≥98%(GC) for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Room temperature,Argon charged Ships Normal 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 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Übersicht
3-Thiophenecarbonitrile can be used to synthesize the following:
2,4-dinaphthyl-3-cyanothiophene via reaction with iodonaphthalene
2,5-bis-tri(n-butyl)tin-3-cyanothiophene, a building block for the synthesis of new alternating (3-alkyl/3-cyano)thiophene copolymers
This compound belongs to the class of organic compounds known as heteroaromatic compounds. These are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
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
Not applicable as a ready-to-use biological reagent. No validated protocols for WB, IHC, IF, FC, or related assays are provided for this item.
General laboratory handling suggestions (chemistry focus):
For reaction setup: Use oven-dried glassware, inert atmosphere (argon/nitrogen), and anhydrous solvents, particularly for organometallic or moisture-sensitive steps.
For stock solutions (analytical assays): Prepare in dry DMSO or acetonitrile at known concentration (e.g., 10–100 mM), filter (PTFE) if required, and store aliquots under inert gas to minimize hydrolysis/oxidation.
Item-specific protocol details are Not specified for this item; refer to CoA/Spec Sheet and SDS.
Biological Roles
This product is a small synthetic heteroaromatic building block without intrinsic biological function in cells or organisms when used as a laboratory reagent.
Not a buffer, enzyme cofactor, or metabolite.
Any biological interactions reported in literature (e.g., binding to macromolecules) are context-specific to designed derivatives or formulations and do not constitute a use-case for this reagent.
Research-use note (from Product Data): For research use only.
For bio-oriented experiments where this scaffold is incorporated into probes or materials:
Consider DMSO stock solutions for assay preparation; confirm solubility and assay compatibility.
Ensure that residual solvent and reagent carryover are controlled to prevent assay interference.
No organism-specific pathway or signaling role is attributed to 3-cyanothiophene as supplied.
Buffer Applications
Not typically applicable. 3-Cyanothiophene is not a buffering agent and does not participate in defined acid/base equilibria suitable for preparing laboratory buffers.
Practical note: If handling this reagent in biochemical assays, prepare buffer systems independently (e.g., phosphate, HEPES) and dissolve 3-cyanothiophene in a compatible organic co-solvent (DMSO, DMF) before spiking into the buffered medium, keeping final organic content within assay tolerance.
Green Alternatives
While 3-cyanothiophene itself is the target reagent, greener choices can be made around solvent and reagent selection during its transformations. Below is practical guidance (literature-based):
Prefer greener solvents where compatible:
Replace THF with 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) for metalations and reductions; both have higher boiling points, better stability, and can be sourced from renewable feedstocks (2-MeTHF).
Use toluene or ethyl acetate instead of chlorinated solvents when extraction/processing allows.
For cross-coupling, 2-MeTHF or aqueous micellar media (e.g., designer surfactants) can reduce solvent impact compared with dioxane/DMF.
Reagent selection and conditions:
For nitrile hydrolysis, consider catalytic acidic resins or enzymatic approaches (where feasible) to reduce strong mineral acid/base usage.
Apply catalytic hydrogenation (H2, Pd/C) instead of stoichiometric metal hydrides when over-reduction is acceptable and selectivity can be managed.
Energy and workup efficiency:
Exploit higher-boiling green ethers (2-MeTHF/CPME) to conduct reactions at moderate reflux and facilitate phase separations (reduced water use).
Comparison snapshot (general):
THF vs 2-MeTHF: similar polarity; 2-MeTHF greener, less peroxide-prone than ethers like THF/dioxane; may alter lithiation kinetics/selectivity—re-optimize base equivalents and temperature.
DCM vs EtOAc/toluene: DCM offers fast extraction but higher environmental/health concerns; EtOAc/toluene are preferable when partitioning allows.
Note: Validate reaction performance under greener conditions; yields and selectivities may vary and require optimization.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item. It is not offered as a GMP-grade substance.
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical):
3-Cyanothiophene can serve as a synthetic intermediate for discovery chemistry, enabling access to amides, acids, aldehydes, and amines on a thiophene scaffold. Such intermediates may be used in medicinal chemistry campaigns for structure–activity relationship (SAR) studies.
In process development settings, selection of solvent and workup methods should consider ICH Q3C residual solvent guidance if downstream use is intended, even though this catalog item is for research use only.
No therapeutic or clinical claims are made or implied for this product.
Physical Properties
Only item-specific specifications appearing on the Product Data are authoritative. Values below are provided as general literature information for context and method development; they are not specifications for this specific lot.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Phase at ambient conditions (literature): low-volatility liquid or low-melting solid; typically handled as a liquid in labs.
Boiling point (literature): typically reported in the ~210–225 °C range at 1 atm for 3-cyanothiophene; consult primary data for exact value prior to distillation work.
Melting point (literature): often reported near or below room temperature (sub-ambient); verify before low-temperature handling.
Density (literature): commonly near 1.15–1.20 g/mL at 20–25 °C for comparable thiophene nitriles; confirm experimentally.
Refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general, literature):
Water: very low (aromatic nitrile, non-ionizable under neutral conditions).
Organic: miscible or highly soluble in polar aprotic solvents (DMF, DMSO, NMP, acetonitrile), chlorinated solvents (DCM, CHCl3), ethers (THF, 2-MeTHF), and aromatics (toluene).
Partitioning (general): aromatic nitriles often exhibit moderate hydrophobicity; exact logP for this isomer is not provided here.
Note: Treat these values as starting points; always confirm with the item’s CoA/SDS and your own measurements where process-critical.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on common grades (general information):
General reagent grade: Suitable for routine synthesis and method development when trace impurities are not critical.
High-purity/synthetic grade: Tighter control of organic/metal impurities; recommended for organometallic steps (e.g., directed lithiation) and materials synthesis (optoelectronic applications) where trace impurities can poison catalysts or impact device performance.
Chromatography/HPLC grade solvents (not applicable here as this is a building block) are specified for low UV background; if using 3-cyanothiophene as a GC reference or standard, consult analytical-grade offerings.
Stabilizers/inhibitors:
None specified for this item. Many nitrile aromatics are supplied neat without stabilizers. If your application is moisture- or acid-sensitive (e.g., metalation), consider brief drying (e.g., molecular sieves) and use of inert atmosphere handling.
Quality control recommendations (practical):
Verify identity and purity by 1H/13C NMR and GC/MS prior to scale-up. The nitrile carbon often appears near 115–120 ppm (13C, literature), and the thiophene protons display characteristic downfield aromatic signals.
For polymer/materials applications, consider additional specs (water by Karl Fischer, metal content by ICP-MS, and UV–Vis background). These are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Use-cases reflect the dual reactivity of a thiophene ring and a nitrile handle. Below are representative applications (literature) and practical notes.
Building block for conjugated materials: 3-Cyanothiophene is a precursor to push–pull thiophene motifs used in organic electronics (OPV, OFET, OLED). The nitrile tunes electron affinity and lowers LUMO; subsequent functionalization at 2/5-positions enables polymerization.
Directed metalation/functionalization:
Cyano group facilitates regioselective lithiation at the 2- or 5-positions using n-BuLi or LDA at −78 to −20 °C in THF, followed by electrophiles (carbonyls, halides, borylation reagents). TMEDA can improve selectivity/yield.
Full reduction (LiAlH4, catalytic hydrogenation) to corresponding primary amines.
Hydrolysis to amide (mild) or carboxylic acid (stronger acid/base, heat) enabling access to 3-thiophenecarboxamide/acid.
Nucleophilic additions (Grignard/organolithium) to the nitrile to give imines/ketimines, hydrolyzed to ketones upon workup.
Halogenation/cross-coupling:
Electrophilic bromination/chlorination at activated positions (often 2-position) followed by Suzuki–Miyaura, Stille, Negishi, or Kumada couplings to construct aryl–aryl linkages.
Cycloaddition/annulation:
Conversion of nitrile to amidoxime/imidate can open routes to heterocycle annulations.
Practical tips:
Maintain anhydrous/inert conditions for organometallic steps (consistent with argon-charged storage).
Monitor nitrile reductions carefully to avoid over-reduction when aldehyde stage is desired.
For scale-up, validate heat removal during exothermic metalations and quench steps.
Reaction Conditions
Representative literature conditions for common transformations of 3-cyanothiophene (guidance only; optimize for your system):
Directed lithiation/electrophile trapping:
Base: n-BuLi (1.1–1.5 equiv) or LDA (1.2–1.5 equiv)
Solvent: anhydrous THF or 2-MeTHF; −78 to −40 °C, 0.5–2 h
Electrophiles: DMF (formylation), B(OMe)3 or iPrOB(pin) systems (borylation), RX (alkylation), CO2 (carboxylation)
Typical isolated yields: 50–85% depending on electrophile and quench.
Nitrile partial reduction to aldehyde (DIBAL-H):
Reagent: DIBAL-H (1.2–1.5 equiv per nitrile)
Solvent: toluene or DCM; −78 to −20 °C, 0.5–2 h
Quench: MeOH, then aqueous Rochelle’s salt; keep cold to avoid over-reduction
Outcome: 3-formylthiophene derivatives; moderate to high yields with careful control.
Full reduction to amine:
LiAlH4 in THF/ether, 0–25 °C, 2–6 h; or H2 (1–5 bar), Pd/C in EtOH/THF at 25–60 °C
Workup: cautious quench of hydrides; filtration from catalyst; yields often 60–90%.
Hydrolysis to amide/acid:
Amide: aqueous EtOH with H2SO4 or base (Na2CO3/NaOH) at reflux (2–8 h)
Acid: stronger acid/base, extended reflux; isolate via acid–base extraction.
Halogenation/cross-coupling (after bromination):
Bromination: NBS in DMF or AcOH at 0–25 °C
Suzuki–Miyaura: Pd(PPh3)4 (1–3 mol%), K3PO4, 1,4-dioxane/H2O or 2-MeTHF/H2O, 60–100 °C, 2–12 h
Stille/Negishi: standard Pd catalysts, toluene/DMF, 60–110 °C.
Note: All parameters are literature-style generalizations; confirm with small-scale trials and adjust for your substrate and equipment.
Safety and Handling
Safety data specific to this catalog item are not provided here. Always consult the SDS for authoritative guidance.
GHS status (item-specific): Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General safety profile for thiophene nitriles (literature/experience-based):
Hazards: Combustible organic liquid/solid; may cause skin and eye irritation; harmful if swallowed or inhaled. Nitriles can release toxic gases upon thermal decomposition (e.g., HCN, NOx, SOx under fire conditions).
PPE: Wear lab coat, safety glasses or splash goggles, and nitrile gloves; use in a fume hood to minimize inhalation exposure.
Incompatibilities: Strong oxidizers; very strong bases/acids under forcing conditions (can drive hydrolysis or side reactions). Avoid contact with reducing alkali metals unless intentionally performing directed metalation.
Special risks: Although not an ether, aromatic nitriles can slowly hydrolyze under strongly acidic/basic conditions; keep containers dry and tightly closed. High-boiling organics can accumulate static—ground equipment when transferring larger volumes.
First aid (overview; defer to 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 advice for persistent irritation.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: Use dry chemical, CO2, alcohol-resistant foam. Combustion may generate irritating/toxic fumes (SOx, NOx, HCN).
Storage note (from Product Data): Store at room temperature under argon; keep container tightly closed. Shipped under normal conditions.
Solvent Selection
This product is a heteroaromatic building block, not used as a bulk solvent. Solvent selection here refers to choosing media for reactions and workups involving 3-cyanothiophene.
Polarity/miscibility (general): 3-Cyanothiophene is nonpolar-to-moderately polar and typically dissolves well in common organic solvents: ethers (THF, 2-MeTHF, CPME), aromatics (toluene), chlorinated (DCM, chloroform), and polar aprotics (DMF, DMSO, NMP, MeCN). Water solubility is very low.
Choosing a solvent by transformation type (literature guidance):
Directed metalation (n-BuLi, LDA): anhydrous THF, 2-MeTHF, or CPME at −78 to −20 °C; add TMEDA if needed to enhance regioselectivity.
Nitrile reductions (DIBAL-H to aldehyde; LiAlH4/Catalytic hydrogenation to amine): toluene/hexanes or DCM for DIBAL at −78 to 0 °C; ether/THF for LiAlH4 at 0–25 °C.
Hydrolysis to amide/acid: aqueous-organic biphasic (MeCN/H2O) or polar protic (EtOH/H2O) under acid/base catalysis.
Cross-coupling (after halogenation or borylation): toluene, 1,4-dioxane, CPME, or DMF with appropriate base (K3PO4, Cs2CO3) under Pd catalysis.
Workup/extraction: Partitioning favors organic phase; DCM or EtOAc extractions are typically efficient, followed by brine washes to remove polar residues.
Drying: If used in moisture-sensitive steps, pre-dry solvent and reagent (3 Å molecular sieves or distillation) and maintain argon atmosphere (aligns with item’s argon-charged storage).
Storage and Reconstitution
Storage conditions (from Product Data): Room temperature; argon charged. Keep container tightly closed and under inert gas to minimize oxidation/moisture exposure. Shipped under normal conditions.
Stability: Nitrile aromatics are generally stable under dry, inert conditions. Avoid prolonged exposure to air and moisture, and protect from strong light/UV if long-term storage is anticipated.
Reconstitution/handling (general):
Use anhydrous, oxygen-free solvents for air/moisture-sensitive transformations (e.g., directed metalation). Suitable solvents include THF, 2-MeTHF, CPME, toluene, DCM, DMF, or acetonitrile depending on the application.
If solids precipitate at low temperature, warm gently to ambient and swirl under inert gas to re-liquefy (if applicable). Appearance is Not specified for this item; refer to CoA/Spec Sheet.
For analytical stocks, prepare in dry acetonitrile or DMSO, sparge or blanket with argon, and store in sealed vials. Prepare small aliquots to avoid repeated headspace exposure.
Shelf-life/retention samples: Not specified for this item; refer to CoA/Spec Sheet. For GMP-adjacent research workflows, retain a reference sample under identical storage for comparison by NMR/GC-MS over time.
Disposal: Collect organic waste according to institutional and local regulations. Do not discharge to drains.
Structure and Identity
Brief overview: 3-Cyanothiophene is a heteroaromatic nitrile comprising a thiophene ring bearing a cyano group at the 3-position; it serves as a compact, electron-withdrawing, π-rich building block.
Item-specific identifiers (from Product Data)
SKU: C153346
Product Name: 3-Cyanothiophene
CAS: 1641-09-4
CID: 74231
InChIKey: 110691 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Core structural features (general description)
Ring system: five-membered aromatic thiophene (C4S) with alternating C=C bonds and one sulfur heteroatom.
Functional group: a terminal nitrile (–C≡N) at the 3-position of the ring (meta to sulfur by ring numbering), providing a strongly electron-withdrawing substituent capable of diverse downstream transformations (hydrolysis, reduction, metalation-directed functionalization).
2D structure in words: A planar, aromatic thiophene ring with sulfur at position 1; the cyano substituent is attached at position 3. Remaining ring positions are unsubstituted.
Composition (literature/computed)
Molecular formula (literature): C5H3NS
Molecular weight (literature): ~109.14 g/mol
Stereochemistry: none (achiral, no stereocenters).
Resonance/electronic notes (general): The cyano group withdraws electron density inductively and via resonance, deactivating the ring toward electrophilic substitution and favoring directed lithiation at the 2- or 5-positions under strong base.
Synthetic Utility
Key reactivity derives from the conjugated nitrile and the heteroaromatic thiophene.
Nitrile handle:
Hydrolysis: Amide (mild, e.g., H2O/ROH with acid/base catalysis), carboxylic acid (stronger conditions), expanding into coupling chemistry (amide bond formation, esterification).
Reduction: DIBAL-H to aldehyde (low T), LiAlH4 or catalytic hydrogenation to primary amine; borane complexes can also effect reduction with different chemoselectivity profiles.
Nucleophilic addition: RMgX/RLi afford imines/ketimines leading to ketones after hydrolytic workup.
Thiophene ring:
Directed metalation: n-BuLi/LDA at −78 to −20 °C (THF/2-MeTHF) guided by the cyano substituent; quench with electrophiles (carbonyls, CO2, halogens, B(OR)3) to introduce 2- or 5-substituents.
Oxidation: Controlled oxidation to thiophene S-oxides can activate for further rearrangements/functionalizations (specialized conditions).
Retrosynthetic value:
Serves as a masked carboxyl/aldehyde/amine handle on the thiophene core, allowing late-stage diversification while preserving the aromatic framework.
Provides electron-withdrawing modulation to tune reactivity and regioselectivity in subsequent steps (e.g., coupling or annulation sequences).
Practical guidance:
Employ inert atmosphere and dry glassware. Quench organolithium reactions cautiously at low temperature. Monitor by TLC/GC where possible; nitriles give characteristic IR band near ~2230 cm−1 (literature) useful for in-process control.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent (heteroaromatic nitrile) and does not possess antigen/epitope specificity, clone information, isotype, or species reactivity. For biochemical targeting applications, consider conjugating derived motifs to biological ligands or using orthogonal affinity handles.
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