Methylammonium Acetate - ≥99% , CAS No.6998-30-7

CAS: 6998-30-7 Cat. No.: M1524294 Formula: C₃H₉NO₂ Molecular Weight: 91.11 EC Number: 835-899-6 PubChem CID: 5259270

GRADE & PURITY ≥99%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Specifications

Specifications & Purity

≥99%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

Canonical Smiles

CC1=C(C=CC(=C1)C2=NN(C=C2C=C3C(=O)N4C(C(=C(N=C4S3)C)C(=O)OC(C)C)C5=CC=C(C=C5)SC)C6=CC=CC=C6)OCC=C

IUPAC Name

propan-2-yl 7-methyl-2-[[3-(3-methyl-4-prop-2-enoxyphenyl)-1-phenylpyrazol-4-yl]methylidene]-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate

InChIKey

QILUFVJSEAEPCY-UHFFFAOYSA-N

INCHI

1S/C38H36N4O4S2/c1-7-19-45-31-18-15-27(20-24(31)4)34-28(22-41(40-34)29-11-9-8-10-12-29)21-32-36(43)42-35(26-13-16-30(47-6)17-14-26)33(37(44)46-23(2)3)25(5)39-38(42)48-32/h7-18,20-23,35H,1,19H2,2-6H3

Isomeric SMILES

CC1=C(C=CC(=C1)C2=NN(C=C2C=C3C(=O)N4C(C(=C(N=C4S3)C)C(=O)OC(C)C)C5=CC=C(C=C5)SC)C6=CC=CC=C6)OCC=C

PubChem CID

5259270

Molecular Weight

91.11

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Azoles
      • Subclass Pyrazoles

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Azoles
• Subclass: Pyrazoles
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyrazoles
• Alternative Parents: Thiophenol ethers Phenoxy compounds Phenol ethers Toluenes Alkyl aryl ethers Alkylarylthioethers Thiazoles Enoate esters Heteroaromatic compounds Lactams Isothioureas Azacyclic compounds Sulfenyl compounds Monocarboxylic acids and derivatives Hydrocarbon derivatives Carbonyl compounds Organic oxides Organonitrogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylpyrazole - Phenoxy compound - Aryl thioether - Thiophenol ether - Phenol ether - Alkyl aryl ether - Toluene - Alkylarylthioether - Benzenoid - Monocyclic benzene moiety - Thiazole - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Heteroaromatic compound - Carboxylic acid ester - Lactam - Isothiourea - Carboxylic acid derivative - Ether - Azacycle - Monocarboxylic acid or derivatives - Sulfenyl compound - Thioether - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Organonitrogen compound - Organooxygen compound - Organosulfur compound - Organic nitrogen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl 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

Chemical and Physical Properties

• Solubility: High soluble in organic solvent.
• Sensitivity: Moisture sensitive
• Boil Point(°C): 53 °C/3 mmHg
• Melt Point(°C): 75 °C

Application Protocols

No assay-specific protocols are provided for this small-molecule salt. This section is not typically applicable.

• General preparation guidance (literature/practice)
  • LC-MS mobile phase: dissolve the required amount in water (or water/MeOH or water/ACN) to desired molarity (e.g., 10 mM), adjust pH with acetic acid if needed, filter (0.2 µm), and use freshly prepared solutions.
  • Buffering solution: for an acetate buffer in the acidic range, mix methylammonium acetate with acetic acid to the desired pH; verify at working temperature and solvent composition.
  • Drying before synthesis: if low water content is critical, dry under vacuum at ambient temperature in a desiccator, then transfer and weigh quickly under inert gas as indicated by the product’s argon-charged packaging.

For validated, application-specific protocols, consult primary literature corresponding to your method or reaction class.

Biological Roles

• General biochemical context (literature; not product-specific and not medical)

  • Acetate is a central metabolite in carbon metabolism, feeding into acetyl-CoA biosynthesis and the TCA cycle. In biochemical systems, acetate participates in acetylation reactions and energy production via acetyl-CoA (literature).
  • Methylammonium is the protonated form of methylamine. Methylamine can be produced microbially and metabolized by methylotrophs; in cells it can be deaminated or incorporated into one-carbon pools (literature). The methylammonium ion itself can be transported by certain ammonium transporters as an analogue/probe (literature).

• Laboratory use relevance

  • In vitro enzyme assays: acetate buffers are commonly used in the acidic to neutral range; using a volatile counterion (methylammonium) facilitates downstream MS-based analyses of enzymatic products by minimizing nonvolatile salt load.
  • Protein/peptide work: volatile acetate salts are sometimes employed during desalting or lyophilization steps to enable removal without leaving nonvolatile residue, although ammonium salts are more prevalent.

• Note

  • The above roles are general to the ions; specific biological testing or suitability for cell culture/diagnostics is not established for this item. For research use only, as stated by the manufacturer.

Buffer Applications

• Item-specific buffer data: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general guidance for using methylammonium acetate in buffers (not product specifications)

  • Buffering chemistry: composed of HOAc/AcO− (pKa ≈ 4.76) and MeNH3+/MeNH2 (pKaH ≈ 10.6). The salt itself provides ionic strength near neutrality; buffering capacity is established by adding acetic acid (for acidic buffer, pH ~3.8–6) or methylamine (for basic buffer, pH ~9–11), respectively.
  • LC-MS mobile phases: prepare 1–50 mM methylammonium acetate in water or water/MeOH or water/ACN, adjust pH with acetic acid for desired selectivity; filter (0.2 µm) and degas. Concentration choice balances buffering capacity, ionization efficiency, and background.
  • Volatility advantage: the counterion is volatile, aiding MS detection and lyophilization without nonvolatile residue, similar to ammonium acetate.

• Practical notes

  • Prepare fresh; acetate systems can show pH drift on standing due to CO2 absorption or microbial growth; store cold where feasible.
  • Verify pH at working temperature and solvent composition, as activity coefficients in water/organic mixtures shift apparent pKa values.
  • For enzymology, confirm compatibility with metal cofactors; acetate can chelate weakly or compete in active sites in some systems.

Green Alternatives

Methylammonium acetate is already relatively benign compared with many non-volatile ionic modifiers; it is aqueous-compatible and composed of low-toxicity ions. Nonetheless, alternatives may offer benefits depending on use.

• Comparison (literature/general; select the option that matches your constraints)

  | Option | Volatility (MS-friendliness) | Typical pH window | Notes | | --- | --- | --- | --- | | Ammonium acetate | High | ~3–7 (with HOAc/NH3) | Widely used LC-MS buffer; extremely common, excellent baseline behavior. | | Methylammonium acetate | High | ~3–7 (with HOAc/MeNH2) | Similar to ammonium; can tune selectivity/ion-pairing; this product. | | Ammonium formate | High | ~3–7 (with HCO2H/NH3) | Lower UV background; slightly different ionic strength per mol. | | Triethylammonium acetate | Moderate | ~3–7 | Better solubility in organic-rich phases; less volatile, can increase MS background. | | Bicarbonate/carbonate (ammonium) | High (for NH4HCO3) | ~8–10 | Greener for basic LC; decomposes to CO2/NH3, excellent for MS. |

• Green chemistry considerations

  • Use water-rich mobile phases where feasible; minimize organic solvent content.
  • Favor volatile buffer systems (ammonium/methylammonium salts) to reduce nonvolatile waste and facilitate solvent recycling.
  • Prepare only required volumes fresh to limit waste and degradation.

• Tradeoffs

  • Methylammonium vs ammonium: potential for slightly altered retention/selectivity but similar volatility; choose empirically based on target analytes.
  • Heavier trialkylammonium acetates improve retention of hydrophobic acids but at the expense of MS ionization efficiency and greenness.

Pharmaceutical Uses

• Item-specific pharmacopeial status/grade: Not specified for this item; refer to CoA/Spec Sheet.

• General, non-clinical use cases (literature/practice; no therapeutic claims)

  • Analytical development: volatile acetate buffers are commonly used during LC/LC-MS method development for drug substances and impurities, allowing easy removal during sample prep and minimizing nonvolatile residue.
  • Process analytical support: volatile salts facilitate downstream solvent recovery and reduce salt fouling in equipment relative to nonvolatile buffers.
  • Excipients: while ammonium salts are more commonly cited, alkylammonium acetates may serve in research formulations as pH modifiers or transient counterions during API salt screening; suitability must be established case-by-case.

• Considerations

  • Assess extractables/leachables impact when used in contact with polymers; acetate can influence corrosion or swelling in some materials.
  • For MS-based bioanalysis, evaluate ion suppression compared to ammonium acetate; methylammonium may modulate ESI response differently for acidic analytes.
  • Regulatory: use is limited to research unless supported by appropriate pharmacopeial monographs and quality documentation; this product is labeled For research use only.

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/typical properties for methylammonium acetate (reference only; not specifications)

  • Physical state: typically a hygroscopic crystalline solid (literature, common to small ammonium carboxylates).
  • Odor: may exhibit faint amine/acetic acid notes due to trace equilibrium dissociation (literature).
  • Solubility: expected to be very soluble in water and polar protic solvents (e.g., MeOH, EtOH); low solubility in nonpolar solvents (literature, by analogy to ammonium/alkylammonium acetates).
  • Acid–base behavior: comprised of the conjugate acid of methylamine (pKaH ≈ 10.6, literature) and the conjugate base of acetic acid (pKa ≈ 4.76, literature). Aqueous solutions can act as a modest buffer near these regimes when paired with the appropriate acid/base.
  • Hygroscopicity: small ammonium carboxylate salts often absorb moisture and may cake or deliquesce under humid air (literature observation).

• Refractive index, melting point, boiling point, density, logP: Not specified for this item; refer to CoA/Spec Sheet. Where needed, consult primary literature or measure under your method conditions.

Quality & Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on interpreting grades for this material (general)

  • Research/biochemical grade salts emphasize low inorganic/metallic contaminants and controlled water content to ensure reproducibility in catalysis, organometallic compatibility, and analytical workflows.
  • LC/MS or MS-grade buffering salts typically control volatile/nonvolatile residue and UV background to minimize ion-suppression and baseline drift.
  • Dry/anhydrous designations for hygroscopic salts indicate packaging under inert atmosphere with low headspace moisture; verify with Karl Fischer on receipt if critical.

• Stabilizers/additives: None stated for this item. If a stabilizer or anti-caking agent is present, it will be listed on the CoA; absence is generally preferred for analytical applications.

• What to check on receipt

  • Appearance and flow (caking indicates moisture uptake).
  • Assay or titratable content if provided on CoA.
  • Residual solvents/metals/UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

• Suitability notes

  • For LC/MS uses, prepare fresh solutions, use high-purity water/solvents, and 0.2 µm filter to reduce particulates and background.
  • For moisture-sensitive syntheses, handle rapidly under inert gas as indicated by the product’s argon-charged storage recommendation.

Reaction & Applications

• General roles (literature)

  • Volatile acetate source and buffering component for analytical separations (e.g., LC-MS mobile phase additive), where minimal nonvolatile residue is required.
  • Mild base/nucleophile source via acetate, and proton shuttle via the ammonium function in organic synthesis and catalysis.
  • Ionic medium component: can contribute to protic ionic liquid/deep eutectic systems when paired with appropriate partners (e.g., acetic acid), modifying viscosity and polarity.

• Synthetic contexts (examples from literature/general practice)

  • Metal-catalyzed C–H activation: acetate acts as an internal base/ligand in Pd- or Rh-catalyzed transformations (concerted metalation–deprotonation). A soluble acetate source can improve rates/selectivity depending on solvent.
  • Acylation equilibria and transesterifications: acetate salts can participate in acyl transfer or buffer adventitious acidity that would otherwise catalyze side reactions.
  • Phase-transfer or biphasic neutralizations where a volatile cation is desired to aid downstream removal.

• Analytical/separations

  • Used as a mobile phase modifier to adjust pH and ionic strength while maintaining volatility for MS detection; methylammonium can tune retention and peak shapes relative to ammonium.

• Practical notes

  • Drying: if anhydrous conditions are required, dry under vacuum at ambient or mild temperature; avoid overheating to prevent decomposition to methylamine/acetic acid or amide formation.
  • Degassing: for LC work, helium sparging or vacuum sonication reduces dissolved gases that can cause baseline noise.
  • Always validate with small-scale trials, as retention and reactivity can be sensitive to concentration and solvent composition.

Reaction Conditions

The following are literature-based, general guidelines for using alkylammonium acetate salts; they are not specifications for this item.

• As a volatile buffer/additive in LC and synthesis

  • Typical concentrations: 1–50 mM in aqueous or aqueous–organic solutions for LC-MS; 0.1–0.5 M stock solutions for preparative work where stronger buffering/ionic strength is needed.
  • Solvents: water, MeOH, EtOH, ACN/water. Filter through 0.2 µm PTFE/nylon depending on solvent.
  • Temperature: ambient to 40 °C for dissolution; avoid prolonged heating to prevent decomposition.

• In metal-catalyzed reactions (e.g., Pd-catalyzed C–H activation using acetate as a base)

  • Solvents: polar aprotic (DMF, DMSO, DMAc) or mixed aqueous media, depending on substrate; sometimes MeCN/H2O.
  • Base/additive loading: catalytic to stoichiometric acetate; optimize empirically.
  • Atmosphere: air or inert depending on catalyst; moisture tolerance varies.
  • Time/yield: substrate-dependent; small-ion acetates often improve initial rates by enhancing solubility of ionic intermediates (literature trend).

• In deep eutectic media formation

  • Combine methylammonium acetate with acetic acid or other HBDs at defined ratios; mix at room temp to mild heating until homogeneous. Validate conductivity/viscosity before use.

• Workup considerations

  • Volatility aids removal by rotary evaporation or lyophilization; rinse residues with minimal water/alcohol to strip remaining salt prior to extraction into organics.

Safety & Handling

• Item-specific hazard data

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

• General safety considerations for alkylammonium carboxylate salts (literature/experience; defer to SDS for authoritative guidance)

  • Likely hazards: may cause skin/eye irritation; inhalation of dust should be avoided. Thermal decomposition can release methylamine and acetic acid vapors, both irritants.
  • PPE: lab coat, safety glasses or face shield, nitrile gloves; use in a fume hood when weighing large quantities, preparing hot solutions, or when aerosol formation is possible.
  • Storage incompatibilities: keep away from strong oxidizers and strong acids/bases that could liberate corrosive vapors (acetic acid) or amines (methylamine). Avoid moisture uptake due to probable hygroscopicity.
  • Special risks: as a protic salt, it can alter pH; avoid mixing with acid chlorides/anhydrides/isocyanates to prevent uncontrolled reactions. Heating to dryness can lead to decomposition and amide formation in some systems.
  • First-aid overview: rinse eyes/skin with water for ≥15 min after contact; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Always consult the SDS for detailed measures.

• Environmental: aqueous solutions are expected to be biodegradable but may alter local pH; dispose via appropriate neutralization and in accordance with institutional and regulatory requirements.

Solvent Selection

• Polarity and miscibility (literature/general)

  • Highly polar, ionic, protic compound; expected to be freely soluble in water and polar protic solvents (MeOH, EtOH). Limited solubility in polar aprotics (MeCN, DMSO) can vary; aqueous-organic mixtures generally improve handling.

• Choosing media for use

  • Aqueous buffers: ideal when a volatile acetate system is desired (e.g., LC-MS mobile phases) where ammonium acetate might be substituted by alkylammonium acetate to tune ion-pairing.
  • Alcoholic media: useful when water-sensitive substrates are marginally compatible yet some proticity is acceptable; MeOH/EtOH can dissolve the salt while maintaining volatility.
  • Nonpolar solvents (e.g., hexanes, toluene): typically unsuitable; use a biphasic or phase-transfer strategy if needed.

• Comparison snapshot (literature/general)

  • Methylammonium acetate vs ammonium acetate: the methylated cation can modestly alter volatility, ion-pairing, and chromatographic selectivity; both are generally volatile and MS-friendly.
  • Versus triethylammonium acetate: triethylammonium salts have higher organic solubility but are less volatile and may cause more ESI ion suppression.

• Practical tips

  • For LC use, prepare solutions in water or water/MeOH or water/ACN; filter (0.2 µm) and degas to improve baseline stability.
  • Avoid highly basic or strongly acidic co-solvents that may shift equilibria and release methylamine or acetic acid.

Storage & Reconstitution

• Item-specific storage and shipping

  • Storage Conditions: Store at 2–8 °C, Argon charged (from Product Data).
  • Shipped In: Wet ice (from Product Data).
  • Research Use Note: For research use only (from Product Data).

• Practical storage guidance (general)

  • Keep tightly capped under inert gas to minimize moisture and CO2 uptake; hygroscopic salts can cake and show pH drift upon dissolution after exposure.
  • Store in the original container within secondary containment to prevent condensation ingress during refrigeration.
  • Allow container to equilibrate to room temperature before opening to avoid moisture condensation.

• Reconstitution/preparation (general; not item-specific specs)

  • Solvents: dissolve in high-purity water or suitable polar solvents (MeOH, EtOH). For LC use, prepare fresh solutions and filter through 0.2 µm.
  • Concentration: prepare only what is needed; acetate systems can support microbial growth—store solutions at 2–8 °C and discard if turbidity/odor develops.
  • Drying (if required): dry gently under vacuum at ambient temperature; avoid heating to prevent decomposition to methylamine/acetic acid.

• Stability notes

  • Long-term stability, water content, and assay: Not specified for this item; refer to CoA/Spec Sheet.
  • Avoid contact with strong acids/bases and oxidizers during storage.

Structure & Identity

A simple organic salt composed of the methylammonium cation and the acetate anion; an ionic, protic compound useful as a volatile acetate source and buffering component.

• Item-specific identifiers (from Product Data)

  • SKU: M1524294
  • Product Name: Methylammonium Acetate
  • CAS: 6998-30-7
  • CID: 5259270
  • InChIKey: 297838
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity details (for reference; not specifications for this item)

  • Overall empirical formula (combined salt): C3H9NO2 (literature)
  • Formula components: CH3NH3+ (methylammonium), CH3COO− (acetate) (literature)
  • Molecular weight: ~91.11 g/mol (literature, calculated from C3H9NO2)
  • Representative SMILES (salt pair, literature): C[NH3+].CC(=O)[O-]

• Structural features (general chemistry description)

  • Functional groups: protonated primary amine (ammonium), carboxylate anion.
  • No stereocenters; consists of two small ions associated by electrostatics and hydrogen bonding.
  • 2D structure description: a methyl-substituted ammonium cation (tetrahedral N center bearing three N–H bonds and one N–C bond) ion-paired with a planar acetate anion (sp2 carbonyl carbon, delocalized negative charge over two oxygens).

Synthetic Utility

• Functional roles (literature/general)

  • Acetate source: provides a weakly basic, nucleophilic counterion useful in substitution, elimination, and metal-catalyzed reactions (e.g., as a base in Pd-catalyzed C–H activation via CMD pathways).
  • Protic, ionic additive: methylammonium can modulate medium polarity, hydrogen-bonding, and ion pairing, influencing rates/selectivity in polar reactions.
  • Volatile counterion strategy: facilitates temporary salt formation or neutralization where downstream removal by evaporation/lyophilization is desired.

• Transformations and contexts

  • C–H functionalization: acetate assists as an internal base; choice of cation (methylammonium vs alkali metal) can change solubility in organic/aqueous media.
  • Acyl transfer equilibria: acetate buffers acidity and can participate in ester interchange under appropriate conditions.
  • Desilylation/neutralizations: acetate sources have been used for mild deprotection or quench steps where strong nucleophiles are undesirable.
  • Ionic liquid/DES precursor: combining with acetic acid or other H-bond donors yields low-melting mixtures useful as alternative reaction media.

• Practical notes

  • For water-sensitive substrates, employ mixed solvents (e.g., MeOH/MeCN) and limit water content; confirm solubility of all components.
  • Avoid high temperatures that could decompose the salt to methylamine and acetic acid, altering stoichiometry and introducing odor/pressure.
  • If metal-catalyzed processes are moisture-sensitive, pre-dry the salt (vacuum, ambient temp) immediately before use.

Target Specificity

This product is a small-molecule salt and does not possess immunological target specificity (no antigen/epitope, clone, or isotype). This section is not typically applicable. For practical information, refer to Reaction & Applications, Buffer Applications, and Synthetic Utility.