Ethylstyrene (mixed isomers) - ≥95% , CAS No.7564-63-8

CAS: 7564-63-8 Cat. No.: E1071096 分子式: C₁₀H₁₂ 分子量: 132.200 EC番号: EINECS231-464-4

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

仕様と純度

≥95%

保管条件

Room temperature

純度

≥95%

名前と識別子

• カノニカル・スマイル: CCC1=CC=CC=C1C=C
• IUPAC Name: 1-ethenyl-2-ethylbenzene
• InChIKey: VTPNYMSKBPZSTF-UHFFFAOYSA-N
• INCHI: 1S/C10H12/c1-3-9-7-5-6-8-10(9)4-2/h3,5-8H,1,4H2,2H3
• 分子量: 132.200

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • 分類 Benzene and substituted derivatives
      • Subclass Styrenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 分類: Benzene and substituted derivatives
• Subclass: Styrenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Styrenes
• Alternative Parents: Aromatic hydrocarbons Cyclic olefins
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Styrene - Aromatic hydrocarbon - Cyclic olefin - Unsaturated hydrocarbon - Olefin - Hydrocarbon - Aromatic homomonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.
• 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

化学的性質と物理的性質

• 分子量: 132.200 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 132.094 Da
• Monoisotopic Mass: 132.094 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 105.000
• 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

Not applicable. No bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this chemical monomer.

For chemical transformations or polymerizations involving ethylstyrene, refer to the Reaction Conditions and Synthetic Utility sections for literature‑based procedural guidance.

Biological Roles

Ethylstyrene is a synthetic aromatic hydrocarbon monomer and does not play a natural biological role.

• General notes (literature)
  • No known role in metabolic pathways; not a biological buffer or nutrient.
  • Hydrophobic and largely inert in aqueous biochemistry; may partition into lipid phases due to its aromatic/alkenyl structure.
  • In toxicology research, styrenic aromatics are studied for their environmental fate and potential bioaccumulation; such discussions are outside the scope of product use and should rely on the SDS and regulatory literature.

For life science workflows, ethylstyrene is primarily relevant as a chemical intermediate or for materials synthesis (e.g., monomers for polymer supports), not as a biomolecule.

Buffer Applications

Not typically applicable. Ethylstyrene is a hydrophobic organic monomer and is not used to prepare aqueous buffer systems or to control pH.

If your workflow involves ethylstyrene in contact with aqueous phases, select compatible emulsifiers/surfactants and buffers based on your biological system, but the compound itself does not contribute buffering capacity.

Green Alternatives

Context: Ethylstyrene is an aromatic vinyl monomer. Greener considerations focus on solvent choice, process conditions, and monomer selection.

Greener processing options (literature guidance)

• Solvent selection for reactions on ethylstyrene
  • 2‑MeTHF vs toluene vs THF
    • 2‑MeTHF: bio‑derived, good solvency for aromatics, higher bp (80 °C) than THF, forms fewer peroxides, water‑immiscible (facilitates separations).
    • Toluene: effective hydrocarbon solvent; petro‑based; VOC concerns but easy recovery by distillation.
    • THF: polar ether; facilitates organometallics but peroxide‑forming and often higher EHS burden.
• Polymerization media
  • Bulk polymerization minimizes solvent use but raises heat‑management issues; consider solution polymerization in toluene/ethyl acetate/2‑MeTHF to moderate viscosity and improve safety.
• Energy and initiation
  • Photopolymerization (LED) or low‑temperature ATRP/RAFT can reduce energy input compared to high‑temperature thermal initiations.

Alternative monomers (tradeoffs; literature)

• Bio‑based or lower‑toxicity monomers (e.g., limonene‑derived vinyl monomers, isosorbide di(meth)acrylates) can substitute in some applications but differ in Tg, modulus, and compatibility.

Waste and inhibitor management

• Recover and recycle unreacted monomer via vacuum distillation with proper stabilization.
• Avoid large excesses of chlorinated solvents; choose greener extraction solvents (EtOAc, MeTHF) where compatible.

Note: No item-specific green certifications are provided; consult the CoA/SDS and your EHS program.

Pharmaceutical Uses

No therapeutic or clinical use is claimed or implied. For research use only.

Formulation/manufacturing context (general)

• Ethylstyrene may be used in research on polymeric excipients or model styrenic copolymers for coatings and device materials. Any such application requires thorough toxicological and extractables/leachables assessment.
• It is not an established pharmacopeial excipient. If used in device/material R&D, ensure compliance with relevant material standards and perform appropriate purification to minimize residual inhibitor and volatiles.

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

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: 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/typical values for ethylstyrene isomers (for reference only; not item specifications)

• Physical state: clear, colorless to pale yellow liquid (styrenic monomers typically color on storage if unstabilized).
• Boiling point: ~185–190 °C at 1 atm (isomer-dependent; literature).
• Melting point: below 0 °C (liquid at ambient; literature).
• Density (20/25 °C): ~0.90–0.92 g/mL (literature, aromatic vinyl monomers).
• Refractive index nD20: ~1.525–1.535 (literature ranges for o/m/p‑ethylstyrene).
• Vapor pressure (25 °C): on the order of a few Pa to tens of Pa (lower than styrene; literature trend).
• LogP (octanol/water): ~3.5–3.9 (calculated/literature for isomers).
• Solubility: insoluble in water; miscible with common organic solvents (toluene, ethers, chlorinated solvents, esters) — literature.
• Viscosity (25 °C): low to moderate for a monomeric aromatic liquid (literature qualitative).

Notes

• Actual values depend on isomer distribution and purity. For regulatory, process, or QC use, rely on the CoA/Spec Sheet for the shipped lot.

Quality and Grades

• Item-specific quality information

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizer/inhibitor: Not specified for this item; refer to CoA/Spec Sheet.

• Context for styrenic monomers (general)

  • Many suppliers ship styrenic monomers with trace polymerization inhibitors (e.g., TBC, MEHQ) to improve storage stability. Presence/level of inhibitor affects suitability for anionic, radical, or coordination polymerizations and may necessitate inhibitor removal (e.g., alumina, basic wash) before use.
  • “Monomer grade” typically implies low peroxide content, low color, and controlled inhibitor content; “Analytical” or “Purified” grades may emphasize low UV background or defined inhibitor levels. Confirm with the CoA.

• What to check on receipt

  • CoA parameters often include assay (%), water (Karl Fischer), acidity, color (APHA), inhibitor type/ppm, and GC area % for isomer distribution. For this item, these are Not specified for this item; refer to CoA/Spec Sheet.
  • If polymerization or advanced synthesis is intended, verify inhibitor content and remove only immediately prior to use; store re‑inhibited for safety when appropriate.

• Quality control tips

  • Assess by GC/FID for isomer ratio and purity; monitor peroxides if long storage is expected.
  • Record refractive index and density as fast checks for identity consistency (literature ranges provided in Physical Properties, non‑spec).

Reaction and Applications

Ethylstyrene (mixed isomers) is a styrenic aromatic alkene used as a monomer and versatile aryl–alkenyl building block.

Typical applications (literature; non-exhaustive)

• Free‑radical polymerization: bulk, solution, or emulsion polymerization to give poly(ethylstyrene) or copolymers (e.g., with acrylates, maleic anhydride, butadiene). The ring ethyl substituent modulates Tg and solubility compared to polystyrene.
• Controlled radical polymerizations: ATRP, RAFT, NMP can provide well‑defined poly(ethylstyrene) blocks; inhibitor removal may be needed.
• Electrophilic additions at the double bond: hydrohalogenation, sulfenylation, and carbocationic additions proceed with Markovnikov selectivity typical of styrenes.
• Oxidation/epoxidation: epoxidation (e.g., m‑CPBA) of the vinyl group; subsequent ring‑opening yields 1,2‑diols or beta‑functionalized derivatives.
• Hydroboration–oxidation and hydrosilylation: anti‑Markovnikov alcohols or benzylic silanes via catalytic processes (e.g., BH3·THF then H2O2/NaOH; Pt or Karstedt’s catalysts for hydrosilylation).
• Cross‑coupling at the benzylic/vinylic position: Heck and Fujiwara–Moritani type arylations on the vinyl group; C–H activation on the ring is influenced by the ethyl substituent (o/p‑directing through hyperconjugation).
• Radical additions (ATO, Giese‑type): thiol–ene and radical Giese additions across the double bond under photoinitiation.

Practical tips

• Dry, oxygen‑poor conditions suppress inhibitor carryover and unwanted polymerization; use degassing and nitrogen/argon blankets.
• For polymerizations, monitor exotherms; consider solution/bulk viscosity and heat removal. Employ appropriate inhibitors for storage between runs if monomer is purified.
• Isomer mixture: reaction regioselectivity on the ring (SEAr, nitration, halogenation) may vary with o/m/p content; vinyl chemistry is largely insensitive to the ring substitution pattern.

Reaction Conditions

General, literature‑based guidance for common transformations of ethylstyrenes (not item specifications)

• Free‑radical polymerization

  • Initiators: AIBN (0.1–1 mol%), peroxides (BPO, TBHP) per standard protocols.
  • Solvents: bulk, toluene, xylene, ethylbenzene; temperatures 60–120 °C depending on initiator half‑life.
  • Atmosphere: inert (N2/Ar); inhibitor removal may be needed immediately before use; control exotherm.

• ATRP/RAFT of ethylstyrene

  • ATRP: CuBr/ligand (e.g., PMDETA) with alkyl bromide initiator in anisole/toluene/bulk; 60–110 °C; ppm‑ATRP variants feasible.
  • RAFT: trithiocarbonate or dithiobenzoate CTAs; AIBN at 60–80 °C in toluene/anisole.

• Epoxidation of the vinyl group

  • Reagent: m‑CPBA (1.1–1.5 eq) in DCM at 0–25 °C; typical times 1–4 h; quench with Na2SO3/NaHCO3; yields often 70–90%.

• Hydroboration–oxidation

  • BH3·THF or 9‑BBN (1.0–1.2 eq) in THF/2‑MeTHF at 0–25 °C; oxidize with H2O2/NaOH; anti‑Markovnikov alcohol formation; 60–85% typical yields reported.

• Hydrosilylation

  • Catalyst: Pt(0) (Karstedt’s) 10–100 ppm or Speier’s catalyst; solvent toluene or neat; 25–80 °C; hours to completion.

• EAS on the ring

  • Friedel–Crafts acylation: Acyl chloride/AlCl3 in DCM/CS2 at 0–25 °C; o/p selectivity influenced by isomer; careful control to avoid polymerization of the vinyl group.

Notes

• Mixed isomer feedstocks can complicate regioselectivity for ring reactions; purify to a single isomer when selectivity is critical.
• Always confirm conditions at small scale; presence/absence of inhibitors and trace peroxides affects outcomes.

Safety and Handling

Safety overview (general guidance for styrenic monomers; defer to product SDS for authoritative information)

• Likely hazards (literature-based for ethylstyrenes)
  • Flammable liquid and vapor; keep away from ignition sources and hot surfaces.
  • May cause skin and eye irritation; inhalation of vapors can cause respiratory irritation and CNS effects at high concentrations.
  • Polymerization hazard: may undergo exothermic polymerization, especially upon heating, exposure to light, peroxides, or radical initiators.
• GHS/CLP for this specific item: Not specified for this item; refer to SDS.
• Signal word/Pictograms/H-statements: Not specified for this item; refer to SDS.

Recommended precautions

• Engineering controls: handle in a fume hood; use explosion‑proof ventilation where large volumes are handled.
• PPE: safety glasses or chemical goggles; lab coat; suitable chemical‑resistant gloves (e.g., nitrile); use a face shield for bulk transfers.
• Incompatibilities: strong oxidizers; strong acids; radical initiators and peroxides (unless intentionally used under controlled polymerization conditions); avoid copper/bronze catalysts unless intended.
• Handling notes: minimize exposure to heat, light, and air; purge headspace with inert gas when feasible. Avoid contamination with peroxides or amines that can initiate polymerization.

First aid (general)

• Inhalation: move to fresh air; monitor breathing; seek medical attention if symptoms persist.
• Skin contact: wash with soap and water; remove contaminated clothing.
• Eye contact: rinse cautiously with water for several minutes; remove contacts if easy; seek medical attention for persistent irritation.
• Ingestion: rinse mouth; do not induce vomiting; seek medical advice.

Spill/Fire response

• Spill: absorb with inert material (vermiculite, sand); collect in non‑sparking containers.
• Fire: use dry chemical, CO2, foam; water spray to cool containers. Combustion can produce CO/CO2 and irritant smoke.

Always consult the SDS for the lot-specific hazard classification and emergency measures.

Solvent Selection

This product is an organic monomer/building block rather than a laboratory solvent. A dedicated “solvent selection” section is not typically applicable.

Practical guidance (when using Ethylstyrene as a substrate/monomer)

• Solubility/miscibility (literature): immiscible with water; miscible with hydrocarbons (hexanes, toluene), ethers (THF, MTBE), esters, and chlorinated solvents.
• Polarity class: nonpolar to weakly polar aromatic hydrocarbon; suitable as a substrate in nonpolar or moderately polar aprotic media.
• For polymerizations or functionalizations, common medium choices include toluene, xylene, heptane, or bulk (neat) conditions, depending on heat removal and viscosity control.

If you are seeking a solvent for your process, consider toluene or 2‑MeTHF for reactions on ethylstyrenes, balancing solvency, boiling point, and greener solvent credentials (see Green Alternatives).

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Protect from heat and direct sunlight. Store in tightly closed containers.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizer/inhibitor: Not specified for this item; refer to CoA/Spec Sheet.

Best practices (general for styrenic monomers)

• Store under inert gas (N2/Ar) if possible to limit oxidation and premature polymerization; amber bottles help minimize light exposure.
• If supplied with inhibitor, keep as received for storage; remove inhibitor only immediately prior to use, and consider re‑inhibiting any recovered monomer before re‑storage for safety.
• Avoid elevated temperatures; refrigerating at 2–8 °C further slows polymerization for long‑term storage (verify acceptability with the supplier if crystallization/viscosity is a concern).

Reconstitution/Preparation

• Typically supplied as a ready‑to‑use liquid; no reconstitution required.
• Before use, bring to ambient temperature, mix thoroughly, and, if needed for sensitive chemistry, pass through basic alumina to remove phenolic inhibitors (only if inhibitor removal is confirmed necessary by your method).

Research Use Note: For research use only.

Structure and Identity

Brief description: Ethylstyrene (mixed isomers) denotes an isomeric mixture of ring‑ethyl‑substituted styrenes (vinylethylbenzenes), typically comprising 2‑, 3‑, and 4‑ethylstyrene.

• Item-specific identifiers (from Product Data)

  • SKU: E1071096
  • Product Name: Ethylstyrene (mixed isomers)
  • CAS: 7564-63-8 (mixture)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature description for ethylstyrenes)

  • Core: benzene ring bearing a vinyl (–CH=CH2) substituent (styrenyl group) and an ethyl (–CH2CH3) substituent.
  • Isomerism: positional isomers differ by the relative position (ortho/meta/para) of the ethyl group to the vinyl group on the ring.
  • Functional groups: aromatic ring, terminal alkene (styrenyl), alkyl (ethyl) substituent.
  • 2D description: an sp2 aromatic hexagon with one vinylic substituent (–CH=CH2) and one ethyl substituent (–CH2–CH3) located at o/m/p positions relative to each other.

• Composition (literature values for individual isomers; examples)

  • 2‑Ethylstyrene: MF C10H12; example SMILES: C=CC1=CC=CC(CCC)=C1 (varies by notation); InChIKey (example): may differ by supplier—consult primary databases.
  • 3‑Ethylstyrene: MF C10H12; example SMILES: C=Cc1cccc(CC)c1.
  • 4‑Ethylstyrene: MF C10H12; example SMILES: C=Cc1ccc(CC)cc1.

• Molecular formula and weight (literature, for each isomer)

  • Molecular formula (all isomers): C10H12
  • Molecular weight (all isomers): ~132.20 g/mol

Note: Exact composition and identifiers for the shipped lot may vary in isomer ratios; consult the item’s CoA/Spec Sheet for definitive identity data.

Synthetic Utility

Functional group analysis (literature)

• Terminal alkene (styrenyl)
  • Undergoes electrophilic additions, radical additions (thiol–ene), catalytic hydrofunctionalizations (hydroboration, hydrosilylation, hydrocyanation), and oxidations (epoxidation, dihydroxylation).
  • Serves as a handle for polymer growth (radical, ATRP/RAFT/NMP), enabling block/graft copolymer synthesis.
• Aromatic ring with ethyl substituent
  • Slightly activating, ortho/para‑directing for electrophilic aromatic substitution (EAS). Useful for halogenation, Friedel–Crafts acylation/alkylation, nitration (careful control required), and sulfonation.
  • Benzylic C–H positions of the ethyl group are amenable to oxidation (to ketones/carboxylates) and radical functionalization.

Retrosynthetic value

• Ethylstyrenes can serve as masked benzyl cation equivalents via radical/cationic pathways and as precursors to 1,2‑diols/epoxides useful in further diversification.
• The isomer mixture provides access to regioisomeric product arrays for SAR/materials screening, though isomer separation may be required for structure–property studies.

Derivatization examples (general)

• m‑CPBA epoxidation → ring opening with nucleophiles (ROH, amines) → beta‑substituted benzylic alcohols.
• Hydroboration–oxidation → 2‑phenethyl alcohol derivatives (anti‑Markovnikov).
• Heck coupling on the double bond with aryl halides to extend conjugation.

Note: For chiral or position‑selective synthesis, begin with a defined isomer rather than a mixed isomer feed.

Target Specificity

Not applicable. This product is a small‑molecule monomer, not a biological targeting reagent (e.g., antibody, ligand, or probe). No antigen/epitope specificity applies.