This compound belongs to the class of organic compounds known as benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
External Descriptors
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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. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For practical laboratory use, refer to Reaction Conditions and Application sections for synthetic procedures and handling.
Biological Roles
This product is a small aromatic halonitrile used as a synthetic building block. It does not have a known intrinsic biological role.
General context (literature)
Aromatic nitriles appear in numerous bioactive scaffolds as metabolically stable, polar, and compact substituents that can modulate binding via dipolar interactions. The ortho arrangement can influence conformation in biaryl systems after coupling.
The compound itself is intended strictly for laboratory research and chemical synthesis; it is not formulated for biological assays or in vivo use.
Biotransformation considerations (general)
Nitriles can be hydrolyzed by nitrilases/nitrile hydratases in microorganisms, but halogenated aromatics are typically resistant and persistent; any such processes are context-specific and not a use recommendation.
Research Use Note: For research use only (per Product Data). No medical or clinical applications are implied.
Buffer Applications
Not typically applicable. 2-Iodobenzonitrile is a nonionic organic building block, not a buffering agent. It is not used to prepare biological buffers or to control pH. For practical use, see the Synthetic Utility, Reaction & Applications, and Reaction Conditions sections for guidance in synthetic chemistry contexts.
Green Alternatives
Greener strategies typically focus on solvent choice, halide selection, and catalyst loading rather than changing the core building block when the ortho nitrile is required.
Greener solvent replacements (literature/general)
Replace DMF/NMP with 2-MeTHF, CPME, propylene carbonate, or aqueous ethanol/dioxane systems for Suzuki couplings.
For Sonogashira, consider EtOH, 2-MeTHF, or water/organic micellar media with modern ligand systems.
Halide economy and alternative substrates
Aryl iodides offer high reactivity but poorer atom economy compared to bromides/chlorides. If reactivity allows, 2-bromobenzonitrile or 2-chlorobenzonitrile can be greener/cheaper alternatives; however, they typically require more active catalysts/ligands and higher temperatures.
Catalyst and base choices
Use lower Pd loadings (≤0.5–1 mol%) with high-activity ligands (e.g., SPhos, XPhos) or Ni catalysis where feasible.
Favor inorganic bases with lower EHS impact (K2CO3, K3PO4) and aqueous workups.
Comparison snapshot (general)
2-Iodobenzonitrile vs 2-bromobenzonitrile: iodide gives faster oxidative addition (lower temperature, shorter time) but worse atom economy and potentially higher E-factor if iodide waste is not recovered.
Solvent swap impact: moving from DMF/NMP to 2-MeTHF/H2O typically improves worker exposure profile and waste treatability, with similar coupling performance in many cases.
Always confirm that greener substitutions maintain yield/selectivity for the specific transformation.
Pharmaceutical Uses
Role in formulation: Not used as an excipient or buffer. Instead, 2-iodobenzonitrile serves as a synthetic intermediate to access benzonitrile-containing drug candidates and advanced intermediates via cross-coupling and subsequent functional group manipulations (literature/general).
Pharmacopeia status: Not a compendial excipient; no monograph use is indicated.
Process chemistry relevance (general)
Aryl iodide substrates like this are leveraged in route scouting for rapid SAR generation, enabling lower-temperature couplings and late-stage diversification.
After establishing structure–activity relationships, process routes often transition to aryl bromides/chlorides for cost and sustainability, retaining the ortho-nitrile motif.
No therapeutic claims are made. This product is for research and manufacturing development use only, not for human or veterinary applications.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical physical data (for reference; varies with sample and measurement method)
State at ambient: typically a low-melting solid or high-melting liquid near room temperature (literature reports describe a low-melting crystalline solid).
Melting point: literature reports generally in the ~30–40 °C range depending on purity and polymorph (literature).
Boiling point: aromatic iodides of this size typically distill at elevated temperatures (>250 °C at 1 atm); reduced at vacuum (literature trend; consult primary data before distillation).
Solubility: sparingly soluble in water; soluble in common organic solvents (e.g., dichloromethane, chloroform, THF, acetone, acetonitrile, DMF, toluene) (literature/general).
Polarity/partitioning: expected moderate hydrophobicity due to aryl iodide; nitrile adds modest polarity; typically favorable logP for organic phases (literature trend).
Spectral handles: strong C≡N stretch in IR near ~2220–2240 cm−1; aryl iodide C–I stretch in the 500–650 cm−1 region (literature).
Note: Do not treat literature values as product specifications. Verify with the item’s CoA/SDS for operational planning.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical grades for this class of material (general)
Research grade: Suitable for synthetic chemistry, including cross-couplings (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Heck) where aryl iodides often provide higher reactivity via facile oxidative addition.
High-purity (>98–99% typical for many catalogs) is preferred for catalytic reactions to minimize poisons (sulfur, halides, peroxides, metal contaminants). UV-Vis/HPLC grade specifications focus on low UV background and trace impurity control; such specifications are not provided here for this item.
Stabilizers: None are typically added to simple aryl iodides; if stabilizers or inhibitors are present, they will be stated on the CoA/SDS. For this item, no stabilizer information is provided.
Verification
For exact assay, residual solvents, metals, water (Karl Fischer), and chromatographic purity: Not specified for this item; refer to CoA/Spec Sheet.
Always confirm lot-specific data (melting point, GC/HPLC purity, ICP-MS for metals if coupling catalysts will be used).
Reaction and Applications
2-Iodobenzonitrile is a versatile aryl iodide building block; the ortho nitrile and the reactive C–I bond enable broad cross-coupling and directed functionalization chemistry.
Cross-coupling (literature/general)
Suzuki–Miyaura: couples with boronic acids/esters to access 2-substituted benzonitriles; aryl iodides typically display rapid oxidative addition, enabling milder conditions and broad functional group tolerance.
Sonogashira: forms o-cyanophenyl alkynes under Pd/Cu (or Pd-only) catalysis; useful in preparing alkynylated nitriles for further cyclizations.
Buchwald–Hartwig amination: installation of anilines and N-heterocycles; the nitrile survives many amination conditions.
Heck: vinylation at the iodide position to generate o-cyanostyrenes.
Directed ortho-metalation and annulation
The nitrile is a strong directing group; treatment with bases (e.g., s-BuLi/TMEDA) can effect metalation adjacent to CN for subsequent electrophile quench (literature practice). Careful temperature control required.
Cyclization strategies: alkynylation followed by intramolecular nucleophilic additions can construct isoquinoline/quinazolinone frameworks (literature routes).
Nitrile transformations
Hydrolysis (acidic or basic) to amide or carboxylic acid derivatives, often after coupling to set the substitution pattern.
Reduction to primary amine (e.g., catalytic hydrogenation or hydride reagents), enabling access to o-iodobenzylamines or, post-coupling, o-aminobenzene derivatives.
Practical notes
Dry, oxygen-limited conditions typically improve Pd-catalyzed couplings.
Aryl iodides can undergo dehalogenation; choose ligands and bases to suppress reduction.
The ortho nitrile can influence regioselectivity and reactivity—account for potential chelation or coordination to metals.
Reaction Conditions
General literature conditions for common transformations of 2-iodobenzonitrile (verify and optimize for your substrate/catalyst system; not item-specific specifications):
Suzuki–Miyaura coupling
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd2(dba)3/XPhos–SPhos (0.5–1 mol% Pd).
Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
Solvent: dioxane/H2O, THF/H2O, 2-MeTHF/H2O, or MeOH/H2O.
Temperature/time: 40–90 °C, 1–12 h. Aryl iodides often couple efficiently at the lower end.
Sonogashira coupling
Catalyst: PdCl2(PPh3)2 (1–2 mol%) with CuI (5–10 mol%) or copper-free systems with bulky phosphines/NHCs.
Base/solvent: Et3N, DIPEA, or Cs2CO3 in THF, toluene, or DMF; 25–80 °C.
Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) with BINAP, BrettPhos, or XPhos; NaOtBu or K3PO4 as base.
Solvent: toluene, dioxane, or tBuOH; 60–110 °C.
Heck reaction
Catalyst: Pd(OAc)2/PPh3 or PdCl2(dppf); base: Et3N or K2CO3; solvent: DMF, NMP, or toluene; 80–120 °C.
Ortho-metalation (nitrile-directed)
Base: s-BuLi (1.1–1.5 equiv) with TMEDA in THF; −78 to −40 °C; quench with electrophiles (e.g., MeI, CO2). Strict anhydrous technique required.
Typical isolated yields in literature for aryl iodide couplings range 70–95% when optimized. Always run small-scale screens to tune ligand/base/solvent and manage dehalogenation.
Safety and Handling
Item-specific hazard classification
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl iodides and aromatic nitriles (literature/good practice)
Hazards: May cause skin/eye irritation and respiratory irritation; harmful if swallowed. Nitriles can release toxic fumes under fire (HCN, NOx); aryl iodides can produce hydrogen iodide and iodine vapors upon decomposition.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of vapors or dust.
Incompatibilities: Strong bases can induce metalation; avoid strong oxidizers and strong reducing agents. Under coupling conditions, base and transition metals are common—control exotherms and oxygen/moisture as appropriate.
First aid (overview; defer to SDS): Move to fresh air if inhaled; wash skin with soap and water; rinse eyes cautiously with water for several minutes; seek medical attention if symptoms persist.
Fire: Use CO2, dry chemical, or foam. Combustion may produce CO/CO2, NOx, HCN, and iodine-containing fumes.
Storage and shipping (item-specific)
Storage Conditions: Protected from light, Room temperature (per Product Data).
Shipped In: Normal (per Product Data).
Keep container tightly closed; store in a dry, well-ventilated place. Use amber or light-protective packaging as indicated.
Solvent Selection
2-Iodobenzonitrile is a moderately hydrophobic, polarizable aryl iodide bearing a nitrile. Solvent choice should balance substrate solubility, catalyst stability, and byproduct handling.
Functions well in polar aprotic media (DMF, DMAc, NMP, MeCN) for Pd-catalyzed couplings; also compatible with mixed aqueous-organic systems (dioxane/H2O, THF/H2O) for Suzuki couplings.
When to choose specific solvents (general guidance)
Suzuki–Miyaura: dioxane/H2O, THF/H2O, or MeOH/H2O with K2CO3, K3PO4, or Cs2CO3; switch to toluene/H2O or 2-MeTHF/H2O for greener options.
Sonogashira: amine bases in THF, toluene, or DMF; avoid excess water to limit Glaser-type homocoupling.
Buchwald–Hartwig: toluene, dioxane, or tBuOH often improve catalyst lifetimes.
S_NAr or metalation: use strong bases in THF or CPME at low temperature; nitrile can direct ortho-metalation.
Practical tips
Ensure complete dissolution at reaction temperature; a slurry can be acceptable for cross-coupling if mass transfer is adequate.
Remove high-boiling dipolar solvents (DMF/DMSO) under reduced pressure after aqueous workup; or use extractive workups from mixed aqueous systems to simplify isolation.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Protected from light, Room temperature (per Product Data). Store in a tightly sealed container in a dry, ventilated area. Use amber glass or light-protective packaging.
Shipped In: Normal (per Product Data).
Stability and handling (general guidance)
Keep away from strong bases/acids and oxidants. Avoid prolonged exposure to light and air to limit potential discoloration or decomposition.
If low-melting, store below the melting range to maintain a solid for easier handling, if compatible with your lab conditions.
Reconstitution
Not applicable. This is a neat organic compound typically used as received. If preparing stock solutions, dissolve in an appropriate dry solvent (e.g., DCM, THF, toluene, MeCN, DMF) and store aliquots under inert gas at low temperature, protected from light. Label solutions with solvent, concentration, and date.
Always consult the product’s CoA/SDS for lot-specific stability and safe handling details.
Structure and Identity
2-Iodobenzonitrile (o-iodobenzonitrile) is an ortho-iodinated benzonitrile, combining an aryl iodide and a nitrile on the same benzene ring, enabling orthogonal reactivity.
Item-specific identifiers (from Product Data)
CAS: 4387-36-4
SKU: I103576
InChIKey: 157247 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity data (for reference only; not item-specific specifications)
Common name: 2-iodobenzonitrile (o-iodobenzonitrile)
Functional groups: aryl iodide (C–I) and nitrile (–C≡N) para-orthogonal pair on a benzene ring; iodine is ortho to the nitrile.
The nitrile is strongly electron-withdrawing and can direct ortho-metalation; the C–I bond is highly polarizable and undergoes oxidative addition readily.
2D description: a benzene ring bearing a cyano substituent at C1 and an iodine at C2 (adjacent position), with no stereocenters.
Synthetic Utility
2-Iodobenzonitrile unites two powerful handles: a highly reactive aryl iodide for cross-coupling and a directing nitrile for site-selective transformations.
Functional group leverage (general)
Aryl iodide: rapid oxidative addition in Pd/Ni catalysis; compatible with Suzuki, Sonogashira, Heck, Negishi, Stille, and Buchwald–Hartwig couplings.
Nitrile: directs ortho-metalation; convertible to amides/acids/amines; participates in cycloadditions and serves as a hydrogen-bond acceptor in ligand design.
Retrosynthetic value
As a linchpin, it enables fast entry to 2-substituted benzonitriles. Subsequent nitrile manipulation diversifies functionality without re-installing halide.
Strategic sequence: (1) Cross-coupling at I; (2) Nitrile transformation (hydrolysis/reduction); (3) Directed ortho-functionalization if the iodide is first replaced.
Selectivity and regiocontrol
Ortho nitrile can chelate to metals, affecting migratory insertions and C–H activations—useful in designing regioselective couplings and annulations.
Practical points
Protect from light (item-specific) to minimize any photoinitiated side reactions or discoloration.
Use dry, oxygen-controlled conditions to reduce dehalogenation and improve catalyst turnover.
Monitor for proto-deiodination; adjust ligand/basicity and employ mild hydride scavengers if needed.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, probe, or biological reagent with defined target binding parameters. No antigen/epitope or isotype information applies.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 4387-36-4, the molecular formula is C7H4IN, and the molecular weight is 229.02 g/mol. InChIKey JDDAFHUEOVUDFJ-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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