h23H,3-20H2,1-2H3

Molecular Weight

341.600

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty amides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty amides
• Intermediate Tree Nodes: Not available
• Direct Parent: N-acyl amines
• Alternative Parents: Tertiary carboxylic acid amides Alkanolamines Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: N-acyl-amine - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Alkanolamine - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Organonitrogen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
• 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

Chemical and Physical Properties

• Molecular Weight: 341.600 g/mol
• XLogP3: 7.400
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 18
• Exact Mass: 341.329 Da
• Monoisotopic Mass: 341.329 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 269.000
• 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 vendor‑validated biological assay protocols are provided for this small‑molecule amphiphile. Nevertheless, the following general laboratory approaches can be useful when incorporating it into research workflows. These are literature‑based best practices and not item‑specific specifications.

• Preparing stock solutions

  • DMSO: 50–200 mg/mL at room temperature typically achievable; warm to 40–50 C if needed. Filter through 0.45 μm PTFE while warm to remove particulates.
  • Ethanol/i‑PrOH: 10–100 mg/mL with gentle heating and stirring. Use immediately or store aliquots tightly sealed to limit evaporation.

• Formulating aqueous dispersions

  • Prepare a concentrate in ethanol or propylene glycol, then add slowly into warm (40–50 C) aqueous phase under high‑shear mixing. Use a higher‑HLB co‑surfactant (e.g., polysorbate) as needed. Final organic cosolvent ≤5% v/v is typical for stable dispersions.
  • Sonication (bath or probe) for 1–5 min can reduce droplet size; avoid overheating.

• Polymer/wax incorporation

  • Pre‑melt the host matrix (50–90 C, depending on matrix) and add the compound with stirring until homogeneous. Cast films or pellets and cool under controlled conditions to manage crystallinity.

• Analytical QC checkpoints

  • Verify concentration by gravimetry or by HPLC with ELSD/CAD; confirm absence of undissolved solids microscopically or by light scattering.

For any bio‑related testing, establish system‑specific compatibility and safety beforehand. For research use only (per Product Data).

Biological Roles

This compound is a synthetic fatty acid amide bearing a C18 saturated tail and a polar tertiary amide/primary alcohol headgroup. It is not a known endogenous metabolite.

• General biochemical context (literature/general)

  • Fatty acid amides (FAAs) occur in biology (e.g., N‑acylethanolamines). The present molecule is an N‑methylated, hydroxyethyl analog of stearamide and is not reported as a natural signaling lipid. Its amphiphilicity may enable interfacial interactions with lipid assemblies in model systems.
  • In membrane‑mimetic research, such amphiphiles can partition into bilayers or micelles, modulating surface tension and microviscosity. The tertiary amide nitrogen is non‑protonatable under physiological pH, while the terminal alcohol can engage in hydrogen bonding.

• Research utility in life sciences (non‑clinical)

  • Surfactant/co‑surfactant in the preparation of liposomes, nanoemulsions, or lipidic particles for method development and physicochemical studies (e.g., size distribution, zeta potential). Any biological testing should be preceded by compatibility and cytotoxicity screening appropriate to the model system.
  • Model substrate for enzyme assays probing amidase stability (typically low reactivity toward primary amidases due to tertiary amide substitution) or for studying non‑enzymatic hydrolysis in varied media.

• Important caveats

  • No medical, diagnostic, or therapeutic use is intended or implied. For research use only (per Product Data).
  • Biological behavior (e.g., membrane partitioning) is system‑dependent; verify experimentally under your specific conditions.

Buffer Applications

This compound is a hydrophobic, nonionic amphiphile and is not used as a buffering agent. It does not provide significant acid/base capacity in the physiological pH range.

• Practical guidance

  • For dispersing this material into aqueous buffers, use co‑solvents (e.g., ethanol, DMSO, propylene glycol) and/or nonionic surfactants, with gentle heating and sonication to aid incorporation.
  • Select buffer systems based on the needs of your biomolecules (e.g., phosphate, Tris, HEPES); this compound will not materially affect buffer pH but may interact with proteins and membranes—verify compatibility experimentally.

• Recipes and pKa data

  • No relevant pKa for buffering action; any pKa associated with the terminal alcohol is far above the aqueous range and the tertiary amide is essentially nonbasic in water (literature generality).

For detailed work with buffered dispersions, focus on the Solvent Selection and Application Protocols sections rather than buffer chemistry.

Green Alternatives

Selection of solvents and processes strongly influences the environmental profile when working with long‑chain amide surfactants.

• Process design (general guidance)

  • Favor solvent‑minimized or solvent‑free methods (melt blending, reactive extrusion) whenever feasible due to the compound’s low volatility and melt‑processable nature.
  • For solution work, consider greener solvent choices that still solubilize long hydrophobes.

• Greener solvent comparisons (literature/general)

  Option | Conventional choice | Greener alternative | Pros of alternative | Trade‑offs ---|---|---|---|--- Dissolution for coating | Toluene/xylene | 2‑MeTHF or CPME | Bio‑based (2‑MeTHF), better safety/air emissions | Slightly lower solvency; water uptake (2‑MeTHF) Polar aprotic media | DMF/NMP | Cyrene, propylene carbonate | Lower toxicity (non‑reprotoxic), higher boiling points | Viscosity; slower drying Alcoholic media | i‑PrOH | EtOH/EtOH‑water with cosolvent | Lower toxicity, renewable | May require heating; limited water tolerance

• Energy and waste reduction

  • Use moderate heating (40–60 C) and efficient stirring/ultrasonication to accelerate dissolution without reflux.
  • Employ solid dosing/melt incorporation to avoid solvent waste in polymer/wax applications.

• Safer reagents for transformations (general)

  • For esterifications of the hydroxyethyl group, catalytic organocatalysts (e.g., DMAP, TBD) under azeotropic water removal can avoid acid chlorides.
  • For amide reduction to amines, BH3·SMe2 is often more chemoselective than LiAlH4 and can reduce waste of inorganic salts; however, it still demands strict controls—assess EHS profiles before scale‑up.

• Verification

  • Confirm that greener substitutions meet performance criteria (solubility, film quality, micelle formation) through small‑scale DoE rather than one‑to‑one solvent swaps.

Pharmaceutical Uses

No clinical or therapeutic claims are made. For research and development use only.

• Potential roles in formulation research (literature/general)

  • Nonionic surfactant/co‑surfactant: may assist in forming/stabilizing emulsions or self‑emulsifying systems for hydrophobic actives during preformulation screening.
  • Wetting and penetration‑modifying excipient (screening stage): fatty amide amphiphiles can alter interfacial properties of semi‑solid bases and hot‑melt matrices in prototype dosage form development.
  • Processing aid: lubrication and slip modifier in melt‑extruded matrices due to oriented adsorption at interfaces.

• Pharmacopeial/compendial status

  • No specific pharmacopeial monograph is known for N‑hydroxyethyl‑N‑methylstearamide (literature check); if compendial compliance is required, alternative listed excipients should be considered.

• Evaluation considerations

  • Assess compatibility with actives and other excipients (DSC/TG, isothermal stress, FT‑IR) since tertiary amides can participate in hydrogen bonding.
  • Determine HLB contribution empirically; the compound lacks a strong ionic headgroup, so it typically functions as a co‑surfactant alongside higher‑HLB materials in aqueous systems.
  • Characterize residual impurities (free stearic acid, secondary/primary amides) and color/odor for acceptability in prototype formulations.

• Regulatory note

  • Any progression beyond laboratory R&D requires comprehensive safety, impurity, and stability assessments specific to the intended route and product class.

Physical Properties

Only limited item-specific physico‑chemical data are provided with this listing; do not treat literature values as certificate specifications.

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (informational; not item specifications)

  • Empirical formula (computed from structure): C21H43NO2
  • Formula weight (computed): ~341.58 g/mol
  • Expected physical state: waxy solid or highly viscous paste at ambient temperature (typical for C18 amide derivatives)
  • Polarity: amphiphilic; nonionic headgroup (tertiary amide + primary alcohol) with a dominant hydrophobic C18 tail.
  • Solubility (qualitative, literature):
    • Water: very low at room temperature; dispersible with surfactants/cosolvents.
    • Organic solvents: soluble in hot alcohols (EtOH, i‑PrOH), chlorinated solvents, ether esters (EtOAc), and hydrocarbons upon warming; good solubility in polar aprotic solvents (DMF, DMSO).
  • Partitioning: high lipophilicity expected due to C18 chain (logP large; specific value not established for this compound in standard databases).
  • Melting range/softening: long‑chain fatty amide analogs typically soften between ~40–70 C depending on substitution (literature trend; specific MP for this compound not established).
  • Refractive index, density, dielectric constant, UV cutoff: Not established in literature for this exact compound.

• Notes for practitioners

  • Gentle heating (40–60 C) commonly reduces viscosity and aids dissolution in organic media. Sonication can assist preparation of stock solutions or emulsions. Verify any critical property for your use case on the item’s CoA/Spec Sheet.

Quality & Grades

• Item-specific quality details

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
  • UV cutoff, residual solvents, water/peroxide ppm, metals: Not specified for this item; refer to CoA/Spec Sheet.

• Understanding grade implications (general guidance)

  • Research grade fatty amide surfactants are typically assessed for assay (e.g., % by GC/HLPC or 1H NMR), acid value (free stearic acid), amide value, hydroxyl value (for the hydroxyethyl), and moisture (Karl Fischer). If HPLC/LC–MS applications are intended, low UV background and low nonvolatile residue are advantageous; however, such attributes must be confirmed on the item’s CoA.
  • Stabilizers are generally not required for saturated long‑chain amides; absence/presence of antioxidants (e.g., BHT) should be disclosed on the CoA if applicable.

• What to check on receipt (practical tips)

  • Visual: uniform waxy solid/paste without discoloration. Any rancid/oxidized odor or significant yellowing can indicate oxidative impurities (free acid/aldehydes).
  • Identity: confirm by NMR/IR (strong amide C=O ~1630–1680 cm−1; broad O–H 3200–3600 cm−1), MS (MW ~341.58), and, if needed, elemental analysis consistent with C21H43NO2.
  • Purity: assess by GC with high‑temperature column or HPLC with ELSD/CAD for non‑chromophoric materials; monitor residual stearic acid and secondary amides.

• Suitability by application class (general)

  • For materials/formulations research, assay and color are often primary. For analytical/reference use, tighter specs on identity/purity, residual solvents, and water content may be required—use the CoA to ensure fit for purpose.

Reaction & Applications

This tertiary fatty amide with a terminal primary alcohol is a versatile amphiphile for materials and surface‑science research.

• Research/formulation uses (general; expand on catalog category “life sciences”)

  • Nonionic surfactant/emulsifier: the C18 chain drives interfacial adsorption, while the hydroxyethyl amide headgroup provides hydrogen‑bonding capacity—useful in stabilizing oil‑in‑water emulsions or modifying micellar systems in method development.
  • Lubricity/antistatic additive: incorporation into polymer/wax matrices can reduce friction and modify surface energy due to oriented monolayer formation.
  • Crystal habit modifier: fatty amides can influence nucleation/growth of hydrophobic actives in crystallization studies.

• Transformations (synthetic leverage of this scaffold; literature)

  • Selective reduction of the amide carbonyl (e.g., BH3·THF, BH3·SMe2, or LiAlH4) affords N‑methyl‑N‑(2‑hydroxyethyl)stearylamine, a tertiary amine that can be further quaternized or protonated for cationic surfactant studies.
  • O‑functionalization of the hydroxyethyl group: esterification (acyl chlorides, anhydrides; DMAP or acid catalysis) to modulate HLB; carbonate or sulfonate formation (e.g., tosylate) to create leaving groups for subsequent nucleophilic substitutions.
  • Urethane/urethane network formation: reaction with isocyanates yields carbamates, enabling tethering onto polyurethanes as slip/compatibilizing additives.

• Analytical/characterization notes

  • IR: amide C=O band (ca. 1630–1680 cm−1), broad O–H stretch, and aliphatic C–H at 2850–2950 cm−1.
  • NMR: long methylene envelope (1.2–1.3 ppm), terminal CH3 (~0.88 ppm), N‑CH3 (ca. 2.8–3.1 ppm), CH2 adjacent to N and O (ca. 3.2–3.7 ppm), and OH (exchangeable).

• Practical tips

  • Ensure dry conditions for acylation/esterification steps; remove residual acids to prevent hydrolysis during storage. When reducing amides, prefer borane reagents for selectivity in the presence of the primary alcohol.

Reaction Conditions

The following conditions are general literature guidance for transformations of N‑hydroxyethyl‑N‑methylstearamide; they are not item‑specific specifications.

• Amide reduction to tertiary amine (literature)

  • Reagents: BH3·THF (1.5–3.0 equiv per amide) or BH3·SMe2; alternative LiAlH4 (2–4 equiv) if compatible with other groups.
  • Solvent: dry THF or 2‑MeTHF; 0–25 C addition, then 50–70 C for 4–18 h.
  • Workup: careful quench with MeOH/H2O at 0 C; extract into organic solvent; neutralize and dry.
  • Notes: borane is typically more selective than LiAlH4 in the presence of the primary alcohol.

• O‑Acylation (esterification of the hydroxyethyl group)

  • Reagents: acyl chloride or anhydride (1.1–1.5 equiv), base (pyridine, Et3N), catalytic DMAP (0.05–0.20 equiv).
  • Solvent: DCM, toluene, or 2‑MeTHF; 0–25 C for addition, then 25–60 C for 2–12 h.
  • Notes: ensure anhydrous conditions; monitor by TLC (UV inactive—use staining) or LC with ELSD/CAD.

• Carbonate formation

  • Reagents: triphosgene (substoichiometric) with alcohol and base, or dialkyl carbonates under transcarbonation with organocatalysts (TBD).
  • Conditions: 25–80 C depending on method; remove byproducts under reduced pressure.

• Tosylation/mesylation (activation as leaving group)

  • Reagents: TsCl or MsCl (1.1–1.5 equiv), base (pyridine or Et3N), catalytic DMAP; 0–25 C then 25–40 C for 1–6 h.

• Urethane formation with isocyanates

  • Catalyst: DBTDL (50–500 ppm) or organocatalysts; 25–60 C in dry toluene/2‑MeTHF.

• Typical yields (qualitative)

  • For O‑acylations and sulfonylations, good to excellent isolated yields are commonly reported for analogous long‑chain alcohols (60–90%), contingent on mixing/solubility. Always optimize for your system.

Safety & Handling

Safety information specific to this catalog item is limited in the Product Data. Always consult the SDS for authoritative guidance before use.

• Item-specific hazard data (from Product Data)

  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal word / Pictograms / H‑Statements: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (as provided).

• General hazards for long‑chain amide surfactant analogs (literature/general)

  • Expected to be of low volatility and low acute inhalation hazard; dust generation is minimal for waxy solids but avoid aerosolization of fine particulates.
  • May cause skin or eye irritation on contact; prolonged contact with molten material can cause thermal injury.
  • Combustible organic solid; combustible dust hazard is typically low but standard controls should be applied when milling/powdering.

• Handling recommendations (good laboratory practice)

  • PPE: lab coat, safety glasses or face shield, and chemical‑resistant gloves (e.g., nitrile). Use heat‑resistant gloves if working above the softening point.
  • Engineering controls: handle solids/pastes in a fume hood when heating or when using volatile solvents; provide local exhaust during transfers of hot melts or solutions.
  • Incompatibilities: strong oxidizing agents; strong acids or bases can promote hydrolysis/transamidation at elevated temperature.
  • First‑aid overview: rinse skin/eyes with water for ≥15 min upon contact; remove contaminated clothing; if inhaled (dust/aerosol), move to fresh air; if ingested, rinse mouth—seek medical attention in all cases. Follow SDS.

• Fire safety

  • Extinguishing media: dry chemical, CO2, foam. Cool containers with water spray. Thermal decomposition may emit CO/CO2; self‑contained breathing apparatus recommended for firefighters.

• Hygienic measures

  • Wash hands after handling; avoid eating/drinking in the work area; decontaminate tools that contact molten material.

Solvent Selection

N‑Hydroxyethyl‑N‑methylstearamide is amphiphilic yet strongly hydrophobe‑dominated; solvent choice should balance solvency for the C18 chain with compatibility for the polar headgroup.

• Polarity/miscibility (general/literature)

  • Water: very low intrinsic solubility; dispersible with surfactants, co‑solvents, or upon heating.
  • Alcohols: soluble in hot ethanol/isopropanol; often forms clear solutions above ~40–60 C depending on concentration.
  • Polar aprotics: good solubility in DMF, DMSO, NMP—useful for analytical solutions and polymer modifications.
  • Esters/ethers: soluble in ethyl acetate, 2‑MeTHF, and CPME on warming.
  • Hydrocarbons/chlorinated: soluble in toluene, xylene, and chlorinated solvents, especially when warmed.

• Practical selection by task

  • Stock solutions for bio‑materials research: DMSO or ethanol/propylene glycol blends allow meter‑scale dosing, sometimes followed by dilution into aqueous media with surfactants.
  • Coatings/polymer work: toluene, xylene, or ethyl acetate provide fast evaporation; 2‑MeTHF or CPME are greener alternatives to THF/Et2O with comparable solvency for long‑chain amides.
  • Thermal processing: melt‑mixing into polymers or wax matrices avoids solvents entirely.

• Small comparison (general)

  • DMSO vs EtOH: DMSO provides higher solvency at room temperature; ethanol may require heating but offers easier removal and lower toxicity profile.
  • Toluene/xylene vs 2‑MeTHF/CPME: aromatics give strong hydrophobe solvency; 2‑MeTHF/CPME can be preferable for greener workflows with adequate performance.

• Tips

  • Warm and stir to accelerate dissolution; avoid excessive heating that could promote hydrolysis in the presence of water/strong acid/base. Use mild vacuum to remove high‑boiling solvents post‑processing if thermal sensitivity is a concern.

Storage & Reconstitution

• Item-specific storage/shipping

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (applicable to long‑chain amide waxes)

  • Keep tightly closed in a dry, well‑ventilated place away from strong oxidizers. Protect from prolonged exposure to heat and direct sunlight to minimize discoloration or oxidative byproducts.
  • For long‑term storage, containers with minimal headspace and inert gas blanketing (nitrogen) can help preserve color/odor, although saturated C18 amides are comparatively oxidation‑resistant.
  • If partial solidification or phase separation occurs, gently warm (40–60 C) and mix to restore uniformity before use.

• Reconstitution and solution handling

  • To prepare concentrated stock solutions, warm solvent (e.g., ethanol, isopropanol, DMSO, 2‑MeTHF) to 40–60 C and add the solid with stirring until fully dissolved; filter warm solutions through PTFE membranes if clarity is required.
  • For aqueous dispersions, pre‑dissolve in a suitable cosolvent and introduce into the aqueous phase under shear while maintaining temperature above the softening point.

• Stability notes

  • The tertiary amide is hydrolytically robust under neutral conditions; avoid strong acids/bases at elevated temperature to prevent hydrolysis/transamidation.
  • Freeze–thaw is generally not relevant for the neat solid; for formulated dispersions, minimize cycles to avoid phase separation.

Always consult the SDS and the item’s CoA/Spec Sheet for definitive handling and storage instructions.

Structure & Identity

N‑Hydroxyethyl‑N‑methylstearamide is a fatty‑acid–derived tertiary amide bearing a long, saturated C18 aliphatic chain and a pendant primary alcohol.

• Item-specific identifiers (Product Data)

  • SKU: N970453
  • CAS: 35699-24-2
  • InChIKey: 364962 (as provided; note this does not follow the standard 27-character InChIKey format)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structure information (general; not item-specific specifications)

  • Preferred IUPAC-style name (descriptive): N-methyl-N-(2-hydroxyethyl)octadecanamide (literature)
  • Molecular formula (computed from structure): C21H43NO2 (literature/computed)
  • Molecular weight (computed): ~341.58 g/mol (literature/computed)
  • Core functional groups: tertiary amide [–C(=O)–N(CH3)–CH2CH2OH], primary alcohol (on the hydroxyethyl), saturated C18 alkyl chain (stearoyl).
  • Stereochemistry: None (all atoms achiral in the parent chain; no defined stereocenters).

• 2D structural description (verbal)

  • A linear C18 alkyl chain (CH3–(CH2)16–CH2–) terminates at a carbonyl carbon forming an amide. The amide nitrogen bears two substituents: a methyl group and a 2‑hydroxyethyl group (–CH2–CH2–OH). No additional rings or unsaturations are present beyond the amide carbonyl.

• Structural features and implications (general knowledge)

  • Amphiphilic motif combining a hydrophobic tail and polar headgroup (amide + alcohol), consistent with nonionic surfactant behavior and interfacial activity in formulations and materials research.

Synthetic Utility

The scaffold combines a tertiary amide (electrophilically inert under many conditions) with a terminal primary alcohol that is readily derivatized—useful for building amphiphilic materials and surfactant libraries.

• Functional handles and typical transformations (literature/general)

  • O‑Derivatization: form esters (acyl chlorides/anhydrides, EDCI/DMAP) to modulate polarity and HLB; install carbonates (e.g., with phosgene alternatives like triphosgene or organic carbonates) for degradable linkers; convert to sulfonates (tosylate/mesylate) for subsequent SN2 substitutions creating ether derivatives.
  • Amide reduction: BH3·THF or BH3·SMe2 selectively reduces the amide to the tertiary amine without affecting the alcohol, yielding N‑methyl‑N‑(2‑hydroxyethyl)stearylamine—a precursor to cationic surfactants (via quaternization) or zwitterions.
  • Crosslinkable motifs: reaction of the alcohol with diisocyanates or diepoxides enables incorporation into polyurethane or epoxy networks as a flexible, hydrophobe‑rich side chain.

• Retrosynthetic value

  • Serves as a branch point to probe structure–property relationships across fatty amide amphiphiles by systematic variation at the O‑substituent while keeping the stearoyl tail constant.

• Characterization strategies

  • O‑acylation/etherification progress is conveniently tracked by disappearance of the O–H signal in 1H NMR and changes in IR (loss of broad OH, emergence of new C=O or S=O bands). For amide reduction, monitor by IR (loss of amide C=O) and 13C NMR (carbonyl carbon absence).

• Practical notes

  • Use dry, oxygen‑limited conditions for derivatizations to minimize side hydrolysis/oxidation of long‑chain substrates. For viscous reaction media, employ high‑solids mixing, overhead stirring, and moderate heating (40–80 C) to maintain homogeneity.

Target Specificity

Not applicable. This product is a small‑molecule fatty amide, not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular specificity). No antigen/epitope, clone, isotype, or species reactivity attributes apply.