Acrylic acid - ≥98%(GC), contains 180-220 ppm MEHQ as inhibitor, used for Acrylic acid can be primarily used as a monomer to produce various acrylic polymers, including polyacrylic acid, polymethyl methacrylate (PMMA), acrylonitrile butadiene styrene (ABS

CAS: 79-10-7 Cat. No.: A1523893 Formule: C₃H₄O₂ Poids moléculaire: 72.06 Beilstein Registry Number: 635743 Numéro CE: 201-177-9

GRADE & PURITY ≥98%(GC), contains 180-220 ppm MEHQ as inhibitor

Storage

Protected from light,Room temperature,Argon charged

Shipped In

FedEx DG Service

Vue d’ensemble

Acrylic acid is an unsaturated carboxylic acid that is commonly used as a versatile building block in the chemical industry because of its reactive double bond between the carbon and oxygen atoms. It is used to prepare various acrylic acid-based polymers, which are used for various applications such as adhesives, paints & coatings, medical devices, organic semiconductors,thin-film transistors, hydrogels and lithium-ion batteries. Additionally, acrylic acid also serves as one of the polyelectrolytes in the self-assembled polymeric film used for hydrogen generation.

Specifications

Spécifications et pureté

≥98%(GC), contains 180-220 ppm MEHQ as inhibitor

Application

Acrylic acid can be primarily used as a monomer to produce various acrylic polymers, including polyacrylic acid, polymethyl methacrylate (PMMA), acrylonitrile butadiene styrene (ABS), and many others. These polymers exhibit a wide range of properties, suc

Conditions de stockage de stockage

Protected from light,Room temperature,Argon charged

Expédié en

FedEx DG Service

Pureté

≥98%(GC)

Noms et identifiants

Sourires canoniques

C=CC(=O)O

IUPAC Name

prop-2-enoic acid

InChIKey

NIXOWILDQLNWCW-UHFFFAOYSA-N

INCHI

1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)

Isomères SMILES

C=CC(=O)O

WGK Allemagne

1

RTECS

AS4375000

Numéro ONU

2218

Groupe d'emballage

II

Poids moléculaire

72.06

Beilstein

635743

Reaxy-Rn

635743

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=635743&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Acrylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Acrylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acrylic acids
• Alternative Parents: Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acrylic acid - Monocarboxylic acid or derivatives - Carboxylic acid - 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 acrylic acids. These are organic compounds containing acrylic acid CH2=CHCO2H.
• External Descriptors: Unsaturated fatty acids

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

• Solubilité: Soluble in water, chloroform, ethanol, methanol, and DMF.
• Sensibilité: Hygroscopic,Light & Air sensitive.
• Indice de réfraction: 1.4192-1.4212
• Point d'éclair (°F): 119.3 °F - closed cup
• Point d'éclair (°C): 48.5 °C - closed cup
• Point d'ébullition (°C): 139°C
• Point de fusion (°C): 13°C
• Poids moléculaire: 72.060 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 72.0211 Da
• Monoisotopic Mass: 72.0211 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 5
• Formal Charge: 0
• Complexity: 55.900
• 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

Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical guidance, refer to the Reaction & Applications and Reaction Conditions sections for synthetic and polymerization workflows.

Biological Roles

General biochemical context (literature):

• Acrylic acid (prop-2-enoic acid) is not a primary metabolite in humans but can arise transiently from environmental exposure or as an intermediate in microbial pathways. It is a strong irritant/corrosive compound.
• Microbial transformations: Certain bacteria convert 3-hydroxypropionic acid ↔ acrylic acid via dehydration/oxidation pathways. Industrial bioprocess research explores fermentative or chemo-enzymatic routes to acrylic acid from renewable feedstocks (glycerol, lactic acid), leveraging dehydratases and oxidoreductases.
• Reactivity with biomolecules: As an α,β-unsaturated acid, acrylic acid can undergo Michael addition with thiol-containing residues (e.g., cysteine) in vitro, potentially modifying proteins. Such reactions underlie some immobilization/bioconjugation chemistries using acrylic-functional surfaces.
• Polyelectrolyte behavior: Poly(acrylic acid) and its salts exhibit pH-responsive swelling and ion-exchange properties relevant to biointerfaces, hydrogel scaffolds, and controlled-release matrices. While the monomer is hazardous, its polymers (carbomers, sodium polyacrylate) are widely used in biomedical materials development.

Note:

• No medical or therapeutic claims are made. Any biological use of acrylic acid must consider its corrosivity and potential to alkylate nucleophiles; appropriate containment and quenching protocols are essential.

Buffer Applications

Applicability note: Acrylic acid is a reactive, polymerizable monomer and is not typically chosen as a laboratory buffer component despite having a monoprotic pKa ~4.25 (literature). Its tendency to self-polymerize and to undergo Michael addition with nucleophiles makes it unsuitable for stable buffer systems.

Guidance (literature):

• If a carboxylic acid buffer near pH 4–5 is required, conventional systems such as acetate (acetic acid/sodium acetate) or citrate are strongly preferred due to stability and well-characterized buffering capacity.
• Using acrylic acid for electrophoresis, cell culture, or protein work is not recommended given reactivity toward thiols and amines.

Recommendation:

• Select standard, non-reactive buffer systems for pH control. Reserve acrylic acid for synthetic or materials applications where its reactive double bond is essential.

Green Alternatives

Assessment context: Acrylic acid is widely used but poses hazards (corrosive, flammable, polymerization risk) and is typically petro-derived. Greener strategies focus on solvent choices, bio-based routes, and safer functional equivalents when feasible.

Greener route/options (literature):

• Bio-based acrylic acid: Emerging routes from glycerol or lactic acid to acrylic acid can reduce carbon footprint but are supply-limited.
• Itaconic acid (bio-based) as a Michael acceptor: Less volatile, solid at room temp; can substitute in some polymerizations or conjugate additions, though reactivity and Tg differ.
• Maleic acid/anhydride: Electron-poor alkenes for copolymerizations; lower volatility but anhydride is also corrosive; hydrolyzes to diacid.

Process-level improvements:

• Use water or alcohols as reaction media when compatible; avoid chlorinated solvents.
• Continuous-flow polymerization or esterification for improved heat/mass transfer and safer inhibitor control.
• Energy: operate near ambient temperature/pressure where kinetics allow; apply LED photoinitiation for radical processes.

Comparison snapshot (literature; qualitative):

• Acrylic acid: high reactivity, volatile (bp ~140 °C), corrosive; excellent monomer versatility.
• Itaconic acid: solid, lower volatility, bio-derived; slower radical kinetics; different copolymer reactivity ratios.
• Crotonic acid: less reactive Michael acceptor; lower polymerization hazard but diminished performance in many applications.

Trade-offs:

• Substituting can alter material properties (Tg, adhesion, water uptake). Conduct pilot-scale evaluations to confirm performance and life-cycle benefits.

Pharmaceutical Uses

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

Formulation/manufacturing context (literature; non-therapeutic):

• While the monomer acrylic acid itself is not used directly as a pharmaceutical excipient due to corrosivity and reactivity, its polymers (poly(acrylic acid), carbomer/carbopol resins) and copolymers (e.g., with alkyl acrylates) are prominent excipients. They function as rheology modifiers, mucoadhesive agents, and controlled-release matrix formers in topical, oral, and ophthalmic products.
• Acrylic acid serves as a building block for crosslinkers and functional monomers used to tailor polymer excipients (e.g., hydrogels with pH-responsive swelling). Residual monomer specifications in such polymers are tightly controlled to minimize patient exposure; processing includes thorough purification and validated analytical release testing.
• In medical device manufacturing, acrylic-acid-derived surface primers and grafting strategies are used to enhance wettability, adhesion, and to introduce carboxyl functionality for bioconjugation.

Practical notes:

• For any GMP-relevant process, ensure polymer-grade monomers, documented inhibitor levels, validated removal of residuals, and pharmacopeial compliance of the final excipient or device per applicable compendia.
• This product is for research use only and not for use in humans or clinical applications.

Physical Properties

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

Literature/typical values (non-binding, for method development):

• Appearance: colorless, corrosive liquid; may appear slightly yellow upon aging due to impurities/polymerization (literature).
• Melting point: ~13–14 °C (literature).
• Boiling point: ~139–141 °C at 1 atm; ~86–88 °C at 100 mbar (literature).
• Density: ~1.051 g/mL at 20 °C (literature).
• Refractive index (nD20): ~1.422 (literature).
• pKa (25 °C, water): ~4.25 (monoprotic acid; literature).
• LogP (octanol/water): ~−0.3 (literature), indicative of high hydrophilicity.
• Solubility: miscible with water and many polar organics (alcohols, acetone); limited in nonpolar hydrocarbons (literature).
• Vapor pressure: ~3–4 hPa at 20 °C (literature).
• Viscosity: ~1.3–1.5 mPa·s at 20 °C (literature).

Notes for practitioners:

• Acrylic acid readily self-polymerizes, especially near or above its melting point and under light/heat; physical constants can shift with inhibitor content and impurity profile.
• Commercial materials are often stabilized (e.g., with MEHQ + trace oxygen). Stabilizer content significantly affects UV absorbance and downstream polymerization kinetics; verify via CoA for critical applications.

Quality and Grades

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

General guidance for acrylic acid quality (literature/industry practice):

• Commercial acrylic acid is often supplied with polymerization inhibitors (e.g., 10–200 ppm MEHQ, sometimes with trace copper salts) and requires dissolved oxygen for stabilization. Inhibitor presence impacts UV background and reactivity in radical processes—critical for polymer synthesis and analytical methods.
• Typical purity designations include “monomer grade,” “glacial” (low water), and high-purity grades for specialty polymer or electronics use. “Glacial” generally indicates low water content but is not a substitute for Karl Fischer values—confirm via CoA.
• Low-UV or HPLC grades control absorbance in 200–300 nm range to minimize baseline drift in chromatographic detection. For kinetic polymerization studies, low-metal specifications (Cu/Fe) may be requested, as trace metals can quench radicals.

Recommendations:

• Verify inhibitor type/level, water content, acidity profile, and metals by consulting the item’s CoA.
• If inhibitor-free acrylic acid is required (e.g., for certain organic syntheses), plan immediate use under inert conditions, with temperature control, light exclusion, and suitable risk assessment.

Reaction and Applications

General applications (literature; expand pragmatically for professional use):

• Radical polymerization: Core monomer for poly(acrylic acid) and copolymers (superabsorbents, dispersants, carbomer precursors). Copolymerizes readily with acrylates, styrenics, maleic anhydride, and vinyl monomers. Inhibitor management (e.g., MEHQ + O2) is essential; initiators include AIBN, V-50, and peroxides.
• Michael acceptor: The α,β-unsaturated system undergoes conjugate addition with thiols (thiol–ene “click”), amines (aza-Michael), malonates, and enolates. Rate/order: thiol > secondary amine > primary amine > carbon nucleophiles; base catalysis accelerates but increases polymerization risk.
• Esterification/transesterification: Acid-catalyzed reaction with alcohols affords acrylate esters (e.g., n-butyl acrylate, 2-HEA). Water removal (Dean–Stark or reactive distillation) improves conversion; inhibitors should be maintained to suppress vinyl polymerization.
• Amidation: Via activation (e.g., DCC/EDC/NHS) to acrylamides; direct coupling is limited by poor leaving group ability of –OH.
• Reduction/oxidation: Hydrogenation to propionic acid; epoxidation across the C=C yields glycidic derivatives; ozonolysis affords carboxylic fragments.
• Diels–Alder/dipolar cycloadditions: Behaves as an electron-poor dienophile, forming adducts with electron-rich dienes; useful in materials patterning and protecting-group strategies.

Materials science context:

• Precursor to crosslinked hydrogels (via divinyl crosslinkers), ionomers (neutralized polyacrylate salts), and surface-grafted layers (SI-ATRP). Neutralization state (–COOH vs –COO– M+) tunes water uptake, Tg, and adhesion.

Practical cautions:

• Temperature rise from polymerization is significant; ensure heat removal.
• Stabilizers and trace oxygen profoundly affect kinetics; document conditions meticulously.

Reaction Conditions

General, literature-based guidance (verify for your system):

• Radical polymerization of acrylic acid:

  • Initiators: AIBN (0.1–1 mol%), persulfates (0.1–1 wt% in water), or peroxides; temperature 50–80 °C (AIBN ~60–70 °C half-life window), inert or controlled O2 depending on inhibitor strategy.
  • Solvents: bulk, water (neutralized to acrylate for aqueous), alcohols, DMF/dioxane; solids content 10–60% for solution polymerization.
  • Notes: Include inhibitor maintenance (MEHQ) to control runaway; use staged feeds and cooling.

• Michael (thiol–ene) additions:

  • Conditions: Base catalysis (TEA, DBU, 1–10 mol%) at RT–50 °C, or photoinitiation (365–405 nm) with radical sources (Irgacure 651/2959) at ambient temperature.
  • Solvents: MeCN, MeOH, DMF, or bulk; typical conversions >90% within 0.5–4 h.

• Esterification to acrylates:

  • Fischer: H2SO4 or p-TsOH (1–5 mol%), reflux in the corresponding alcohol; Dean–Stark (with toluene) or continuous water removal. Maintain inhibitor (e.g., 10–200 ppm MEHQ) and a small O2 bleed.
  • Steglich: DCC (1.1–1.5 eq), DMAP (0.05–0.1 eq) in DCM/THF at 0–25 °C; 2–12 h.

• Amide formation:

  • EDC·HCl (1.1–1.5 eq) with NHS (1.1 eq) in DMF/MeCN, base (DIPEA), 0–25 °C, 2–16 h.

• Cross-metathesis:

  • Catalyst: Grubbs II/III (1–5 mol%) in DCM/toluene at 25–60 °C; ethylene purge for driving equilibrium when appropriate.

Safety overlay:

• Avoid strong base at elevated temperature (polymerization risk). Exclude light/heat; do not distill to dryness. Maintain documented inhibitor and oxygen profiles.

Safety and Handling

Item-specific storage and logistics (from Product Data):

• Storage: protected from light; room temperature; argon charged.
• Shipping: FedEx DG Service (dangerous goods).

GHS and hazard guidance (literature; consult the SDS for authoritative classification):

• Typical classifications: Flammable liquid (Cat. 3), Skin corrosion/irritation (Cat. 1), Serious eye damage (Cat. 1), Acute toxicity (Cat. 4, inhalation), Specific target organ toxicity – single exposure (respiratory irritation). Pictograms commonly: GHS02 (flame), GHS05 (corrosion), GHS07 (exclamation). Exact categories may vary by supplier/inhibitor content; defer to the SDS provided with this item.
• Polymerization hazard: May undergo exothermic self-polymerization. Inhibitors (e.g., MEHQ) require dissolved oxygen to function; strictly anoxic storage without inhibitor can increase risk.

Handling/PPE:

• Work in a fume hood; avoid inhalation and skin/eye contact.
• Wear chemical-resistant gloves (e.g., butyl rubber, laminated barrier), goggles/face shield, lab coat; use splash protection due to corrosivity.
• Ground/bond containers; keep away from ignition sources and heat.

Incompatibilities and precautions (literature):

• Avoid strong oxidizers, strong bases (rapid exotherm, salt formation), strong acids (accelerates polymerization), free-radical initiators, peroxides, and reactive metals.
• Do not distill to dryness; maintain inhibitor during distillation and include a small oxygen bleed if MEHQ-stabilized.

First aid (overview; see SDS):

• Skin/eyes: Immediate copious water rinse ≥15 minutes; remove contaminated clothing; seek medical evaluation.
• Inhalation: Fresh air, monitor for respiratory irritation; medical attention if symptoms persist.
• Ingestion: Rinse mouth; do not induce vomiting; seek medical care.

Solvent Selection

Applicability note: Acrylic acid is a reactive monomer/reagent rather than a general-purpose solvent. Nevertheless, solvent choice is crucial when using it in synthesis or polymerization.

Solubility and polarity (literature):

• Highly polar, protic acid (pKa ~4.25); miscible with water and polar organics (alcohols, acetone, acetonitrile) and moderately soluble in ethers; limited solubility in alkanes/aromatics unless co-solvent is present.
• Dielectric constant (estimated by analogy to similar acids) is moderate-to-high; hydrogen bonding strongly influences solvation.

Solvent selection guidance:

• Radical polymerization: Bulk or solution polymerization in water, alcohols, dioxane, DMF, or toluene (with co-solvent) depending on target molecular weight and heat removal strategy. For aqueous systems, neutralization to sodium/potassium acrylate improves water-phase polymerizations.
• Michael additions and conjugate chemistry: Polar aprotic solvents (MeCN, DMF, DMSO) often enhance rates; methanol/ethanol can participate in esterification—use with intent.
• Esterification to acrylates: Employ the corresponding alcohol as solvent/reactant under azeotropic or continuous-water-removal conditions.

Comparison (general):

• Water: green, excellent heat capacity; may require pH control to suppress hydrolysis/side reactions.
• Alcohols: dual role (solvent/reactant); favor transesterification/ester formation.
• Aprotic (MeCN/DMF): good for nucleophile-driven conjugate additions; mind base-promoted polymerization.

Practical tips:

• Control inhibitor and oxygen content to manage radical activity.
• Avoid strong basic media unless salt formation is intended (acrylate).

Storage and Reconstitution

Item-specific storage (from Product Data):

• Store protected from light, at room temperature, argon charged.

Additional handling considerations (literature; not item-specific):

• Acrylic acid can self-polymerize; storage under inert gas and light exclusion reduce risk. Many commercial lots include polymerization inhibitors (e.g., MEHQ) that require dissolved oxygen to function. Inhibitor presence/level for this item: Not specified for this item; refer to CoA/Spec Sheet.
• If long-term storage is anticipated, maintain temperature stability (cool, well-ventilated area), avoid contact with metals and bases, and keep containers tightly closed. Do not allow contact with UV sources or heat.
• Upon receipt, inspect for discoloration or viscosity increase (possible polymerization). If necessary for sensitive syntheses, acrylic acid may be purified by vacuum distillation in the presence of inhibitor and with careful oxygen control; do not distill to dryness.

Reconstitution: Not applicable; typically supplied as a neat liquid. If solidifies near/below ~13 °C, gently warm in a water bath to liquefy, avoiding hot spots and light exposure.

General note:

• Always consult the SDS and the product’s CoA/specification sheet for definitive guidance on stabilizers, inhibitor levels, and safe storage durations.

Structure and Identity

Item-specific (from Product Data):

• SKU: A1523893
• Product name: Acrylic acid
• CAS: 79-10-7
• PubChem CID: 6581
• InChIKey: 239738 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed identity (for reference only):

• Preferred IUPAC name: prop-2-enoic acid
• Molecular formula: C3H4O2 (literature)
• Molecular weight: 72.06 g/mol (literature)
• Canonical SMILES: C=CC(=O)O (literature)
• InChIKey: CTQNGGLPUBDAKN-UHFFFAOYSA-N (literature)

Structural features (general chemistry description):

• Contains an α,β-unsaturated carboxylic acid: a vinyl group (CH2=CH–) conjugated to a carboxyl (–C(=O)OH).
• Planar alkene (sp2–sp2) conjugated with the carbonyl; the molecule supports conjugate (Michael) addition at the β-carbon.
• No stereocenters; E/Z not applicable to terminal alkene.
• Functional groups: carboxylic acid (acidic, hydrogen-bond donor/acceptor), activated double bond (electron-poor olefin).

Synthetic Utility

Functional group synopsis (literature):

• Dual reactivity: carboxylic acid (acid/base, esterification, amidation after activation) and activated alkene (Michael acceptor, cycloaddition, radical polymerization). Conjugation stabilizes an enone-like transition state, enhancing nucleophilic attack at the β-carbon.

Key transformations:

• Michael additions: Thiol–ene reactions under base or photoinitiation; aza-Michael additions with amines; soft carbanions (malonates, β-ketoesters) add under basic or Lewis acid catalysis.
• Esterification to acrylates: Fischer conditions (mineral acid, azeotrope) or Steglich (DCC/DMAP) at room temperature to preserve the alkene.
• Amide formation: EDC/NHS or DCC/HOBt couplings provide acrylamides; maintain inhibitor to suppress polymerization.
• Cross-metathesis: With terminal alkenes using Ru-catalysts (e.g., Grubbs), enabling elaboration while retaining/transforming the acid functionality.
• Hydrogenation: Selective C=C reduction to propionic acid (Pd/C, H2) or full reduction to propanol derivatives after activation.
• Cycloadditions: Diels–Alder with electron-rich dienes; 1,3-dipolar cycloadditions (e.g., with nitrile oxides) across the alkene.

Retrosynthetic value:

• Serves as a versatile linchpin to access acrylate esters/amides, hydrogels, and functional surfaces. The carboxylate handle enables salt formation and phase behavior tuning; the alkene allows grafting and post-polymerization modifications.

Operational cautions:

• Manage exotherms, inhibitor content, and oxygen; low temperatures and light exclusion reduce unwanted polymerization during coupling or metathesis.

Target Specificity

Not applicable. This product is a small-molecule reagent/monomer, not an affinity reagent or biologic. No antigen/epitope/clone/isotype information applies.