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Proprietà chimiche e fisiche
Peso molecolare
130.190 g/mol
XLogP3
-0.600
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Exact Mass
130.111 Da
Monoisotopic Mass
130.111 Da
Topological Polar Surface Area
41.100 Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
83.100
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
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Recensioni
Recensioni dei clienti
Application Protocols
No tested biological assay protocols (e.g., WB, IHC, IF, FC) are provided for this item. Typical usage is as a synthetic intermediate or building block. For chemical applications, follow standard organic synthesis protocols appropriate to amines/amides (e.g., acylation, reductive amination, salt formation) and consult the Reaction Conditions and Synthetic Utility sections for guidance.
If preparing solutions for screening or reactions:
Prepare stock solutions in DMSO, MeOH, or water (as protonated salt) as needed; filter if particulate is present.
Verify concentration by weight and, if required, by quantitative NMR or UV (if a suitable chromophore is introduced in an assay context).
Always adapt procedures to your specific substrates and consult primary literature.
Biological Roles
Item-specific note
Category Path indicates life science relevance, but no biological function is specified. Research Use: For research use only.
General biochemical context (not product-specific, no medical claims)
3-ethylamino-N-methyl-propanamide is not a known endogenous metabolite or cofactor. As a small, polar, H-bonding molecule, it can serve as a fragment or motif in probe/ligand design where an amide–amine arrangement modulates solubility, basicity, and binding through dual donor/acceptor interactions.
The secondary amine (likely pKa ~9–10, literature) will be predominantly protonated near physiological pH, potentially enhancing interactions with acidic residues (Asp/Glu) in protein active sites when incorporated into larger ligands.
The N-methyl amide can influence conformational preferences (cis/trans rotamers) and reduce H-bond donor count versus a primary amide, often used strategically to tune permeability and solubility in medicinal chemistry scaffolds.
Practical lab implications
In biochemical assays, the free base may alter pH; prepare buffered solutions and consider using defined salt forms (e.g., HCl) for reproducible potency measurements.
High aqueous compatibility (as protonated species) facilitates screening in enzyme or receptor assays when embedded in small-molecule libraries.
No specific biological pathways, targets, or activities are assigned to this item by the manufacturer; consult the primary literature for structure–activity relationships of related amide–amine motifs.
Buffer Applications
This compound is not a standard buffering agent and is not typically used to prepare defined buffer systems.
Practical notes (general)
The secondary amine could, in principle, provide limited buffering capacity around its conjugate acid pKa (literature: ~9–10 for typical secondary aliphatic amines), but the presence of the amide and lack of standardized titration data make it unsuitable as a reference buffer.
For experiments requiring controlled pH, use established buffers (Tris, HEPES, MOPS, phosphate). The compound may be dissolved in those buffers for biological assays as needed.
Recommendations
If aqueous handling is required, prepare solutions in an appropriate buffer and verify pH after addition, especially at millimolar-to-higher concentrations where the protonated amine can shift pH.
Consider using a defined salt form (e.g., hydrochloride) for consistent pH impact and solubility.
Buffer formulations, buffering ranges, and recipes are not applicable to this item beyond dissolution in an external, validated buffer.
Green Alternatives
This product is a reagent/building block rather than a process solvent; “greener alternatives” pertain to the media and auxiliaries used with it.
Greener solvent choices (general guidance)
Replace DMF/NMP with MeCN, EtOAc, 2-MeTHF, CPME, or propylene carbonate where mechanistically acceptable.
Use ethanol/i-PrOH or water–ethanol mixtures for salt formation/crystallization and work-ups when feasible.
For amide couplings, consider aqueous micellar media (e.g., TPGS-750-M) or EtOAc with green coupling reagents.
Reagent and process alternatives
Amide couplings: prefer carbodiimide (EDC·HCl) with Oxyma/HOAt alternatives avoiding HOBt hazards; or enzyme-catalyzed couplings in water for sensitive substrates.
Reductive aminations: switch from NaBH3CN (CN-containing) to NaBH(OAc)3, or catalytic hydrogenation (H2/Pd, H2/Raney Ni) under controlled conditions.
Comparison snapshot (general)
DMF vs 2-MeTHF: similar polarity for many couplings; 2-MeTHF offers renewable sourcing and easier removal but may require higher temperatures.
DCM vs EtOAc: EtOAc is less hazardous and biodegradable; may need larger volumes due to solubility differences.
Waste minimization
Employ telescoped steps (e.g., in situ salt formation/crystallization) and aqueous extractions optimized for amines (pH swings) to reduce solvent usage.
Note: Select alternatives based on reaction compatibility with secondary amines/amides and required selectivity.
Pharmaceutical Uses
Item-specific status
No pharmacopeial grade or excipient designation is provided. Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
For research use only. Not for human or veterinary use.
General formulation/manufacturing context (no therapeutic claims)
As a small amide/amine building block, this compound may serve as an intermediate in the synthesis of drug candidates or as a fragment in SAR programs. Its secondary amine allows salt formation (e.g., HCl, mesylate, sulfate) to tune crystallinity and processability of intermediates.
The N-methyl amide contributes to polarity without adding a strong basic site, which can be leveraged to balance permeability and solubility in lead optimization when incorporated into larger APIs.
Handling considerations in process R&D (general)
Hygroscopicity and CO2 uptake (common for amines) can impact assay on scale; control atmosphere during weighing and store tightly capped.
Choice of counterion for salt intermediates should consider hygroscopicity, filterability, and downstream displacement (e.g., volatile acids for easy removal).
No compendial monographs or excipient roles are asserted for this specific item.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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 values (typical for the named structure; not product specifications)
Empirical formula (derived from name): C6H13N2O
Formula weight (calculated): ~129.18 g/mol
Acid-base properties: one secondary amine (conjugate acid pKa typically ~9–10 for unhindered aliphatic secondary amines); amide N is non-basic; amide carbonyl pKa (for deprotonation) extremely weakly acidic (not practical).
LogP/logD: expected low logP (hydrophilic) as a free base; logD strongly pH-dependent (protonated under acidic to neutral aqueous conditions).
Solubility (qualitative, literature expectation): very soluble in polar protic and aprotic solvents (water, alcohols, DMSO); forms water-soluble salts with mineral acids.
High H-bond donor/acceptor count implies strong solvation in polar media.
Protonation state will dominate handling in aqueous systems; expect cationic form near physiological pH, enhancing aqueous solubility.
Note: Definitive physical constants (mp, bp, density, refractive index, UV cutoff, residual water/peroxide/metals) are Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific status
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers, inhibitors, or additives: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades (general information)
Research grade: suitable for most synthetic and discovery workflows; impurity profiles may include traces of residual solvents and related amines/amides.
Analytical/GC/HPLC grade (when applicable): emphasizes low non-volatile residue and low UV background—useful if the compound is deployed as a reference or in trace analytical work.
Pharmaceutical/USP/EP grade: not applicable unless specifically stated on CoA/spec; would require compendial testing and documentation.
Quality considerations specific to amide/amine building blocks (general)
Assay/purity: verify by 1H/13C NMR and LC–MS; amide rotamers can broaden NMR signals—variable-temperature NMR can help.
Identity confirmation: high-resolution MS and, if a salt form is used, confirm counterion content.
Residual water and protic impurities: can influence reactivity in coupling/activation steps; Karl Fischer may be relevant if moisture-sensitive downstream chemistry is planned.
Amines can absorb CO2 to form ammonium carbamates; brief drying under vacuum can restore free base prior to use.
Refer to the Aladdin Scientific CoA/Spec Sheet for this specific lot’s assay, impurity limits, and analytical methods.
Reaction and Applications
Functional profile
Bifunctional handle combining a secondary amine (nucleophilic, basic) and a secondary amide (polar, weakly nucleophilic; H-bond donor/acceptor). The two-carbon spacer enables intramolecular or tethering strategies.
Amide N-modification: conversion to tertiary amides via alkylation (e.g., Eschweiler–Clarke not applicable to amides; use alkyl halides with strong base, or acyl activation for N→C rearrangements in advanced settings).
Amine derivatization: acylation to give diamide derivatives; carbamate formation (e.g., with chloroformates) to transiently mask basicity for chromatographic handling.
Reductive alkylation: condense the amine with aldehydes/ketones followed by NaBH3CN or H2/Pd to access tertiary amines.
Urea/sulfonamide formation: treat with isocyanates or sulfonyl chlorides to prepare ureas/sulfonamides, useful in SAR libraries.
Coupling as a spacer: the terminal amide can serve as a polarity anchor while the amine engages in coupling (EDC/HATU/HBTU) to carboxylic acids, yielding diamide-linked constructs.
Medicinal chemistry context (general)
The amide contributes to aqueous solubility and H-bonding patterns; the secondary amine affords tunable pKa/logD via salt selection or N-alkylation, aiding ADME optimization.
Practical tips
Drying: brief high-vacuum or co-evaporation with toluene can remove adventitious water before moisture-sensitive couplings.
Base choice: for SN2 alkylations, use K2CO3/Cs2CO3 in MeCN/acetone; for acylations, use non-nucleophilic bases (DIPEA, triethylamine).
Avoid over-alkylation by using limiting electrophile or transient protection of the amine.
Reaction Conditions
General conditions below are literature-based guidance for this functional motif; they are not product specifications.
Acylation of the secondary amine
Typical: acid chloride or activated acid (EDC/HATU + base) in DCM, DMF, or MeCN; base such as DIPEA or Et3N; 0–25 °C; 1–4 h. Monitor to avoid over-acylation.
Reductive amination to form tertiary amines
Carbonyl partner (aldehyde/ketone) in MeOH/MeCN with NaBH(OAc)3 (acetic acid additive, pH ~5–6) at rt for 2–16 h; or H2 (1–5 bar)/Pd-C in EtOH at rt–40 °C.
Sulfonylation/carbamoylation
TsCl or MsCl with base (Et3N, NaHCO3) in DCM or MeCN at 0–25 °C; 1–3 h.
Chloroformates (e.g., Boc2O or ethyl chloroformate) in DCM with base at 0–25 °C for carbamates/protection.
SN2 alkylation of the amine
Alkyl bromide/iodide (1.0–1.5 equiv) with K2CO3/Cs2CO3 in MeCN or acetone at 25–50 °C for 2–12 h; minimize dialkylation by stoichiometry and slow addition.
Amide stability and transformations
The N-methyl amide is robust to moderate base/acid; avoid strong dehydrating agents unless activation is intended. Lactamization or rearrangement requires specific activating reagents and elevated temperatures.
Work-up notes
Acid/base extraction: protonate amine with 1–2 M HCl to transfer to aqueous; basify to liberate free base for extraction with EtOAc/MTBE.
Drying agents: Na2SO4 or MgSO4; avoid prolonged exposure to strong bases that can lead to amide hydrolysis under forcing conditions.
Safety and Handling
Item-specific hazard data (from Product Data)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification and pictograms: Not specified for this item; refer to SDS.
General safety guidance for small aliphatic amides/amines (literature; not product-specific)
Likely hazards: may cause skin/eye irritation and respiratory irritation; secondary amines can be sensitizers in some cases. Avoid inhalation, ingestion, and contact.
PPE: lab coat, nitrile gloves, safety goggles; work in a fume hood to minimize exposure to vapors/aerosols.
First aid (overview):
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Incompatibilities: strong oxidizers; acid chlorides/anhydrides and isocyanates (reactive with amine); strong acids/bases can lead to salt formation or hydrolysis under forcing conditions.
Secondary amines can nitrosate in the presence of nitrosating agents under acidic conditions—avoid contact with nitrite sources in acid.
Handling/storage best practices
Store tightly closed at room temperature (per Product Data), protected from moisture and CO2 (to avoid adventitious salt formation) and from strong oxidants.
For weighing/transfer, minimize air exposure if long-term purity is critical; inert gas blanket is optional.
Always consult the product’s SDS for authoritative hazard classifications and response measures.
Solvent Selection
This product is a polar, hydrogen-bonding organic base (secondary amine) combined with a polar amide. It is not used as a solvent itself; solvent choice pertains to its use in reactions or formulations.
Polarity and miscibility (literature expectations)
Highly polar; expected to be freely miscible with water as the protonated form; good solubility in MeOH, EtOH, i-PrOH, DMSO, DMF, and acetonitrile.
Limited solubility anticipated in nonpolar hydrocarbons unless co-solvents are used or the amine is protected.
Choosing media for typical operations
N-acylation/amide couplings: DMF, NMP, DCM, or MeCN with base; for greener profiles, consider 2-MeTHF or EtOAc when compatible.
Alkylation of the secondary amine: polar aprotic solvents (MeCN, acetone, DMSO) facilitate SN2; control base to minimize over-alkylation.
Salt formation/crystallization: ethanol/ether/MTBE or EtOAc/hexanes mixtures often enable isolation of amine salts (HCl, HBr, TsOH).
Brief comparison (general)
DMF/DMSO: maximal solubilization of polar substrates; harder work-up and EHS concerns.
MeOH/EtOH: greener, facile work-up, but may engage in transesterification or H-bonding that slows some reactions.
2-MeTHF/EtOAc: greener, good for extractions and crystallizations; may require co-solvent to fully dissolve the free base.
Consult your reaction’s compatibility with amines and amides when selecting solvent and base.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance/state: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (amines/amides)
Keep tightly closed in a dry, well-ventilated place. Protect from moisture and CO2 to avoid adventitious salt/carbamate formation.
For long-term storage, consider an inert atmosphere (nitrogen/argon) and desiccant. Avoid strong oxidizers in proximity.
Reconstitution and solution handling
Solubility: readily soluble in polar organic solvents (DMSO, MeOH, EtOH) and aqueous acidic media as a salt (literature expectation).
To prepare aqueous stocks, dissolve the material in a minimal volume of water or water–alcohol, optionally adding a stoichiometric acid (e.g., HCl) to form a clear salt solution. Verify pH and adjust to target.
Filter solutions (0.22 µm) for sterile applications; store aliquots at 2–8 °C if extended storage is needed. Avoid repeated freeze–thaw of aqueous solutions.
Stability monitoring
Check by LC–MS or NMR periodically if stored for extended periods; look for signs of oxidation or amide hydrolysis under harsh conditions.
Refer to the product’s CoA/Spec Sheet for any lot-specific storage notes and the SDS for safety-related storage instructions.
Structure and Identity
Brief description: 3-ethylamino-N-methyl-propanamide is a small bifunctional molecule containing a secondary amide (N-methyl) and a secondary aliphatic amine (ethylamino) separated by a two-carbon linker.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "112446", which is not a standard InChIKey format.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature
Literature/computed identity details (for reference; not item specifications)
Suggested molecular formula: C6H13N2O (derived from the name)
Approximate molecular weight: ~129.18 g/mol (computed from formula)
Representative (non-authoritative) SMILES describing the named structure: O=C(NC)CCNCC (depicts an N-methyl amide linked via –CH2–CH2– to a secondary ethylamino group)
Structural features (general chemistry)
Functional groups: secondary amide (–CONH–) methylated on N; secondary amine (–NH–) bearing an ethyl substituent.
Connectivity (2D description): carbonyl carbon (amide) –CH2–CH2–NH–CH2–CH3, with the amide nitrogen substituted by –CH3.
Hydrogen-bonding capacity: one amide carbonyl acceptor; one amide N–H donor; one secondary amine N–H donor; the amine lone pair is a strong H-bond acceptor.
Polarity: high; expected to be water-miscible as the free base or readily water-soluble as a protonated salt.
Synthetic Utility
Functional group reactivity
Secondary amine: undergoes acylation, sulfonylation, carbamoylation, urea formation, reductive amination, and SN2 alkylation; can be protected (Boc, Cbz, Fmoc) to modulate reactivity.
Secondary amide (N-methyl): comparatively inert toward nucleophilic substitution; can participate in H-bonding and directivity; under strong activation (e.g., CDI, Ghosez reagent), can be transformed but typically serves as a stable handle.
Roles in synthesis
Linker/spacer: the –CH2–CH2– tether separates the amine from the amide, enabling bifunctional coupling to generate diamides, peptidomimetics, or urea–amide hybrids.
Polarity enhancer: incorporation into scaffolds increases aqueous solubility; amine salt formation aids crystallization and isolation.
Late-stage diversification: amine handles facilitate rapid library expansion (sulfonylation/alkylation); amide remains intact under many conditions, preserving the core.
Retrosynthetic value
Disconnection at the amine: access via reductive amination of 3-oxopropanamide derivatives or via nucleophilic substitution on 3-halo/N-protected 3-aminopropanamides with ethylamine followed by N-methylation of the amide.
Alternative approach: acylate N-methylethylenediamine with 2-bromoacetyl derivatives, then intramolecular adjustments to install the –CH2–CH2–C(=O)– motif.
Analytical/handling
Verify purity by LC–MS; amide rotamers may show duplicated peaks in NMR.
Convert to a crystalline salt (e.g., HCl) for solid handling and improved shelf stability if needed.
All strategies above are general literature guidance and should be adapted to your specific substrates.
Target Specificity
Not applicable. This product is a small organic building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity is defined for this item.
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