| HS Code | 264184 |
| Casnumber | 94994-61-5 |
| Molecularformula | C11H8F6O |
| Molecularweight | 270.17 g/mol |
| Exactmass | 270.0475 g/mol |
| Iupacname | 2-(4-ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol |
| Synonyms | 2-(4-vinylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol; 4-vinyl-alpha,alpha-bis(trifluoromethyl)benzyl alcohol |
| Smiles | C=CC1=CC=C(C=C1)C(O)(C(F)(F)F)C(F)(F)F |
| Inchi | InChI=1S/C11H8F6O/c1-2-7-3-5-8(6-4-7)9(18,10(12,13)14)11(15,16)17/h2-6,18H,1H2 |
| Appearance | Colorless to pale yellow liquid |
| Boilingpoint | 58-60 °C at 1 mmHg |
| Density | 1.30 g/mL at 25 °C |
| Refractiveindex | 1.4470 |
| Flashpoint | 110 °C (closed cup) |
| Solubility | Soluble in methanol, ethanol, ether, and chloroform; practically insoluble in water |
| Storageconditions | Store in a cool, dry, dark place under inert atmosphere |
As an accredited 2-(4-Ethenylphenyl)-1,1,1,3,3,3-Hexafluoropropan-2-Ol factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 5 g packaged in amber glass bottle with PTFE-lined cap, under inert atmosphere. Label includes hazard warnings and lot number. |
| Container Loading (20′ FCL) | 20′ FCL: packed in sealed drums on pallets, lashed and blocked, with proper labeling and segregation to ensure safe transport. |
| Shipping | Ship as: **UN 3265 Corrosive Liquid, Acidic, Organic, N.O.S. (2-(4-ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol), Class 8, Packing Group II**. Use UN-certified, corrosion-resistant containers, kept tightly sealed, cool, dry, and protected from light. Avoid strong oxidizers, bases, heat, and polymerization triggers. Follow IATA/IMDG/ADR regulations and provide SDS. |
| Storage | Store in a tightly sealed, light-resistant container under an inert atmosphere (e.g., nitrogen or argon). Keep in a cool, dry, well-ventilated area away from heat, sparks, flames, and incompatible materials such as strong oxidizers, acids, and bases. Avoid prolonged exposure to air or moisture to prevent polymerization or degradation. Use proper labeling and secondary containment. |
| Shelf Life | Stable for at least two years when stored cool, dry, and tightly sealed, protected from light and moisture. |
At the 193 nm immersion lithography node, 2-(4-ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol is fed into solution polymerization as a fluorinated alcohol comonomer at a monomer feed ratio of 20–35 mol% relative to total vinyl monomer. This range is selected because feed ratios below 20 mol% produce insufficient alkaline solubility in 0.26 N tetramethylammonium hydroxide developer, while ratios above 35 mol% increase resist film water uptake and reduce plasma etch resistance under fluorocarbon-based gate and contact etch chemistries. The resin is typically polymerized in PGMEA or methyl ethyl ketone at 65–80 °C under nitrogen with 0.5–1.0 mol% AIBN relative to monomer, using alicyclic methacrylates and tertiary-ester acid-labile comonomers to tune glass transition temperature and dry etch resistance. After precipitation in n-heptane, redissolution, and 0.05 µm filtration, the resin is blended with photoacid generator, quencher, and solvent to form a positive-tone chemically amplified resist. Semiconductor-grade materials are controlled under SEMI C1 trace metal guidelines, REACH Regulation (EC) No 1907/2006 Article 31 safety data sheet and Annex XVII restriction screening, and RoHS Directive 2011/65/EU for restricted substances in end-of-life equipment. Terminal product types include dry and immersion ArF photoresists for logic and memory patterning at 7 nm and 5 nm nodes, where the monomer functions as a low-absorbance replacement for phenolic hydroxyl functionality.
Post-exposure bake latitude in EUV and electron-beam resists based on HFIP-styrene copolymers is limited by acid diffusion and leaving-group deprotection rather than by the fluorinated alcohol substituent. The copolymer feed typically contains 25–40 mol% HFIP-styrene, with cycloaliphatic methacrylates and acid-labile tertiary-ester monomers forming the balance; this ratio maintains exposure sensitivity while preventing development-out of unexposed regions. PEB is commonly run at 90–130 °C on a hotplate for 60–90 s. Below 90 °C, deprotection is incomplete and line edge roughness increases; above 130 °C, photoacid migration degrades critical dimension uniformity at 24 nm half-pitch and below. Film formation uses a 300 mm coat/develop track at spin speeds from 1,000 rpm to 1,800 rpm, producing 100–200 nm thickness after prebake. Exposure is carried out at 13.5 nm EUV or 50–100 keV electron beam. Development uses 0.26 N aqueous tetramethylammonium hydroxide with surfactant-controlled wetting. Compliance evaluation includes SEMI S2/S8 equipment and environmental qualification, ASTM E595 total mass loss and collected volatile condensable materials testing for vacuum exposure environments, and REACH Regulation (EC) No 1907/2006 Article 33 communication for candidate list substances. Terminal products are EUV chemically amplified resists for sub-10 nm node development, electron-beam resists for photomask fabrication, metrology pattern referencing, and advanced defect review wafers.
For planar optical waveguide and interposer applications, HFIP-styrene is incorporated into amorphous copolymers to depress refractive index and suppress moisture-related transmission loss. Copolymer feed ratios are commonly 35–55 mol%, yielding refractive index values in the 1.46–1.50 range at 633 nm depending on the second comonomer; polymer batches outside this ratio window are rejected for cladding use because core-clad index contrast falls below 0.003. The polymer is synthesized in dried tetrahydrofuran or PGMEA, isolated by repeated precipitation into methanol or water, and redissolved at 10–15 wt% solids for spin coating. Casting on silicon or glass substrates is performed at 1,500–3,000 rpm under ≤45% RH to avoid dewetting and thickness nonuniformity. Pattern generation uses UV photolithography with reactive ion etching in oxygen-containing plasma or direct laser writing when a photoactive comonomer is included. Compliance testing follows ASTM D542 for refractive index, ASTM D1003 for optical transmittance, ISO 1183 for polymer density, and Telcordia GR-1221-CORE for passive optical component reliability including damp heat and thermal cycling. Terminal product types include polymer-based planar lightwave circuit claddings, optical interposer layers, and waveguide couplers used in data center board-level optical interconnects.
During redistribution-layer fabrication for advanced packages, spin-on dielectrics based on HFIP-styrene copolymers are processed on 300 mm wafer coaters to provide low-dielectric-constant insulation between copper traces and passivation layers. The copolymer is dissolved in PGMEA at 10–25 wt% solids and cast at spin speeds from 1,200 rpm to 2,200 rpm. After casting, the film undergoes a two-stage cure: 100–130 °C hotplate solvent removal followed by 250–350 °C nitrogen furnace cure to densify and drive off residual hydroxyl-associated moisture. Dielectric constant targets are typically 2.8–3.2 at 1 MHz, and cured film thickness is controlled in the 1–10 µm range by solids content and spin speed. The processing window is bounded on the upper end by thermolytic cleavage; thermal gravimetric analysis is therefore specified with 5% mass loss above 350 °C under nitrogen. Qualification testing applies ASTM D150 and IEC 60250 for permittivity and dissipation factor, ASTM E1356 and ISO 11357-2 for glass transition temperature, ISO 11358-1 for decomposition temperature, ASTM D3359 for crosshatch adhesion, and ASTM D570 for moisture uptake. Terminal product types include low-k interlayer dielectric films for fan-out wafer-level packaging, redistribution layers, and chip-last panel-level processes.
| Qualification parameter | Test method | Standard designation |
|---|---|---|
| Dielectric constant and dissipation factor at 1 MHz | Capacitance method | ASTM D150, IEC 60250 |
| Glass transition temperature | Differential scanning calorimetry | ASTM E1356, ISO 11357-2 |
| Thermal decomposition | Thermogravimetric analysis | ISO 11358-1 |
| Adhesion to silicon oxide | Crosshatch tape test | ASTM D3359 |
| Moisture absorption | Immersion method | ASTM D570 |
Gas separation membranes based on HFIP-styrene copolymers utilize the hexafluoroisopropanol group as a CO₂-philic hydrogen-bonding site to improve CO₂ solubility selectivity in CO₂/CH₄ and CO₂/N₂ feeds. In thin-film composite production, the polymer is dissolved at 10–20 wt% solids in tetrahydrofuran or cyclopentanone and slot-die coated onto a porous polyacrylonitrile or polyimide support. The selective layer is controlled at 0.2–1.0 µm thickness, with in-line reflection interferometry used to maintain coating uniformity. HFIP-styrene feed ratio is generally held at 20–40 mol%; below 20 mol%, CO₂ permeability becomes too low for competitive membrane area, while above 40 mol%, mixed-gas selectivity at feed pressures above 10 bar declines due to CO₂-induced plasticization of the copolymer matrix. Permeation testing follows ISO 15105-1 and ASTM D1434 at 35 °C and feed pressures from 2 bar to 20 bar. Module-level compliance is assessed under Directive 2014/68/EU for pressure equipment, REACH Regulation (EC) No 1907/2006 for chemical registration and safety data sheet requirements, and ISO 9001:2015 for manufacturing quality control. Published production-scale field data for this specific monomer in commercial biogas units remain limited; the above ranges are drawn from laboratory-scale mixed-gas permeation studies. Terminal products include spiral-wound and hollow-fiber membrane cartridges for biogas upgrading, natural gas sweetening, and post-combustion CO₂ capture pilot units.
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2-(4-Ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol is a para-substituted styrenic monomer in which the phenyl ring carries a hindered CF3-substituted tertiary alcohol. The molecular formula is C11H8F6O, the monoisotopic mass is 270.0479 g mol−1, and the calculated fluorine mass fraction is 42.2%. The structure contains one polymerizable vinyl group and one strongly hydrogen-bonding hexafluoropropan-2-ol group, also described as a hexafluoro-2-hydroxy-2-propyl substituent. The vinyl moiety participates in radical, anionic, or thiol-ene chemistries, while the fluorinated alcohol group provides acidity, polarity, and base-solubility switching not available from non-fluorinated styrenics such as styrene or 4-vinyltoluene.
No internationally standardized model designation is assigned to this monomer. Procurement is normally specified by the IUPAC name and a supplier-specific catalogue identifier; commercial listing suffixes may refer to assay grade or inhibitor loading. A typical release model for research and pilot use specifies a GC-FID assay of ≥ 98.0%, a related-impurity total of ≤ 2.0%, and controlled inhibitor content. Because public reference data for this exact derivative are limited to individual certificates of analysis and polymer-science literature, batch-specific values should be obtained from the supplier before scale-up.
The CF3-substituted tertiary alcohol exerts a strong electron-withdrawing effect on the para-styrenic double bond, reducing electron density at the vinyl carbon and altering copolymerization reactivity ratios relative to styrene. The electron-poor olefin can be polymerized through conventional free-radical initiation with azobis(isobutyronitrile) at 60–70°C, but the induction period and propagation rate are influenced by dissolved oxygen, inhibitor carryover, and solvent polarity. In copolymerizations with electron-rich monomers, the compound can exhibit alternating tendency by radical stabilization; the exact Mayo–Lewis reactivity ratios should be measured by nonlinear regression of polymer composition data rather than assumed from substituted-styrene analogues.
The hexafluoropropan-2-ol proton is substantially more acidic than a conventional primary or secondary alcohol. The aqueous pKa of the hexafluoropropan-2-ol state is approximately 9.3, compared with approximately 10.0 for phenol and approximately 17.1 for 2-propanol. In a polymer chain, the resulting conjugate base can be generated with aqueous tetramethylammonium hydroxide developers, commonly 0.26 N, enabling solubility switching in photoresist-type films. The hydroxyl group is sterically shielded by two CF3 groups, which reduces chain-transfer activity through labile hydrogen abstraction relative to unprotected 4-vinylphenol; however, controlled radical polymerization with copper halide complexes can be complicated by coordination or deactivation, so the free alcohol may require protection with a silyl ether when ATRP conditions are used.
The following representative analytical panel is used for lot release of research-grade fluorinated styrenic monomers. The supplier certificate of analysis is normative for any given batch.
| Property | Method or instrument | Release target |
|---|---|---|
| Assay by gas chromatography | GC-FID, flame ionization detector | ≥ 98.0% |
| Total related impurities | GC-FID area normalization | ≤ 2.0% |
| Water content | Coulometric Karl Fischer, ISO 15512:2019 | ≤ 0.10% |
| Inhibitor concentration | HPLC–UV | 10–20 ppm 4-tert-butylcatechol |
| Melting transition | Differential scanning calorimetry, 10 K min−1, ASTM E967-18 | Lot-specific, one sharp endotherm on CoA |
Release testing is normally conducted under an ISO 9001:2015-documented quality system. Karl Fischer water determination follows ISO 15512:2019, and differential scanning calorimetry follows ASTM E967-18. Residual water and inhibitor variation are batch-relevant because both alter radical polymerization induction time. Laboratories receiving the monomer should verify assay after transit, particularly where the material has been exposed to ambient light or repeated freeze–thaw cycles. The vinylic absorption near 1630 cm−1 and the broad O–H stretch in the 3400–3450 cm−1 region are used by FT-IR for rapid identity confirmation; electron-impact mass spectra exhibit the molecular ion at m/z 270.
Replacement of 4-vinylphenol with the title monomer changes several polymer properties simultaneously. The phenolic O–H is replaced by a hindered tertiary alcohol that is more acidic, more fluorinated, and less prone to oxidative coupling to quinoidal species. The fluorine mass fraction rises from 0.0% to 42.2%, lowering expected water uptake and increasing free volume in thin films while maintaining a hydrogen-bond-donor site for adhesion or dissolution-inhibitor interaction. Compared with 2,2,2-trifluoroethyl methacrylate, the present compound introduces a styrenic rather than methacrylic double bond, which affects propagation rate and copolymer microstructure. Compared with 1,1,1,3,3,3-hexafluoroisopropyl methacrylate, the present monomer retains an acidic proton, enabling base-solubility switching, whereas the methacrylate is a nonacidic ester.
| Monomer | Monoisotopic mass | Calculated fluorine mass fraction | Acidic hydrogen character | Reactive olefin type |
|---|---|---|---|---|
| 2-(4-Ethenylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol | 270.0479 g mol−1 | 42.2% | tertiary HFIP alcohol, pKa ≈ 9.3 | para-styrenic |
| 4-Vinylphenol | 120.0575 g mol−1 | 0.0% | phenolic, pKa ≈ 10.0 | para-styrenic |
| 2,2,2-Trifluoroethyl methacrylate | 168.0398 g mol−1 | 33.9% | nonacidic ester | methacrylic |
| 1,1,1,3,3,3-Hexafluoroisopropyl methacrylate | 236.0278 g mol−1 | 48.3% | nonacidic ester | methacrylic |
The difference between the styrenic HFIP monomer and the methacrylate esters matters in applications requiring an acidic proton for aqueous-base development or for post-polymerization ionic interaction. The styrenic olefin also produces an aromatic backbone repeat unit with higher glass-transition potential than a methacrylate backbone at equal functionality. However, the methacrylate esters are generally available as lower-melting liquids, whereas the title compound is typically handled as a crystalline or waxy solid at 2–8°C. Published data for this exact configuration are limited; therefore, direct substitution into an established formulation should be preceded by thermal and rheological screening of the resulting copolymer under the intended processing conditions.
In solution polymerization, the monomer is blended in anhydrous tetrahydrofuran, 2-butanone, or propylene glycol monomethyl ether acetate under nitrogen. Dissolved oxygen is reduced by freeze–pump–thaw cycling or inert-gas sparging to below 5 ppm before initiator addition. A jacketed glass reactor with a PTFE mechanical stirrer and reflux condenser is adequate for trial quantities. Inhibitor removal by neutral alumina or vacuum distillation may be required for controlled radical polymerization; however, bulk distillation of the free alcohol should be performed only under reduced pressure because the tertiary alcohol can undergo acid-catalyzed dehydration at elevated wall temperatures. The compound is incompatible with strong bases beyond controlled deprotonation, and contact with concentrated sulfuric acid or aluminum chloride should be avoided.
For thin-film photoresist evaluation, the monomer is incorporated into a base-soluble copolymer by radical polymerization, then formulated with a photoacid generator. The hexafluoropropan-2-ol repeat unit provides hydrogen-bonding sites for dissolution inhibitors and remains largely transparent at 193 nm because the aromatic ring and fluorinated alcohol do not introduce a strong irradiation-absorbing chromophore. Development is performed with aqueous tetramethylammonium hydroxide at approximately 0.26 N, and line-clearing dose can be adjusted by controlling the molar fraction of the HFIP-containing repeat unit. Storage of the monomer should be at 2–8°C under argon or nitrogen, protected from light, with relative humidity maintained below 60% during handling. Repeated exposure to moisture increases water content and shifts polymerization kinetics; molecular sieves should not be added directly to bulk monomer unless the sieve is first dried and inhibitor compatibility has been verified by GC-FID.
