GRADE & PURITYfor Synthesis?Synthesis grade — practical purity for chemical synthesis and preparative work. Use as a cost-effective reagent when analytical purity isn't required.
This compound belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
External Descriptors
Branched fatty acids
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.
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Application Protocols
Not applicable. No validated immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic or analytical applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance and tailor protocols to your specific substrates and instrumentation.
Biological Roles
General biochemical context (literature; not product-specific and not implying clinical/therapeutic use):
Chemical class: branched-chain fatty acid (BCFA) isomeric with hexanoic acid. BCFAs occur in bacterial membranes and certain mammalian lipid pools at low levels.
Metabolism: aliphatic carboxylic acids are typically activated to acyl‑CoA thioesters by acyl‑CoA synthetases. Branching at the α‑carbon influences downstream metabolism; classical β‑oxidation is sterically hindered at α‑branched substrates, sometimes favoring alternative pathways (e.g., ω‑oxidation followed by truncated β‑oxidation or α‑oxidation for some branched systems, literature generality).
Biophysical effects: incorporation of branched acyl chains into lipids can decrease membrane packing density relative to straight-chain analogs, altering fluidity (observed with BCFAs in microbial systems, literature generality).
Protein acylation: aliphatic acids can serve as acyl donors to proteins (e.g., via acyl transfer chemistry) in biochemical assays; branching can modulate enzyme selectivity (enzyme-dependent; literature examples exist but are system-specific).
Important usage notice:
The above pertains to fundamental biochemistry. SKU E434316 is supplied strictly for research and laboratory use. No claims are made regarding biological activity, safety, or suitability for use in humans or animals. For any biological experimentation, ensure appropriate containment, approvals, and risk assessment.
Buffer Applications
2‑Ethylbutyric acid is a monocarboxylic acid with pKa typical of aliphatic fatty acids (~4.8–4.9, literature). However, it is not commonly used as a laboratory buffer component because:
Low aqueous solubility and hydrophobicity complicate preparation of well-defined aqueous buffer systems.
Pronounced odor and volatility relative to common buffering acids disfavor routine use.
Practical guidance:
If a carboxylate buffer near pH 4.8–5.0 is desired, more conventional systems (acetate, formate, citrate, MES) are preferred for better solubility, lower odor, and well-characterized buffering ranges.
For biphasic or nonaqueous systems where a weak carboxylic acid is needed (e.g., controlling basicity in organic media), 2‑ethylbutyric acid can function as a Brønsted acid, but this is not a conventional “buffer” application. Titrate in situ and monitor pH (or acid equivalents) appropriate to the solvent system.
Item-specific buffer specs (concentration ranges, recipes): Not applicable/not specified for this item; refer to CoA/Spec Sheet if needed.
Green Alternatives
Because 2‑ethylbutyric acid is a substrate/reagent rather than a solvent, “greener alternatives” focus on reaction media and coupling strategies that reduce hazard and waste when transforming this acid.
Greener choices and trade-offs (literature/general):
Solvents:
Prefer 2‑MeTHF, CPME, EtOAc, or alcoholic media (when compatible) over chlorinated solvents (e.g., DCM) for esterifications and couplings.
Water or water‑lean biphasic systems (with surfactants or phase-transfer catalysts) can enable some esterifications and amide formations.
Coupling reagents:
Shift from HATU/HBTU (benzotriazole-based; explosive risk) to EDC·HCl with OxymaPure or to CDI when feasible; consider catalytic peptide coupling with recyclable reagents.
Catalysis and process intensification:
Use solid acids (Amberlyst‑15, Montmorillonite K‑10) or heteropolyacids for Fischer esterification, enabling easier recovery/reuse and less corrosive waste.
Employ enzyme-catalyzed esterifications/amidations in green solvents or solvent-free media to lower E-factor and energy input.
Workup/waste:
In-situ azeotropic water removal or reactive distillation reduces solvent volume and drives equilibrium without stoichiometric dehydrating agents.
Illustrative comparison (general):
DCM + HATU amidation: fast, efficient, but chlorinated waste and hazardous coupling byproducts.
EtOAc or 2‑MeTHF + EDC/Oxyma: comparable conversions with reduced environmental impact and improved safety profile.
Note: Selection should consider substrate solubility and required purity. Validate greener conditions at small scale before scale-up.
Pharmaceutical Uses
Formulation/excipient context (general; no therapeutic claims):
2‑Ethylbutyric acid is not a common pharmacopeial excipient. Its primary value in pharmaceutical R&D is as a synthetic building block to introduce the 2‑ethylbutanoyl moiety into intermediates, prodrugs, or conjugates to modulate lipophilicity, permeability, and metabolic stability (literature/general medicinal chemistry practice).
Formation of 2‑ethylbutanoyl esters of alcohol-containing APIs to explore pro-moieties with altered release or absorption (requires full development and safety evaluation; research use only).
Preparation of amide-linked side chains in small molecules or linkers where α‑branching imparts steric bulk near the carbonyl, potentially affecting receptor binding and hydrolytic stability (system-dependent).
Use as a reference standard or impurity marker in impurity profiling when branched C6 carboxylates are process-related impurities.
Regulatory/quality notes:
No pharmacopeial monograph is implied for this specific item. If use in GMP or regulated settings is contemplated, obtain full qualification data (CoA, residual solvent profile, elemental impurities, bioburden, stability) and assess against relevant guidelines (ICH Q3A/B, Q3D, Q7) before use.
Item-specific compliance status: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Exact BP/MP, density, refractive index, UV cut-off, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values for 2-ethylbutanoic acid (for context; not product specifications):
Phase at ambient conditions: typically a colorless to pale liquid carboxylic acid with fatty-acid-like odor
Solubility: limited solubility in water; miscible with common organic solvents (alcohols, ethers, chlorinated solvents) (literature, qualitative)
Volatility: lower than straight-chain hexanoic acid due to branching effects; still distillable under atmospheric or reduced pressure (literature, qualitative)
Partitioning: expected to be moderately hydrophobic (positive logP typical for C6 aliphatic acids) (literature, qualitative)
Practical implications (general):
The branched structure usually lowers melting point relative to straight-chain isomers, making handling as a liquid straightforward at room temperature.
Odor control (use of vented enclosures) and secondary containment are recommended due to fatty-acid-like smell and potential for surface adsorption.
Important: Do not treat the above as specifications for SKU E434316. For exact values applicable to this item (and for chromatographic suitability, trace impurities, etc.), consult the current CoA and SDS.
Quality and Grades
Grade/Purity (as provided): for Synthesis
Meaning: “For synthesis” denotes a grade appropriate for general laboratory and preparative chemistry where ultra-trace impurities, low-UV background, or bio/pharma compliance are not specifically required. It is suitable for reaction setup, building-block use, and routine R&D operations.
What this implies for use:
Chromatography-sensitive applications (e.g., HPLC/UV detection) or trace analysis may require higher grades (HPLC, spectroscopy) with guaranteed low UV absorbance and tighter impurity controls.
Metal content, residual solvents, moisture content, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/impurities:
No stabilizer is stated for this product. If your transformation is base- or acid-catalyzed and sensitive to trace inhibitors, consider a pre-screen: quick GC or 1H NMR to confirm purity, and, if needed, short-path distillation under reduced pressure immediately prior to use.
Fit-for-purpose guidance:
Synthesis grade is typically adequate for:
Formation of acid chlorides/anhydrides, esterifications, and amide couplings
Routine derivatization or salt formation
For bioassays or impurity profiling, request a CoA with analytical data for your lot or consider upgrading to a higher analytical grade where available.
Reaction and Applications
As a branched aliphatic carboxylic acid, 2-ethylbutyric acid is a versatile acyl source and hydrophobic motif for derivatization.
Common reaction families (literature/general):
Esterifications: formation of 2‑ethylbutanoate esters under Fischer conditions or via acid chloride/anhydride intermediates. Useful for tuning lipophilicity and volatility in materials and fragrance research (research use only).
Amide couplings: EDC/HOBt, DIC/Oxyma, HATU/DIPEA in DMF/DCM/MeCN to furnish 2‑ethylbutanamides; branching near the carbonyl modulates sterics and basicity of resultant amides.
Acid chloride formation: SOCl2 or (COCl)2 (cat. DMF) to give 2‑ethylbutanoyl chloride; employed for acylation of nucleophiles (alcohols, amines, arenes via Friedel–Crafts under Lewis acidity).
Anhydrides and mixed anhydrides: pivaloyl chloride or isobutyl chloroformate strategies enable subsequent rearrangements or couplings.
Reductions: BH3·THF or LiAlH4 to primary alcohol (2‑ethylbutanol); DIBAL-H or Rosenmund-type conditions to the aldehyde (2‑ethylbutanal) when selectivity is required.
Decarboxylative transformations: photoredox/Ni dual catalysis can enable decarboxylative cross-couplings from pre-activated carboxylates (e.g., redox-active esters) to build C–C bonds while retaining α‑branching.
Practical tips:
Drying: for coupling chemistry, ensure dryness (molecular sieves) to minimize hydrolysis and O→N acyl transfer side products.
Stoichiometry: use slight excess of acid for esterification; for amidation, equimolar with coupling reagent control.
Workup: acid-base extractions often efficient; the branched C6 chain partitions into organic layers—adjust salt strength (brine) to break emulsions.
Characterization: 1H NMR shows characteristic downfield broad singlet for –CO2H; IR ν(C=O) ~1710 cm−1 (carboxylic acid dimers, literature).
Reaction Conditions
General, literature-based guidance for transforming 2‑ethylbutyric acid (not product specifications; optimize per substrate):
Fischer esterification:
Conditions: ROH (solvent/reagent), catalytic H2SO4 or p‑TsOH (1–10 mol%). Reflux at solvent bp (e.g., MeOH 65 °C, EtOH 78 °C, iPrOH 82 °C) with water removal (Dean–Stark for higher alcohols or 3Å molecular sieves).
Typical times: 2–24 h depending on alcohol and catalyst loading.
Notes: Excess alcohol or azeotropic water removal drives conversion. Branching minimally affects equilibrium but can slow rate with hindered alcohols.
Amide coupling:
Reagents: EDC·HCl (1.1–1.5 eq) + Oxyma/HOAt (0.1–1.0 eq), base (DIPEA 2–3 eq) in DMF/MeCN/DCM at 0–25 °C.
Alternative: DIC (1.1–1.5 eq) + DMAP (cat.) in DCM; or HATU (1.1 eq) in DMF for difficult amines.
Typical times: 1–16 h. Monitor by TLC/LC–MS.
Acid chloride formation:
SOCl2 (1.5–3 eq) in DCM/toluene, cat. DMF, 0–25 °C to reflux until gas evolution ceases (1–3 h). Remove volatiles under reduced pressure; use immediately or store cold under inert gas.
Reductions:
BH3·THF (1–1.5 M in THF), 1.2–1.5 eq at 0 °C to rt; quench carefully with MeOH then aqueous base.
DIBAL‑H (1.0–1.5 eq) at −78 to −20 °C on corresponding acid chloride/Weinreb amide to access aldehyde.
Friedel–Crafts acylation (from acid chloride):
Catalyst: AlCl3 (1–2 eq), solvent CH2Cl2 or CS2, 0 °C to rt; electron-rich arenes preferred; branching helps suppress polyacylation.
Yields: substrate-dependent; esterifications and amide couplings commonly 70–95% under optimized conditions (literature ranges). Validate conditions on small scale first and observe standard safety protocols.
Safety and Handling
Provided hazard information for this item:
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
General safety profile for saturated aliphatic carboxylic acids (literature; not product-specific classification):
Hazards: causes skin and eye irritation; may cause respiratory irritation if aerosolized or heated; unpleasant, persistent odor. Ingestion may cause GI irritation.
Incompatibilities: strong oxidizers; strong bases (exothermic neutralization); reactive acid derivatives (acid chlorides/anhydrides) form under dehydrating conditions; avoid reactive metals that form carboxylates with H2 evolution under strongly basic conditions.
PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to mitigate odor and vapors.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin: wash with soap and water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: combustible liquid; use CO2, dry chemical, or foam. Thermal decomposition can generate acrid fumes.
Spill response: contain, absorb with inert material (vermiculite, sand), transfer to waste container; wash area with mild detergent while preventing environmental release.
Always consult the product-specific SDS for authoritative classification, exposure limits, and emergency measures.
Solvent Selection
This product is a carboxylic acid reagent rather than a solvent. Solvent selection therefore pertains to how best to use 2-ethylbutyric acid in synthesis or processing.
General solvent compatibility (literature):
Miscible with: common organic solvents (alcohols, ethers such as THF/Et2O, esters, chlorinated solvents). Limited solubility in water due to hydrophobic backbone.
Polarity class: moderately polar protic compound; behaves as a hydrogen-bond donor/acceptor; prefers polar aprotic or protic organic media for homogeneous reactions.
Recommended solvent choices by transformation (general guidance):
Fischer esterification: anhydrous alcohols (MeOH, EtOH, iPrOH) as both reagent and solvent; use acid catalysis (e.g., H2SO4, TsOH). Remove water (Dean–Stark or molecular sieves) to drive equilibrium.
Amide coupling: polar aprotic solvents (DCM, DMF, DMAc, NMP, MeCN) with carbodiimides (EDC/DIC) or uronium reagents; consider base (DIPEA) and additives (HOBt/HOAt/Oxyma).
Acid chloride formation: inert solvents (toluene, DCM) with SOCl2 or oxalyl chloride; catalytic DMF optional.
Reductions to alcohol/aldehyde: BH3·THF in THF or DIBAL-H in toluene/hexane at controlled temperature.
Comparison notes:
Versus longer-chain acids (C8+): improved solubility in medium-polar solvents and lower viscosity.
Versus straight-chain C6 (hexanoic acid): similar compatibility; branching can slightly alter solubility and boiling behavior, often easing distillation.
Always align solvent choice with downstream workup, safety, and waste considerations.
Storage and Reconstitution
Storage conditions (as provided): Room temperature
Shipped in: Normal
Container recommendations: Store tightly closed in a corrosion-resistant cap/liner (e.g., PTFE-lined) to minimize odor egress and prevent atmospheric moisture/contaminant ingress.
Atmosphere: Ambient air is acceptable for most handling; for long-term storage of opened containers, an inert headspace (N2/Ar) can help limit oxidative discoloration or odor carryover.
Light sensitivity: Aliphatic carboxylic acids are generally light-stable; store away from direct sunlight as good practice.
Stability: Typically stable at room temperature under dry, clean conditions. Avoid prolonged exposure to strong bases or oxidizers.
Reconstitution: Not applicable; supplied neat (no reconstitution required). If solidification occurs at lower temperatures, warm gently to room temperature and mix before use.
Spill/odor control in storage areas: Secondary containment and absorbent pads help manage potential leaks and persistent odors from fatty-acid-like compounds.
Always refer to the current CoA and SDS for lot-specific stability or storage notes and for guidance on safe handling and disposal. For sensitive reactions, consider drying or distilling immediately prior to use to achieve the lowest moisture content.
Structure and Identity
Product: 2-Ethylbutyric acid (SKU: E434316)
CAS: 88-09-5 (as provided in product data)
Category: Chemical and Biochemical Reagents; for research use only
Item-specific identifiers (as supplied):
InChIKey: 270200 (as provided; consult CoA/SDS for definitive identifier)
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.
Common name: 2-ethylbutanoic acid; a branched C6 monocarboxylic acid (isomeric with hexanoic acid)
Expected molecular formula (literature): C6H12O2; typical formula for branched C6 carboxylic acids
Expected molecular weight (literature): ~116.16 g/mol for C6H12O2 isomers
Functional groups: one terminal carboxylic acid (–CO2H); saturated, aliphatic backbone with one ethyl substituent at the α-carbon
Structural features: the α-carbon (C2 relative to the carboxyl carbon) bears an ethyl substituent, creating a stereogenic center; commercial material is typically racemic unless specified otherwise
2D description in words: a carboxylate carbonyl attached to a chiral methine; that methine is bonded to an ethyl group and a methylene that continues to a terminal methyl (overall a branched six-carbon chain terminating in –CO2H)
Notes:
Where exact identifiers (canonical SMILES, definitive InChIKey) are required for informatics, verify against the Certificate of Analysis (CoA) or an authoritative database for this specific lot/item.
Synthetic Utility
Key reactivity features (general chemistry):
Carboxylic acid functionality enables diverse transformations: acyl activation (chlorides/anhydrides), nucleophilic substitution (ester/amide formation), reductions, and decarboxylative couplings.
α‑Branching (ethyl at C2) introduces steric bulk near the carbonyl:
Often slows acylation of hindered nucleophiles, potentially improving selectivity against over-acylation.
Can influence conformational bias in resultant amides/esters and alter physical properties (solubility, volatility).
Representative transformations:
2‑Ethylbutanoyl chloride via SOCl2/(COCl)2 (cat. DMF) → electrophile for:
Alcohol acylation (Steglich-type alternatives also viable using DCC/DMAP)
Amide formation with amines (Schotten–Baumann in biphasic systems)
Mixed anhydrides (isobutyl chloroformate) for peptide-like couplings with reduced racemization risk when acylating chiral amines/alcohols.
Reductions:
BH3·THF → 2‑ethylbutanol
Rosenmund or DIBAL-H (via acid chloride/Weinreb amide) → 2‑ethylbutanal
Decarboxylative couplings:
Ni/photoredox-enabled cross couplings from N‑hydroxyphthalimide (NHPI) esters to forge C(sp3)–C(sp2)/C(sp3) bonds; α‑branching retained in the product.
Salt formation:
Preparation of sodium/potassium 2‑ethylbutyrates for phase-transfer catalysis or as masked bases in organic media.
Utility in design:
The 2‑ethylbutanoyl group is a compact hydrophobe; installing it can finely tune logP and sterics without the rigidity of aromatic acyls.
Target Specificity
Not applicable. This product is a small-molecule carboxylic acid reagent, not a biological targeting agent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies to SKU E434316.
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