GRADE & PURITYMoligand™?Moligand™ — Aladdin's line of ligands and bioactive small molecules. Use for receptor, pathway, and binding studies needing defined small-molecule tools.90% (v/v)
This compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
External Descriptors
Straight chain 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
No antibody/assay-specific protocols are associated with this small-molecule reagent. For practical laboratory use, consult the following sections for detailed guidance:
Reaction & Applications: solvent/reagent roles and practical tips.
Buffer Applications: preparation of acetate buffers and mobile phases.
Reaction Conditions: representative procedures and conditions.
If you require a standard operating procedure (SOP) tailored to your workflow (e.g., esterification in acetic acid or preparation of 0.1 M acetate buffer), refer to primary literature and internal method validation, and verify suitability with the item’s CoA.
Biological Roles
This section summarizes acetic acid’s roles in biochemistry (general literature) and is not product-specific, nor a medical claim.
Central metabolite precursor:
Acetate is converted to acetyl-CoA by acetyl-CoA synthetase, feeding the TCA cycle, fatty acid biosynthesis, and numerous acetylation reactions.
Acetyl donor (indirect):
Through acetyl-CoA, acetate contributes to protein acetylation (e.g., histone acetylation) and small-molecule acetylations influencing gene regulation and metabolism.
Microbial metabolism:
Produced by fermentation (e.g., acetogens, mixed-acid fermentation). Serves as carbon/energy source in many bacteria; key intermediate in anaerobic digestion (methanogenesis via acetate cleavage/oxidation pathways).
Acid–base and transport:
Weak acid (pKa ~4.76); at physiological pH, exists largely as acetate anion, transported by monocarboxylate transporters (MCTs) across membranes.
Buffering and cellular pH:
Acetate/HOAc pairs buffer in mildly acidic environments; used in vitro to stabilize enzymes that prefer pH 4–6.
Osmolyte/ionic effects:
Acetate salts influence ionic strength and can modulate protein solubility and folding differently than chloride or phosphate due to specific ion effects (Hofmeister series).
Note: The above roles describe endogenous chemistry and in vitro applications; this product is for research use only, not for clinical/therapeutic use.
Buffer Applications
Acetic acid and its conjugate base (acetate) form a versatile buffering system for pH ~3.8–5.8 (literature). Suitable for enzyme assays, nucleic acid staining, and certain protein procedures where mildly acidic conditions are required.
Practical pKa: 4.76 at 25 °C; optimal buffering ±1 pH unit.
Common formulations (general guidance):
0.1 M Acetate buffer, pH 4.5: Mix appropriate volumes of 0.1 M acetic acid and 0.1 M sodium acetate; fine-adjust with acid/base; verify with calibrated pH meter.
50 mM Acetate buffer, pH 5.2 (nucleic acid staining): Prepare from glacial HOAc and NaOAc·3H2O; filter (0.22 µm) for sterile work.
Ionic strength and additives:
Add NaCl (e.g., 50–150 mM) to modulate ionic strength; include EDTA (0.5–1 mM) to chelate divalent cations when required by assay.
Chromatography/mobile phases:
HPLC/CE often uses 0.1–1% v/v acetic acid in water–organic systems for improved peak shapes of basic analytes; volatile and MS-compatible (though formic acid often enhances ESI sensitivity).
Compatibility considerations:
Proteins with acid-labile PTMs or requiring neutral pH may denature in acetate buffer.
Avoid acetate with reagents forming insoluble acetates (e.g., some heavy metal salts) if precipitation would interfere.
Item-specific buffer-grade specs (metal, UV, microbial limits): Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Acetic acid is comparatively favorable on several green chemistry metrics (renewable routes, biodegradability, low chronic toxicity), yet it is corrosive and flammable. Consider context-specific alternatives or optimizations.
Strengths of acetic acid (literature/general):
Non-halogenated, readily biodegradable; available from bio-based fermentation (ethanol oxidation) or CO2/biomass routes.
Replaces mineral acids in some processes, reducing salt waste upon neutralization.
Potential concerns:
Corrosive and volatile (odor, inhalation irritation); flammable (flash point ~39 °C).
Comparison examples (general guidance):
For acidification/pH control in aqueous work:
Alternative: Citric acid or lactic acid (solid, less volatile, reduced odor). Tradeoff: different pKa profiles, potential complexation effects, less volatility for MS.
Alternative: 2-MeTHF or CPME with catalytic solid acids (e.g., Amberlyst) to reduce corrosivity and aid separation. Tradeoff: need water removal; may alter selectivity and rate.
For acetoxylation chemistry:
Alternative: Acetic anhydride (more efficient acetyl donor) or catalytic acetyl transfer using isopropenyl acetate. Tradeoff: hazard class for anhydride; cost/selectivity considerations.
Greener process tips with acetic acid:
Use aqueous acetic acid at the lowest effective concentration; recover via distillation.
Implement closed transfer and vapor scrubbing to mitigate emissions.
Employ corrosion-resistant equipment to extend asset lifetime.
Pharmaceutical Uses
For research and manufacturing context only; no therapeutic claims.
Typical roles (literature/general):
pH adjuster and buffer component (with sodium acetate) in parenteral and ophthalmic formulations where mildly acidic conditions are desired.
Processing solvent or reagent in synthesis of active pharmaceutical ingredients (APIs), especially for esterifications/acetylations or as a crystallization co-solvent.
Volatile acid modifier in LC–MS analytical methods for QC of drug substances and products.
Compendial status:
Acetic Acid appears in major pharmacopeias (e.g., USP/NF, Ph. Eur.) with defined impurity and assay tests for specific pharmaceutical grades (glacial and diluted). Compliance must be verified per lot and grade.
Materials compatibility:
Corrosive to metals; prefer glass or high-grade polymers (PTFE, PFA, HDPE). For stainless steel, select corrosion-resistant grades and monitor for stress corrosion in hot/acidic service.
Residual solvent/control:
As a process solvent/reagent, residual levels in APIs/intermediates must be controlled per ICH Q3C (Class 3 solvent) and validated analytical methods (e.g., GC headspace).
Item-specific pharmacopeial compliance, endotoxin/bioburden, and excipient grade status: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific numeric specifications are not provided. Where applicable, literature values are listed for reference; do not treat them as product specs.
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Selected physical constants (literature):
Melting point (glacial acetic acid): 16.6 °C (solidifies near cool-room temperatures)
Boiling point: 118.1 °C at 1 atm
Density: 1.049 g/mL at 25 °C (neat)
Refractive index: n20 D ≈ 1.371
Dielectric constant (25 °C): ~6.2 (polar, protic)
pKa (in water, 25 °C): 4.76 (weak monoprotic acid)
logP (octanol/water): approximately −0.3 (fully miscible with water when unionized fraction is considered in bulk)
Vapor pressure: ~11.6 mmHg at 20 °C (odoriferous, volatile enough for inhalation exposure)
Flash point (closed cup): ~39 °C (flammable, Cat. 3, literature)
Autoignition temperature: ~427 °C (literature)
Solubility (literature):
Miscible with water, ethanol, acetone; dissolves many polar organics; limited solubility for nonpolar hydrocarbons.
Spectral/analytical notes (literature):
Characteristic IR: strong C=O at ~1710 cm−1 (broad due to H-bonding), O–H stretch ~2500–3300 cm−1.
1H NMR (D2O suppressed exchange complicates; neat/CDCl3): singlet ~2.08 ppm (3H), very broad OH.
Always verify property values and acceptance ranges on the item’s CoA for your specific lot.
Quality & Grades
Item grade/purity (from Product Data): Moligand™.
What this means: “Moligand™” is a proprietary Aladdin line designation. Specific assay, impurity, water, metal ion, or UV-absorbance limits are not listed in the Product Data for this item.
Assay/purity: Not specified for this item; refer to CoA/Spec Sheet.
Water content (e.g., Karl Fischer): Not specified for this item; refer to CoA/Spec Sheet.
Residual metals/ash: Not specified for this item; refer to CoA/Spec Sheet.
UV cut-off/absorbance profile: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: None indicated; Not specified for this item; refer to CoA/Spec Sheet.
Concentration/form (glacial vs aqueous): Not specified for this item; refer to CoA/Spec Sheet.
Practical implications:
If planning chromatographic use (UV detection), request the UV-Vis trace for your lot to ensure low background at your detection wavelength.
For moisture-sensitive transformations, verify KF water and consider drying (e.g., acetic anhydride treatment followed by distillation) if needed; only after confirming suitability on CoA.
For metal-catalyzed reactions, check metal ion content on CoA to avoid catalyst poisoning or side reactions.
Documentation: For regulated workflows or QC, ask for CoA/Specification Sheet and, where applicable, lot-specific SDS and analytical traces (GC, NMR, KF).
Reaction & Applications
Acetic acid is both solvent and reagent across diverse transformations. Below are representative applications and practical notes (literature/general guidance).
Esterifications and transesterifications:
Fischer esterification of alcohols under acid catalysis; HOAc as solvent moderates rate and improves handling. Water removal (Dean–Stark with toluene/benzene azeotrope or molecular sieves) shifts equilibrium to esters.
Acetylation chemistry:
While acetic anhydride or acetyl chloride are common acetyl donors, acetic acid can acetylate activated substrates under coupling (DCC/DMAP) or catalytic conditions (e.g., Pd-catalyzed C–H acetoxylation with PhI(OAc)2).
Reductive amination and imine chemistry:
Small amounts of HOAc promote imine formation from aldehydes/ketones and amines, controlling pH and suppressing over-reduction with NaBH3CN/NaBH(OAc)3; can be used as co-solvent.
Metal-catalyzed reactions:
Heck/Suzuki couplings occasionally tolerate HOAc as co-solvent to solubilize amine salts and modulate base strength; Pd-catalyzed oxidative acetoxylations (e.g., Wacker-type variants) employ HOAc as medium/additive.
Oxidations and brominations:
Solvent in selective oxidations (e.g., PCC/CrO3) and electrophilic brominations (NBS/Br2) of activated aromatics or alkenes; acidity can influence regioselectivity and suppress side reactions.
Polymer and materials processing:
Solvent for cellulose acetate dope preparations; medium for chitosan dissolution (with water) and for silica surface treatments.
Analytical uses:
Additive in HPLC/CE mobile phases (typically 0.1–1% v/v) to adjust pH and improve peak shapes for basic analytes; volatile for MS compatibility (though formic acid is often preferred for ESI sensitivity).
Practical tips:
Drying: Distill from acetic anhydride or P2O5/drying agents; confirm water content by KF when critical.
Corrosion: Use glass or suitable PTFE-lined components; avoid reactive metals. Ensure adequate ventilation due to strong odor and vapors.
Reaction Conditions
General literature guidance; optimize per substrate and consult primary sources.
Fischer esterification (aliphatic alcohols):
Typical: HOAc as solvent (3–10 equiv) with catalytic H2SO4 or p-TsOH (1–10 mol%). Reflux (118 °C) 2–24 h; azeotropic water removal (Dean–Stark with toluene) boosts conversion. Isolated yields commonly 60–95% depending on sterics and water removal efficiency.
Reductive amination (ketone/aldehyde + amine):
Solvent: MeOH/HOAc or MeCN/HOAc (0.1–1 equiv HOAc). Reductant: NaBH3CN or NaBH(OAc)3. Temperature: 0–25 °C (sensitive substrates) to rt–reflux. Reaction time: 1–18 h. Control pH ~5–6 to favor iminium formation while suppressing over-reduction.
Pd-catalyzed C–H acetoxylation (Ar–H → Ar–OAc):
Catalyst: Pd(OAc)2 (5–10 mol%); Oxidant: PhI(OAc)2 or O2 with cocatalyst; Solvent: HOAc/Ac2O mixtures. Temperature: 60–120 °C; Time: 4–24 h. Directing groups often required; yields vary (30–80%).
Bromination of activated aromatics/alkenes:
Reagents: Br2 or NBS; Solvent: HOAc (neat or mixed with DCM). Temperature: 0–25 °C; Time: 0.5–4 h. Acidic medium enhances electrophilicity; monitor to prevent over-bromination.
Oxidations (e.g., Jones/PCC variants):
HOAc as co-solvent to dissolve substrates and control acidity; 0–25 °C for PCC; 0–10 °C for Jones. Times vary minutes to hours; quench and neutralize carefully.
Operational tips:
Dry HOAc when water-sensitive equilibria limit conversion (use sieves or distill from Ac2O). Confirm water by KF.
Use corrosion-resistant apparatus; avoid prolonged contact with reactive metals. Employ efficient scrubbing/venting for HBr/Cl off-gases in halogenations.
Always validate on small scale; exotherms possible when mixing with strong acids/bases/oxidants.
Safety & Handling
Authoritative safety information must be taken from the SDS for this catalog item. No item-specific GHS fields are specified in the Product Data. The following is typical for glacial acetic acid (literature) and is provided for general guidance only.
Typical GHS classification (literature, for concentrated acetic acid):
Signal word: Danger
Pictograms: GHS02 (Flame), GHS05 (Corrosion)
Hazards: Flammable liquid Cat. 3; Skin corrosion/irritation Cat. 1A; Serious eye damage Cat. 1; Specific target organ toxicity – single exposure (respiratory irritation) Cat. 3.
Primary risks:
Corrosive to skin/eyes; inhalation of vapors causes severe irritation to mucosa and respiratory tract.
Flammable liquid with relatively low flash point (~39 °C). Vapors may form explosive mixtures with air.
Use chemical splash goggles and face shield for bulk handling; acid-resistant gloves (e.g., nitrile, butyl) and lab coat/apron.
Work in fume hood to control vapors and avoid inhalation.
First aid (overview; consult SDS):
Skin/eye contact: Immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air, monitor breathing, seek medical attention.
Ingestion: Rinse mouth, do NOT induce vomiting, seek immediate medical care.
Storage/handling practices (also see Storage tab):
Keep tightly closed in corrosion-resistant container with venting consideration; segregate from oxidizers/bases; ground/bond when dispensing; control ignition sources.
Solvent Selection
Acetic acid functions as a polar, protic, weakly acidic solvent and reagent. Its selection depends on the reaction’s tolerance for acidity and water.
Solvent class (literature/general):
Polar protic; dielectric constant ~6.2 (25 °C). Capable of hydrogen bonding (donor and acceptor) and ion solvation.
Miscibility profile (literature):
Miscible with water, alcohols, acetone; mixes with many polar organics; poor for nonpolar hydrocarbons.
When to choose acetic acid:
Acid-catalyzed transformations (e.g., Fischer esterifications) where HOAc acts as both solvent and Brønsted acid.
Reactions requiring acetate as a weak nucleophile/base (e.g., acetoxylations under metal catalysis, in situ buffering).
Processes benefitting from a water-tolerant, non-halogenated medium (e.g., certain oxidations with permanganate or chromium reagents where control of acidity is desired).
Workup facilitation: easy removal by aqueous base washes and vacuum stripping; forms water-miscible phases.
When to avoid:
Base-sensitive substrates (acid-labile protecting groups) or base-catalyzed reactions (aldol, Claisen) where acidity suppresses reactivity.
Strongly moisture-sensitive reagents (e.g., Grignards, strong metal hydrides) that are quenched by protic solvents.
Comparisons (general):
vs. Formic acid: stronger reducing ability of HCO2H in transfer hydrogenations; lower bp; stronger acidity; more volatile/odoriferous.
vs. Propionic acid: higher bp and lower acidity; solvation of some nonpolar substrates slightly improved.
vs. Halogenated solvents (DCM, chloroform): acetic acid is non-halogenated and biodegradable, but acidic and higher boiling.
Shipping (from Product Data): Shipped via FedEx DG Service.
Container/compatibility:
Store in tightly closed, corrosion-resistant containers (glass with PTFE-lined cap or compatible HDPE). Segregate from oxidizers/bases and away from ignition sources. Secondary containment recommended to manage leaks.
Stability considerations (literature/general):
Chemically stable under ambient conditions; avoid prolonged exposure to air in open vessels to limit vapor emissions and moisture uptake. Freezes at ~16.6 °C; if solidified in cold rooms or winter transit, warm gently to room temperature to liquefy before use.
Handling after opening:
Minimize headspace and cap promptly to control odor and emissions. For analytical or moisture-critical work, consider aliquoting and using septum-sealed bottles or sure/seal systems.
Reconstitution:
Not applicable; supplied as a neat liquid or defined solution. If concentration/grade is critical (e.g., glacial vs aqueous), verify on CoA/label. For buffer preparation, dilute with deionized water to target molarity and adjust pH with NaOH/HOAc as needed.
Shelf life and QC:
Item-specific expiry/retest period: Not specified for this item; refer to CoA/Spec Sheet. Inspect periodically for container corrosion, discoloration, or contamination; confirm assay/water (KF) where required by process controls.
Always defer to the product label and SDS for authoritative storage and handling instructions.
Structure & Identity
Acetic acid is the simplest aliphatic carboxylic acid after formic acid and a cornerstone reagent/solvent in organic synthesis.
Item-specific identifiers (from Product Data):
SKU: A291630
Product name: Acetic Acid
CAS: 64-19-7
CID: 176
InChIKey (as provided): 305771
Structure and common identifiers (literature/general values):
Structural features (general chemistry description):
Functional group: a single, terminal carboxylic acid (–CO2H) attached to a methyl group.
No rings, no stereocenters, fully acyclic and planar at the carboxylate moiety.
Acidic proton on the hydroxyl; conjugate base is acetate (CH3CO2–), resonance-stabilized over the carboxylate.
2D structure in words:
A methyl carbon (sp3) bonded to a carbonyl carbon (sp2); the carbonyl is doubly bonded to oxygen and singly bonded to a hydroxyl oxygen. The –OH is the acidic site; the carbonyl oxygen is the primary H-bond acceptor.
Synthetic Utility
From a retrosynthetic and functional group perspective (literature/general), acetic acid is valuable both as a building block and as a medium that tunes reactivity.
Functional group behavior:
Weak Brønsted acid enabling protonation of carbonyls/alkenes to accelerate nucleophilic additions without harsh conditions.
Acetate as a leaving group precursor (e.g., formation of ROAc, Ar–OAc) under activation or catalysis.
Oxidative C–H acetoxylation (Pd-catalyzed with hypervalent iodine oxidants).
Reductive amination with NaBH3CN/NaBH(OAc)3 where HOAc adjusts equilibrium toward imines/iminium ions.
Cleavage/deprotection under mild acidic conditions for acid-labile groups that survive mineral acids poorly (careful substrate-dependent optimization).
As solvent:
Facilitates nitrations/halogenations of deactivated aromatics by stabilizing cationic electrophiles; modulates ionic strength and dielectric environment.
Supports chromium- and permanganate-based oxidations where aqueous mineral acids are less compatible with organics.
Workup and isolation advantages:
Neutralization with bicarbonate/carbonate affords CO2 venting and water-soluble acetate salts; simplifies phase separations and minimizes halogenated waste.
Limitations:
Incompatible with strong bases and moisture-/proton-sensitive reagents; may induce acetyl migration or hydrolysis in certain protecting groups (e.g., acetals under prolonged exposure).
Target Specificity
Not applicable to this product type. Acetic acid is a small-molecule reagent/solvent and does not possess antigen/epitope specificity, clone identity, isotype, or species reactivity. For experimental applicability, see Reaction & Applications, Synthetic Utility, and Buffer Applications sections.
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