Ethyl 2-(methylamino)propanoate - ≥95% , CAS No.56428-90-1

CAS: 56428-90-1 Cat. No.: E1024249 Fórmula: C₆H₁₃NO₂ Peso molecular: 131.170

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CCOC(=O)C(C)NC

IUPAC Name

ethyl 2-(methylamino)propanoate

InChIKey

KHRLPZJTPHCMSQ-UHFFFAOYSA-N

INCHI

1S/C6H13NO2/c1-4-9-6(8)5(2)7-3/h5,7H,4H2,1-3H3

Peso molecular

131.170

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Alpha amino acid esters
• Alternative Parents: Alanine and derivatives Carboxylic acid esters Monocarboxylic acids and derivatives Dialkylamines Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-amino acid ester - Alanine or derivatives - Carboxylic acid ester - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Secondary amine - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Amine - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
• 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

Propriedades químicas e físicas

• Peso molecular: 131.170 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 131.095 Da
• Monoisotopic Mass: 131.095 Da
• Topological Polar Surface Area: 38.300 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 93.100
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 assay or bioanalytical protocols are specified for this item in the Product Data. As a synthetic building block, usage protocols depend on the transformation of interest. See Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for representative conditions and workflow guidance.

For analytical qualification on receipt (general recommendations):

• Confirm identity by 1H/13C NMR and LC–MS (ESI+). The β-amino ester typically shows an O–CH2 quartet (~4.1–4.3 ppm) and an ethyl CH3 triplet (~1.2–1.3 ppm), with amine-associated signals near 2–3 ppm (literature, general).
• Assess purity by HPLC/GC as appropriate; check water (KF) if moisture-sensitive chemistry is planned.
• If stereochemistry matters, evaluate ee by chiral HPLC or derivatize with Marfey’s/DNA-based chiral reagents after hydrolysis (literature approaches).

Biological Roles

This product is a synthetic amino-ester building block. No biological/clinical claims are made; for research use only.

• Context (literature/general)

  • N-Methylated amino acids occur in natural products and peptides, influencing conformation and protease resistance. N-methylalanine units are commonly used in peptidomimetic design to adjust backbone hydrogen-bonding patterns.
  • As an ethyl ester, this compound is a derivatized form of N-methylalanine; the ester serves as a protecting/masking group for the carboxylate, not a natural metabolite in standard pathways.

• Biochemical behavior (general)

  • The secondary amine can be protonated under physiological pH, increasing hydrophilicity; the neutral ester reduces acidity and increases membrane permeability relative to the free acid (conceptual, literature-based).
  • Hydrolysis (enzymatic or chemical) would regenerate N-methylalanine; however, rates and pathways are system-dependent and are not specified for this item.

• Utility in biological research

  • Employed as a precursor to N-methylalanine-containing peptides or peptidomimetic fragments for SAR studies.

No organism-specific roles, receptor interactions, or pathway activities are assigned to this compound in the Product Data.

Buffer Applications

This compound is not a conventional buffering agent. As a neutral amino ester, it lacks a conjugate acid/base pair with a useful buffering range in aqueous media.

• Practical note
  • For aqueous workups, its protonated amine can confer temporary water solubility under acidic conditions, but this is not buffering. Choose standard buffers (e.g., phosphate, acetate, HEPES) for pH control in reactions or biological assays.

Refer to Reaction & Applications and Synthetic Utility sections for relevant usage information.

Green Alternatives

While Ethyl 2-(methylamino)propanoate is a building block rather than a process solvent, greener choices can be made for the media and reagents used with it.

• Greener solvent swaps (general guidance)

  • Replace DCM with 2-MeTHF or CPME for acylations and extractions when compatible with reagents.
  • Favor ethyl acetate or IPA over chlorinated solvents for workup and crystallization.
  • Use water/MeOH or water/EtOH mixtures for hydrolysis steps where feasible.

• Reagent considerations

  • Prefer coupling agents with improved safety/greenness profiles (e.g., EDC·HCl with OxymaPure) over benzotriazole-based additives.
  • Minimize excess alkylating agents; explore catalytic phase-transfer to reduce solvent/reagent load.

• Comparison snapshot (literature/general)

  • DCM vs 2-MeTHF: 2-MeTHF is biorenewable, higher boiling, lower halogenated waste; may require longer reaction times but often similar outcomes for acylations.
  • THF vs CPME: CPME offers lower peroxide formation tendency and higher hydrophobicity, aiding separations; THF is more polar and may dissolve salts better.

• Waste and safety

  • Amines generate malodorous waste; maintain closed systems and activated carbon traps where needed.
  • Neutralize aqueous acidic/basic hydrolysis streams before disposal; follow local regulations.

These recommendations are general and should be validated for compatibility with your specific transformation involving this substrate.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the Product Data. The following notes describe common research/manufacturing contexts for amino-ester building blocks; no therapeutic claims are made.

• Typical roles (literature/general)

  • Synthetic intermediate: Precursor to N-methylalanine amides, carbamates, and peptide fragments in API/intermediate synthesis.
  • Pro-moiety exploration: Amino esters are sometimes evaluated as transient masking groups to modulate physicochemical properties in discovery research; suitability depends on stability/hydrolysis profile.

• Considerations for process development

  • Selection of salt form (e.g., HCl) can improve crystallinity, handling, and purge of impurities.
  • Control of residual solvents, water, and enantiomeric purity may be critical for downstream steps; define specifications early and monitor by validated methods (GC/LC/Chiral HPLC).

• Regulatory note

  • For GMP or clinical manufacturing, ensure source qualification, full CoA review, and alignment with ICH guidelines on impurities and solvent residues.

Item-specific pharmacopeial listing or excipient grade: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific specifications are not provided for this product. For authoritative values, consult the CoA/Spec Sheet.

• Item-specific specs

  • 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/general properties for the neutral free base (for context only; not product specifications)

  • Molecular formula (literature): C6H13NO2
  • Molecular weight (literature): ~131.17 g/mol
  • Physical state: typically a colorless liquid or low-melting solid for small amino esters with secondary amines (literature)
  • Acid–base: secondary amine pKaH (conjugate acid) commonly around 10–11 (literature, general secondary aliphatic amines); actual value depends on solvent/temperature
  • Solubility: expected to be miscible with many polar organic solvents (e.g., alcohols, ethers, chlorinated solvents) and moderately soluble in water due to the basic amine (literature, qualitative)
  • Volatility: small aliphatic amino esters usually distill under reduced pressure; risk of thermal decomposition at elevated temperatures (literature, general)

• Optical activity

  • If supplied as racemate, no optical rotation; if enantiopure, [α]D would be specified on the CoA. Not specified for this item; refer to CoA/Spec Sheet.

Note: Do not treat these literature notes as specifications for SKU E1024249. Always verify with the product’s CoA/SDS prior to use.

Quality and Grades

• Item-specific quality information

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

• Guidance on typical grades for amino-ester building blocks (general)

  • Research grade: Suitable for routine synthesis and screening where ultra-low trace impurities are not critical.

  • 95–99% purity (typical literature ranges): Beneficial for direct use in coupling or acylation steps to minimize byproducts; actual purity for this SKU must be confirmed on the CoA.

  • Optical specification: If enantioenriched material is required, the CoA typically lists ee and [α]D. This item’s stereochemical specification is not provided; confirm before use in chiral syntheses.

• Impurity considerations (general best practices)

  • Water promotes ester hydrolysis; Karl Fischer water content, if reported on CoA, helps assess suitability for moisture-sensitive reactions.
  • Residual solvents (GC), and amine/ester related impurities (e.g., hydrolyzed acid, transesterified species) can impact reaction performance; check CoA analytics (GC/HPLC, NMR) as applicable.

• Documentation and traceability

  • For regulated or critical-path synthesis, request batch-specific CoA, lot traceability, and analytical reports (NMR, LC/GC purity, residual solvents, water).

Reaction and Applications

Ethyl 2-(methylamino)propanoate is a versatile β-amino ester used as a building block for N-methylated alanine derivatives, peptidomimetic fragments, and small-molecule libraries.

• Representative transformations (literature/general)

  • N-Acylation: Formation of N-acyl-N-methylalaninate derivatives using acid chlorides, anhydrides, or activated acids (e.g., HATU, EDCI). Control base strength to limit ester cleavage.
  • N-Alkylation: Exhaustive or selective N-alkylation under SN2 conditions (alkyl halides) with appropriate base; monitor for O-alkylation and quaternization.
  • Transesterification: Exchange of the ethyl group (e.g., to methyl, benzyl, or tBu) via acid/base catalysis; remove ethanol to drive equilibrium.
  • Hydrolysis/saponification: Conversion to N-methylalanine (free acid) with aqueous base or strong acid; subsequent coupling to form amides/peptidomimetics.
  • Reductive and condensative chemistry: Formation of ureas/carbamates (with phosgene equivalents, CDI); reductive acylations to assemble N-methylated peptide motifs.

• Applications

  • Peptidomimetics: Incorporation of N-methyl-α-amino acid units to modulate backbone conformation and proteolytic stability.
  • Prodrug/intermediate chemistry: Amino-ester handles enable masked acids and tunable polarity for lead optimization (research context).
  • Asymmetric synthesis: If enantiopure starting material is available, retains stereochemistry during N-functionalization; racemic material can be resolved via salt formation or chiral chromatography (general).

• Practical tips

  • Maintain anhydrous conditions for acylations and N-alkylations to minimize ester hydrolysis.
  • For N-alkylation, use hindered, non-nucleophilic bases (e.g., K2CO3, DIPEA) and polar aprotic solvents; consider phase-transfer catalysis for heterogeneous systems.
  • Monitor reactions by LC/MS; the secondary amine ionizes readily under ESI+.

Reaction Conditions

General, literature-based guidance for typical transformations involving Ethyl 2-(methylamino)propanoate. Optimize for your substrate and scale; these are not specifications for this item.

• N-Acylation (to secondary amides)

  • Solvent: DCM or DMF (anhydrous).
  • Base: DIPEA or pyridine (1.5–2.5 equiv).
  • Electrophile: acyl chloride or EDC/HATU-activated acid.
  • Temperature: 0–25 °C; cool during additions to control exotherm.
  • Notes: Minimize water; monitor for ester cleavage.

• N-Alkylation (SN2)

  • Solvent: MeCN, DMF, or acetone.
  • Base: K2CO3, Cs2CO3, or DIPEA.
  • Electrophile: primary alkyl halide/sulfonate.
  • Temperature: 20–60 °C depending on reactivity.
  • Notes: Avoid strong bases that induce transesterification; consider phase-transfer catalysis (toluene/50% KOH, TBAB) for heterogeneous systems.

• Ester hydrolysis (to N-methylalanine)

  • Base-mediated: NaOH or KOH (1–2 M) in MeOH/H2O or THF/H2O, 0–25 °C to reflux; work up by acidification and extraction or salt isolation.
  • Acid-mediated: HCl (6 M) under reflux for complete cleavage; generates ammonium salt.

• Carbamate formation

  • Reagents: ethyl/benzyl chloroformate or CDI with alcohols.
  • Solvent: DCM or THF; base: triethylamine/DIPEA; 0–25 °C.

• Analysis and control

  • Track by LC–MS (ESI+), 1H NMR (disappearance of NH, shifts near 3–4 ppm for O–CH2), and IR (C=O ~1735 cm−1 for ester; amide shift upon acylation, literature).

Scale-up: control heat evolution and maintain adequate mass transfer; consider continuous addition of electrophile to suppress over-reaction.

Safety and Handling

Safety information specific to this item is not provided in the Product Data. Always consult the SDS for definitive guidance.

• GHS classification and hazard statements

  • GHS/Signal word/Pictograms: Not specified for this item; refer to SDS.

• Likely hazards (general, literature-based for small aliphatic amino esters)

  • Irritant to skin, eyes, and respiratory tract; amines are often sensitizers/irritants.
  • Vapors may be unpleasant; use in a fume hood.

• Incompatibilities and reactivity (general)

  • Avoid strong oxidizers (risk of exothermic reactions).
  • Strong acids or bases may catalyze ester hydrolysis; isolate from acid chlorides/anhydrides unless acylation is intended.
  • Reacts with electrophiles at nitrogen; may form salts with strong acids (e.g., HCl) that alter handling.

• Storage conditions

  • Product Data indicates: store at room temperature.
  • Keep tightly closed, under inert gas if long-term storage is anticipated, to limit moisture uptake and hydrolysis.

• Personal protective equipment (PPE)

  • Lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use a fume hood.

• First-aid overview (general)

  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do NOT induce vomiting; seek medical advice.

Defer to the current SDS for SKU-specific hazard classifications and emergency procedures.

Solvent Selection

This product is a reactive amino-ester building block rather than a bulk solvent. Solvent selection below pertains to using Ethyl 2-(methylamino)propanoate in synthesis and purification.

• Polarity and solubility (general)

  • Amphiphilic: combines a basic secondary amine with an ethyl ester. Typically soluble in polar organics (alcohols, ethers, esters, chlorinated solvents) and moderately soluble in water (amine protonation enhances aqueous solubility).

• Common solvent choices by operation

  • Acylation/alkylation at nitrogen: anhydrous dichloromethane (DCM), acetonitrile, THF, or toluene; add non-nucleophilic base (e.g., DIPEA) if needed.
  • Carbodiimide/HATU couplings (acylation of N): DMF, DCM, or NMP are typical; maintain low water to suppress hydrolysis.
  • Hydrolysis/saponification of the ester: aqueous THF/MeOH or dioxane; base (NaOH, K2CO3) or acid (HCl) as catalyst.
  • Reductive amination/derivatization: MeOH, EtOH, or DCE/MeOH mixtures depending on reagent solubility.

• Workup and isolation

  • The free base partitions into organic solvents at basic pH; the protonated amine partitions into aqueous phase at acidic pH, useful for acid–base extractions.
  • Convert to a crystalline salt (e.g., HCl salt) for improved handling; choose alcohol/ether or EtOAc/hexanes mixtures for precipitation (general guidance).

• Comparison with alternatives (general)

  • If higher aqueous solubility is required, the corresponding hydrochloride salt may be preferred.
  • For greener choices, consider Me-THF or CPME over DCM/THF where compatible (see Green Alternatives).

Storage and Reconstitution

• Storage (item-specific)

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Container: Keep tightly closed in a dry, inert atmosphere to minimize hydrolysis and oxidation. Use amber glass if prolonged light exposure is expected (general best practice).

• Stability considerations (general)

  • Amino esters can undergo hydrolysis under moist or strongly acidic/basic conditions. Avoid prolonged exposure to humidity and extremes of pH.
  • Forming a crystalline acid-addition salt (e.g., HCl salt) may enhance shelf stability and handling; verify compatibility with intended chemistry.

• Reconstitution and use

  • This material is typically used neat or dissolved in anhydrous organic solvent (e.g., DCM, THF, MeCN, DMF, EtOAc) immediately before use.
  • For aqueous operations, pre-adjust pH to control protonation state: protonated amine increases aqueous solubility; free base partitions into organics during extractions.
  • If solidification occurs at low temperature, warm gently to ambient and vortex/sonicate to homogenize before dispensing.

• Freeze–thaw guidance

  • Not typically stored frozen; if chilled for stability, avoid repeated freeze–thaw by aliquoting into dry, inert vials.

Always consult the product’s CoA and SDS for lot-specific stability, handling, and compatibility information.

Structure and Identity

Ethyl 2-(methylamino)propanoate is the ethyl ester of N-methylalanine, featuring a secondary amine adjacent to an ester carbonyl (a β-amino ester motif).

• Item-specific identifiers (from Product Data)
  • CAS: 56428-90-1
  • CID: 13353058
  • InChIKey: 180374 (as provided for this item)
  • SKU: E1024249
• Names and composition
  • Preferred name: Ethyl 2-(methylamino)propanoate
  • Synonym (literature): Ethyl N-methylalaninate; Ethyl 2-(methylamino)propionate (literature)
• Structure description (general)
  • Functional groups: secondary amine (–NH–CH3), ethyl ester (–CO2Et), and an α-branching methyl substituent at C2
  • Backbone: CH3–CH(NHCH3)–C(=O)–O–CH2–CH3
  • Ring systems: none; acyclic, aliphatic
  • Stereochemistry: the 2-position is stereogenic; unless specified otherwise, commercial material is typically racemic (literature)
• Molecular descriptors (literature/computed)
  • Molecular formula (literature): C6H13NO2
  • Molecular weight (literature): ~131.17 g/mol
  • SMILES (literature): CCOC(=O)C(NC)C

2D structure in words: an ethyl ester terminus (–CO2Et) is bonded to a chiral α-carbon bearing a methyl substituent and a secondary amino group N-methylated (–NHCH3). The molecule is overall neutral, with a basic amine and a polar ester, conferring amphiphilic character.

Synthetic Utility

Key functional handles: a secondary amine (nucleophilic, basic) and an ethyl ester (electrophilically activatable, hydrolyzable). Together they enable streamlined assembly of N-methylalanine derivatives.

• Transformations centered at nitrogen (literature/general)

  • Acylation with acyl chlorides/activated acids to form secondary amide derivatives (N-acyl-N-methylalaninates).
  • Alkylation to access tertiary amines or quaternary ammonium salts; careful control prevents over-alkylation.
  • Carbamate/urea formation using chloroformates or CDI.

• Transformations at the ester

  • Hydrolysis/saponification to the corresponding N-methylalanine (free acid) for peptide couplings.
  • Transesterification to tune protecting groups or volatility (e.g., methyl, benzyl, or tBu esters).
  • Amidation via activation (e.g., mixed anhydrides, EDC/HATU) to give N-methylalanine amides while retaining the N-methyl substituent.

• Retrosynthetic value

  • Serves as a convergent intermediate where the N-methyl group is preinstalled, avoiding late-stage N-methylation (often challenging on peptides).
  • Amenable to salt formation for purification; acid–base extraction simplifies workups.

• Selectivity notes

  • Competing O-acylation/alkylation can occur; employ conditions favoring N-selectivity (non-nucleophilic bases, appropriate solvents, stoichiometry control).
  • Ester stability requires control of pH and temperature to suppress unwanted hydrolysis during N-functionalization.

Target Specificity

Not applicable. This product is a small-molecule amino-ester building block, not a biological targeting reagent (e.g., antibody, ligand with defined biological specificity). No target, epitope, or species reactivity is provided in the Product Data.

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 56428-90-1, the molecular formula is C6H13NO2, and the molecular weight is 131.170 g/mol. InChIKey KHRLPZJTPHCMSQ-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.