This compound belongs to the class of organic compounds known as acyl chlorides. These are organic compounds containing the functional group -CO-Cl.
External Descriptors
Not available
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. This listing does not represent an assay kit, antibody, or enzyme with defined bioassay protocols.
General lab guidance
For acylation workflows, a typical protocol involves: drying glassware and solvents; charging base and nucleophile; cooling; slow addition of 2-ethylacryloyl chloride; in-process IR/TLC/GC monitoring; cautious quench; and purification under minimized moisture exposure.
Because no item-specific validated protocols are provided, develop and optimize methods based on your substrates and intended application.
Biological Roles
This product is an industrial/synthetic reagent and is not intended for biological assays in its native form.
General chemistry perspective
Acyl chlorides are highly reactive and not typically encountered as natural metabolites or stable biomolecules; in aqueous biological systems they hydrolyze rapidly to the corresponding acids with HCl evolution (literature/general).
α,β-Unsaturated systems can act as Michael acceptors toward biological nucleophiles (thiols, amines), which underlies their strong irritancy and potential to modify proteins non-specifically in vitro (literature/general). Such reactivity precludes specific physiological “roles.”
Research caution
Any work involving biological matrices should be conducted with rigorous quenching/neutralization prior to contact with cells/enzymes. No claims are made for biocompatibility or suitability in vivo.
Data status for this item
No item-specific bioactivity data or biological function is provided. Refer to the SDS and perform appropriate risk assessments for any laboratory exposure scenarios.
Buffer Applications
Not typically applicable. As a moisture-sensitive, strongly reactive acyl chloride, this material is incompatible with aqueous buffers and will hydrolyze rapidly, releasing HCl.
Guidance
If downstream chemistry requires aqueous workup, conduct acylation in anhydrous organic solvent, then quench and neutralize before transferring to buffered systems. Select buffer after conversion to a stable product (amide/ester), not for the acyl chloride itself.
Green Alternatives
Sustainability considerations (general)
Acid chlorides are inherently hazardous (corrosive, HCl evolution) and moisture-sensitive; greener strategies often replace them with less hazardous acyl-transfer reagents.
Alternative reagents/routes (literature/general)
Direct coupling of carboxylic acids (e.g., 2-ethylacrylic acid) using carbodiimides (EDC, DIC) or uronium reagents (T3P, COMU) to form amides/esters under milder, often aqueous-tolerant conditions; avoids HCl gas but introduces other waste streams.
Activated esters (e.g., NHS esters) or anhydrides can serve as safer acyl donors in many contexts.
Enzyme-catalyzed esterifications or amidations in solvent-minimized systems can be considered for select substrates.
Process-intensification
Employ microreactors/flow chemistry for acid chlorides to reduce inventory, improve heat/mass transfer, and contain HCl byproducts.
Solvent greening
Preferably use 2-MeTHF, CPME, or toluene over chlorinated solvents where compatible; balance against reactivity and stability of the acyl chloride.
Comparison (general)
Metric | Acid chloride route | Alternative (e.g., EDC/T3P)
Atom economy | Good but generates HCl | Adds coupling reagent mass; waste streams
Moisture tolerance | Low | Moderate to good
Scalability | High with controls | High; often simpler PPE/venting
Trade-offs
For highly hindered or less nucleophilic substrates, acid chlorides may be superior. Selection should weigh EHS, cost, and performance.
Pharmaceutical Uses
Scope of use
For research use only. No medical, diagnostic, or therapeutic use is intended or implied.
Formulation/excipient context
Acid chlorides, including α,β-unsaturated variants, are generally too reactive and corrosive to serve as excipients. They may, however, be employed as synthetic intermediates in the preparation of active pharmaceutical ingredient (API) building blocks or pro-moieties under strictly controlled manufacturing conditions (literature/general).
Regulatory note
No pharmacopeial monograph is indicated for this specific substance in the provided data. Any GMP-relevant use would require appropriate specifications, impurity controls (e.g., residual chloride, related acids), and validated handling to prevent HCl exposure and hydrolysis.
Process chemistry considerations
When used upstream, ensure effective quench, neutralization, and purge of residual acyl chloride and HCl. Apply orthogonal analytics (e.g., GC for residual solvent, titration/IR for acid chloride) to demonstrate absence in drug substance intermediates.
Physical Properties
Item-specific specs
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-/general-property guidance (for α,β-unsaturated acyl chlorides; for reference only)
Physical state: typically colorless to pale yellow, moisture-sensitive liquids with pungent, lachrymatory odor (literature/general).
Density, refractive index, and boiling point can vary with substitution; values for this specific compound are not provided here (consult SDS/primary literature).
Solubility: reactive with water; miscible with many aprotic organic solvents (e.g., DCM, toluene, ether, acetonitrile) but subject to solvolysis with alcohols and amines (literature/general).
Stability: prone to hydrolysis generating HCl and the corresponding acid; may slowly polymerize or self-condense in the presence of nucleophiles or bases; light and heat can accelerate decomposition (literature/general).
Practical notes
Handle under anhydrous conditions; use dry solvent and inert atmosphere to preserve integrity.
For any exact numeric values required in method development or hazard assessment, defer to the SDS and the item-specific CoA/Spec Sheet.
Quality & Grades
Item-specific quality fields
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grade (general guidance)
For moisture- and base-sensitive acyl chlorides, “high-purity” or “anhydrous” grades typically emphasize low hydrolyzable chloride impurities and minimal acid content; HPLC/GC assays are commonly used. Low UV-absorbing grades are relevant if spectroscopic monitoring is critical.
If an inhibitor is present to suppress polymerization of the α,β-unsaturation (e.g., traces of acid or radical scavenger), it may influence downstream polymerizations or radical additions; processes may require inhibitor removal (e.g., basic wash is contraindicated for acyl chlorides; instead, distillation under inert can be considered).
What to check on receipt
Verify COA for assay %, water (Karl Fischer), acid content, and color index if provided. Because acyl chlorides hydrolyze readily, confirm packaging integrity and absence of HCl odor/fuming beyond expectations.
For materials-science applications (as per Category Path), confirm that impurity profile (e.g., residual solvent, stabilizer) is compatible with polymerization or surface-modification steps.
Documentation
For any regulatory or method-validation needs, request the latest Specification Sheet and batch CoA to obtain exact limits; this listing intentionally avoids asserting unstated specifications.
Reaction & Applications
Materials-science relevance (per category): precursor to functionalized polymers and surfaces via acylation or conjugate-addition strategies; potential to introduce pendant acyl chloride motifs for post-functionalization.
Common transformations (literature/general)
Acylation of amines to secondary/tertiary amides; acylation of alcohols/phenols to esters; reactions typically use a non-nucleophilic base (Et3N, pyridine, DIPEA) or an inorganic base (Na2CO3) in biphasic variants (though water-free conditions preferred for acid chlorides).
Formation of anhydrides with carboxylates; conversion to corresponding acid via controlled hydrolysis.
Conjugate (Michael) additions of soft nucleophiles to the α,β-unsaturated system under catalytic conditions, enabling C–C, C–S, or C–N bond formation; the acyl chloride can be transformed in situ to thioesters/amides for tandem processes.
Precursors to enones/enamides via chloride displacement/elimination pathways.
Practical tips
Maintain strict anhydrous conditions; predry glassware and solvents. Charge base first, cool to 0–5°C, and add 2-ethylacryloyl chloride dropwise to moderate exotherm and capture HCl.
Use IR (strong νC=O ~1800 cm−1; literature) to monitor consumption; a new amide/ester νC=O typically appears lower (~1640–1750 cm−1 depending on product).
For polymer-related workflows, consider immediate use after opening or prepare stabilized solutions under inert atmosphere to minimize hydrolysis/premature polymerization.
Reaction Conditions
General conditions for representative transformations (literature/general; optimize per substrate)
Amide formation: 0–25°C in DCM or THF; amine (1.0–1.2 eq), base (1.1–2.0 eq, e.g., Et3N, DIPEA, or pyridine). Add acyl chloride slowly to cooled amine/base solution; stir 0.5–4 h. Quench with cold, dilute aqueous bicarbonate; extract and wash to remove amine salts. Typical conversions are high with fast kinetics; yields depend on substrate basicity and sterics.
Esterification: alcohol/phenol (1.1–1.5 eq), catalytic DMAP (0–10 mol%, if compatible), base (2.0 eq) in DCM or toluene at 0–25°C. Monitor for side reactions (polymerization); minimize DMAP if conjugate reactivity is problematic.
Ketone synthesis: reaction with organocuprates (Gilman reagents) at −78 to −20°C in ether/THF to give ketones selectively from acid chlorides; work up at low temperature to suppress overreaction.
Michael-type additions: soft nucleophiles (e.g., thiols) with base or catalyst at 0–25°C in polar aprotic solvent; competition with acylation must be managed by reagent order and stoichiometry.
Monitoring and control
IR (acid chloride νC=O ~1800 cm−1) and in-process HCl capture (gas trap or amine salts) are recommended. Maintain anhydrous environment to prevent hydrolysis.
Note: Exact, item-specific operating ranges and performance metrics are not specified; consult primary literature and perform pilot trials.
Safety & Handling
Authoritative source: Always consult the product SDS for definitive hazard, first-aid, and disposal information.
Item-specific safety fields
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General hazards for acyl chlorides and α,β-unsaturated acid chlorides (literature/general)
Strongly corrosive; causes severe burns to skin and eyes; vapors are irritating and often lachrymatory due to HCl evolution.
Reacts exothermically with water, alcohols, amines, bases; liberates HCl gas.
May fume in moist air; avoid inhalation and exposure to moisture.
Keep spill control materials (sodium bicarbonate, inert absorbent) available; neutralize cautiously after sorption to inert material.
Storage incompatibilities and handling
Store tightly sealed under inert gas in a desiccated, light-protected secondary container.
Segregate from water, alcohols, amines, strong bases, oxidizers, and active metals.
Use dry syringes/needles or cannula transfer; cool before additions to moderate exotherm.
First-aid overview (general)
Skin/eye contact: Immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; seek medical attention.
Ingestion: Do not induce vomiting; seek medical attention promptly.
Solvent Selection
Applicability: As a reactive liquid acyl chloride, solvent choice strongly affects stability and selectivity.
General solvent compatibility (literature/general)
Preferred aprotic, non-nucleophilic solvents: dichloromethane (DCM), chloroform, toluene, chlorobenzene, heptane/hexanes, anhydrous ethers (diethyl ether, TBME) when base is controlled; acetonitrile can be suitable for some catalytic processes.
Avoid: Protic solvents (water, alcohols), and strongly nucleophilic solvents (DMF, DMSO) unless intentionally used as reagents (e.g., Vilsmeier-type activation) due to potential side reactions.
Polarity and heat transfer
DCM and toluene offer good heat removal and manageable boiling points for controlling exotherms during acylation of amines/alcohols.
Hydrocarbon solvents can enhance selectivity in Schotten–Baumann alternatives conducted under strictly anhydrous, non-aqueous conditions.
Practical selection tips
For amide/ester formation with bases (e.g., Et3N, DIPEA), DCM or THF under cooling minimize HCl accumulation; add acyl chloride slowly.
For polymer or surface grafting workflows (materials science), low polarity solvents (toluene, xylene) can promote film formation and limit premature hydrolysis at interfaces.
When monitoring by IR, choose solvents with minimal overlap around 1800 cm−1 (acid chloride C=O) for clearer tracking.
Storage & Reconstitution
Item-specific storage and shipping
Storage conditions: Store at −20°C (as provided in Product Data). Keep container tightly closed under inert gas in a dry, light-protected environment.
Shipped in: Ice chest + ice pads (as provided), to limit temperature excursions and suppress decomposition.
Handling after receipt
Allow to equilibrate to room temperature before opening to prevent moisture ingress via condensation; purge headspace with dry nitrogen/argon after each use.
If frequent use is anticipated, consider preparing aliquots in flame-dried vials under inert atmosphere to minimize freeze–thaw and moisture exposure.
Stability notes (general)
Sensitive to moisture, heat, and light. Hydrolyzes to the corresponding acid with HCl evolution; may polymerize at the double bond. Store away from acids/bases that could initiate side reactions.
Reconstitution/solution preparation
No reconstitution is required. For solution use, prepare in anhydrous, non-nucleophilic solvents (e.g., DCM, toluene, dry ether) immediately before use. Concentration and solvent choice should be dictated by the target reaction and stability window.
Documentation
For precise shelf-life and impurity evolution, refer to the batch CoA/Spec Sheet and SDS; this listing does not assert unstated stability specifications.
Structure & Identity
Item-specific identifiers (from Product Data)
SKU: E477289
Product name: 2-Ethylacryloyl chloride
CAS: 4390-96-9
CID: 4227818
InChIKey: 142192 (as provided)
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.
Structural features (general chemistry description)
Functional groups: an acid chloride (–COCl) conjugated to an α,β-unsaturated system (acryloyl-type). The “2-ethyl” substituent denotes an ethyl group on the vinylic carbon of the acryl framework, yielding a substituted enoyl chloride.
Key reactivity motifs: highly electrophilic acyl chloride carbonyl; conjugated C=C that can participate in conjugate (Michael-type) chemistry under appropriate conditions; potential for polymerization of the enoyl moiety.
2D structure (verbal): a short C=C chain (acryloyl backbone) bearing an ethyl substituent at the 2-position, terminated by a carbonyl bound to chloride; planar around the C=C and trigonal planar at the acyl carbon.
Stereochemistry (general)
The C=C can exhibit E/Z geometry in substituted enoyl systems; acyl chlorides of this class are commonly handled as mixtures unless specifically isomerized/purified. Specific stereochemical composition is not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional-group leverage
Dual reactivity: (1) highly electrophilic acyl chloride carbonyl for rapid acyl transfer; (2) conjugated C=C enabling Michael chemistry or downstream elaboration to enones/enamides.
Key transformations (literature/general)
Amide formation with primary/secondary amines under non-nucleophilic base; esters from alcohols/phenols; acylation of organometallics to furnish ketones (via acid chloride to ketone under Cu or Pd catalysis).
Conversion to acid anhydrides or mixed anhydrides (e.g., with pivalate or trifluoroacetate) to tune reactivity/selectivity.
Cross-coupling manifolds: Pd-catalyzed carbonylative couplings from acid chlorides to access aryl/alkenyl ketones; Ni-catalyzed reductive couplings for C–C bond construction.
Generation of enones via base-mediated elimination after nucleophilic substitution, or via Weinreb amide intermediates for controlled monoacylation.
Retrosynthetic value
As an activated version of 2-ethylacrylic acid, it streamlines convergent assembly of amides/esters/enones where mild conditions and short contact times limit side reactions (polymerization, isomerization).
Practicalities
Use low temperatures and inverse addition to manage exotherm; scavenge HCl with tertiary amines. Consider in situ formation from the corresponding acid (e.g., oxalyl chloride, Ghosez reagent) when freshness is critical; otherwise, employ freshly opened bottled material under inert atmosphere.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody.
No antigen/epitope, species reactivity, clone, or isotype information applies.
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