This compound belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
164.990 g/mol
XLogP3
1.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
163.947 Da
Monoisotopic Mass
163.947 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
7
Formal Charge
0
Complexity
87.700
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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Recensioni
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Application Protocols
Not applicable for antibody/assay protocols. No validated WB, IHC, IF, or FC protocols are associated with this chemical reagent.
For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for representative procedures and optimization guidance.
Biological Roles
This is a synthetic organic intermediate and is not a biomolecule. No specific biological role is associated with methyl (E)-3-bromoacrylate.
General biochemical considerations (literature/practice):
Acrylate esters are electrophilic Michael acceptors and can alkylate nucleophilic residues (e.g., cysteine) in proteins under suitable conditions. This underlies their use as chemical probes/warheads in research chemistry, not as biological metabolites.
Hydrolysis: In aqueous basic conditions, ester hydrolysis can yield 3-bromoacrylic acid; further reactions (e.g., elimination, addition) may occur depending on pH and nucleophiles.
Research use only note (item-specific):
As stated in the catalog: For research use only. Not for food, drug, cosmetic, or household use.
Buffer Applications
Not typically applicable. This compound is a reactive organic reagent, not a buffering agent. For aqueous work, choose established buffer systems (e.g., phosphate, Tris, HEPES) compatible with your transformation, and keep this acrylate in non-aqueous media to prevent hydrolysis and undesired Michael additions.
Green Alternatives
Greener choices depend on the synthetic goal. Because this reagent is both a vinyl bromide and a Michael acceptor, alternatives may target one or both functions.
If only a Michael acceptor is needed: Use methyl acrylate or methyl (E)-cinnamate derivatives (halogen-free) to avoid bromine-containing waste.
If cross-coupling to install a vinyl ester is desired: Consider directly coupling boron/organometallic partners with methyl acrylate via Heck-type processes, bypassing preformed bromides.
For solvent selection: Prefer 2-MeTHF, CPME, propylene carbonate, or green aromatics (e.g., anisole) over chlorinated solvents where compatible.
Methyl acrylate: Lower hazard profile (no organobromine); supports Michael additions and Heck reactions but lacks direct halide handle.
2-MeTHF solvent vs THF: Similar polarity; 2-MeTHF is bio-derived, higher bp, and more water-tolerant, reducing energy for solvent recovery.
Trade-offs:
Eliminating bromine may require additional steps or different catalysts to reach the same substitution pattern.
Some greener solvents may alter rates/selectivity; modest re-optimization of catalysts/base/temperature is often needed.
Pharmaceutical Uses
No excipient or pharmacopeial use is indicated for this item.
General context (literature/practice):
Methyl (E)-3-bromoacrylate may serve as a synthetic building block in medicinal chemistry programs to access substituted acrylates, enamides, and related motifs common in APIs and intermediates. Any such use is confined to R&D and process development.
Regulatory considerations: Organobromine intermediates typically require control of residual halides and related impurities in GMP settings; selection of coupling chemistry and quench/workup conditions should reflect ICH guidelines.
Note: This product is for research use only and not intended for human or veterinary therapeutic applications.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values and expectations (for methyl (E)-3-bromoacrylate; for reference only):
Physical state: typically a colorless to pale liquid acrylate ester (may be lachrymatory)
Solubility: expected to be miscible with many organic solvents (e.g., Et2O, THF, DCM, toluene, MeCN) and poorly soluble in water due to ester functionality and vinylic bromide
Volatility: moderate; handle in a fume hood to limit vapor exposure and odor
Reactivity: prone to radical polymerization typical of acrylates; vinylic bromide participates in Pd-catalyzed cross-couplings
Notes:
The above are general literature characteristics of bromoacrylate esters; consult the item’s CoA/SDS for definitive specifications for SKU P997209.
Quality and Grades
Item-specific grade/purity details are not provided in this listing.
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for interpreting grades (context for acrylate esters):
Research grade: Suitable for most synthetic applications; may contain trace stabilizer to suppress polymerization (e.g., MEHQ/BHT). If inhibitor content matters (e.g., radical or anionic polymerizations), remove immediately before use by appropriate methods (basic alumina, vacuum distillation) while observing safety.
Low-water/anhydrous material: Often preferred for base- or metal-catalyzed couplings. Verify water and inhibitor content on CoA before moisture-sensitive steps.
Chromatography-grade solvents/reagents: Feature lower UV absorbance and particulates; usually not relevant for this reagent unless used as a reference standard.
Quality notes specific to this chemistry:
E/Z purity can influence stereochemical outcomes in couplings/Michael additions. If stereochemical fidelity is critical, request geometric isomer ratio documentation on the CoA.
Halide purity (absence of iodide/chloride) can affect catalytic coupling rates; metals/residual peroxides should be within acceptable limits when running sensitive Pd/Ni catalysis.
Reaction and Applications
Methyl (E)-3-bromoacrylate is a bifunctional electrophile that combines a conjugated Michael acceptor with a vinylic bromide, enabling diverse bond formations.
Key application families (literature/practice):
Palladium-catalyzed cross-couplings: As a vinyl bromide, it participates in Suzuki–Miyaura (with boronic acids), Stille (with stannanes), Negishi (with organozincs), Kumada (with Grignards under Ni/Pd), and Sonogashira (with terminal alkynes) couplings, generally preserving E-geometry.
Heck reactions: Coupling with alkenes to elaborate substituted acrylates while controlling double-bond geometry; the ester activates the alkene and can direct regioselectivity.
Conjugate (Michael) additions: Soft nucleophiles (thiols, malonates, enolates, amines) add to the β-position of the α,β-unsaturated ester. The vinylic bromide can be leveraged in tandem sequences (e.g., conjugate addition followed by intramolecular cyclization or further coupling).
Cyclizations/annulations: Intramolecular couplings after prefunctionalization offer routes to heterocycles and carbocycles.
Radical chemistry: Atom-transfer radical additions (ATRA) and Giese-type additions to the activated alkene, with the C–Br bond enabling radical initiation or functionalization.
Practical tips:
Control polymerization: Work cold and/or with inhibitor present for storage; remove inhibitor immediately before metal-catalyzed steps if required.
Stereocontrol: Verify E-content; many cross-couplings proceed with retention of configuration under mild conditions.
Base selection: Use non-nucleophilic bases (e.g., DIPEA, K2CO3, Cs2CO3) to reduce undesired addition/polymerization. Avoid strong nucleophiles unless purposeful (Michael).
Order of operations: In sequences, many practitioners couple the vinyl bromide first (under Pd) and then perform conjugate addition; others exploit conjugate addition then cross-couple the resulting (now allylic/benzylic-like) site depending on design.
Reaction Conditions
Typical literature conditions for common transformations of methyl (E)-3-bromoacrylate (guidance only; optimize per substrate):
Suzuki–Miyaura coupling (vinyl–aryl): Pd(PPh3)4 (1–5 mol%), K2CO3 or Cs2CO3 (2–3 equiv), dioxane/H2O or MeCN/H2O, 50–90 °C, 2–12 h. Often proceeds with retention of E-geometry; water co-solvent can accelerate.
Sonogashira coupling (vinyl–alkynyl): PdCl2(PPh3)2 (1–3 mol%), CuI (5–10 mol%), Et3N or i-Pr2NH, THF or DMF, 25–60 °C, 2–8 h. Copper-free variants reduce Glaser coupling.
Heck coupling (vinyl–alkenyl/aryl): Pd(OAc)2 (1–2 mol%) with PPh3 or bulky phosphines, Et3N or K2CO3, DMF/toluene, 80–130 °C, 6–16 h; control of regio- and stereochemistry via ligand/base/temperature.
Negishi/Stille: Pd(PPh3)4 (1–3 mol%), THF/DMF or toluene, 25–80 °C; excellent for sensitive partners.
Michael additions: Soft nucleophile (e.g., malonate, thiol) with base (K2CO3, DBU) or Lewis acid (Sc(OTf)3, Cu catalysts) in MeCN, THF, or toluene, 0–25 °C to limit polymerization; 1–6 h typical.
Conjugate reduction: Hydrosilylation (Pt/CatKarstedt or CuH) or Stryker’s reagent variants in toluene/THF at 0–25 °C.
Operational tips:
Oxygen exclusion improves Pd-catalyzed couplings and minimizes inhibitor consumption if present.
Maintain moderate concentrations (0.05–0.3 M) in acrylate chemistry to reduce polymerization risk.
Quench couplings with aqueous NH4Cl; for Michael additions, acidic quench minimizes retro-addition.
Note: Yields and exact conditions vary widely with substrates/ligands; consult primary literature for system-specific optimization.
Safety and Handling
Authoritative hazard classification for this specific item is not provided here. Always consult the product SDS before use.
Product data (item-specific):
Storage conditions: Room temperature
GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to SDS.
General safety information for bromoacrylate esters (literature/practice; not a substitute for SDS):
Likely hazards: Irritation to skin, eyes, and respiratory tract; acrylates can be sensitizers and strong lachrymators. Vinylic bromides may release HBr upon decomposition.
Polymerization risk: Acrylates can undergo exothermic radical polymerization. Avoid heat, peroxides, and contaminant radical initiators; do not distill to dryness.
Incompatibilities: Strong bases and nucleophiles (uncontrolled Michael additions), strong oxidizers/reducers, strong acids (HBr formation), and amines without temperature control.
PPE: Chemical-resistant gloves (e.g., nitrile), splash goggles, lab coat; use in a functioning fume hood.
First aid (overview): Rinse eyes/skin with water for ≥15 minutes upon contact; remove contaminated clothing. If inhaled, move to fresh air. Seek medical attention as indicated by SDS.
Fire: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and HBr.
Handling tips:
Work under inert atmosphere for air/moisture-sensitive transformations.
Keep containers tightly closed; minimize headspace and light exposure to reduce polymerization.
For scale-up, consider inhibitor checks and calorimetry due to potential runaway polymerization (general acrylate guidance).
Solvent Selection
This product is an organic reagent rather than a solvent. However, choosing an appropriate reaction solvent is crucial for its common transformations.
General solvent compatibility (literature/practice):
Polar aprotic solvents (e.g., DMF, DMAc, DMSO, MeCN, THF, 2-MeTHF) promote cross-couplings, nucleophilic substitutions on activated positions, and conjugate additions.
Moderately polar chlorinated solvents (e.g., DCM, 1,2-DCE) are effective for Lewis-acid-catalyzed additions and some radical reactions.
Nonpolar aromatics (e.g., toluene) are common for Pd-catalyzed couplings at elevated temperatures.
Miscibility/handling notes (general):
Expected to be soluble in most organic media; limited water solubility.
For base-sensitive steps, avoid highly basic solvents that may induce polymerization or undesired Michael addition.
Comparison (typical choices):
THF/2-MeTHF: good for organometallic additions and conjugate additions; 2-MeTHF offers greener profile and higher boiling point.
MeCN/DMF: strong solvents for Pd-catalyzed couplings; MeCN is easier to remove, DMF excels at high-temperature couplings.
Toluene/1,4-dioxane: suited to high-temperature Heck/Suzuki conditions; dioxane has regulatory considerations.
General guidance for this class of materials (literature/practice):
Atmosphere: Store under inert gas (N2/Ar) when possible to limit oxidation and polymerization; minimize headspace.
Light/heat: Protect from light and heat sources. Do not store near radical initiators or peroxides.
Stabilizers: Acrylates are often shipped with polymerization inhibitors. If the presence/level of any stabilizer matters to your application, consult the CoA. Remove immediately prior to sensitive reactions if necessary, using validated methods.
Packaging: Use amber glass with PTFE-lined caps. For long-term storage, small aliquots reduce repeated air exposure.
Reconstitution: Not applicable; supplied neat as a liquid reagent. If solidification occurs at low temperatures, warm gently to ambient and homogenize before use.
Shelf-life and specs:
Appearance, purity, inhibitor content, and E/Z ratio: Not specified for this item; refer to CoA/Spec Sheet and SDS for definitive guidance.
Research use only: As noted by the manufacturer, this product is for research use only.
Structure and Identity
Brief description: 2-Propenoic acid, 3-bromo-, methyl ester, (E)- is the E-configured vinyl bromide ester commonly called methyl (E)-3-bromoacrylate; it features a conjugated C=C–C(=O)OMe system bearing a vinylic bromine atom.
Functional groups: α,β-unsaturated methyl ester (Michael acceptor) and a vinylic bromide (C(vinyl)–Br)
Geometry/stereochemistry: E-configuration across the C=C bond; the higher-priority substituents (–C(=O)OMe and –Br) are on opposite sides of the double bond
2D description: CHBr=CH–C(=O)–OCH3 with trans relationship between Br and the carbonyl substituent across the C=C
Conjugation: The C=C is conjugated to the carbonyl; vinylic bromide enables cross-coupling while the ester activates the double bond for conjugate addition
Synthetic Utility
Functional group profile and reactivity (literature/practice):
Vinylic bromide (C(sp2)–Br): Excellent handle for cross-coupling (Suzuki, Stille, Negishi, Sonogashira, Heck), permitting rapid diversification at the β-position of the acrylate while often maintaining E-stereochemistry.
α,β-Unsaturated ester: Activated alkene for conjugate addition of soft nucleophiles (thiols, malonates, nitroalkanes, silyl enol ethers, amines) under base/Lewis acid catalysis.
Strategic uses:
Divergent synthesis: Orthogonal reactivity enables sequences like (a) Pd-coupling to install aryl/alkynyl substituents, then (b) conjugate addition or reduction to build complexity.
Annulation: Tandem intramolecular Heck or Michael additions from suitably tethered nucleophiles produce lactones/lactams and carbocycles.
Late-stage modification: Introduction of acrylate motifs into complex scaffolds via mild cross-coupling; ester can be further transformed (hydrolysis to acid, reduction to alcohol, amidation).
Stereochemical relay: E-configuration can influence downstream diastereocontrol in cycloadditions (e.g., Diels–Alder on substituted derivatives) and additions.
Downstream transformations:
Ester chemistry: Hydrolysis, transesterification, amidation (via acid or mixed anhydride), and reduction (DIBAL or LiAlH4) to corresponding alcohols/aldehydes.
Practical note: Verify and, if necessary, preserve E/Z geometry throughout sequences; some conditions (high T, strong base) can isomerize the double bond.
Target Specificity
Not applicable. This product is a small-molecule reagent and does not possess antibody/biological target specificity. No antigen, epitope, clone, or isotype information applies.
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