4-Ethoxystyrene - ≥95%, stabilized with ~0.1% TBC , CAS No.5459-40-5

CAS: 5459-40-5 Cat. No.: E477029 Formula: C₁₀H₁₂O Molecular Weight: 148.20 EC Number: 226-729-6

GRADE & PURITY ≥95%, stabilized with ~0.1% TBC

Synonyms

4-Ethoxystyrene | EINECS 226-729-6 | 4-Vinylphenetole | 1-Ethoxy-4-vinylbenzene | MFCD00009097 | XML26X6K54 | 4-Ethoxystyrene, technical grade, 90% | p-Vinylphenetole | A857153 | F87405 | SCHEMBL181498 | AKOS009156981 | NSC 24179 | EN300-1243725 | Benzene

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

4-Ethoxystyrene | EINECS 226-729-6 | 4-Vinylphenetole | 1-Ethoxy-4-vinylbenzene | MFCD00009097 | XML26X6K54 | 4-Ethoxystyrene, technical grade, 90% | p-Vinylphenetole | A857153 | F87405 | SCHEMBL181498 | AKOS009156981 | NSC 24179 | EN300-1243725 | Benzene

Specifications & Purity

≥95%, stabilized with ~0.1% TBC

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

Pubchem Sid

504755384

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504755384

Canonical Smiles

CCOC1=CC=C(C=C1)C=C

IUPAC Name

1-ethenyl-4-ethoxybenzene

InChIKey

OBRYRJYZWVLVLF-UHFFFAOYSA-N

INCHI

1S/C10H12O/c1-3-9-5-7-10(8-6-9)11-4-2/h3,5-8H,1,4H2,2H3

Isomeric SMILES

CCOC1=CC=C(C=C1)C=C

Molecular Weight

148.20

Reaxy-Rn

1935209

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1935209&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Phenol ethers

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Phenol ethers
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenol ethers
• Alternative Parents: Styrenes Phenoxy compounds Alkyl aryl ethers Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Phenoxy compound - Styrene - Phenol ether - Alkyl aryl ether - Monocyclic benzene moiety - Ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
• External Descriptors: Not available

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

Chemical and Physical Properties

• Sensitivity: heat sensitive
• x_refractive_index: n20/D 1.549 (lit.)
• x_boil_point_char: 99-100 °C/11 mmHg (lit.)
• Molecular Weight: 148.200 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 148.089 Da
• Monoisotopic Mass: 148.089 Da
• Topological Polar Surface Area: 9.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 112.000
• 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

No biochemical/assay protocols are specified for this item. For synthetic or polymerization workflows, see Reaction Conditions for representative setups. Always tailor stoichiometry, temperature, and atmosphere to your catalyst/initiator system and verify purity/inhibitor content on receipt (refer to the CoA/SDS).

Biological Roles

This product is a synthetic organic monomer and is not typically used to probe biological pathways or functions. 4-Ethoxystyrene has no established endogenous biological role. Any biological testing, if performed, should treat it as an exogenous hydrophobic small molecule and follow standard lab safety and waste-handling practices. No claims are made regarding bioactivity; see SDS for exposure guidance.

Buffer Applications

Not typically applicable. 4-Ethoxystyrene is a hydrophobic vinyl-arene and is not used to prepare aqueous buffer systems. For experimental work involving this monomer, select organic solvents as outlined in Solvent Selection and Reaction & Applications.

Green Alternatives

Greener process considerations focus on solvent choice, energy input, and stabilization strategy rather than on the monomer itself.

• Solvent selection (comparative, general):

  • 2-MeTHF: bio-based, good solvency for styrenes, forms fewer peroxides than THF, facilitates phase splits. Tradeoff: odor and cost.
  • CPME: hydrophobic ether with broad liquid range, lower peroxide formation tendency, high boiling point. Tradeoff: sourcing and limited regulatory familiarity.
  • Ethyl acetate: low toxicity/biodegradable; suitable for many addition and oxidation reactions. Tradeoff: moderate solvency and lower bp can limit temperature window.
  • Anisole: higher boiling, good for polymerizations; not bio-based but less hazardous than chlorinated media.

• Process intensification:

  • Flow polymerization or flow functionalization can improve heat/mass transfer and mitigate runaway risks.
  • Photocatalytic and electrochemical variants of alkene functionalizations may allow milder conditions and greener oxidants/reductants (e.g., O2, electricity) in place of stoichiometric reagents.

• Waste and stabilization:

  • Use minimal inhibitor load compatible with safe storage (verify via CoA/SDS). Remove inhibitor only immediately before use and restabilize leftovers to reduce waste.

Note: The above are literature-based best practices and do not modify this item’s specifications. Confirm compatibility with your process safety and quality systems.

Pharmaceutical Uses

No direct excipient or pharmacopeial role is established for 4-ethoxystyrene. In a pharmaceutical R&D context it may serve only as a synthetic intermediate or as a comonomer for specialty polymeric materials used in device or packaging research. This listing is for research use only and is not intended for human or veterinary applications. Always evaluate extractables/leachables and residual monomer content if materials derived from this monomer are studied for formulation or device research.

Physical Properties

Item-specific specifications (this product):

• Appearance, purity/grade, density, refractive index, water/peroxide/metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general data for 4-ethoxystyrene (for planning; not product specifications):

• Phase at ambient conditions: typically a colorless to pale liquid (styrenic monomer class).
• Molecular weight: ~148.20 g/mol (C10H12O).
• Qualitative solubility: sparingly soluble in water; miscible with common organic solvents (e.g., toluene, ethyl acetate, dichloromethane, THF, acetone). Aromatic/ether character favors good solubility in nonpolar to mid-polar media.
• Polarity/logP (inferred from structure): expected hydrophobic (aromatic ring + alkene) with modest polarity from the aryl ether; partitions strongly into organic phases.

Notes:

• Exact physical constants (bp, mp, density, nD, pKa/logP) vary among references for substituted styrenes and are not provided for this specific item. For regulated or scale-up work, confirm with primary literature or measure directly.
• As with many styrenics, viscosity and refractive index are typically higher than the parent alkene but below those of long-chain vinyl aromatics.

Quality and Grades

Item-specific quality information:

• Grade/purity, stabilizer/inhibitor content, GC assay, UV specs, trace metals: Not specified for this item; refer to CoA/Spec Sheet.

Context and guidance (general; not product-specific):

• Styrenic monomers are often supplied with a polymerization inhibitor (e.g., tert-butylcatechol or hydroquinone derivatives) to enhance storage stability. If inhibitor content affects your polymerization or synthesis, verify the inhibitor type/level on the CoA and consider pre-treatment (e.g., basic alumina) when appropriate.
• Analytical/Reagent grades: For materials science and synthetic work, typical qualifiers include GC purity (e.g., ≥98–99%), residual solvents, and inhibitor content. HPLC-grade is less common for monomers but low-UV-background solvents are relevant if spectroscopic monitoring is required.
• Quality control suggestions:
  • Confirm identity by 1H/13C NMR (diagnostic vinyl signals ca. 6–7.2 ppm; ethoxy –CH2– near 4.0–4.2 ppm), and GC–MS.
  • Check for early-stage polymerization by GC baseline rise or by 1H NMR broadening/high-mass signals.
  • If oxygen-sensitive processes are planned, consider degassing and testing peroxide levels prior to use (if applicable).

Reaction and Applications

4-Ethoxystyrene serves both as a functional monomer and as a versatile vinyl-arene substrate.

• Polymer/materials applications (general):

  • Free-radical polymerization to poly(4-ethoxystyrene) or copolymers with styrene, acrylates, maleic anhydride, etc. The para-ethoxy substituent increases electron density of the ring, altering Tg and dielectric properties versus polystyrene.
  • Post-polymer modification via ether cleavage or O-functionalization can tailor polarity and adhesion.

• Representative transformations (literature):

  • Electrophilic additions to the alkene: hydroboration–oxidation (to give para-ethoxyphenethyl alcohols), hydrohalogenation, thiol–ene couplings.
  • Oxidations of the alkene: epoxidation (m-CPBA), dihydroxylation (OsO4/NMO), or Wacker-type oxidation to give p-ethoxyacetophenone derivatives under suitable conditions.
  • Cyclopropanation (Simmons–Smith; metal-carbene transfer) to access arylcyclopropanes.
  • Cross-coupling on the aryl ring (after halogenation) or Heck reactions using the alkene partner to form C–C bonds with aryl/vinyl halides.
  • Friedel–Crafts chemistry on the electron-rich ring (nitration, acylation) with the para position blocked; ortho-directing effects dominate.

Practical tips:

• Dry, oxygen-lean conditions minimize undesired radical initiation during storage and handling.
• If an inhibitor is present (check CoA), passage through basic alumina just prior to polymerization can restore activity; re-stabilize any remainder for storage.
• Monitor conversions by GC or 1H NMR; vinyl signals (ca. 5.2–6.8 ppm) diminish as reactions proceed.

Reaction Conditions

General literature guidance for common transformations (verify and optimize experimentally):

• Free-radical polymerization

  • Initiators: AIBN (0.5–2 mol%), peroxides (e.g., BPO, TBPB)
  • Solvents: toluene, anisole, xylene, ethyl acetate, 2-MeTHF
  • Temperature: 60–120 °C depending on initiator t1/2
  • Atmosphere: inert (N2/Ar); exclude oxygen to avoid inhibition
  • Notes: monitor exotherm; consider RAFT/ATRP for controlled architectures

• Hydroboration–oxidation of the alkene

  • Reagents: 9-BBN or BH3•THF; then H2O2/NaOH
  • Solvent: THF or 2-MeTHF
  • Temp: 0–25 °C (addition), then 25–50 °C (oxidation)
  • Outcome: benzylic alcohols (Markovnikov/anti-Markovnikov per reagent/catalyst)

• Epoxidation

  • Reagent: m-CPBA (1.1–1.5 eq)
  • Solvent: DCM, CHCl3, or EtOAc
  • Temp: 0–25 °C; buffer acid formed (add NaHCO3)

• Heck coupling (as alkene partner)

  • Catalyst: Pd(OAc)2 or Pd(PPh3)4 (1–5 mol%)
  • Base: Et3N, DIPEA, K2CO3
  • Solvent: DMF, DMAc, NMP, or toluene
  • Temp: 80–130 °C; inert atmosphere

• Cyclopropanation

  • Reagent: ethyl diazoacetate or CH2I2/Zn–Cu (Simmons–Smith)
  • Solvent: DCM, toluene
  • Temp: 0–25 °C; add slowly; control exotherm

These are representative conditions reported for styrenes; adjust for substituent effects of the para-ethoxy group and scale/safety constraints.

Safety and Handling

Item-specific hazard information:

• Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to the SDS.

General safety guidance for styrenic monomers (literature/industry practice; not product-specific):

• Likely hazards: flammable liquid and vapor; skin/eye irritation; harmful if inhaled; may polymerize exothermically if contaminated or heated excessively. Always review the SDS for authoritative classification and PPE.
• Personal protective equipment (PPE): chemical-resistant gloves, lab coat, splash goggles; use in a fume hood to control vapors.
• Handling practices:
  • Avoid heat, sparks, and open flames. Ground/bond when transferring.
  • Minimize exposure to air and light if long-term storage is intended, as many styrenes can gradually form peroxides or self-polymerize.
  • Prevent contact with strong acids, Lewis acids, and radical initiators unless intentionally used for reaction.
• First-aid overview (consult SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Fire-fighting: use alcohol-resistant foam, dry chemical, or CO2; cool containers with water spray.
• Spills: absorb with inert material; contain vapors; dispose per regulations. Defer to institutional EHS procedures.

Solvent Selection

Compound-solvent behavior (general guidance for 4-ethoxystyrene):

• Polarity class: nonpolar to moderately polar, aromatic/ether character.
• Miscibility: immiscible with water; miscible with common organic solvents (toluene, xylene, ethyl acetate, acetone, MTBE, DCM, chloroform, THF, CPME, 2-MeTHF).
• Dielectric environment: reactions and polymerizations are commonly run in aromatic solvents (toluene, xylene) or ethers (THF, 2-MeTHF, CPME) to balance solubility and volatility control.

Choosing solvents by application:

• Radical polymerization: toluene, anisole, or xylene for thermal stability; ethyl acetate or 2-MeTHF for greener profiles and heat transfer. Bulk polymerization is also practiced but demands rigorous thermal control.
• Transition-metal catalysis (e.g., Heck, hydrofunctionalizations): polar aprotic media (DMF, DMAc, NMP) or greener ethers (2-MeTHF, CPME) often enhance rates while maintaining solubility; aromatic solvents are common for high-temperature runs.
• Oxidations/dihydroxylations/epoxidations: chlorinated solvents or acetonitrile are frequent in literature; greener replacements like EtOAc or 2-MeTHF may be viable depending on catalyst.

Comparison snapshot (general):

• Toluene: high solubility, good thermal window; not renewable.
• 2-MeTHF/CPME: good solvency for styrenes, lower peroxide tendency than THF (CPME), partially bio-based (2-MeTHF), easier workup.
• EtOAc: greener profile, moderate solvency; lower boiling range may limit some transformations.

Storage and Reconstitution

Item-specific guidance (from Product Data):

• Storage conditions: Store at 2–8 °C.
• Shipping: Shipped on wet ice.

General best practices for styrenic monomers (literature/industry guidance; not product-specific):

• Protect from heat, light, and sources of radical initiation. Store in airtight containers; consider inert headspace (N2/Ar) for extended storage.
• If supplied with an inhibitor (check CoA/SDS), retain inhibitor during storage. If removal is necessary before use (e.g., via basic alumina), only treat the portion required for immediate experiments and restabilize any remainder prior to returning to storage.
• Avoid freeze–thaw cycles that can lead to moisture ingress; bring to room temperature before opening to minimize condensation.
• Inspect periodically for signs of polymerization (increased viscosity, haziness). If observed, do not use; follow institutional disposal procedures.

Reconstitution: Not applicable (neat liquid). If dilution is needed for handling or dosing, prepare solutions in a compatible, dry organic solvent under inert atmosphere as appropriate for the planned reaction.

Structure and Identity

Brief overview: 4-Ethoxystyrene is a para-ethoxy-substituted vinylbenzene (a styrenic monomer), combining an electron-rich anisole-like ring with a terminal styrenyl alkene.

• Item-specific (from Product Data)

  • SKU: E477029
  • CAS: 5459-40-5
  • PubChem CID: 79570
  • InChIKey: 253689 (as provided)
  • Storage: 2–8 °C; shipped on wet ice
  • Research Use: For research use only

• Computed/literature identification (general reference; verify against CoA/SDS)

  • Preferred IUPAC name (literature): 1-ethenyl-4-ethoxybenzene (p-ethoxystyrene)
  • Molecular formula (literature): C10H12O
  • Molecular weight (literature): ~148.20 g/mol
  • SMILES (literature): CCOc1ccc(cc1)C=C

• Structural features (general)

  • Aromatic ring bearing two para-disposed substituents: an ethoxy group (–O–CH2CH3) and a vinyl group (–CH=CH2).
  • Functional groups: electron-donating aryl ether, terminal alkene (styrenyl). No defined stereocenters; the vinyl substituent is terminal (E/Z not applicable).
  • 2D description: A benzene ring with –OCH2CH3 at the para position relative to a –CH=CH2 group; the ethoxy oxygen is directly bound to the ring (aryl ether).

Synthetic Utility

Functional group portfolio and reactivity (general, literature-based):

• Terminal styrenyl alkene:
  • Radical additions (thiol–ene), atom-transfer radical additions, and polymerization.
  • Carbene transfer/cyclopropanation and epoxidation/dihydroxylation to access richly functionalized benzylic motifs.
  • Hydrofunctionalizations (hydroboration, hydrosilylation, hydrocyanation) enabling downstream oxidation or cross-coupling.
• Electron-rich aryl ether:
  • Strongly activating, ortho/para-directing for electrophilic aromatic substitution (EAS); para site is blocked, biasing to ortho.
  • Ether can serve as a handle for O-alkylation/acylation or, under specific conditions, demethylation/ether cleavage analogs (adapted to ethoxy).

Retrosynthetic value:

• As a vinyl-arene linchpin, it enables convergent assembly: install the p-ethoxy unit first (via anisole ether synthesis), then append vinyl via Wittig, Heck, or vinylation chemistry—or vice versa.
• Access to p-ethoxyacetophenone scaffolds via oxidative routes (e.g., Wacker-type or benzylic oxidation of the corresponding ethyl derivative) provides entry to numerous fine-chemical targets.

Orthogonality:

• The alkene can be chemoselectively transformed while leaving the aryl ether intact under many conditions (e.g., hydroboration–oxidation), enabling stepwise elaboration.

Target Specificity

Not applicable. This product is a small-molecule monomer, not a biological targeting reagent (no antigen/epitope, clone, isotype, or species reactivity). Refer instead to Reaction & Applications and Synthetic Utility for relevant use-cases.