This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
208.210 g/mol
XLogP3
0.100
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
208.085 Da
Monoisotopic Mass
208.085 Da
Topological Polar Surface Area
78.400 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
225.000
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
Lösungsrechner
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Application Protocols
Not applicable. No tested bioassay or analytical protocols are provided for this item. For use in your workflow:
Prepare stock solutions in DMSO, DMF, or ethanol based on solubility screening.
Filter through 0.2 µm PTFE before use in analytical systems to remove particulates.
For solid-state studies, dry under high vacuum prior to weighing to ensure accurate mass and consistent crystallization behavior.
Refer to your internal SOPs; no item-specific protocols are supplied.
Biological Roles
Applicability note: This is a synthetic small molecule intended for research use only; no biological activity or clinical claims are made for this item.
General context (literature; not item-specific claims)
Amide functionality: Amide linkages are pervasive in biomolecules (peptides, proteins) and contribute to conformational stability via resonance and hydrogen bonding.
Oxalamide motif: Known in supramolecular chemistry as a bidentate H-bonding unit that can mediate self-assembly and host–guest interactions; used as a scaffold to study hydrogen-bond-driven recognition in aqueous or mixed solvents.
Hydroxyethyl substituent: Provides increased hydrophilicity and potential for additional H-bonding or covalent attachment to biomaterials (e.g., via carbonate/urethane formation) in research settings.
Phenyl group: Offers an aromatic probe for spectroscopic studies (UV absorbance in near-UV) and can modulate lipophilicity in model membrane partitioning experiments.
Potential research uses in biochemistry (non-clinical)
Model compound for studying amide hydrogen exchange rates by NMR.
Calibration or training sample for chromatographic methods (reversed-phase retention vs. H-bonding capacity).
Building block for preparing conjugates to polymers or surfaces for biointerface research via the terminal OH.
All biological context above is general literature knowledge and not a statement of performance or suitability for any specific biological assay.
Buffer Applications
Not typically applicable. N-(2-hydroxyethyl)-N'-phenylethanediamide is not a buffering agent and does not constitute a standard acid/conjugate base pair with a well-defined pKa window for buffer preparation.
Practical guidance
If dissolution in aqueous buffers is required for a study, prepare concentrated stock solutions in DMSO, DMF, or ethanol, then dilute into the buffer with vigorous mixing to avoid precipitation. Assess solubility empirically across pH 2–10.
Common biological buffers (PBS, HEPES, Tris) may be used as media for testing, but the compound itself does not provide buffering capacity.
For quantitative buffer recipes and pH control, select purpose-designed buffers (e.g., phosphate pH 6–8, HEPES pH 6.8–8.2, acetate pH 3.6–5.6).
Green Alternatives
Perspective: While the compound itself is a research substrate rather than a solvent or reagent to be “replaced,” greener choices can be made for its synthesis, manipulation, and purification.
Greener solvent choices (literature guidance)
Replace DMF/NMP with more benign polar aprotics when feasible:
Substitute DCM with EtOAc or 2-MeTHF for many acylations/extractions.
Crystallization/workup:
Favor ethanol or isopropanol over methanol where solubility allows.
Comparison (qualitative, literature)
2-MeTHF vs THF: 2-MeTHF is bio-based, higher boiling (safer distillation), and more hydrophobic—useful for phase splits; THF is fully miscible with water and may be preferred for homogeneous conditions.
EtOAc vs DCM: EtOAc is biodegradable and less toxic; higher boiling point may lengthen evaporation times.
Cyrene vs DMF: Cyrene mimics DMF polarity without the same reproductive toxicity profile; higher viscosity may impede mass transfer in large-scale operations.
Process-intensity considerations
Use catalytic promoters (DMAP, TBD) to reduce stoichiometric activators.
Telescoping: Combine activation and coupling steps to minimize isolations and solvent swaps.
Energy: Leverage room-temperature couplings and mechanochemistry (ball milling) to cut solvent volumes (emerging literature).
Note: No item-specific process data are provided; adapt green alternatives after bench solubility screens and pilot trials.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item; it is supplied strictly for research use only.
General formulation context (literature; not item-specific claims)
Role in discovery workflows: Amide-rich linkers like oxalamides are explored as structural motifs in early-stage medicinal chemistry. This compound may serve as a research intermediate for SAR exploration or conjugation to polymers/surfaces via its hydroxyethyl group.
Solubilization strategies for formulation studies: Co-solvents (ethanol, PEG 400), cyclodextrin inclusion, or formation of salts/ion pairs is generally not applicable here due to neutral functionality; instead, rely on co-solvents and nanosuspension approaches if aqueous delivery is required for non-clinical testing.
Analytical development: The aromatic ring facilitates UV detection (210–230 nm) for HPLC method development; confirm linearity and extinction in your matrix.
Regulatory note
No compendial monograph, dosage form, or clinical use is implied. Any use must remain within non-clinical, laboratory-scale research.
Physical Properties
Item-specific specifications
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 (for context; not item specifications)
Typical MW (from name-based inference): ~208.22 g/mol for C10H12N2O3
Hydrogen-bonding: 2× amide C=O acceptors, 2× amide N–H donors, 1× alcohol donor/acceptor; often leads to high melting point and low volatility
Solubility profile (qualitative, literature):
Likely sparingly soluble in water, but enhanced by H-bonding; more soluble in polar protic and dipolar aprotic solvents (MeOH, EtOH, DMSO, DMF)
Poor solubility expected in nonpolar solvents (hexanes, toluene) unless warmed or with co-solvent
Partitioning: logP expected to be low-to-moderate (aromatic ring increases lipophilicity; three heteroatoms decrease it)
UV characteristics: aromatic phenyl ring absorbs in near-UV (typical λmax ~200–230 nm, shoulder ~250–270 nm; literature, qualitative)
Thermal behavior: amide-rich solids often exhibit decomposition near/above melting; drying under high vacuum at ≤40–50 °C is customary prior to analysis (general practice)
Notes
Exact numerical values (mp, bp, density, pKa, refractive index, water content) are not specified for this item; refer to CoA/Spec Sheet. Always verify solvent and temperature dependence experimentally.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general)
Research grade: Suitable for most synthetic and analytical workflows. If your application is moisture/trace-metal sensitive (organometallics, catalysis), request a CoA with residual water, metals, and LC/HPLC purity.
HPLC/LC-MS suitability: For UV/LC detection, aromatic amides typically show clean UV profiles. If using as an internal standard or analyte, confirm low non-volatile residue and UV cutoff. Item-specific UV data are not provided here.
Impurity considerations for oxalamides (general):
Possible residuals: starting amines (aniline, 2-aminoethanol), mono-oxalamide congeners, over-acylated species (carbonate/oxalate esters), and inorganic salts from coupling bases.
Recommended QC: 1H/13C NMR (amide NHs, carbonyls at ~155–165 ppm), IR (amide I/II bands), HRMS for exact mass, HPLC purity with diode-array to check aromatic absorbers.
Batch-to-batch control: Document water content (KF), residual solvents (GC), and polymorph/solid form if relevant; request orthogonal identity tests (NMR + MS).
Contact Aladdin Scientific for the latest CoA/Spec Sheet to obtain definitive grade, purity, and test methods for SKU N938237.
Reaction and Applications
This oxalamide bearing both an N-phenyl and a 2-hydroxyethyl substituent serves as a versatile, bifunctional building block for research synthesis.
Two amide carbonyls and two NHs offer dense H-bonding; amide activation is possible under dehydrative coupling (e.g., CDI, EDC/HOBt) to form imidates or mixed anhydrides, though the oxalamide core is relatively inert to mild nucleophiles.
The N-phenyl group imparts aromatic character—electrophilic aromatic substitution is feasible only under forcing conditions; cross-coupling would require prefunctionalization (not present here).
Representative application domains
Linker chemistry: Oxalamides are used as rigid, H-bonding linkers in supramolecular assemblies and polymer conjugates.
Probing H-bond networks: Serves as a model compound for studying intramolecular vs. intermolecular H-bonding in solids and solutions.
Precursor to cyclic carbamates/oxazolidinones: Conversion of the 2-hydroxyethyl to an activated leaving group followed by intramolecular cyclization onto an amide-derived center (under specific activation) can generate heterocycles (method-dependent).
Practical tips
Drying: Because of strong H-bonding, residual solvent and water can be retained; dry under high vacuum at ≤40–50 °C before analytical work.
Protection strategies: The alcohol can be protected (e.g., TBDMS, acetyl) when performing amide-directed transformations.
Analytics: Assign NH/OH by variable-temperature 1H NMR or D2O shake; carbonyls typically appear ~158–164 ppm in 13C NMR for oxalamides (literature ranges).
Reaction Conditions
General literature guidance for related transformations (not item-specific specifications)
Formation of N-(2-hydroxyethyl)-N′-phenyl oxalamide
Route A (sequential acyl chloride amidation): Generate oxalyl chloride mono-activated intermediate or bis-oxalyl chloride from oxalic acid; couple first with 2-aminoethanol (base: Et3N, pyridine) in DCM or THF at 0–25 °C, then with aniline under similar conditions to form the asymmetric oxalamide. Control stoichiometry and order to limit symmetric byproducts. Typical times: 1–4 h per step; work cold to suppress overacylation.
Route B (CDI-mediated): Activate oxalic acid or oxamide derivative with CDI in DMF/THF, then add 2-aminoethanol followed by aniline. Temperatures 0–25 °C; catalytic DMAP can accelerate O-acyl side reactions—monitor by TLC/HPLC.
Downstream derivatizations
Tosylation of the alcohol: TsCl (1.1–1.5 eq), pyridine or Et3N, DCM 0–25 °C, 1–3 h; isolate as the tosylate for displacement.
Carbonate formation: React with p-nitrophenyl chloroformate (1.1–1.3 eq) in DCM with base at 0–25 °C to yield activated carbonates for coupling with nucleophiles.
Hydrolysis (stability testing): Aqueous base (e.g., 1–2 M NaOH) at reflux can cleave amide linkages over hours; acidic hydrolysis typically slower. Such conditions are for stress testing, not routine handling.
Solvents and atmosphere
Prefer anhydrous DCM, THF, MeCN, or DMF for couplings; nitrogen/argon atmosphere improves reproducibility with acid chlorides.
Expected yields
Literature for asymmetric oxalamide couplings often reports 50–80% isolated yields after chromatographic separation from symmetric side products; actual yields depend on order of addition and purification strategy.
Safety and Handling
Item-specific safety data
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General safety guidance for amide/aryl alcohol solids (literature; not item-specific)
Hazards: Neutral, non-volatile amides are generally of low acute volatility hazard; dust may cause mechanical irritation to eyes/respiratory tract. Avoid ingestion and skin/eye contact.
PPE: Laboratory coat, safety glasses, and nitrile gloves. Use a dust mask or work in a fume hood if powdering or weighing fine solids.
Handling: Minimize dust formation. Use clean, dry tools. For solution work, prefer closed vessels; purge with inert gas if moisture-sensitive transformations are planned.
Incompatibilities: Strong oxidizers (may affect the benzylic/aromatic moieties under forcing conditions), strong acids/bases can promote hydrolysis or transamidation upon heating; reactive acid chlorides/anhydrides without base can acylate the hydroxy group.
First aid (overview; defer to SDS):
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Organic solid; combustible. Use CO2, dry chemical, or foam. Thermal decomposition may release CO/CO2 and nitrogen oxides.
Always consult the product-specific SDS for authoritative hazard classification and response.
Solvent Selection
Relevance: This compound is a polar, hydrogen-bond-rich organic solid. Solvent choice matters for dissolution, crystallization, and downstream transformations at the hydroxy or amide sites.
Polarity and miscibility (literature guidance)
Preferred solvents for dissolution: DMSO, DMF, NMP, methanol, ethanol, isopropanol.
Moderately suitable with heating or co-solvent: acetonitrile, ethyl acetate, acetone.
Generally poor: nonpolar hydrocarbons (hexanes, heptane) and weakly polar aromatics (toluene) unless cosolvated.
Dielectric considerations
High dielectric solvents (DMSO, DMF, MeOH) disrupt the amide H-bond network and improve solubility. Water co-solvent can be used, but complete aqueous dissolution may be limited.
Use-case recommendations
NMR: DMSO-d6 or CD3OD typically provide sharp resonances for NH/OH; CDCl3 may give broadening/insolubility.
Recrystallization: EtOAc/EtOH or EtOAc/hexanes (with polar modifier) are common starting points; optimize empirically.
Reactions at the OH (e.g., tosylation/esterification): dichloromethane, THF, or MeCN with base; include catalytic DMAP as needed.
Amide transformations (hydrolysis/coupling): polar aprotics (DMF, DCM) or biphasic systems, depending on reagent.
Small comparison (literature, qualitative)
DMSO vs DMF: DMSO gives superior solubility and NMR behavior; DMF easier to remove and less viscous.
MeOH vs EtOH: MeOH dissolves better; EtOH preferred for workup and lower toxicity profile.
Note: No item-specific UV cutoff, water content, or stabilizer information is provided; verify compatibility with moisture- or base-sensitive reagents experimentally.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data). Keep tightly closed.
General handling and reconstitution (literature guidance)
Protect from moisture: Although amides are not highly hygroscopic, the hydrogen-bonding network can retain adventitious water. Store in a dry place with desiccant.
Light: The aryl group is not overtly photosensitive, but standard protection from prolonged light is prudent to avoid discoloration.
Solution stability: In aprotic solvents (DMSO, DMF, MeCN, DCM), solutions are typically stable for days at ambient conditions. For long-term storage, keep solutions at 2–8 °C and under inert gas; inspect for precipitation or degradation before use.
Reconstitution: For analytical or biological assays, dissolve in DMSO (common high-solubility choice) to prepare concentrated stocks (e.g., 10–100 mM), then dilute with compatible media. If using alcohols (MeOH/EtOH), verify final solvent tolerance of your system.
Freeze–thaw: Store aliquots to minimize freeze–thaw of solutions. Solid material tolerates ambient temperature storage; avoid repeated warming of chilled solutions to reduce moisture uptake.
Shipping
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Always follow your institution’s chemical storage and waste disposal policies and consult the SDS for definitive stability and compatibility information.
Structure and Identity
Brief description: N-(2-hydroxyethyl)-N'-phenylethanediamide is an asymmetrically N,N′-disubstituted oxalamide featuring one N-phenyl and one N-(2-hydroxyethyl) substituent on the oxalamide core (–NH–CO–CO–NH–).
Item-specific identifiers (from Product Data)
CAS: 69433-42-7
CID: 2249822
InChIKey: 244758 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Representative SMILES (literature): O=C(C(=O)N(Ph))NCCO or more explicitly: O=C(C(=O)N(c1ccccc1))NCCO
2D structure in words
Two adjacent carbonyl carbons (oxalamide backbone). One amide nitrogen is bound to a phenyl ring and hydrogen; the other amide nitrogen is bound to a 2-hydroxyethyl chain and hydrogen. The terminal hydroxyl provides an additional hydrogen-bond donor/acceptor site, while both amide carbonyls and NHs afford a dense H-bonding array.
Synthetic Utility
Strategic features (literature)
Bifunctional handle set: A terminal primary alcohol (–CH2CH2OH) and an oxalamide core with two carbonyls and two NH donors provide orthogonal chemistry for stepwise elaboration.
H-bond-dense scaffold: Useful as a recognition element in supramolecular assemblies, organogels, and crystal engineering studies.
Representative transformations
Alcohol derivatization: Formation of mesylate/tosylate followed by SN2 to install azides, halides, or amines; carbonate and carbamate formation using chloroformates or CDI + alcohol/amine partners.
Cyclization: Conversion of the 2-hydroxyethyl arm to oxazolidinone-like motifs via activation and intramolecular nucleophilic attack (conditions vary; often require carbonyl activation and base).
Amide editing: Though amide bonds are robust, oxalyl derivatives can be selectively activated (e.g., with POCl3, SOCl2, or CDI) to access imidazoles, mixed anhydrides, or to perform stepwise N-acyl migrations.
Conjugation: The hydroxyethyl group enables attachment to polymers (PEGylation analogs via carbonate/urethane linkages) and surface immobilization chemistries (silica, resins) for affinity materials.
Analytical cues for route confirmation
IR: Amide I ~1640–1690 cm−1; Amide II ~1530–1560 cm−1; broad O–H 3200–3500 cm−1.
NMR: Distinct NH signals (often broad; temperature- and solvent-dependent), benzylic/aryl resonances 7.0–7.6 ppm; –CH2–CH2–OH around 3.4–4.0 ppm in 1H.
These are general literature practices; optimize protections and order of operations to avoid undesired acyl transfers.
Target Specificity
Not applicable. This product is a small-molecule research chemical and is not an antibody, enzyme, or affinity reagent. No target, epitope, species reactivity, clone, or isotype information applies.
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