ethyl (2R)-2-aminopropanoate , CAS No.30959-96-7

CAS: 30959-96-7 Cat. No.: E1073353 Formula: C₅H₁₁NO₂ Peso molecolare: 117.150

Storage

Room temperature

Specifiche

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CCOC(=O)[C@@H](C)N

IUPAC Name

ethyl (2R)-2-aminopropanoate

InChIKey

ROBXZHNBBCHEIQ-SCSAIBSYSA-N

INCHI

1S/C5H11NO2/c1-3-8-5(7)4(2)6/h4H,3,6H2,1-2H3/t4-/m1/s1

Peso molecolare

117.150

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 Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-amino acid ester - Alanine or derivatives - Carboxylic acid ester - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Amine - Aliphatic acyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 117.150 g/mol
• XLogP3: 0.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 117.079 Da
• Monoisotopic Mass: 117.079 Da
• Topological Polar Surface Area: 52.300 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 82.500
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent in the Product Data. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.

Biological Roles

This compound is a non-natural derivative (ethyl ester) of the proteinogenic amino acid L-alanine. As such, it is primarily a synthetic intermediate and does not have a direct physiological role. The following points are general context from biochemistry literature and should not be construed as medical or clinical claims.

• Relation to L-alanine: L-Alanine participates in glucose–alanine cycling, transamination, and protein biosynthesis. Conversion of the ethyl ester back to L-alanine (e.g., by hydrolysis) restores compatibility with metabolic pathways (literature).
• Transport/uptake: Protonated amino acid esters can sometimes traverse membranes differently from the parent amino acid due to altered polarity; however, ethyl (2R)-2-aminopropanoate is not a standard metabolite and specific transporters/kinetics are not established (literature/general).
• Enzymatic transformations: Lipases and esterases may hydrolyze the ethyl ester under physiological-like conditions, generating L-alanine and ethanol; rates depend on enzyme and medium (literature).

Research use only: Any biological testing should be designed for laboratory research, with appropriate controls to differentiate effects of the ester vs. the liberated amino acid and ethanol.

Buffer Applications

Not typically used as a buffering agent. The molecule contains a primary amine but lacks the carboxylate functionality of free amino acids at neutral pH due to esterification, which limits zwitterionic buffering capacity. For buffer needs, consider standard systems (e.g., phosphate, Tris, HEPES) or free L-alanine in specific contexts.

Green Alternatives

While ethyl (2R)-2-aminopropanoate is a target reagent rather than a volatile solvent or auxiliary, greener practices can still be applied when using it.

• Feedstock considerations (general):

  • L-Alanine can be sourced via fermentation (bio-based), offering a renewable starting material for preparing the ester.
  • Preparation via enzymatic esterification (lipase-catalyzed) in green solvents or solvent-free systems reduces energy input and minimizes hazardous reagents (literature).

• Solvent choices: Prefer biorenewable or safer solvents when compatible with the transformation:

  • 2-MeTHF or CPME vs. THF for non-protic media.
  • EtOAc or Me-THF vs. DCM for extractions and couplings (when reagent/catalyst systems allow).
  • Water/EtOH systems for salt formation or enzymatic steps.

• Comparison snapshot (general, literature):

  • DCM: Excellent for coupling and workup; environmental and toxicity concerns; consider EtOAc/MeCN alternatives.
  • DMF/DMSO: High solvating power; poor EHS and workup; consider MeCN or green dipolar solvents (e.g., propylene carbonate) where feasible.
  • EtOH/2-MeTHF: Renewable content, easier recovery; watch for transesterification in alcoholic media.

• Waste minimization:

  • Use coupling systems with benign byproducts (e.g., T3P in EtOAc).
  • Crystallize intermediates/salts to reduce chromatographic solvent consumption.

Note: Evaluate solvent substitutions for reaction rate, selectivity, and risk of ester exchange.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet. The following are general, non-clinical notes common to amino acid esters in process chemistry.

• Role in development/manufacturing (literature/general):
  • Intermediate for synthesizing alanine-containing amides, peptidomimetics, and small-molecule APIs via amide bond formation followed by ester hydrolysis.
  • Potential pro-moiety in medicinal chemistry programs exploring ester prodrugs; the ethyl ester can modulate lipophilicity and permeability, with subsequent in vivo or in vitro hydrolysis—application-specific and requires separate qualification.
• Salt handling: The hydrochloride salt is often preferred for stability, crystallinity, and accurate dosing in process steps; free base is more volatile/odorous and can absorb CO2/H2O.
• Regulatory note: Any use in cGMP or clinical settings requires independent qualification and sourcing to compendial standards; this catalog item is for research use only (as stated by the manufacturer).

Physical Properties

Item-specific specifications for this product are not provided in the Product Data. Do not use the following as product specifications; consult the CoA/Spec Sheet for item-specific values.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, boiling/melting point (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

General literature/computed information for ethyl (2R)-2-aminopropanoate (for context only):

• Physical state: Typically a low-melting solid or viscous liquid depending on purity and salt form (literature). Primary amine can form hydrogen bonds; ester lowers melting relative to the free acid.
• Solubility: Miscible or highly soluble in polar organic solvents (MeOH, EtOH, acetone) and partially soluble in water due to the amine; increased solubility in water as salts (e.g., HCl salt) (literature).
• Acid–base: Primary amine pKaH typically ~9–10 for α-amino esters; overall molecule is basic and can form salts with mineral acids (literature).
• LogP/logD: α-Amino acid ethyl esters often exhibit modest lipophilicity (logP near 0 to 1 when unprotonated); logD is pH-dependent due to the amine (literature).

Note: Exact BP/MP, density, and refractive index vary with enantiomeric purity, water content, and salt/solvent content; verify against the supplied CoA for this catalog item.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Salts: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for amino acid ester quality:

• Enantiomeric purity: For chiral building blocks like ethyl (2R)-2-aminopropanoate, enantiomeric excess (ee) is critical. Techniques for verification include chiral HPLC, derivatization with chiral reagents (e.g., Marfey’s), or NMR with chiral shift reagents.
• Residual water/solvents: Water promotes hydrolysis and racemization under base. Karl Fischer titration and GC headspace are commonly used for QC.
• Low inorganic content: Important for coupling chemistry to avoid side reactions; ash/metals are typically minimized in high-purity synthetic reagents.
• UV profile: For HPLC monitoring of derivatized amino esters, low baseline absorbance in the detection range (200–220 nm) is desirable for eluents/solvents; the neat ester itself has weak UV above 210 nm.
• Impurities of concern: Racemized (2S) epimer, hydrolyzed alaninate (alanine), transesterification products (e.g., methyl/butyl esters), and acylated/byproducts from prior steps. Confirm identity by 1H/13C NMR and MS.

Reaction and Applications

Ethyl (2R)-2-aminopropanoate is a versatile chiral building block for constructing L-alanine-containing motifs and for broader asymmetric synthesis.

Key application areas (literature):

• Peptide and amide synthesis: Serves as the nucleophilic amine component in coupling with activated carboxylic acids (acid chlorides, anhydrides) or modern coupling systems (e.g., EDCI/HOBt, HATU, T3P) to give N-acyl alaninate esters, which can be hydrolyzed later to L-alanine amides.
• Urea/thiourea/Carbamate formation: Reaction with isocyanates, carbonates, or chloroformates affords protected derivatives and organocatalyst precursors.
• Reductive amination/alkylation: The amine can undergo reductive alkylation to introduce side chains while preserving the ester (with careful conditions), useful in preparing N-alkyl alaninate derivatives.
• Salt formation and resolution: The chiral center can be used to form diastereomeric salts with achiral acids/bases for resolution studies; conversely, racemization can be studied under base to access both enantiomers.
• Transesterification and hydrolysis: The ethyl ester can be selectively transformed—acid/base-catalyzed hydrolysis to L-alanine; enzymatic resolution or lipase-catalyzed transesterification enables mild transformations.

Practical tips:

• Maintain neutral to mildly basic conditions (avoid strong base) to limit racemization at the α-carbon.
• Protect the amine (e.g., Boc, Cbz, Fmoc) prior to transformations that might otherwise lead to undesired acylation or polymerization.
• For couplings, pre-form the hydrochloride salt to improve handling, then liberate the free base in situ with organic base.

Reaction Conditions

General, literature-based guidance for common transformations of ethyl (2R)-2-aminopropanoate. These are not product specifications; optimize per substrate.

• N-Acylation (amide formation):

  • Solvents: DMF, DCM, or MeCN.
  • Bases: DIPEA, NMM, or NaHCO3 (aqueous-organic biphasic for acid chlorides).
  • Coupling reagents: HATU, HBTU, EDCI (with HOBt/HOAt), or T3P.
  • Temperature: 0–25 °C typically; keep cool to minimize racemization.
  • Workup: Acidic quench to remove residual base/coupling byproducts.

• Ester hydrolysis (to L-alanine):

  • Acidic: 1–6 M HCl, reflux to room temp depending on time scale; yields the hydrochloride salt of L-alanine.
  • Basic: Aqueous NaOH/KOH in MeOH/H2O or THF/H2O at 0–25 °C; neutralize carefully to avoid racemization.

• Aminolysis (ester → amide):

  • Reagents: Primary/secondary amines (2–5 equiv), catalytic DMAP or base.
  • Solvent: MeCN, toluene, or neat amine; 25–80 °C as needed.
  • Note: Protect the α-amine first to avoid polymerization/cyclization side reactions.

• Salt formation (HCl):

  • Medium: Anhydrous Et2O/THF, HCl(g) or 2 M HCl in ether.
  • Outcome: Crystalline hydrochloride improves handling and stability.

• Reductive amination (on the α-amine):

  • Carbonyl partner with NaBH3CN or BH3·THF; mildly acidic buffer (AcOH) in MeOH/MeCN; 0–25 °C.

Caution: Strong base, high temperature, or prolonged reaction times can induce α-racemization; monitor ee by chiral HPLC.

Safety and Handling

Item-specific GHS classification and hazard statements are not provided in the Product Data. Always consult the SDS for authoritative safety information.

• GHS/Classification (item-specific): Not specified for this item; refer to SDS.
• Anticipated hazards (general/literature for amino acid ethyl esters): May cause skin/eye irritation and respiratory irritation. Amines can be sensitizers in some individuals and are generally harmful if swallowed in significant amounts.
• PPE: Use appropriate lab PPE—lab coat, nitrile gloves, splash goggles. Handle in a fume hood to avoid inhalation of vapors or aerosols.
• Incompatibilities (general): Strong oxidizers; strong acids/bases (risk of hydrolysis under strong acid/base; base can promote racemization). Isocyanates and acyl chlorides react readily with the amine.
• Reactivity notes: Primary amine is nucleophilic; ester is susceptible to hydrolysis and aminolysis. Avoid prolonged exposure to moisture and elevated temperatures.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spills: Absorb with inert material; avoid release to drains. Dispose according to local regulations.
• Fire: Use CO2, dry chemical, or foam. Combustion can produce NOx and COx.

Solvent Selection

This product is itself an organic reagent/solute rather than a general-purpose solvent. Nevertheless, selecting suitable media for handling and reactions with ethyl (2R)-2-aminopropanoate is important.

• Polarity/miscibility (literature):
  • Highly soluble in polar protic solvents (MeOH, EtOH) and polar aprotic solvents (DMF, DMSO, MeCN).
  • Moderate solubility in less polar ethers (THF) and chlorinated solvents (DCM, CHCl3) depending on protonation state.
  • Water solubility increases significantly upon protonation (e.g., as HCl salt).
• Selection tips:
  • For amide couplings: DMF, DCM, or MeCN are common; base choice (DIPEA, NMM) influences solubility of the aminium salt.
  • For hydrogenation or deprotection steps: Alcohols (MeOH, EtOH) are practical if avoiding ester exchange; to prevent transesterification, use non-alcoholic solvents.
  • For salt formation/handling: Dissolve in minimal Et2O/THF and gas with HCl (anhydrous) to precipitate the hydrochloride, which is easier to weigh and is less volatile/hygroscopic.
• Comparison (general):
  • DMF/DMSO maximize solubility for polar substrates but are harder to remove.
  • DCM/EtOAc facilitate workup and crystallization of salts/derivatives but may require ion-pairing or co-solvents for complete dissolution.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated place.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Stability considerations (general):
  • Sensitive to hydrolysis under acidic/basic aqueous conditions; keep dry and avoid prolonged moisture exposure.
  • The free base can absorb CO2/H2O and may slowly oxidize/acylate in air; consider storing under inert gas for long-term stability.
  • Racemization risk increases under basic conditions and heat—store neutral and cool when possible.
• Form considerations:
  • Free base vs. acid salt: The hydrochloride salt often exhibits improved crystallinity and shelf stability; if material is supplied as the free base, salt formation just prior to use can aid handling (general literature guidance).
• Reconstitution/dissolution: Dissolves readily in common polar organic solvents (MeOH, EtOH, DMF, DCM) and in water when protonated; filter if particulate is present. Warm gently if needed, avoiding prolonged heating.
• Research Use Note: For research use only (per Product Data).

Structure and Identity

Ethyl (2R)-2-aminopropanoate is the ethyl ester of L-alanine (often referred to as ethyl L-alaninate), a chiral amino acid ester used as a building block in asymmetric synthesis and peptide chemistry.

• Item-specific identifiers (Product Data):

  • SKU: E1073353
  • CAS: 30959-96-7
  • InChIKey: 321458 (as provided)
  • Storage Conditions: Room temperature
  • Category: Small molecules and compound library (全部 / 可售 / 小分子和化合物库)

• Literature/computed identifiers and structure (general reference values):

  • Common name: Ethyl L-alaninate; ethyl (2R)-2-aminopropanoate
  • Molecular formula: C5H11NO2 (literature)
  • Molecular weight: ~117.15 g/mol (literature)
  • SMILES: CCOC(=O)C@HC (literature; R configuration at C-2)

• Structural features (general):

  • Functional groups: Primary amine (–NH2), ethyl ester (–CO2Et), aliphatic chiral center at the α-carbon.
  • Ring systems: None (acyclic).
  • Stereochemistry: Single stereocenter at C-2; (2R) corresponds to the L-enantiomer for α-amino acids.
  • 2D description: An ethyl ester chain (–COO–CH2–CH3) attached to a carbonyl linked to a chiral α-carbon bearing a methyl substituent and a primary amine.

Synthetic Utility

As a chiral α-amino ester, ethyl (2R)-2-aminopropanoate provides both a nucleophilic amine and a transformable ester handle, making it highly versatile in synthesis.

• Chiral pool entry: Fixed (2R) stereochemistry enables transfer of L-configuration into target molecules without asymmetric catalysis.
• Functional group interconversions:
  • Ester → acid: Controlled hydrolysis (aq. base or acid) affords L-alanine without epimerization under mild conditions.
  • Ester → amide: Aminolysis or two-step coupling/hydrolysis strategies deliver primary or secondary alaninamides.
  • Amine protection: Boc, Cbz, Fmoc protections enable orthogonal manipulations; carbamate install/remove sequences avoid racemization when properly buffered.
• Formation of higher-order structures:
  • Peptidic linkages via coupling to carboxylic acids/activated esters.
  • Ureas/thioureas and guanidines from isocyanates, isothiocyanates, and carbodiimides.
• Named/representative methods (literature):
  • HATU/HOBt or EDCI/HOAt couplings for N-acylation.
  • T3P-mediated amidations in EtOAc as a greener option.
  • Enzymatic kinetic resolution or dynamic kinetic resolution of racemates (when applicable) using lipases to set or maintain stereochemistry.

Selectivity notes: Avoid strong base and elevated temperatures that can promote enolization and racemization at C-2.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent (e.g., antibody, ligand with defined biomolecular target) and no target specificity is provided in the Product Data.