Methyl 2-methylvalerate - ≥95% , CAS No.2177-77-7

CAS: 2177-77-7 Cat. No.: B300583 Formule: C₇H₁₄O₂ Poids moléculaire: 130.18 Numéro CE: 218-543-9

GRADE & PURITY ≥95%

Synonyms

(+/-)-METHYL 2-METHYLPENTANOATE | 2-Methylpentanoic acid methyl ester | 2-Methylvaleric acid methyl ester | Methyl 2-methylpentanoate # | Methyl 2-methylpentanoate, >=98% | FEMA No. 3707 | METHYL 2-METHYLPENTANOATE, (+/-)- | Pentanoic acid, 2-methyl-, met

Storage

Room temperature

Shipped In

Normal

Specifications

Synonymes

(+/-)-METHYL 2-METHYLPENTANOATE | 2-Methylpentanoic acid methyl ester | 2-Methylvaleric acid methyl ester | Methyl 2-methylpentanoate # | Methyl 2-methylpentanoate, >=98% | FEMA No. 3707 | METHYL 2-METHYLPENTANOATE, (+/-)- | Pentanoic acid, 2-methyl-, met

Spécifications et pureté

≥95%

Conditions de stockage de stockage

Room temperature

Expédié en

Normal

Pureté

≥95%

Noms et identifiants

• Pubchem Sid: 504759046
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504759046
• Sourires canoniques: CCCC(C)C(=O)OC
• IUPAC Name: methyl 2-methylpentanoate
• InChIKey: ZTULNMNIVVMLIU-UHFFFAOYSA-N
• INCHI: 1S/C7H14O2/c1-4-5-6(2)7(8)9-3/h6H,4-5H2,1-3H3
• Isomères SMILES: CCCC(C)C(=O)OC
• Numéro ONU: 3272
• Groupe d'emballage: III
• Poids moléculaire: 130.18
• Reaxy-Rn: 1721233
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1721233&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Methyl esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Methyl ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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

• Point d'éclair (°C): 35°C
• Point d'ébullition (°C): 85°/18mmHg
• Poids moléculaire: 130.180 g/mol
• XLogP3: 2.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 130.099 Da
• Monoisotopic Mass: 130.099 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 88.900
• 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

Références

1. Yan Zhao, Chen-Yang Shao, Han Yan, Yue Zhang, Qun-Hua Peng, Zhi Lin, Xiao-Ting Zhai, Hai-Peng Lv, Yin Zhu.  (2026)  Unraveling the aromatic essence of baked green tea using sensomics: insights from three representative cultivars.  FOOD CHEMISTRY,      [PMID:41544474] [10.1016/j.foodchem.2026.147878]

Application Protocols

No antibody/assay application protocols are associated with this small-molecule reagent. For practical usage, see Reaction Conditions, Synthetic Utility, and Reaction & Applications for detailed, literature-based guidance on transformations (hydrolysis, transesterification, amidation, and reductions).

Biological Roles

Item-specific biological data are not provided. The following notes are general/literature context for aliphatic methyl esters and are not clinical claims.

• Metabolic fate: Aliphatic methyl esters are commonly hydrolyzed by carboxylesterases to the corresponding carboxylic acid and methanol. For methyl 2-methylvalerate, hydrolysis would yield 2-methylpentanoic acid and methanol (literature).
• Biochemical relevance: The acid product (2-methylpentanoic acid) is a branched short-chain fatty acid isomer; such acids can enter fatty acid metabolism after activation to acyl-CoA thioesters, albeit with isomer- and chain-length-dependent processing (literature).
• Protein interactions: No specific binding roles are established for this ester; interactions are expected to be nonspecific hydrophobic partitioning in membranes or proteins (literature).
• Toxicology context: Methanol release upon hydrolysis is a consideration for in vitro systems; ensure adequate ventilation and quenching. Refer to SDS for hazard details.

Note: These are general biochemical considerations for research planning. This product is for research use only and is not intended for food, drug, or cosmetic applications.

Buffer Applications

Not typically applicable. Methyl 2-methylvalerate is a hydrophobic ester and is not used as a buffering agent. For aqueous systems, consider established buffers (phosphate, HEPES, Tris) selected according to your target pH and ionic strength. See Reaction & Applications and Synthetic Utility for more relevant use-cases of this compound.

Green Alternatives

Consider sustainability at both the solvent and reagent level when working with methyl 2-methylvalerate.

Greener process choices (literature/practice):

• Solvent selection: Replace chlorinated solvents and benzene with greener ethers (2‑MeTHF, CPME), esters (EtOAc), or bio-based alcohols where compatible.
• Catalysis: Employ biocatalytic routes (lipase-catalyzed transesterification or hydrolysis) under mild conditions, minimizing strong acids/bases and lowering E-factor.
• Energy efficiency: Conduct reactions at ambient temperature/pressure when possible; use continuous removal of methanol (e.g., nitrogen sweep or pervaporation) to drive equilibrium with less heat input.

Illustrative comparison (general; not product specifications):

• Conventional: Transesterification in toluene with sodium alkoxide, reflux.
• Greener alternative: Enzymatic transesterification in 2‑MeTHF or solvent-free conditions at 25–40 °C, recyclable enzyme preparations.

Trade-offs:

• Biocatalysis may require longer reaction times and careful water activity control.
• Bio-based solvents (2‑MeTHF) can introduce peroxide-formation risk; implement routine peroxide testing and stabilizer management.
• Switching from methyl to ethyl esters can improve safety (lower methanol generation) but alters volatility and equilibrium constants.

Pharmaceutical Uses

No pharmacopeial/excipient designation is provided for this item. This compound is used in research and process development as a synthetic intermediate or model substrate for ester transformations.

• Potential roles in pharma R&D (general, non-clinical):
  • Intermediate for generating 2-methylpentanoyl motifs in API side chains via amidation or reduction.
  • Volatile component profiling—GC method development for ester-containing matrices.
• Regulatory status: Not specified for this item; verify any compendial requirements (if applicable) via USP/Ph. Eur. monographs for related substances.

Important: No medical or therapeutic claims are made. This product is supplied strictly for research use only.

Physical Properties

Item-specific specifications are not provided in the product data and should be confirmed on the CoA/Spec Sheet.

Literature/general reference values for methyl 2-methylvalerate (for planning only; not product specifications):

• Physical state: Colorless liquid (literature)
• Boiling point: Typically ~148–152 °C at 1 atm (literature)
• Melting point: Expected below 0 °C; often reported < −60 °C for similar C7 methyl esters (literature)
• Density: ~0.86–0.88 g/mL at 20–25 °C (literature)
• Refractive index (n20 D): ~1.404–1.410 (literature)
• Vapor pressure: Low to moderate for a C7 ester; increases substantially with temperature (literature)
• Water solubility: Low (insoluble to slightly soluble; typically a few g/L at ambient temperature). Miscible with most common organic solvents (literature)
• LogP (octanol/water): Approximately 2.1–2.6 (literature/estimated)
• UV cutoff: Not specified for this item; refer to CoA/Spec Sheet. (Aliphatic esters generally have weak UV absorption above ~210–220 nm; literature)

Notes for practitioners:

• As with many aliphatic esters, properties are close to those of methyl hexanoate due to the isomeric C7H14O2 composition. If precise parameters (e.g., density at a defined temperature) are critical, verify on the batch CoA.

Quality and Grades

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

Guidance for interpreting grades (general):

• Analytical reagent (AR) or higher-purity grades typically control trace impurities that can interfere with catalysis (e.g., acids/alcohols, water). For ester substrates, residual acid or alcohol can alter reaction stoichiometry or initiate side reactions (hydrolysis, transesterification).
• Low-UV/HPLC grades emphasize minimal UV-absorbing impurities and low baseline drift, which can be relevant if using the material as a solvent or mobile-phase modifier (less typical for this ester).
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Aliphatic esters generally do not require inhibitors, but trace acid content and water are quality-critical for base- or enzyme-catalyzed transformations.

What to verify on receipt:

• Identity confirmation by GC–MS or 1H/13C NMR.
• Purity/assay by GC with area% normalization; check for 2-methylpentanoic acid and methanol as potential impurities.
• Water content (Karl Fischer) if using in moisture-sensitive chemistry (enolates, strong bases) — Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

As a branched aliphatic methyl ester, methyl 2-methylvalerate is a versatile acyl fragment donor in synthesis.

Typical applications (literature/practice):

• Hydrolysis and saponification: Access to 2-methylpentanoic acid under aqueous base (NaOH, KOH) or acid catalysis. Useful for kinetic studies and method validation of ester hydrolysis.
• Transesterification: Exchange with alcohols (alkoxide catalysis) or via enzymatic methods (lipases) to produce alternative alkyl esters with tailored volatility or solubility.
• Reduction chemistry:
  • DIBAL-H at low temperature (e.g., −78 to −50 °C) to the corresponding aldehyde (2-methylpentanal) with careful quench.
  • LiAlH4/Red-Al to reduce to the primary alcohol (2-methyl-1-pentanol) plus methanol from the methoxy fragment.
• Amidation (aminolysis): Direct conversion to amides using amines at elevated temperature (often with removal of methanol) or with catalysts (e.g., Ti(OR)4, Sc(OTf)3, boronic acids) to improve rates/selectivity.
• Enolate chemistry: The α‑methylene to the carbonyl enables Claisen-type condensations under strong base (e.g., LDA, NaH with ester enolates), though the γ‑branch can influence sterics and outcomes.

Practical tips:

• Control moisture to avoid background hydrolysis.
• For reductions, maintain low temperatures to suppress over-reduction (DIBAL) and ensure controlled quench to prevent exotherms.
• Monitor reactions by GC or GC–MS; aliphatic esters typically give clean chromatographic behavior with short retention windows.

Reaction Conditions

General literature conditions (guidance only; optimize per system):

• Hydrolysis (saponification):
  • Reagents: NaOH or KOH (1–2 equiv) in MeOH/H2O or EtOH/H2O.
  • Temperature: 25–60 °C (or reflux for faster rates).
  • Workup: Acidify to pH ~2 to precipitate/extract 2-methylpentanoic acid.
• Acid-catalyzed hydrolysis:
  • Reagents: Dilute mineral acid (e.g., H2SO4, HCl), aqueous/organic biphasic.
  • Temperature: Reflux; ensure phase transfer or use co-solvent.
• Transesterification:
  • Base: Catalytic NaOMe/KOtBu in the target alcohol; 25–60 °C or reflux depending on alcohol bp.
  • Enzymatic: Candida antarctica lipase B (CAL-B) in 2‑MeTHF or solvent-free, 25–50 °C; control water activity.
• Direct amidation (aminolysis):
  • Neat or in toluene/xylene with an amine (1.2–2.0 equiv); 100–160 °C; remove methanol continuously.
  • Catalysts: Ti(OR)4, B(OPh)3, or Sc(OTf)3 (1–10 mol%) can lower temperature and improve rates.
• Reduction:
  • DIBAL-H (1.0–1.5 equiv) in toluene or CH2Cl2 at −78 to −50 °C to aldehyde; careful, slow quench with MeOH then aqueous Rochelle’s salt.
  • LiAlH4 (1.5–2.0 equiv) in THF/Et2O, 0–25 °C to primary alcohol; aqueous workup with controlled quench.

Analytics: Track by GC/GC–MS or HPLC with RI/UV (short-λ). Typical isolated yields for these standard operations are often high (70–95%) under optimized conditions (literature).

Safety and Handling

GHS details (item-specific): Not specified for this item; refer to the SDS for authoritative hazard classification, pictograms, and H-statements.

General safety information for aliphatic methyl esters (literature/practice guidance):

• Likely hazards: Combustible/flammable liquid, eye/skin irritant; vapors may form ignitable mixtures with air above the flash point. Avoid sources of ignition.
• Incompatibilities: Strong oxidizers; strong acids/bases may promote hydrolysis or transesterification; avoid prolonged moisture exposure to limit hydrolysis to the corresponding acid and methanol.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and safety glasses/goggles. Handle in a fume hood to limit inhalation of vapors.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: Wash with soap and water; remove contaminated clothing.
  • Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
• Fire safety: Use CO2, dry chemical, or foam. Cool containers with water spray if exposed to fire. Vapors are heavier than air; ensure adequate ventilation.

Always consult the product-specific SDS for definitive hazard, exposure limits, and response procedures.

Solvent Selection

This product is primarily a substrate/intermediate rather than a routine reaction solvent. Nevertheless, understanding its solubility profile helps in method development.

• Polarity class: Low-polarity, weakly hydrogen-bond-accepting (ester carbonyl) liquid (literature/general).
• Miscibility: Miscible with most organic solvents (hexanes, toluene, ethers, chlorinated solvents, alcohols); low solubility in water (literature).
• Dielectric constant: Expected in the low-to-mid single digits typical for C7 aliphatic esters; select co-solvents accordingly (literature trend).

Choosing media when using this ester as a reagent:

• Base-catalyzed reactions (transesterification, Claisen-type condensations): Use anhydrous alcohols or aprotic solvents (toluene, THF) with alkoxide or strong base; rigorously exclude water.
• Reductions (DIBAL, LAH): Ethers (Et2O, THF) or toluene at controlled temperatures; avoid protic media.
• Aminolysis (direct amidation): High-boiling hydrocarbons or aromatic solvents (xylene, mesitylene, toluene) may aid methanol removal; consider azeotropic setups.

Quick comparison (literature):

• vs. Methyl hexanoate: Similar solubility and volatility; choose based on desired branching in the acyl fragment.
• vs. Ethyl 2-methylvalerate: Ethyl analog may offer slightly higher bp and altered volatility; otherwise comparable reactivity.

Storage and Reconstitution

• Storage Conditions (item-specific): Room temperature (as provided). Store tightly closed in a dry, well-ventilated place. Minimize exposure to moisture to limit slow hydrolysis to acid and methanol. Protect from heat, sparks, and open flame.
• Shipped In: Normal (ambient) conditions (as provided).
• Reconstitution: Not applicable. This is a ready-to-use liquid; no reconstitution required.
• Handling tips:
  • If using in moisture-sensitive chemistry, consider storing under inert atmosphere (N2/Ar) and dispense via dry syringe techniques.
  • For long-term storage, amber glass and low-permeability caps help preserve composition; periodic GC assay can confirm stability.
• Stability: Item-specific stability data are not provided; refer to CoA/Spec Sheet and SDS. In general, neat aliphatic esters are stable under neutral, dry conditions but can hydrolyze in the presence of acids/bases or water.

Research Use Note: For research use only.

Structure and Identity

Methyl 2-methylvalerate is a branched aliphatic methyl ester derived from 2-methylpentanoic acid (also called 2-methylvaleric acid).

• SKU: B300583
• CAS: 2177-77-7
• PubChem CID: 519890
• InChIKey (item-specific): 466272 (as provided; full-length InChIKey string not specified for this item)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: For reference, methyl 2-methylvalerate is commonly represented as C7H14O2 (literature).
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: Calculated MW for C7H14O2 is ~130.19 g/mol (literature/computed).

Structural features (general description):

• Functional group: Methyl ester (R–C(=O)–O–CH3) on a saturated, branched C5 acyl chain.
• Substitution pattern: One methyl branch at the γ-position relative to the carbonyl (overall “2-methyl” on the pentyl backbone of the parent acid).
• No rings, no heteroatoms beyond the ester oxygen atoms; no stereocenters in the simplest constitutional isomer assignment.
• 2D description: A linear four‑carbon segment (–CH2–CH2–) connects the carbonyl carbon to a branched site (–CH(CH3)–CH3), with the ester methoxy as –OCH3.

Research Use Note: For research use only.

Synthetic Utility

Key functional group: Aliphatic methyl ester.

Transformations (literature/practice):

• Nucleophilic acyl substitution:
  • Aminolysis to amides with primary/secondary amines (heat/catalysis; remove MeOH).
  • Alcoholysis (transesterification) to tailored alkyl esters (acid/base or enzyme catalysis).
• Reductive routes:
  • DIBAL-H partial reduction to aldehyde at low temperature.
  • LAH/borohydride variants to the corresponding primary alcohol.
• Carbon–carbon bond formation:
  • Claisen condensations via enolate of the ester (α‑methylene) with appropriate electrophiles (requires strong base and compatible co-ester).
  • Use as an acyl equivalent after activation (e.g., conversion to acid chloride via hydrolysis then oxalyl chloride) to enter acylation manifolds.
• Biocatalysis: Lipase-mediated dynamic kinetic resolutions and selective transesterifications using this substrate scaffold.

Strategic considerations:

• The γ‑methyl branch modulates sterics and can influence regioselectivity in subsequent C–C bond formations and hydrogenations relative to linear pentanoyl analogs.
• For convergent synthesis, retain the ester through multistep sequences as a protecting group for the acid, then unveil late-stage by hydrolysis.
• Monitor for background hydrolysis and methanol formation in basic media; maintain anhydrous conditions where needed.

Target Specificity

Not applicable. This product is a small-molecule ester, not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity is associated with this item.