Methylethanecarboximidate - ≥95% , CAS No.20258-22-4

CAS: 20258-22-4 Cat. No.: M978313 Formule: C₄H₉NO Poids moléculaire: 87.120

QUALITÉ & PURETÉ ≥95%

Storage

Room temperature

Spécifications

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Pureté

≥95%

Noms et identifiants

Sourires canoniques

CCC(=N)OC

IUPAC Name

methyl propanimidate

InChIKey

PNVXTVKZTGTFIL-UHFFFAOYSA-N

INCHI

1S/C4H9NO/c1-3-4(5)6-2/h5H,3H2,1-2H3

Poids moléculaire

87.120

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboximidic acids and derivatives
      • Subclass Imidoesters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboximidic acids and derivatives
• Subclass: Imidoesters
• Intermediate Tree Nodes: Not available
• Direct Parent: Imidoesters
• Alternative Parents: Organooxygen compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Imido ester - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as imidoesters. These are organic ester derivatives of imidic acid. They have the general structure ROC(CR')=NR\", where R=organyl group, R'-R\"= H or organyl group.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 87.120 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 87.0684 Da
• Monoisotopic Mass: 87.0684 Da
• Topological Polar Surface Area: 33.100 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 51.500
• 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 tested bioassay or immunoassay applications are provided for this item.

General procedural notes (reagent use):

• For amidine installation on amine-bearing substrates: Dissolve substrate in dry aprotic solvent, add base if necessary, then add the imidate dropwise at 0–25 °C; monitor to completion and quench carefully to avoid hydrolysis of product.
• For solution-phase derivatizations in water: Prefer the corresponding hydrochloride salt forms of short-chain imidates; select amine-free buffers (borate/phosphate), pH 8–9, and execute additions quickly to limit hydrolysis.

Item-specific protocols, recommended dilutions, and positive controls: Not specified for this item.

Biological Roles

Item-specific biological data are not provided for this reagent.

General perspective (for small O‑alkyl imidates):

• Not endogenous biomolecules; their primary relevance in life-science labs is as chemical reagents to derivatize primary amines to amidines. This transformation can modulate charge and pKa of amine-containing substrates.
• In biochemical derivatization workflows, the corresponding hydrochloride salts of short-chain imidates are often used because they are more manageable solids and can be dosed into buffered systems. Reaction conditions must be optimized to prevent competing hydrolysis.
• Any interactions with proteins, nucleic acids, or metabolites arise from covalent modification chemistry (nucleophilic addition to the imidate carbon), not from native biological function.

Note: This product is labeled For research use only. No clinical or diagnostic use is implied.

Buffer Applications

This compound is not a buffering agent and does not constitute a classical buffer system.

Practical note (general):

• If used for derivatizing amines in aqueous media, select buffers that do not contain primary/secondary amines (avoid Tris, glycine) and maintain mildly basic pH (often pH 8–9) to promote amine nucleophilicity while minimizing acid-catalyzed hydrolysis. Borate or phosphate buffers are common choices in such derivatizations.
• Keep buffer ionic strength moderate and exclude alcohols if transesterification is undesirable.

Item-specific buffer recipes, pKa, and buffer ranges: Not applicable/not specified for this item.

Green Alternatives

Context: Small imidates are effective acyl-activation equivalents for forming amidines and related functionalities. However, they can be moisture sensitive and may require chlorinated or aprotic polar solvents.

Potential greener strategies (literature/general):

• Solvent substitution: Replace dichloromethane with ethyl acetate, 2‑MeTHF, CPME, or toluene where solubility/reactivity permit. For polar needs, consider acetonitrile or propylene carbonate (with caution re: reactivity) instead of DMF.
• Alternative reagents: For amidine installation, consider using nitriles plus alcohol/HCl (in situ Pinner) or direct oxidative amidination protocols that avoid preformed imidates; enzymatic routes are emerging but substrate-limited.
• Process intensification: Employ flow chemistry with on-demand generation of the imidate from a nitrile to minimize inventory and exposure.

Trade-offs:

• Greener solvents may reduce rate/selectivity; water content control is still critical to prevent hydrolysis.
• In situ generation reduces isolation but adds complexity to control stoichiometry and quench streams.

Illustrative comparison (general):

• Imidate approach: Mild, selective amidine formation; sensitive to moisture; commonly uses aprotic solvents.
• Acid chloride approach: High reactivity; corrosive/byproduct HCl; often requires stricter safety controls.
• Carbodiimide coupling to amidines: Possible but may generate urea waste and require more steps.

Always evaluate EHS metrics (boiling point, toxicity, biodegradability) and life-cycle impacts when selecting solvents/reagents.

Pharmaceutical Uses

No pharmacopeial listing, excipient role, or formulation grade is specified for this item; refer to CoA/Spec Sheet.

General, non-clinical context:

• Small imidates may be employed as synthetic intermediates to access amidines, amides, or heterocycles relevant to medicinal chemistry discovery workflows. They serve as functional group interconversion handle rather than finished excipients.
• For process chemistry, selection of an imidate vs. alternative activating groups (acid chlorides, imidazolides, CDI adducts) balances reactivity, selectivity, stability, and environmental profile.

Compliance reminder: For research use only. Not for human or veterinary use, clinical diagnostics, or as an excipient without appropriate qualification.

Physical Properties

Item-specific specifications:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Other specs (bp, mp, density, refractive index, water/peroxide/metal limits, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for small O-alkyl imidates (qualitative guidance only):

• Physical state: typically low–moderate boiling liquids or low-melting solids; often colorless and moisture sensitive.
• Volatility: can be appreciable due to low molecular mass; use closed systems to limit loss.
• Solubility: high in common organic solvents (ethers, esters, chlorinated, and aprotic polar solvents); limited stability in aqueous media where acid/base-catalyzed hydrolysis can occur.
• Stability considerations: hydrolyzes under protic/acidic conditions to give corresponding amide or ester/alcohol; can undergo exchange with nucleophiles (amines, alcohols). Avoid prolonged exposure to moisture.

Important: Do not treat the above as specifications. For experimental design and safety calculations, consult the product’s CoA/SDS for exact numeric values.

Quality and Grades

Item-specific grade/purity details:

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

Guidance for interpreting grade (general):

• Research grade reagents are suitable for most synthetic and analytical workflows but may not include guarantees on trace metal content, UV background, or residual water.
• If HPLC/UV-grade is required (e.g., for low-background derivatizations), verify that UV absorbance specifications and inhibitor content are appropriate for your method.
• Imidates are moisture sensitive; some suppliers offer them with low water content or packaged under inert gas. If low water is critical (e.g., for sensitive condensations), request Karl Fischer values on the CoA.

Best practices:

• Upon receipt, inspect container integrity and any inert-gas packaging.
• If purity is unspecified, verify by GC/GC–MS or NMR prior to critical applications; check for imidate-to-amide hydrolysis impurities.
• For quantitative derivatizations, standardize concentration by titration against a limiting nucleophile or by quantitative NMR.

Reaction and Applications

This reagent is a small O‑alkyl imidate suited for nucleophile additions and heteroatom substitution chemistry. Typical applications (literature/general):

• Amidine synthesis (Pinner amidine formation): Reaction with primary or secondary amines affords N‑substituted amidines. Useful for installing cationic amidine handles on amine-bearing substrates under relatively mild conditions.
• Alcohol exchange and acyl transfer motifs: In the presence of protic solvents/acids, imidates can equilibrate to esters or hydrolyze to amides; careful control of acidity and water activity is essential.
• Building block for heterocycles: Imidates can participate in cyclizations (e.g., to imidazoles or oxazoles) when combined with appropriate 1,2‑dinucleophiles under dehydrating conditions.
• Derivatization chemistry: Short-chain imidates are used to modify primary amines on small molecules and biomolecules to give amidines that retain positive charge at physiological pH (commonly executed with the corresponding hydrochloride salts); consider pH and buffer composition to minimize hydrolysis.

Practical tips:

• Maintain anhydrous conditions; even trace water accelerates hydrolysis.
• For amination, add the imidate slowly to an amine solution at 0–25 °C, then warm as needed; use an acid scavenger if a salt form is not employed.
• Monitor by TLC/GC/NMR; amidine formation shows characteristic downfield N–H signals and C=N shifts in NMR.

Manufacturer Applications: Not provided in Product Data for this item; the above are common literature uses for imidates.

Reaction Conditions

The following are general, literature-based guidelines for small O‑alkyl imidates; adapt to your substrate and confirm with small-scale trials.

• Amidine formation with primary amines:

  • Solvent: Anhydrous MeCN, THF, toluene, or DCM.
  • Base: Optional tertiary amine (e.g., triethylamine, DIPEA) as HCl scavenger if an acid is generated in situ; molecular sieves (3Å/4Å) to limit hydrolysis.
  • Temperature: 0–25 °C for sensitive substrates; 25–60 °C to drive to completion.
  • Time: 0.5–16 h depending on sterics; monitor by TLC/LC–MS.
  • Workup: Aqueous bicarbonate or brine, then drying; amidines may require buffered extraction to maintain desired protonation state.

• Alcohol exchange/transesterification:

  • Solvent/Reagent: Alcohol (ROH) as co-solvent; catalytic acid (e.g., HCl(g) in alcohol) or base (alkoxide) depending on directionality.
  • Notes: Competes with hydrolysis; maintain low water content and control acidity.

• Heterocycle formation (e.g., imidazoles/oxazoles):

  • Reagents: 1,2‑diamines or amino alcohols; dehydrating conditions (e.g., POCl3, SOCl2, or Dean–Stark in toluene when permissible).
  • Temperatures: 60–110 °C.

Expected outcomes (illustrative, literature): Amidination reactions often give good to excellent yields (60–90%) with unhindered amines under dry conditions; steric hindrance or electron-poor amines slow the rate.

Safety and Handling

Item-specific hazard data:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements/Pictograms: Not specified for this item; refer to SDS.

General safety profile for small imidate esters (literature/good practice):

• Hazards: Can be irritating to skin, eyes, and respiratory tract. Many are lachrymators and may be harmful if inhaled/ingested. Hydrolysis in moist air may release corrosive/byproduct species under acidic or basic conditions.
• Reactivity: Sensitive to moisture and acids/bases; reacts with nucleophiles (amines, alcohols, water). Avoid contact with strong acids, bases, oxidizers, and strong nucleophiles unless intended for reaction.
• Peroxide formation: Not typically a peroxide former (unlike ethers), but always check age/condition and follow SDS guidance.

Handling recommendations:

• Engineering controls: Use in a well-ventilated fume hood; keep containers tightly closed.
• PPE: Lab coat, nitrile gloves (change frequently), splash goggles; consider face shield for scale-up.
• Inert atmosphere: Beneficial for weighing/transfer to minimize hydrolysis; use dry syringes or cannula techniques for liquids.
• Spill/first aid (overview; defer to SDS): Absorb small spills with inert material; avoid water if reaction is exothermic. For skin/eye contact, rinse with water for ≥15 min and seek medical attention as required. If inhaled, move to fresh air.

Always consult the product-specific SDS before use.

Solvent Selection

Profile (general for small O‑alkyl imidates):

• Polarity: Moderately polar, aprotic; compatible with a wide range of organic solvents.
• Preferred media for stability: Anhydrous, neutral, aprotic solvents (e.g., dichloromethane, toluene, acetonitrile, THF, EtOAc). Avoid prolonged residence in protic solvents or aqueous buffers due to hydrolysis.
• Miscibility: Typically miscible with many organics; limited by design with water.

Use-case guidance:

• Nucleophilic additions (e.g., amidine formation with amines): Use dry aprotic solvents; add base scavenger (e.g., triethylamine) if acid is generated.
• Transesterification/exchange with alcohols: Employ alcohol as both reagent and solvent; add catalytic acid or base judiciously while monitoring for imidate stability.

Comparison (general considerations):

• Versus acid chlorides: Imidates are generally milder electrophiles, offering improved selectivity toward amines to give amidines; they are less moisture tolerant than simple esters but often safer than acid chlorides.
• Versus nitriles: Imidates are activated forms derived from nitriles (Pinner chemistry) and are more reactive toward nucleophiles.

Note: Exact dielectric constants/partition data are not specified for this item; consult literature or determine empirically for your solvent system.

Storage and Reconstitution

Item-specific information:

• Storage Conditions: Room temperature (per Product Data). Store in a tightly sealed container.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Best practices for this class of reagents (general):

• Keep dry and protect from moisture; consider storing under inert gas (argon/nitrogen) and using desiccant in the outer container.
• Minimize headspace and temperature cycling; for liquids, use septum-capped vials to enable syringe transfers.
• If material solidifies/crystallizes, gently warm to ambient and ensure homogeneity before aliquoting; avoid overheating.
• Reconstitution: Not typically applicable; if a concentrate/stock solution is desired, prepare in dry aprotic solvent (e.g., MeCN, DCM, THF) immediately prior to use and store refrigerated short-term if necessary. Verify stability by test reaction or analytical check.

Research Use Note: For research use only.

Structure and Identity

Brief overview: Methylethanecarboximidate is an O-alkyl imidate (general motif RC(=NH)OR′). Based on the name, it corresponds to the methyl O‑ester of ethanecarboximidic acid (an “acetimidate” framework), featuring an imino (C=NH) and an alkoxy (–OR) group on the same carbonyl carbon equivalent.

Item-specific identifiers (from Product Data):

• SKU: M978313
• Product Name: Methylethanecarboximidate
• CAS: 20258-22-4
• InChIKey: 282424 (as provided; appears truncated — verify on CoA/SDS)
• SMILES: 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.

Structural features (general, literature-based):

• Functional groups: Imidate (C(=NH)–OR), containing an imino (sp2 N–H) and an alkoxy substituent; no formal carbonyl oxygen (C=N–O).
• Likely substitution pattern implied by the name: a small alkyl group on the acyl carbon (ethane/acetyl level) and a methoxy O-substituent.
• 2D description: An sp2 carbon double-bonded to nitrogen (–C=NH) and single-bonded to an oxygen bearing a methyl group (–OCH3); the remaining substituent on the imidate carbon is an alkyl group consistent with “ethane-”.

Notes:

• Exact stereochemistry is not applicable (acyclic, no chiral centers expected for the simple imidate core).
• Confirm precise identifiers (SMILES/InChIKey, formula, MW) on the product CoA prior to method development.

Synthetic Utility

Key reactivity features (general/literature):

• Electrophilic carbon center of the imidate engages nucleophiles to form C–N (amidine) or C–O bonds (ester exchange). The imino N can participate in tautomerization/equilibration.
• From nitriles to imidates: Prepared via Pinner reaction (nitrile + alcohol + HCl), then neutralization to the imidate; the reverse (hydrolysis) provides access back to amides/esters.

Transformations enabled:

• Amidine synthesis: R–C(=NH)OR′ + R″NH2 → R–C(=NR″)–NH–R′ (amidines; protonation state depends on conditions). Useful for cationic handle installation and heterocycle precursors (e.g., imidazolines).
• Heterocycle construction: Condensation with α‑amino alcohols, diamines, or 1,2‑diamines to form oxazoles, imidazoles, or related rings under dehydrating conditions.
• O- to N‑acyl transfer analogs: Under acid catalysis, imidates can rearrange or exchange with alcohols to yield esters; with water, they give amides.

Strategic value:

• Selectivity over competing functional groups due to tuned electrophilicity; often gentler than acid chlorides, enabling late-stage functionalization.
• Orthogonality: Amines react preferentially; phenols/alcohols require activation or acid catalysis, enabling chemoselective derivatization.

Notes for this specific listing:

• Verify exact substitution pattern and counterion (if any) on the CoA to select optimal base, solvent, and stoichiometry.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting reagent or antibody.

Item-specific targeting data (antigen, epitope, clone, isotype, species reactivity): Not specified for this item.