≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Descripción general
Product description：
4-Ethynyl-1-fluoro-2-methylbenzene has been reported to afford 1,4-disubstituted 1,2,3-triazole on reaction with azide under typical Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC) conditions.
This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
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.
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Application Protocols
No validated bioassay or immunoassay protocols are specified for this item. As a small-molecule building block, usage protocols depend on the chosen synthetic transformation (e.g., Sonogashira coupling, CuAAC, nucleophilic addition).
General pointers (literature-based)
Sonogashira coupling: Charge oven-dried glassware under inert atmosphere; combine aryl/vinyl halide, this alkyne, Pd catalyst (± CuI), base, and solvent; stir at selected temperature; monitor by TLC/GC; work up and purify by silica gel chromatography.
CuAAC: Dissolve azide partner and this alkyne in t-BuOH/H2O (1:1); add CuSO4 and sodium ascorbate (± ligand); stir at RT to 50°C until complete; chelate copper during workup (e.g., with EDTA) before extraction.
Consult primary literature and optimize for your substrates. For batch-specific guidance (stabilizers, purity), refer to the CoA/Spec Sheet.
Biological Roles
Item-specific (Product Data)
No biological function or role is specified. For research use only.
General context (literature; not specific to this item)
Aryl terminal alkynes are not typical endogenous metabolites. However, terminal alkynes are widely used as bioorthogonal handles due to their compatibility with Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC). By appending this motif to biomolecules (via chemical synthesis), researchers can install fluorophores, affinity tags, or other payloads under mild conditions.
The presence of an aryl fluoride and methyl substituent modulates lipophilicity and may influence membrane partitioning or non-specific binding in biological assays; this is a physicochemical consideration, not an inherent biological role.
In enzymology and chemical biology, terminal alkynes can serve as mechanism-based reporters when introduced into substrates/inhibitors; the alkyne can undergo selective ligation post-reaction to visualize or enrich targets (general strategy).
Cautions
Copper required for CuAAC can be cytotoxic in live-cell contexts; copper-free strain-promoted cycloadditions (SPAAC) are preferred in such cases, though they require strained cyclooctynes rather than simple terminal alkynes like this compound.
Any use in cells or organisms must consider DMSO/cosolvent levels and compound hydrophobicity to avoid confounding effects.
No clinical or therapeutic claims are made or implied.
Buffer Applications
This product is a hydrophobic organic building block and is not typically used to prepare aqueous buffers.
Not applicable: It does not serve as a buffering agent or pH stabilizer.
Practical note: When performing bioconjugation (e.g., CuAAC) in aqueous media, select a compatible buffer system (HEPES, phosphate, Tris) that does not coordinate excessively to copper catalysts and include organic co-solvent or surfactant to solubilize the aryl alkyne. Verify that the buffer and additives do not quench catalysts or react with azides.
Green Alternatives
Opportunities to improve sustainability relate primarily to solvent/base choices and catalytic systems rather than substitution of the aryl alkyne itself.
Greener solvent choices (literature/general)
Replace chlorinated solvents (DCM, chloroform) with ethyl acetate, 2-MeTHF, CPME, or dimethyl carbonate where feasible.
For Sonogashira couplings, employ 2-MeTHF or CPME instead of DMF/dioxane when substrate solubility permits.
For CuAAC, use water-rich media with benign co-solvents (t-BuOH/H2O, ethanol/H2O) and water-soluble ligands.
Heterogeneous Pd catalysts or supported nanoparticles can facilitate catalyst recovery.
Micellar catalysis (e.g., TPGS-750-M in water) enables couplings in aqueous media with reduced organic solvent use.
Use carbonate or amine bases with lower EHS profiles (e.g., K2CO3, triethylamine) in place of stronger, more hazardous bases when compatible.
Comparison snapshot (general)
Conventional: Pd/Cu in DMF or dioxane, elevated temperature; chlorinated solvent workups.
Greener alternative: Pd (Cu-free) in 2-MeTHF or aqueous micelles, ambient to moderate temperature, minimal chlorinated solvent usage.
Trade-offs
Greener media may reduce substrate solubility for hydrophobic alkynes; surfactants or co-solvents may be required.
Catalyst turnover numbers and reaction times can vary; small-scale scouting is recommended before scale-up.
Pharmaceutical Uses
Item-specific (Product Data)
No pharmacopeial grade, excipient designation, or formulation role is specified for this item. For research use only.
General (literature context; not specific to this item)
Aryl terminal alkynes are common intermediates in medicinal chemistry programs for structure–activity relationship (SAR) exploration. They enable late-stage diversification via Sonogashira coupling or CuAAC to rapidly access analog series.
The aryl fluoride and methyl substituents are classical medicinal chemistry motifs to tune metabolic stability and lipophilicity, but any such uses here would be as a synthetic building block rather than as an active ingredient or excipient.
If incorporated into an API candidate during discovery, downstream processing may require careful control of residual palladium/copper from coupling steps; scavengers and validated purifications are recommended.
No therapeutic or clinical claims are made. This product is not intended for human or animal administration.
For cGMP or regulatory applications, source or qualify material to appropriate standards and obtain full specifications, residual solvent/metal data, and impurity profiles from the CoA.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values (typical for this structure; provided for planning only)
Molecular formula (calculated): C9H7F
Molecular weight (calculated): ~134.15 g/mol
Acidic proton: terminal alkyne (acetylenic C–H) with pKa ~25 (literature, in DMSO)
Polarity/solubility profile: expected to be non-polar to moderately polarizable; immiscible with water; freely soluble in common organic solvents (e.g., dichloromethane, toluene, THF, ethyl acetate, acetonitrile) — literature/experience-based expectation for aryl alkynes.
Volatility: aromatic alkynes typically have moderate vapor pressures with boiling points in the approximate 170–210°C range depending on substitution; specific BP for this item is not established here (literature context only).
Not specified for this item; refer to CoA/Spec Sheet
Boiling point, melting point
Density, refractive index
UV/Vis cutoff or specific UV absorbance
Water content, residual solvent levels
Trace metal content
Practical notes (general)
The terminal alkyne can weakly hydrogen-bond; however, bulk behavior is dominated by the aromatic core and lipophilicity.
For chromatography, expect strong UV absorbance in the 200–280 nm region typical of substituted benzenes (qualitative). For analytical cutoff or gradient compatibility, verify with an analytical run.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grades (general guidance)
Research grade organic building blocks are typically suitable for synthesis and method development. If HPLC grade or low-UV grade is specified, that would imply stringent control of UV-active impurities for chromatographic applications. Absent such designation, expect standard research-grade quality appropriate for most synthetic uses; confirm by NMR/GC/HPLC as needed.
For cross-coupling and click chemistry, trace metal content and peroxide/oxygenated impurities can affect reactivity and color. If your application is catalyst-sensitive, request metal content and residual solvent data from the CoA.
Practical quality control tips (general)
Verify identity by 1H/13C NMR; look for terminal alkyne proton (ca. δ 3.0–3.5 ppm, literature) and sp carbons (ca. δ 80–90/90–95 ppm). The aromatic F often yields observable 19F resonance and 1H/13C–19F coupling.
Assess purity by GC or HPLC; aromatic alkynes typically give strong UV response at 210–254 nm.
For moisture/air-sensitive transformations (e.g., strong-base deprotonations), consider brief drying over activated molecular sieves or distillation if distillable; confirm that no stabilizer is present if it would interfere (consult CoA).
Reaction and Applications
This terminal aryl alkyne is a versatile synthon across cross-coupling, cycloaddition, and C–C bond-forming chemistries.
Cross-coupling and C–C bond formation
Sonogashira coupling (Pd, often Cu co-catalyst, base): couples with aryl/vinyl halides or triflates to give conjugated diaryl or aryl–vinyl alkynes. Copper-free methods mitigate Glaser homocoupling and are amenable to air- and moisture-tolerant systems.
Nucleophilic additions: deprotonation with strong bases (e.g., n-BuLi, LDA) furnishes the corresponding acetylide for addition to carbonyls (aldehydes, some ketones) to yield propargyl alcohols after quench.
Glaser–Hay oxidative homocoupling (Cu/O2) to form symmetrical diynes — typically a side reaction in Sonogashira; can be leveraged deliberately under controlled conditions.
Cycloadditions and “click” chemistry
CuAAC (Cu(I)-catalyzed azide–alkyne cycloaddition) affords 1,4-disubstituted triazoles under benign conditions (often water/organic mixtures). The aryl terminal alkyne acts as the alkyne partner; ensure copper source and ligand (e.g., TBTA, THPTA) suitability for hydrophobic substrates.
[2+2+2] Cyclotrimerizations (Co/Rh catalysts) with diynes/alkynes to build polysubstituted arenes and heteroarenes.
Electrophilic and radical transformations
Halogenation/iodination of the alkyne (NIS/NBS, I2 with oxidants) to generate haloalkynes for further functionalization.
Hydrofunctionalizations (hydroboration–oxidation to give carbonyl equivalents after rearrangement; hydrostannation; hydrosilylation) under radical or metal-catalyzed conditions.
Practical tips
Dry, oxygen-free conditions limit undesired Glaser coupling in Sonogashira.
The aryl fluoride and methyl influence electronic/steric properties, potentially modulating coupling rates and regioselectivity in downstream chemistry.
Monitor by TLC/GC; terminal alkyne C–H stretch appears near 3270–3330 cm−1 (IR, literature).
Reaction Conditions
General literature guidance for common transformations with aryl terminal alkynes (optimize for your specific substrates):
Sonogashira cross-coupling
Catalyst: Pd(PPh3)2Cl2 (1–3 mol%) or Pd2(dba)3 (0.5–2 mol%) with phosphine ligand; optional CuI (0–5 mol%) for classical protocols.
Base: Et3N, i-Pr2NH, K2CO3, or Cs2CO3.
Solvent: THF, toluene, dioxane, DMF, MeCN, or greener 2-MeTHF/CPME.
Temperature/time: RT to 80°C, 1–16 h. Copper-free conditions reduce homocoupling; use inert atmosphere.
Typical outcomes: internal alkynes in good to excellent yields across aryl/vinyl partners (literature).
Temperature: RT to 60°C; minutes to hours depending on substrates.
Formation of arylacetylides and nucleophilic additions
Base: n-BuLi or LDA (1.0–1.2 equiv) at −78 to 0°C in anhydrous THF or Et2O; subsequent addition to aldehydes yields propargyl alcohols after quench.
Precautions: strict exclusion of moisture/CO2; quench at low temperature.
Glaser–Hay homocoupling (if desired)
CuCl/CuI with diamine (e.g., TMEDA), O2, RT to 60°C in pyridine/Et3N or toluene; furnishes symmetrical diynes.
These conditions are representative literature starting points; adjust catalysts, ligands, temperature, and solvent based on substrate solubility and reactivity.
Safety and Handling
Item-specific (Product Data)
GHS classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
Storage conditions: Store at 2–8°C. Shipped on wet ice.
General safety guidance for aryl terminal alkynes (literature/practice; not a substitute for SDS)
Likely hazards: flammable liquid and vapor; may cause irritation to skin/eyes/respiratory tract; harmful if swallowed or inhaled. Handle in a fume hood.
PPE: safety glasses or splash goggles, lab coat, and nitrile gloves as a baseline. Upgrade to chemical-resistant gloves if prolonged contact is possible. Use flame-resistant lab coat where flammability is a concern.
Engineering controls: handle under local exhaust ventilation. Avoid aerosol formation.
Incompatibilities: strong oxidizers; strong bases (can deprotonate the terminal alkyne to form reactive acetylides); copper salts plus oxygen may promote Glaser-type oxidative homocoupling; avoid contact with halogenating agents.
Special risks: terminal alkynes can form metal acetylides with Cu/Ag; these salts may be shock-sensitive. Prevent unintended contact with copper or silver surfaces in the presence of base/air.
First aid (overview): in case of skin contact, wash with soap and water; eye contact, rinse cautiously for several minutes and seek medical attention; inhalation, move to fresh air; ingestion, rinse mouth and seek medical advice. Always consult the SDS for authoritative instructions.
Fire-fighting: use CO2, dry chemical, or alcohol-resistant foam. Cool containers with water spray.
Solvent Selection
This substance is an aryl terminal alkyne (hydrophobic, moderately polarizable). Solvent choice primarily depends on the intended transformation.
Miscibility and polarity (general/literature)
Water: expected to be insoluble or sparingly soluble.
Organic solvents: typically soluble in ethers (THF, MTBE), aromatics (toluene, xylene), halogenated solvents (DCM, chloroform), esters (EtOAc), and nitriles (MeCN).
Typical selections by application
Pd-catalyzed Sonogashira couplings: THF, toluene, DMF, DMAc, dioxane, MeCN; often with an amine or carbonate base. Copper-free protocols increasingly favor polar aprotic solvents or green ethers (2-MeTHF, CPME) under inert atmosphere.
CuAAC “click” reactions: mixed aqueous–organic media (t-BuOH/H2O, MeOH/H2O, DMSO/H2O) to solubilize azide partners; this alkyne’s hydrophobicity may necessitate surfactants or co-solvents.
Strong-base deprotonation (to form acetylides): anhydrous ethereal solvents (THF, Et2O) or hydrocarbons (toluene, hexane) at low temperature.
Purification: normal-phase silica gel with hexanes/EtOAc or hexanes/DCM gradients; aromatic cores elute in low-to-mid polarity ranges.
Comparison (general considerations)
THF: excellent for base-mediated steps; can coordinate metals; good for low-temperature work.
DCM: effective for workups and chromatography but less green; consider EtOAc or CPME when possible.
Always validate solubility and stability for your specific substrate pairings before scale-up.
Storage and Reconstitution
Item-specific (Product Data)
Storage: Store at 2–8°C.
Shipping: Shipped on wet ice.
General handling and storage guidance (for aryl terminal alkynes)
Keep container tightly closed in a cool, well-ventilated area away from ignition sources.
Protect from strong bases and oxidizers. Avoid prolonged contact with copper/silver surfaces in the presence of air/base to prevent formation of metal acetylides or oxidative coupling.
Inert atmosphere storage (nitrogen/argon) is good practice to limit oxidative side reactions during long-term storage, though not mandated by the item-specific data.
If solidification or crystallization is observed at low temperature (rare but possible depending on impurity profile), gently warm to ambient and swirl to re-homogenize before use.
Reconstitution
Not applicable: supplied as a neat organic reagent. If dilution is required, prepare solutions in dry, compatible organic solvents (e.g., THF, toluene, DCM, MeCN) immediately before use.
For moisture-sensitive operations, pre-dry solvents (molecular sieves, distillation) and use air-free techniques.
Shelf life and quality checks
Periodically verify integrity by NMR/GC if stored for extended periods, especially after multiple openings.
Refer to the CoA/Spec Sheet for any batch-specific stabilizers or storage nuances and for expiry/retest dates.
Structure and Identity
Brief overview: 4-Ethynyl-1-fluoro-2-methylbenzene is an aryl terminal alkyne bearing a para-ethynyl group relative to fluorine and an ortho-methyl group relative to fluorine. It combines a deactivating/ortho–para directing fluoro substituent with a weakly activating methyl and a terminal C≡CH functionality useful for coupling chemistry.
Item-specific (Product Data)
Product name: 4-Ethynyl-1-fluoro-2-methylbenzene
CAS: 351002-93-2
SKU: E331048
Category: 全部 / 可售 / 化学和生化试剂
InChIKey: 110185 (as provided)
Storage: Store at 2–8°C; shipped on wet ice
Research Use: For research use only
Literature/computed (general identity; not item-specific specs)
Typical molecular formula: C9H7F (literature calculation from substitution pattern)
Approximate molecular weight: ~134.15 g/mol (computed from C9H7F)
2D structural description: a benzene ring bearing F at C1, CH3 at C2, and –C≡CH at C4 (para to F). Functional groups: aryl fluoride, aryl methyl, terminal alkyne (acetylenic C–H, sp-hybridized carbon).
Functional features relevant to reactivity: terminal alkyne acidity (pKa ~25, literature), capacity for Pd-catalyzed Sonogashira cross-coupling, CuAAC “click” azide–alkyne cycloaddition, Glaser homocoupling under oxidative Cu conditions.
Not specified for this item; refer to CoA/Spec Sheet
SMILES
Full IUPAC name
Exact elemental analysis or isotopic pattern
Notes: Where exact identifiers (e.g., canonical SMILES, exact InChI) are required for regulatory or informatics use, consult the CoA/Spec Sheet or confirm via independent spectral/registry data for this batch.
Synthetic Utility
Key functional groups and strategic value:
Terminal alkyne (–C≡CH)
Readily engages in Pd-catalyzed Sonogashira coupling with aryl/vinyl halides/triflates to access internal alkynes (diaryl or aryl–vinyl). This enables modular assembly of conjugated systems and late-stage diversification.
Deprotonation with strong bases (e.g., n-BuLi) forms the arylacetylide nucleophile for additions to aldehydes (propargyl alcohol synthesis) or for transmetalation (Cu, Zn) prior to coupling.
Participates in CuAAC with organic azides to give 1,4-triazoles (robust linking motif in discovery chemistry and materials science).
Aryl fluoride and methyl substituents
Influence electronics: F is weakly deactivating through –I with potential o/p directing resonance; Me is weakly activating and o/p directing. These can affect regioselectivity and rates in electrophilic aromatic substitution on downstream products.
Modulate physicochemical properties, often increasing lipophilicity and altering binding in fragment conjugates.
Retrosynthetic roles
Serves as a lynchpin for convergent routes where the aryl alkyne is coupled late to introduce diverse aryl/vinyl partners.
Acts as a precursor to heterocycles via cycloaddition chemistry ([2+2+2] or radical annulations), enabling access to densely substituted frameworks.
Practical considerations
Avoid prolonged exposure to air/Cu salts during storage and reactions to minimize undesired Glaser coupling.
Employ dry, oxygen-free conditions for base-sensitive steps; quench carefully to prevent exotherms with residual strong base.
Target Specificity
Not applicable. This product is a small-molecule organic building block, not a biological macromolecule, antibody, or affinity reagent. No antigen, epitope, clone, isotype, or species reactivity information applies.
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