This compound belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
255.110 g/mol
XLogP3
3.700
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Exact Mass
253.994 Da
Monoisotopic Mass
253.994 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
213.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
1
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
1
Covalently-Bonded Unit Count
1
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Application Protocols
No standardized biological or analytical application protocols are provided for this item.
General laboratory usage tips (chemistry focus):
Purification: Silica gel chromatography using gradients of hexanes/EtOAc or toluene/EtOAc. The conjugated ester absorbs in the near-UV; UV-active for TLC/HPLC.
Handling: If required anhydrous, dry over molecular sieves (3 Å or 4 Å) or sparge with inert gas. Avoid strong bases or nucleophiles unless performing intended conjugate chemistry.
Analysis: Verify identity and E/Z ratio by 1H NMR (vinylic coupling constants), 13C NMR, and HRMS. Monitor metal residues after Pd-catalyzed steps if used downstream in sensitive applications.
For any specific assay or application, please design and validate a fit-for-purpose protocol.
Biological Roles
This compound is a synthetic organic building block without inherent biological role or function. It is not a metabolite, buffer, or cofactor.
Research context: In chemical biology or medicinal chemistry, the aryl bromide can enable late-stage diversification via cross-coupling to access analog libraries. The α,β-unsaturated ester may act as an electrophilic handle for covalent probe development; however, any such use must be evaluated for selectivity and off-target reactivity in a controlled research setting.
ADME-relevant features (general considerations): The ester is hydrolytically labile in biological matrices (esterases), potentially converting to the corresponding acid in vivo; the aryl bromide increases lipophilicity. These are design considerations for probe or intermediate synthesis rather than claims of biological activity.
No medical or therapeutic claims are made. For laboratory research use only.
Buffer Applications
Not typically applicable. Ethyl 3-(3-bromophenyl)acrylate is a hydrophobic synthetic intermediate and does not serve as a buffering agent. For work in aqueous systems, focus instead on appropriate organic cosolvents/emulsifiers if delivering this substrate to water-containing media.
Green Alternatives
While the compound itself is the substrate, greener choices can be made for solvents and reagents used with it.
Greener solvent options (general guidance):
Replace DCM/DCE with ethyl acetate, 2-MeTHF, or CPME when solubility and reaction performance allow.
Use toluene or 2-MeTHF instead of THF when peroxide formation risk and renewability are concerns (2-MeTHF sourced from biomass).
Favor aqueous ethanol/water mixtures for Suzuki couplings where compatible with base and catalyst.
Illustrative comparison (general):
DCM vs EtOAc: EtOAc has lower toxicity and favorable environmental profile; may require longer reaction times but often comparable yields.
THF vs 2-MeTHF: 2-MeTHF offers similar polarity, broader biphasic extraction behavior, and improved safety profile; note different boiling point and possible water content.
DMF/DMAc vs Cyrene or propylene carbonate: For polar aprotic needs, bio-based Cyrene or PC may be considered; assess catalyst compatibility.
Reagent choices:
For reductions, consider transfer hydrogenation (e.g., HCO2H/Et3N or iPrOH) over high-pressure H2 when selectivity permits.
Employ ligand-to-metal atom-efficient Pd sources (e.g., supported Pd or nanoparticle catalysts) and recycle where possible.
Always validate green swaps with small-scale trials to ensure selectivity across the aryl bromide and the Michael-acceptor remains acceptable.
Pharmaceutical Uses
This product is intended for research use only and is not supplied as a pharmacopeial-grade material.
Role in drug discovery/manufacturing (general): Useful as a synthetic intermediate in medicinal chemistry to access cinnamate-derived scaffolds. The aryl bromide enables modular diversification (e.g., Suzuki coupling to introduce heteroaryl pharmacophores), while the ester can be transformed into acids, amides, or alcohols for structure–activity relationship (SAR) studies.
Excipients/Formulation: No known use as a pharmaceutical excipient. Not listed here under any pharmacopeia monograph for excipient applications.
Impurity considerations: For GMP or preclinical route scouting, potential concerns include E/Z isomer ratio, residual Pd or other catalyst metals from couplings, and residual solvents. These must be controlled by appropriate in-process controls and purification, but such specifications are not provided for this catalog item.
No therapeutic claims are made. Any use in regulated manufacturing would require independent qualification and specification setting beyond the scope of this listing.
Physical Properties
Item-specific specs
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Physical state: Typically a colorless to pale yellow liquid for many aryl acrylate esters with similar substitution.
Solubility: Expected to be sparingly soluble in water; readily soluble in common organic solvents (e.g., dichloromethane, toluene, THF, ethyl acetate, acetonitrile) due to aromatic and ester functionality.
Volatility: Moderate; can be handled on the bench, but reduced-pressure techniques are commonly used for purification to limit thermal exposure.
Spectroscopic features: Conjugated C=O stretch typically ~1715–1730 cm⁻¹; alkene vinylic protons ~6.2–7.5 ppm (1H NMR), aromatic region ~7.0–7.7 ppm; ester ethyl quartet/triplet near ~4.2/1.3 ppm. UV–vis shows π→π* bands for cinnamate-like chromophore (near-UV), useful for HPLC/UV tracking.
Density/Refractive Index/MP/BP/LogP/pKa: Not specified here for this exact item; consult primary literature or measure under your conditions if critical.
Note: All numerical property values should be confirmed against the CoA/SDS or measured as needed for your application.
Quality and Grades
Item-specific
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Context and expectations
For synthetic building blocks of this type, quality is typically assessed by GC/HPLC purity and 1H/13C NMR identity. Residual solvent content, isomeric purity (E/Z ratio), and halide content can matter for cross-coupling performance.
If used in catalysis or polymerization-sensitive reactions, low peroxide content and absence of polymerization inhibitors may be important; verify via CoA/SDS if relevant.
Water content and acid value can influence base- or nucleophile-promoted processes (e.g., Michael additions, transesterification). Karl Fischer moisture and titration data may be requested if critical.
What the grade means (general guidance)
“Reagent grade”: Suitable for most synthesis; typical chromatographic purity ≥95% by vendor methods.
“High-purity” or “HPLC grade” solvents/reagents: Often specified for low UV background and tight impurity profiles—useful when tracking by UV-HPLC.
For this catalog item, defer to the CoA for exact specifications, analytical methods, and acceptance criteria.
Reaction and Applications
Ethyl 3-(3-bromophenyl)acrylate is a versatile, bifunctional building block combining an aryl bromide with a conjugated acrylate. This combination supports orthogonal transformations on either the aryl bromide or the Michael-acceptor motif.
Key application families (literature/general):
Cross-coupling at the aryl bromide: Suzuki–Miyaura (to diversify aryl/heteroaryl partners), Sonogashira (introduce alkynes), Heck (extend the conjugation), and Buchwald–Hartwig amination (Ar–N bond formation). Protecting the acrylate functionality from undesired 1,4-addition requires base/catalyst selection.
Conjugate (Michael) additions: Soft nucleophiles (thiols, malonates, enamines) can add 1,4- to the enone, enabling β-functionalized esters. Catalytic asymmetric variants (e.g., chiral Cu or organocatalysts) are reported for similar cinnamate scaffolds.
Conjugate reductions/hydrogenations: Pd/C or Rh catalysts effect selective hydrogenation of the C=C to give the saturated 3-(3-bromophenyl)propanoate; chemoselectivity over Ar–Br managed by catalyst and pressure.
Cycloadditions: As a dienophile in Diels–Alder reactions with electron-rich dienes, affording substituted cyclohexenes that retain or transform the ester handle.
Further elaboration of the ester: Hydrolysis (to acid), transesterification (alcohol exchange), amidation (via the acid or activated intermediates), and Weinreb amide formation for acyl chemistry.
Application domains:
Medicinal chemistry SAR campaigns where meta-bromo enables late-stage diversification while the acrylate modulates electronic properties.
Materials/monomer design leveraging the acrylic motif for polymer-analogous transformations.
Practical notes: Use deoxygenated solvents for Pd-catalyzed couplings; control basicity to avoid undesired aza-/oxa-Michael side reactions; monitor E/Z integrity if stereochemistry is critical.
Reaction Conditions
The following ranges are general literature guidance for molecules of this class; optimize for your system.
Suzuki–Miyaura coupling (Ar–Br): Pd(PPh3)4 or Pd-PEPPSI (0.5–2 mol% Pd), ligand as needed; base K3PO4, K2CO3, or Cs2CO3; solvent toluene/H2O, dioxane/H2O, or MeCN; 60–100 °C; 2–16 h. Boronic acid/ester 1.2–1.5 equiv. Maintain conditions that avoid conjugate addition (avoid strongly nucleophilic amines/alcohols without protection).
Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol% Pd) with dialkylbiaryl phosphine ligands; NaOtBu or Cs2CO3; toluene or dioxane; 80–110 °C; 6–20 h. Monitor for any aza-Michael side processes with primary amines; lower base strength and temperature can help.
Sonogashira: Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%); Et3N or iPr2NH; THF, toluene, or DMA; 25–60 °C; 2–12 h. Copper-free variants reduce Glaser homocoupling.
Conjugate (Michael) addition: Soft nucleophile (e.g., thiol, malonate) with base (DBU, Et3N) or Cu-catalysis; DCM, THF, or MeCN; 0–25 °C; 1–6 h. Asymmetric versions use chiral ligands/organocatalysts.
Hydrogenation/reduction of C=C: Pd/C (5–10 wt%), H2 (1–5 bar), EtOAc or EtOH; rt–40 °C; 1–6 h. For selective conjugate reduction avoiding Ar–Br hydrogenolysis, use carefully tuned catalysts (e.g., Rh/Al2O3) and low pressure.
Diels–Alder: Electron-rich diene, toluene or DCE, 60–120 °C (thermal) or Lewis acid catalysis at lower T; 4–24 h.
Always monitor E/Z integrity if relevant; in many couplings the geometry is retained, but isomerization can occur under basic or high-temperature conditions.
Safety and Handling
GHS/SDS information
Signal Word / H-Statements / GHS Classification / Pictograms: Not specified for this item; refer to SDS.
General laboratory handling (good practice; not a substitute for SDS)
Avoid inhalation of vapors/mists and contact with skin/eyes. Handle in a fume hood with appropriate PPE: lab coat, safety glasses, and nitrile gloves. Wash thoroughly after handling.
Storage compatibility: Keep away from strong bases (can induce Michael addition or transesterification), strong acids (hydrolysis), and strong oxidizing or reducing agents. Avoid prolonged exposure to light/heat that can promote polymerization or isomerization of the C=C.
Spill/cleanup: Absorb small spills with inert material (vermiculite, silica), collect for disposal. Prevent release to drains.
Fire safety: Treat as a combustible organic liquid. Use CO2, dry chemical, or foam for firefighting; cool containers with water spray.
First aid (overview): If inhaled, move to fresh air. On skin, wash with soap and water; remove contaminated clothing. In eyes, rinse cautiously with water for several minutes; remove contact lenses if present and easy to do. If ingested, rinse mouth; do not induce vomiting; seek medical advice.
Waste: Dispose according to institutional and local regulations for halogenated organics.
Always consult the product-specific SDS for definitive hazard and response information.
Solvent Selection
This product is itself an organic substrate rather than a solvent. However, selecting an appropriate reaction or processing solvent is key to its use.
Polarity/behavior (literature, general): Moderately lipophilic aromatic acrylate; dissolves well in ethers (THF, MTBE), chlorinated solvents (DCM, DCE), aromatics (toluene, xylene), esters (EtOAc), and polar aprotics (MeCN, DMF, DMSO). Poorly soluble in water.
Functional handles: Contains an aryl bromide (sensitive to strong nucleophiles) and an α,β-unsaturated ester (sensitive to strong bases and nucleophiles).
Typical solvent choices by transformation (general guidance):
Cross-coupling at Ar–Br (Suzuki, Buchwald–Hartwig): Toluene, 1,4-dioxane, THF, or mixtures with water/EtOH for Suzuki (with aqueous base). MeCN or DMF for challenging couplings.
Conjugate additions/hydrogenations: Alcohols (iPrOH/EtOH), toluene, or EtOAc under catalytic hydrogenation; THF or DCM for organometallic 1,4-additions.
Diels–Alder or radical additions: Toluene, DCE, or acetonitrile depending on kinetics and catalyst.
Comparison notes:
THF vs toluene: THF increases polarity and catalyst solubility; toluene often improves selectivity in cross-coupling and tolerates higher temperatures.
DCM vs EtOAc: DCM offers faster dissolution and inertness; EtOAc is a greener alternative with adequate solubility for many operations.
Dry, oxygen-free solvents are often beneficial for Pd-catalyzed couplings and organometallic additions.
Storage and Reconstitution
Item-specific (from Product Data)
Storage Conditions: Room temperature
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General guidance
Container: Store tightly closed in an amber glass bottle to minimize light-induced isomerization or polymerization of the α,β-unsaturated ester.
Atmosphere: Inert atmosphere (nitrogen/argon) is recommended for long-term storage to limit oxidative or radical processes; keep headspace minimal.
Stability considerations: Avoid prolonged exposure to strong light, heat, and moisture. If solid impurities or crystallization are observed upon cooling, gently warm to redissolve before use and verify purity by NMR/GC/HPLC.
Reconstitution: Not applicable (neat liquid). If preparing stock solutions, use dry, oxygen-free solvents (e.g., anhydrous toluene, THF, or EtOAc), and store aliquots at 2–8 °C if extended storage is needed. Allow solutions to reach ambient temperature before opening to reduce moisture uptake.
Freeze–thaw: Typically not necessary; avoid repeated cycles of warming/cooling that may induce isomerization.
Always consult the product CoA/SDS for definitive storage and stability instructions specific to your lot.
Structure and Identity
Item-specific (from Product Data)
SKU: E1041548
Product Name: Ethyl 3-(3-bromophenyl)acrylate
CAS: 24398-80-9
PubChem CID: 5369361
InChIKey: 227513 (as provided)
Storage: Room temperature
Research Use: For research use only
Literature/Computed (general reference, not item-specific specs)
Preferred IUPAC name (literature): Ethyl 3-(3-bromophenyl)prop-2-enoate
Molecular formula (literature): C11H11BrO2
Molecular weight (literature): ~255.10 g/mol
SMILES (literature): CCOC(=O)/C=C/c1cccc(Br)c1 (E/Z not specified)
Structural features: An α,β-unsaturated ethyl ester (acrylate) conjugated to a meta-bromophenyl ring. The molecule contains an aryl bromide suitable for cross-coupling and a Michael-acceptor enone fragment. No stereocenter; C=C may exist as E/Z isomers (E often encountered in practice for cinnamate derivatives).
2D description: Ethyl ester tail (–CO2Et) attached to an alkene (–CH=CH–) that is in conjugation with a 3-bromophenyl ring; bromine is meta to the vinyl linkage on the aromatic ring.
Synthetic Utility
Functional group ensemble and reactivity (general):
Aryl bromide: Engages in Pd-catalyzed cross-couplings (Suzuki, Stille, Negishi, Kumada, Sonogashira) and nucleophilic aromatic substitution only under forcing conditions (meta-bromo on non-activated ring is typically unreactive to SNAr).
α,β-Unsaturated ester (acrylate): Michael acceptor for 1,4-additions; dienophile in Diels–Alder; subject to selective hydrogenation or conjugate reduction; handle for further derivatization (hydrolysis, amidation, reduction to allylic alcohol under specific conditions).
Strategic value:
Orthogonal functionalization sequence: Couple at Ar–Br first under Pd catalysis (preserving the enone), then perform conjugate chemistry; or invert the order by protecting the enone (e.g., temporary saturation or acetalization) before C–C/C–N bond formation.
Retrosynthesis: Disconnection to ethyl acrylate and 3-bromostyrene via Heck coupling is classic; alternatively, assemble via Wittig/Horner–Wadsworth–Emmons olefination from 3-bromobenzaldehyde and an ethyl phosphonate ester.
Diversification: Late-stage borylation at Ar–Br to give the boronate, enabling further iterative couplings. Use of orthogonal halides (if introduced) can enable sequential couplings with differential reactivity.
Selectivity notes:
Base choice and ligand environment dictate chemoselectivity between cross-coupling and potential aza-/oxa-Michael additions. Employ milder bases (e.g., K3PO4, Cs2CO3) and non-nucleophilic solvents to minimize undesired conjugate reactions.
Target Specificity
Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, enzyme, or biological targeting reagent. No target specificity data are provided for this item.
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