≥95% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Room temperature Spedizione . Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
Specifiche
Specifiche e purezza
≥95%
Condizioni di conservazione di stoccaggio
Room temperature
Purezza
≥95%
Nomi e identificatori
Sorrisi canonici
C#CC1=CN(N=C1)CCF
IUPAC Name
4-ethynyl-1-(2-fluoroethyl)pyrazole
InChIKey
AOTXLHSCPJIQHD-UHFFFAOYSA-N
INCHI
1S/C7H7FN2/c1-2-7-5-9-10(6-7)4-3-8/h1,5-6H,3-4H2
Peso molecolare
138.140
Documentazione
📋 Scheda di dati di sicurezza (SDS)
Documento completo su pericoli, manipolazione, stoccaggio e conformità normativa.
Combine aryl bromide (1.0 equiv), this alkyne (1.2 equiv), Pd(PPh3)2Cl2 (2 mol%), CuI (5 mol%), and Et3N (3–4 equiv) in dry THF (0.1–0.2 M) under N2.
Stir at 50 °C for 4–8 h; monitor by TLC/LC–MS.
Cool, filter through silica/celite, concentrate, and purify by chromatography.
These are illustrative only. Validate on small scale and consult primary literature.
Item-specific recommended protocols/dilutions: Not specified for this item; refer to CoA/Spec Sheet.
Biological Roles
Item-specific biological/clinical data: Not specified for this item; for research use only.
General context (literature) for the scaffold:
Pyrazoles are prevalent heteroaromatic motifs in biochemical probe and medicinal chemistry due to their hydrogen-bond accepting character and planarity, enabling interactions with enzyme active sites and receptors. N-alkylation modulates basicity and lipophilicity, often improving membrane permeability.
The terminal alkyne serves as a bio-orthogonal handle. Through CuAAC, it can be ligated to azide-labeled biomolecules (proteins, glycans, lipids, nucleic acids) to generate triazole-linked conjugates for imaging, pull-downs, and target engagement studies.
Organofluorine (2-fluoroethyl) subtly affects physicochemical properties (e.g., metabolic stability, lipophilicity) relative to ethyl analogs. In probe design, such substitution can influence binding kinetics and resistance to oxidative metabolism (general literature observation).
Practical implications for researchers:
The compound can be incorporated into small-molecule probes where the alkyne enables late-stage tagging or immobilization while the pyrazole imparts heteroaromatic interactions.
For cellular work, ensure residual metal (e.g., Cu from click reactions) is rigorously removed; triazole products are typically robust in biological buffers. Cytotoxicity and off-target effects of this specific compound or its conjugates are not established here and should be determined empirically.
No therapeutic or diagnostic claims are made for this material; it is intended strictly for laboratory research use.
Buffer Applications
This product is a neutral organic building block and is not typically used as a buffering agent.
pH buffering systems: Not applicable. It lacks ionizable groups appropriate for establishing a defined pH range in aqueous media (the N–H is substituted and ring basicity is weak in water).
Use in buffers: If employing in biochemical assays, dissolve first in a compatible co-solvent (e.g., DMSO) and dilute into the aqueous buffer; confirm solubility and absence of precipitation. Typical co-solvent levels for biological assays are ≤1–2% v/v DMSO to minimize perturbation of proteins/cells.
For “click” workflows in aqueous buffers, prepare reactions in tBuOH/H2O or DMSO/H2O with Cu(I) catalysis and appropriate ligands; then remove copper by chelation (EDTA) and buffer exchange as needed.
Item-specific buffer-related specifications: Not specified for this item; refer to CoA/Spec Sheet.
Green Alternatives
Context: The product is a building block, not a bulk solvent. Greener chemistry considerations focus on solvent and reagent choices used with it.
Greener solvent choices (relative to common legacy options; literature guidance):
Replace DCM/CHCl3 with EtOAc, 2-MeTHF, CPME, or toluene when solubility and selectivity permit.
Use water or water/co-solvent systems (e.g., tBuOH/H2O, PEG/H2O) for CuAAC to reduce VOC load.
Prefer acetonitrile or EtOAc over DMF/DMSO when possible for easier workup and lower EHS footprint, acknowledging tradeoffs in solubility and reaction rate.
Comparison snapshot (general):
DCM: Excellent solvating power; high EHS concern; difficult waste stream.
2-MeTHF: Renewable, water-tolerant, good for organometallics; peroxide formation risk over time—monitor and manage.
CPME: Broad utility, low peroxide formation compared to ethers like THF; hydrophobic—may limit CuAAC in aqueous media.
Water/co-solvent: Greenest option for click chemistry; substrate solubility can limit scope.
Reagent choices:
CuAAC: Employ catalytic Cu(I) generated in situ from CuSO4 with sodium ascorbate; minimize copper loading and implement ligand systems (e.g., TBTA) to increase efficiency and reduce waste.
Oxidative couplings: Consider O2/air as the terminal oxidant (with appropriate catalyst control) in place of stoichiometric oxidants.
Workup/waste:
Use aqueous complexation (EDTA/chelation) to strip copper after click reactions.
Aim for telescoped sequences to minimize solvent swaps and chromatographic purifications.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet.
General R&D context (non-clinical, literature):
Role: Heteroaromatic intermediate for discovery chemistry. The terminal alkyne supports modular assembly of libraries via CuAAC, Sonogashira couplings, or hydrofunctionalizations to access diverse, drug-like derivatives.
Formulation relevance: As a small organic intermediate, it is not used as an excipient. If used in screening or tool-compound synthesis, solutions are commonly prepared in DMSO or other organic vehicles before dilution for in vitro assays.
Regulatory considerations: No known monograph in USP/Ph.Eur. for this specific structure. Any use beyond research would require comprehensive quality, safety, and regulatory evaluation.
Manufacturing/process notes (general):
For scale-up, attention to residual copper/palladium from coupling steps is important; plan for metal scavenging and analytical release testing (ICP-MS) if producing advanced intermediates.
Control of potential genotoxic impurities (PGIs), such as haloalkynes or azides used in convergent steps, should be considered under ICH M7 when relevant. These considerations are general; none are specified for this product itself.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values and expectations for 4-ethynyl-1-(2-fluoroethyl)-1H-pyrazole (for general guidance only):
Molecular weight: ~139.15 g/mol (calculated from C7H8FN2)
Exact mass (monoisotopic, literature calc.): ~139.065
Physical state/appearance: not reliably documented in public sources for this exact derivative; small heteroaromatics of this size may be low-melting solids or liquids near ambient temperature (literature expectation only).
Solubility (qualitative, literature expectation):
Miscible/soluble in common organic solvents (e.g., DCM, THF, EtOAc, acetonitrile, toluene, DMF, DMSO) due to moderate polarity and heteroaromatic ring.
Low aqueous solubility expected because of limited hydrogen-bond donor capacity and hydrophobic ring/alkyne.
LogP/logD: Not located for this exact compound; likely low-to-moderate lipophilicity relative to non-fluorinated alkyl pyrazoles (literature expectation).
pKa: The ring N–H is substituted (N1-alkylated), so no acidic N–H; basicity arises from ring nitrogens. No reliable numeric pKa identified for this exact N-substituted species (literature: pyrazoles typically pKaH ~1–3 for conjugate acids, but N-alkylation modifies this).
Boiling point / melting point / density / refractive index: Not found in reliable literature for this specific compound.
Note: Use the product’s CoA/SDS for authoritative, item-specific physical data.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for small-molecule research chemicals like 4-ethynyl-1-(2-fluoroethyl)-1H-pyrazole:
Research grade: Typically suitable for synthetic chemistry, method development, and SAR work. If using in sensitive transformations (e.g., metal-catalyzed coupling, photochemistry), review trace-metal and residual solvent content on the CoA.
HPLC/GC suitability: For analytical applications, choose lots with documented low non-volatile residue and low UV background if applicable. Absent item-specific UV cutoff, treat as “Not specified for this item; refer to CoA/Spec Sheet.”
Stabilizers/inhibitors: None specified for this item. Terminal alkynes generally do not require polymerization inhibitors, but verify on CoA if any stabilizer is present.
Identity confirmation: CoA should provide 1H NMR and/or LC–MS. For alkynes, IR typically shows a sharp C≡C–H stretch near ~3300 cm−1 and C≡C stretch ~2100–2200 cm−1 (literature indicators).
Acceptance testing: Typical release tests may include appearance, purity by HPLC/GC, identity by MS/NMR, and water content by Karl Fischer. Specific numerical limits: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This compound combines a 1-substituted pyrazole with a terminal alkyne, making it a versatile bifunctional building block.
Copper-catalyzed azide–alkyne cycloaddition (CuAAC): Forms 1,4-disubstituted 1,2,3-triazoles anchored to the pyrazole core. Typical conditions: CuSO4·5H2O (1–10 mol%), sodium ascorbate (reducing agent), tBuOH/H2O or DMSO/H2O, rt–50 °C.
Ruthenium-catalyzed azide–alkyne cycloaddition (RuAAC): Access to 1,5-disubstituted triazoles; useful when regiocontrol is required.
Glaser–Hay homocoupling: Dimerization to a diacetylene under Cu-catalysis and O2; controlled conditions can build conjugated linkers.
Sonogashira-type C(sp)–C(sp2) coupling: As a terminal alkyne partner with aryl/vinyl halides (Pd/Cu co-catalysis), expanding aromatic frameworks bearing the pyrazole motif.
Hydrofunctionalizations of the alkyne: Hydrosilylation, hydroboration (leading to vinyl boronates), hydroamination, and carbometalation, enabling downstream diversification.
Electrophilic additions/halogenations: Iodination or bromination across the triple bond to form dihaloalkenes for subsequent cross-coupling.
Pyrazole-directed chemistry:
While N1 is substituted, the pyrazole ring can participate in electrophilic aromatic substitution at C-4/C-5 in other systems; here, the 4-position is occupied. Metalation at C-3/C-5 (with strong bases) may be possible but requires careful control due to the terminal alkyne’s acidity and potential for side reactions.
Practical notes:
Protect the terminal alkyne (e.g., TMS) if conditions risk Glaser coupling or overreaction; deprotect later with mild base.
Monitor for N-dealkylation under harsh conditions; organofluorine is typically robust but avoid strong nucleophiles at elevated temperatures that could induce substitution on the fluoroethyl chain.
Reaction Conditions
General literature conditions involving terminal alkynes on heteroaryl systems (illustrative, not item-specific specifications):
CuAAC (azide–alkyne “click”):
Catalyst: CuSO4·5H2O (1–10 mol%) + sodium ascorbate (2–20 mol%) to generate Cu(I) in situ.
Solvent: tBuOH/H2O (1:1), DMSO/H2O, or DMF/H2O; substrate concentration 0.05–0.5 M.
Temperature/time: rt to 60 °C; 0.5–16 h depending on substrate solubility.
Notes: Add TBTA or THPTA ligands to accelerate and suppress alkyne oxidation; rigorously remove copper post-reaction.
Sonogashira coupling (with aryl/vinyl halides):
Catalyst: Pd(PPh3)2Cl2 (1–3 mol%) + CuI (2–10 mol%); base: Et3N, DIPEA, or K2CO3.
Solvent: THF, toluene, DMF, or 2-MeTHF.
Temperature/time: 25–80 °C; 2–18 h.
Notes: For copper-free variants, use Pd with bulky ligands (e.g., XPhos) and amine bases to avoid Glaser coupling.
Glaser–Hay homocoupling:
Catalyst: CuCl/CuI (5–10 mol%) + TMEDA under O2 (balloon or air).
Solvent: pyridine, DCM, or DMF; 0–25 °C; monitor to avoid overoxidation.
Hydroboration of alkyne:
Reagent: 9-BBN or HBPin with catalysts (e.g., [Ir(cod)Cl]2 + dtbpy) to give vinyl boronates.
Solvent: THF or toluene; 25–60 °C; 1–6 h.
Electrophilic halogenation:
I2/Br2 with catalytic AgNO3 or NIS/NBS variants in acetonitrile or DCM at 0–25 °C.
Yields: Highly substrate- and condition-dependent; for well-matched CuAAC or Sonogashira couplings, isolated yields of 70–95% are common in literature for analogous systems.
Safety and Handling
Item-specific hazard data from Product Data/SDS: Not specified for this item; refer to SDS for definitive classification.
General GHS guidance for small heteroaromatic alkynes (informational, not item-specific):
Potential hazards: May cause skin/eye irritation or respiratory irritation; terminal alkynes and azoles can have moderate acute toxicity and CNS effects at high exposure (literature generalities). Avoid inhalation of vapors/aerosols and contact with skin/eyes.
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; consult the SDS.
Safe handling practices:
Engineering controls: Handle in a fume hood to minimize inhalation; ensure adequate ventilation.
PPE: Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use splash protection for scale-up.
Hygiene: Avoid breathing dust/vapor. Wash thoroughly after handling. Do not eat/drink/smoke in work area.
Incompatibilities (general): Strong oxidizers; strong bases/acids may promote degradation or side reactions (e.g., alkyne polymerization under strongly basic conditions with metals). Avoid azide sources during storage unless intentional CuAAC is performed under controlled conditions.
Special risks: Terminal alkynes can be sensitive to strong bases and copper salts (Glaser coupling under oxygen). Minimize copper contamination and oxygen exposure if preserving the terminal alkyne is critical.
First-aid overview (general):
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 persistent irritation.
Ingestion: Rinse mouth; seek medical advice.
Always defer to the official SDS for authoritative safety and regulatory information.
Solvent Selection
Applicability: This product is a heteroaromatic small-molecule building block, not a solvent. The following guidance concerns choosing solvents to dissolve and react it.
General solvent behavior (literature expectations):
Polarity: Moderately polar because of the pyrazole ring and fluorinated ethyl chain, yet overall hydrophobic; expect good solubility in aprotic organic solvents.
Likely good solvents: DCM, chloroform, THF, 2-MeTHF, EtOAc, acetonitrile, toluene, DMF/DMAc, DMSO. Solubility in alcohols (MeOH, EtOH) is often moderate.
Aqueous solubility: Expected to be low; consider co-solvent strategies for biphasic reactions or click chemistry in tBuOH/H2O mixtures.
When to choose which solvent:
CuAAC (“click” to azides): tBuOH/H2O (1:1) or DMSO/H2O with CuSO4/sodium ascorbate; for water-insoluble azides, DMF or DMSO as primary solvent.
Glaser homocoupling: Polar aprotic solvents (DMF, DMSO) or alcohols under Cu-catalysis with O2; control to avoid overoxidation.
Hydroboration/hydrosilylation of the alkyne: Anhydrous THF or toluene under inert atmosphere with appropriate catalysts.
Electrophilic additions (e.g., halogenation, iodination across alkyne): DCM or acetonitrile; low temperatures to control regioselectivity.
Practical tips:
Dry your solvent for moisture-sensitive steps (e.g., organometallic additions to the alkyne).
Avoid copper contamination if preserving the terminal alkyne; store solutions in glassware free of copper/bronze components.
For scale-up, consider greener options such as 2-MeTHF or EtOAc where compatible (see Green Alternatives).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance for terminal alkynes and heteroaromatics (informational):
Store tightly closed in a dry place, away from strong oxidizers and bases. Although many terminal alkynes are stable, limiting exposure to air/copper minimizes risk of unintended Glaser-type coupling in solution.
If long-term storage of solutions is needed, use dry, oxygen-free solvents in amber vials under inert gas (N2/Ar) at cool room temperature.
Avoid prolonged exposure to light and moisture to preserve purity.
Reconstitution/solubility:
Not applicable as a biologic. To prepare stock solutions for reactions or assays, dissolve in a suitable organic solvent (e.g., DMSO, DMF, THF, acetonitrile, or DCM) to a convenient concentration (e.g., 10–100 mM). Filter if necessary.
Shelf-life and assay:
Specific retest/expiry date and assay range: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the SDS for handling and the CoA for lot-specific quality data before use.
A five-membered pyrazole ring bearing two adjacent nitrogens (N1–N2). At ring position 1, the N–H is replaced by a 2-fluoroethyl substituent. At ring carbon C4, a –C≡CH group projects outward. The remaining ring positions are unsubstituted carbons.
Synthetic Utility
Key functional elements and their reactivity (literature):
Terminal alkyne (C≡CH):
Nucleophilicity upon deprotonation (pKa of terminal alkynes typically ~24–26 in DMSO, literature) allows formation of acetylides for C–C bond formation (e.g., with aldehydes/ketones to give propargyl alcohols; with alkyl halides under SN2 conditions when compatible).
Cycloaddition with azides (CuAAC/RuAAC) to rapidly build triazole-linked architectures from the pyrazole core.
Platform for hydroboration/hydrosilylation to generate vinyl boronates/silanes for further cross-coupling.
N-Substituted pyrazole ring:
Contributes heteroatom coordination ability; can modestly ligate metals or direct metalation at adjacent carbons under strong bases (with caution to avoid alkyne side reactions).
Electronics of the ring can modulate reactivity of the alkyne toward electrophiles via conjugation.
2-Fluoroethyl substituent:
Generally inert under many coupling conditions; provides a handle for later substitution (e.g., via SN2 on the primary carbon adjacent to fluorine under activated conditions) or oxidative elaboration (literature-dependent).
Retrosynthetic value:
Serves as a convergent node: pyrazole core pre-installed, with an outward-facing alkyne for late-stage diversification. Ideal for parallel synthesis where the azide partner defines the diversity element.
Practical considerations:
Protect the terminal alkyne (e.g., TMS) when engaging in strong-base chemistry elsewhere on the molecule.
Avoid copper and oxygen exposure if suppressing Glaser coupling is necessary; include antioxidant/inert atmosphere where appropriate.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biologic or affinity reagent.
Antigen/epitope, species reactivity, clone, and isotype: Not applicable.
Any binding specificity data would pertain to derivatives or conjugates prepared from this compound and are not provided here.
Item-specific target data: Not specified for this item; refer to CoA/Spec Sheet if any selectivity data are supplied for derivative applications.
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