3-Cyanophenylzinc iodide solution - 0.5M in THF , CAS No.288309-53-5

CAS: 288309-53-5 Cat. No.: C465920 Formule: C₇H₄INZn Poids moléculaire: 294.4 PubChem CID: 3294376

GRADE & PURITY 0.5M in THF

Storage

Store at 2-8°C

Shipped In

Wet ice

Vue d’ensemble

Description

3-Cyanophenylzinc iodide can be used:As a reagent/substrate in the palladium-catalyzed synthesis of 5-substituted 2-furaldehydes of biological importance.As a substrate in the di-functionalization of indenes via α-carbonylalkylarylation to yield α-carbonyl- alkylarylated indenes.

Specifications

Spécifications et pureté

0.5M in THF

Informations juridiques

Rieke® Metals, Inc. 产品 ®Rieke Metals, Inc. 的注册商标Rieke is a registered trademark of Rieke Metals, Inc.

Conditions de stockage de stockage

Store at 2-8°C

Expédié en

Wet ice

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

• Sourires canoniques: C1=C[C-]=CC(=C1)C#N.[Zn+]I
• IUPAC Name: benzonitrile;iodozinc(1+)
• InChIKey: HMBFIVLHOWOJRD-UHFFFAOYSA-M
• INCHI: 1S/C7H4N.HI.Zn/c8-6-7-4-2-1-3-5-7;;/h1-2,4-5H;1H;/q-1;;+2/p-1
• Isomères SMILES: C1=C[C-]=CC(=C1)C#N.[Zn+]I
• PubChem CID: 3294376
• Poids moléculaire: 294.4

Application Protocols

No bioassay or immunoassay protocols apply to this organometallic reagent. For practical laboratory use, see Reaction Conditions and Application notes:

• General handling protocol (literature):
  • Dry glassware; establish inert atmosphere (Ar/N2).
  • Cool reaction solvent if exotherm expected.
  • Transfer the solution by cannula or gastight syringe.
  • Rinse the delivery line/syringe with a small portion of solvent to ensure complete transfer.
  • Quench cautiously after completion; filter off inorganic salts; proceed to purification.

Item-specific application parameters (concentration, solvent, additives) are not specified for this item; refer to CoA/Spec Sheet.

Biological Roles

This product is a synthetic organometallic reagent and is not intended for biological systems. No intrinsic biological role is associated with 3-cyanophenylzinc iodide.

General context (literature):

• Aryl nitriles appear widely in bioactive small molecules, but the organozinc reagent here serves purely as a synthetic intermediate donor of the 3-cyanophenyl fragment.
• The nitrile group is a versatile synthetic handle, enabling downstream transformations to motifs common in medicinal chemistry (amides, amines, tetrazoles), but such derivatizations occur after the coupling step and outside biological contexts.

Research use note (from product data): For research use only. Not for human or veterinary use, clinical diagnostics, or consumption.

Buffer Applications

Not applicable. 3-Cyanophenylzinc iodide is an organometallic reagent supplied in an anhydrous organic solvent and is not used to prepare aqueous buffers or biological media. For practical usage, refer instead to Reaction & Applications, Synthetic Utility, and Reaction Conditions.

Green Alternatives

Organometallic solutions are often supplied in ethers such as THF, which have safety and environmental considerations. The solvent for this item is not specified; consult the CoA/Spec Sheet. General greener considerations (literature):

• Alternative solvent choices for cross-coupling/transmetalation:

  • 2-MeTHF: Bio-derived, higher boiling, lower peroxide tendency than THF; often maintains or improves Negishi rates.
  • CPME: Hydrophobic, broad stability window; good phase separation and often lower peroxide formation; may require catalyst/ligand tuning.
  • Toluene/anisole: Non-protic aromatics with favorable EHS profiles relative to halogenated solvents; can work with robust Pd systems.

• Comparison (literature-based):

  • THF vs 2-MeTHF: Similar polarity; 2-MeTHF offers greener sourcing and easier solvent recovery; sometimes slightly slower transmetalation without LiCl.
  • DMF/DMPU vs alternatives: Powerful solvating media but with EHS liabilities; consider Cyrene, propylene carbonate, or NBP when compatible with catalyst and organozinc stability.

• Process tips:

  • Optimize solid’s solubility and catalyst performance first on small scale before switching to greener media.
  • Implement solvent recovery and peroxide monitoring programs for ethers.

Note: If the supplied reagent is in a specific solvent, assess feasibility of in-situ solvent swap under inert atmosphere to a greener alternative while preserving concentration and activity.

Pharmaceutical Uses

No excipient or pharmacopeial status is specified for this item; refer to CoA/Spec Sheet.

General process-chemistry context (literature):

• Role: Arylzinc reagents are used in drug substance synthesis as nucleophiles in Pd/Ni-catalyzed cross-couplings (Negishi) and acylations to access meta-cyanophenyl-containing scaffolds.
• Advantages: High chemoselectivity versus Grignards in the presence of sensitive functional groups; compatibility with a broad range of catalytic systems; typically milder reaction temperatures and reduced side reactions.
• Considerations: Residual zinc salts and iodide byproducts necessitate robust workup/filtration and may impact downstream crystallization; solvent selection (2-MeTHF, CPME) may support greener process metrics relative to THF/DMF when compatible.
• Regulatory/process notes: Ensure control of residual metals (Zn, Pd/Ni) according to ICH Q3D, and validate removal of reaction byproducts and solvents during scale-up. Titrate reagent and monitor water content to ensure batch-to-batch consistency.

Physical Properties

Item-specific properties (as supplied):

• Physical state/appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Solvent and concentration: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water content, metals/peroxide limits: Not specified for this item; refer to CoA/Spec Sheet.

General/literature properties of the neat organozinc species (for context only; the catalog item is a solution):

• Approximate formula mass (C7H4INZn): ~294.4 g/mol (literature/computed)
• Sensitivity: Moisture- and air-sensitive (common for arylzinc halides).
• Solubility behavior: Typically handled in coordinating ethereal/aprotic solvents (THF, 2-MeTHF, DMF, DMPU) due to the Lewis-acidic Zn center (literature).
• Thermal behavior: Generally used at 0–50°C; avoid overheating to limit decomposition (literature).

Practical notes for users (general):

• The solution’s handling characteristics (viscosity, color) and exact properties depend on the solvent and concentration, which are not specified here; consult the CoA/Spec Sheet.
• Verify concentration by titration (e.g., electrophilic quench with iodine or protic titration) if required for stoichiometric accuracy (literature practice).

Quality and Grades

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

Interpretation and practical guidance (general):

• Solution reagents such as arylzinc iodides are commonly supplied in defined molarities in anhydrous solvents (e.g., THF, toluene, DMF). When grade is unspecified, rely on the CoA for:
  • Exact concentration and titer method.
  • Residual halides/salts, base content, and water (Karl Fischer) levels.
  • Trace metal profile and stabilizers, if any.
• For chromatography- or synthesis-critical applications (e.g., Pd-catalyzed cross-coupling), low-halide and low-water content are typically preferred to minimize catalyst inhibition and side reactions (literature guidance).
• Stabilizers: Some organozinc solutions contain additives (e.g., LiCl, TMEDA) to enhance reactivity/solubility; none are specified for this item. If present, such additives can influence catalytic systems and should be considered in reaction design (consult CoA/Spec Sheet).

Recommendation: Prior to scale-up, verify the reagent strength by titration and run a small test reaction to benchmark performance under your catalytic conditions.

Reaction and Applications

3-Cyanophenylzinc iodide is a versatile organozinc nucleophile. The meta-cyano substituent is strongly electron-withdrawing, which modulates aryl–Zn polarity and influences cross-coupling rates and chemoselectivity (literature).

Key reaction families (literature):

• Negishi cross-coupling (Pd or Ni catalysis): Formation of (meta-cyano)biaryls or aryl–alkenyl bonds from aryl/alkenyl halides or pseudohalides. Typical ligands: biaryl phosphines (SPhos, XPhos), Pd(dba)3, Pd-PEPPSI for Ni/Pd.
• Acylation to ketones: Coupling with acid chlorides or mixed anhydrides to give meta-cyanophenyl ketones under Pd/Cu catalysis or direct nucleophilic acyl substitution with appropriate activation.
• Electrophile additions: Reaction with aldehydes/ketones (via transmetalation to Cu or catalytic systems) to provide secondary/tertiary alcohols after workup; the nitrile remains intact and can be leveraged downstream.
• Halogen–zinc exchange platforms: The reagent can serve as a transmetalation partner to transfer the 3-cyanophenyl unit to other metals (Pd, Cu) enabling C–C and C–heteroatom bond formations.

Strategic features of the 3-cyano group (literature):

• Directs regioselectivity and stabilizes anionic/cuprate intermediates; compatible with many catalysts.
• Synthetic handle for diversification: nitrile → amide, acid, amine, tetrazole, imidate, aldehyde (via reduction, hydrolysis, or cycloaddition).

Practical tips:

• Maintain 1.1–1.5 equiv vs electrophile to ensure full conversion; titrate concentration.
• The cyano group tolerates strong base and transition metals; avoid strongly acidic conditions that would prematurely quench the organozinc.
• Employ rigorous anhydrous/inert techniques to preserve activity.

Reaction Conditions

General literature guidance for reactions employing 3-cyanophenylzinc iodide (the catalog item is a solution; solvent/concentration not specified):

• Negishi cross-coupling (aryl/alkenyl halides):

  • Catalyst: 0.5–3 mol% Pd (e.g., Pd(dba)3 + SPhos/XPhos; Pd-PEPPSI; Pd-Precatalysts). Ni catalysts (e.g., NiCl2(dppp)) for aryl chlorides.
  • Solvent: THF, 2-MeTHF, toluene, or mixtures; 0–50°C.
  • Stoichiometry: 1.1–1.5 equiv arylzinc vs electrophile.
  • Time: 0.5–8 h depending on substrate/catalyst.
  • Atmosphere: Inert (Ar/N2). Rigorous exclusion of moisture/air.

• Acylation to ketones (acid chlorides):

  • Catalyst: Pd(0) or Cu(I) salts (e.g., CuI 5–20 mol%) can accelerate; some substrates proceed without catalyst at low temperature.
  • Solvent/Temp: THF or toluene, −20 to 25°C to control exotherm.

• Conjugate additions (after Cu transmetalation):

  • Catalyst: Cu(I) salts with phosphine or NHC ligands; 0–25°C in THF/toluene; affords 1,4-addition products.

• Workup (general):

  • Quench at ≤0–10°C with saturated NH4Cl or dilute NH4Cl/NH4OH depending on catalyst system; extract with organic solvent; remove Zn/I salts by filtration/celite.

All conditions are literature guidance; optimize for your specific catalyst/substrate. Verify reagent concentration by titration before stoichiometric planning.

Safety and Handling

Item-specific hazard data:

• GHS classification, signal word, H-statements, pictograms: Not specified for this item; refer to the product SDS for authoritative safety information.

General safety information for arylzinc halide solutions (literature/practice):

• Hazards: Moisture- and air-sensitive; may react exothermically with water or protic reagents to release flammable gases/vapors (from solvent). Solutions are often in flammable ethers/aprotic solvents.
• Incompatibilities: Water, alcohols, acids/oxidizers, oxygen/air; avoid contact with CO2 where basic additives are present.
• Handling: Work under inert atmosphere (argon/nitrogen) using dry glassware. Employ syringe/Schlenk or glovebox techniques. Additions should be slow and temperature-controlled.
• PPE: Lab coat, safety goggles, chemically resistant gloves (e.g., nitrile), and appropriate face/skin protection when handling larger volumes. Use a fume hood.
• First aid (overview; defer to SDS): Eye/skin contact—immediately rinse with water; remove contaminated clothing. Inhalation—fresh air, seek medical attention. Ingestion—do not induce vomiting; seek medical attention.
• Fire: Solvent-driven fire risk; use CO2, dry chemical, or foam. Do not use water directly on organometallic spills.
• Spills/quench (general guidance): Cover small amounts with dry, inert absorbent; quench cautiously via stepwise alcohol then water addition under cooling, after verifying compatibility. Defer to institutional SOPs and SDS.

Storage (per item data): Store at 2–8°C. Keep tightly sealed under inert gas. Protect from moisture/air and ignition sources. Shipped on wet ice.

Solvent Selection

This product is itself supplied as a solution; the specific solvent is not specified for this item (refer to CoA/Spec Sheet). The following guidance concerns selecting media for reactions employing 3-cyanophenylzinc iodide (general literature):

• Polarity and coordination:

  • Coordinating ethers/aprotics (THF, 2-MeTHF, DME, DMPU, DMF) stabilize R–ZnI through oxygen/nitrogen coordination and typically give higher rates in cross-couplings and nucleophilic additions.
  • Less-coordinating solvents (toluene, CPME) can be advantageous for some catalysts or to improve selectivity, especially with polar substrates or to limit over-transmetalation.

• Miscibility and profiles (literature):

  • THF/2-MeTHF: Miscible with many organic substrates; excellent for Pd-catalyzed Negishi couplings at 0–50°C.
  • DMF/DMPU: Improve solubility of polar electrophiles (acyl halides, heteroaryl halides). Handle with care due to higher boiling points and workup considerations.
  • Toluene/CPME: Better phase separation and often greener than THF; may require ligand/catalyst tuning for optimal transmetalation rates.

• Practical tips:

  • Maintain rigorously anhydrous conditions regardless of solvent.
  • Match solvent to catalyst system: biaryl phosphines/NHCs often tolerate ethers and toluene; SPhos/XPhos-type ligands work broadly across ethers/aromatics.
  • If the supplied solvent differs from your desired medium, pre-mix under inert atmosphere and transfer via cannula to avoid concentration swings.

Note: Because the catalog item’s solvent is not specified, confirm compatibility with your catalyst and substrate on small scale first.

Storage and Reconstitution

Item-specific storage/shipping (from product data):

• Storage conditions: Store at 2–8°C.
• Shipped in: Wet ice.

Additional handling/storage guidance (general to organozinc solutions):

• Keep container tightly closed under an inert atmosphere (argon/nitrogen). Protect from moisture/air and light/heat sources.
• Do not freeze unless explicitly stated on the CoA, as phase separation or concentration changes can occur upon freezing/thawing of organometallic solutions. For this item, freezing guidance is not specified; refer to CoA/Spec Sheet.
• Minimize headspace oxygen/moisture by using septum-capped bottles and positive inert-gas pressure.
• If concentration verification is required after extended storage, perform a titer before use.

Reconstitution: Not applicable—supplied as a ready-to-use solution. If a solvent swap or dilution is needed, perform under inert atmosphere using rigorously dried solvents. Exact solvent identity and concentration for this item are not specified; refer to CoA/Spec Sheet.

Structure and Identity

Brief description: 3-Cyanophenylzinc iodide is an arylzinc halide (organometallic) reagent supplied as a solution. The aryl moiety is a meta-cyano-substituted phenyl, bonded to zinc, with iodide as the counter halide.

• Item identifiers (product data):

  • SKU: C465920
  • Product name: 3-Cyanophenylzinc iodide solution
  • CAS: 288309-53-5
  • PubChem CID: 3294376
  • InChIKey: 125099 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structure description (general/literature):

  • Core features: A benzene ring bearing a nitrile group at the meta position relative to the carbon bearing the Zn–I fragment (i.e., m-cyanophenyl–Zn–I).
  • Functional groups: Aryl–zinc bond (polarized C(sp2)–Zn), nitrile (–C≡N) meta to the organozinc substituent.
  • Stereochemistry: None (planar aromatic system; no stereocenters).

• Empirical composition (literature, for the R–ZnI entity, excluding solvent):

  • Approximate molecular formula (literature): C7H4INZn
  • Approximate formula mass (literature): ~294.4 g/mol

Notes: This product is provided as a solution; solvent, stabilizers, and exact concentration are not specified for this item; refer to CoA/Spec Sheet.

Synthetic Utility

Functional group profile and reactivity (literature):

• Nucleophilic aryl transfer: The aryl–Zn bond enables efficient transmetalation to Pd/Ni/Cu, forging C(sp2)–C(sp2/sp) bonds selectively (Negishi, Liebeskind–Srogl variants, and Cu-mediated additions).
• Chemoselectivity: Compared to Grignard reagents, arylzinc reagents are less basic, often tolerating esters, nitriles, and some heteroaryl halides. The pendant nitrile on the aryl donor remains intact during cross-coupling, enabling late-stage diversification.
• Electrophile scope: Aryl/alkenyl/vinyl halides and triflates; acyl chlorides; certain imidazolyl carboxylates; activated sulfonates. Can participate in conjugate additions after Cu-catalyzed transmetalation.

Downstream elaboration of the 3-cyano group (literature):

• Hydrolysis to acids/amides; reduction to aldehydes/amines; [2+3] cycloaddition to tetrazoles; nucleophilic additions after activation.

Retrosynthetic value:

• Enables convergent assembly of meta-cyanophenyl motifs without resorting to harsh nitrilation or directing-group strategies on the product arene.

Practical guidance:

• Use 1.1–1.3 equiv for couplings; higher loadings may be required with deactivated electrophiles.
• LiCl or TMEDA can enhance solubility/reactivity for some systems; none are specified for this item—add only if compatible with your catalyst.
• Validate reagent strength via titration; maintain strict exclusion of moisture and oxygen.

Target Specificity

Not applicable. This is a small-molecule organometallic reagent, not a biological targeting agent. No antigen/epitope, species reactivity, clone, or isotype information applies.