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
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 biological assay protocols (WB, IHC, IF, FC) apply to this small‑molecule reagent. For chemical use, consider the representative procedures under Reaction Conditions. When preparing analytical samples:
Create stock solutions in dry DMSO, DMF, THF, or MeCN as appropriate to your method.
Filter through PTFE (0.2–0.45 µm) before HPLC/UPLC injections.
For crystallization or purification, see Solvent Selection for recommended solvent systems.
Always adapt protocols to your scale, equipment, and safety requirements; pilot on milligram scale prior to scale-up.
Biological Roles
This compound is a synthetic aromatic building block; it is not known to have intrinsic biological roles.
General background (literature/general)
Aromatic nitriles occur in certain natural products and xenobiotics, but 2‑iodobenzonitrile itself is primarily a laboratory/intermediate substance without established roles in metabolism or signaling.
The nitrile functional group can be metabolically stable; in drug design, aryl nitriles sometimes modulate potency and physicochemical properties, but such context pertains to derivatives, not to 2‑iodobenzonitrile as a reagent.
Biochemical handling
Expect low aqueous solubility and high affinity for organic phases; binders to serum proteins are possible for aryl iodides, but no specific data are assigned here.
Research use only
Per Product Data: For research use only. No food, drug, cosmetic, or household applications.
For any biological testing or screening, ensure appropriate containment and waste management; consult your institutional biosafety and chemical hygiene plans.
Buffer Applications
2‑Iodobenzonitrile is not a buffering agent and is not used to prepare biological buffers or electrophoresis media. It lacks acid/base functionalities in water that would define a useful pKa in the physiological range.
Practical note: If solutions are required for bioassays or materials testing, prepare stocks in suitable organic solvents (e.g., DMSO, DMF) and dilute into assay media with attention to final cosolvent percentages and potential precipitation.
For true buffering needs, select established buffer systems (phosphate, HEPES, Tris, MOPS) appropriate to your pH range and ionic strength.
Green Alternatives
While 2‑iodobenzonitrile itself is the required electrophile in many routes, greener choices can be made around solvent, catalyst, and alternative leaving groups when synthetic flexibility allows.
Greener solvent systems (literature)
Replace DMF/NMP with 2‑MeTHF, CPME, Cyrene, or aqueous ethanol mixtures for Pd couplings where solubility permits.
Favor dioxane alternatives due to hazard profile; 2‑MeTHF or toluene/H2O often deliver similar outcomes.
Catalysis and bases
Use highly active Pd–NHC or palladium-on-carbon in aqueous micellar media (e.g., surfactant-enabled couplings) to cut Pd loading to ppm levels and operate at lower temperatures.
Select inorganic carbonate or bicarbonate bases (K2CO3, KHCO3) in water-rich media to reduce solvent burden.
Alternative electrophiles (route-dependent)
If iodide is not essential, analogous bromo- or triflate precursors may reduce iodinated waste and cost, though at the expense of reactivity. Conversely, the iodide often enables milder, more selective couplings, potentially improving overall E‑factor by reducing protecting-group steps.
Workup and isolation
Prioritize solvent swaps to greener options (EtOAc/heptane) and minimize chlorinated solvent use; employ in‑pot crystallizations when feasible.
Greener pathway: 2‑MeTHF/H2O or EtOH/H2O, heterogeneous Pd or micellar catalysis, mild carbonate base, crystallization‑led isolation.
Note: Optimize on small scale; green gains must be balanced against yield/selectivity and safety.
Pharmaceutical Uses
No excipient or therapeutic uses are assigned. 2‑Iodobenzonitrile is a research-grade synthetic intermediate.
General context (literature/general)
As an aryl iodide bearing an ortho nitrile, it serves as a valuable precursor to substituted benzonitriles, benzamides, benzoic acids, and annulated heterocycles that may appear in drug discovery libraries.
Its high coupling reactivity (Ar–I) facilitates late-stage diversification under comparatively mild conditions, potentially reducing protecting-group manipulations.
Regulatory status
No pharmacopeial monograph is implied. Any GMP use would require independent qualification, impurity profiling, and supplier assessment.
Process considerations
For route scouting, evaluate the balance between iodide reactivity and waste/cost compared to bromide/triflate analogs. If adopted in scale-up, define robust crystallization and purge strategies for iodine-containing impurities.
Research use only: This product is intended solely for laboratory research and development. No clinical, diagnostic, or therapeutic claims are made.
Physical Properties
Item-specific specifications are not provided in the Product Data. Where relevant, consult the item’s CoA/Spec Sheet. The following are general literature values and qualitative guidance for 2‑iodobenzonitrile; do not treat them as product specifications.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Phase: Typically a crystalline solid at ambient conditions (literature, qualitative).
Melting point (literature): commonly reported in the mid‑40s °C range (e.g., ~45–50 °C). Values vary with purity and method.
Boiling point (literature): high-boiling aromatic; often reported around the 270–280 °C range at ambient pressure; thermal sensitivity may be observed near its boiling point.
Density (literature): higher than water, consistent with aryl iodides; specific values vary across sources.
Solubility (literature, qualitative): low in water; soluble in common organic solvents (e.g., DCM, THF, EtOAc, toluene, DMF, DMSO). Solubility can improve upon gentle heating.
LogP (literature): expected to be moderately high for an aryl iodide; exact value varies by source.
UV/Vis: aromatic π–π* absorption in the UV; detailed cutoff/absorbance not specified for this item.
Refractive index: Not applicable for the solid; solution-phase nD depends on solvent and concentration.
Notes
For chromatography/detection planning, rely on pilot runs and standard curves; if HPLC/GC parameters are critical, verify with analytical standards.
Where precise constants matter (e.g., DSC/TGA, vapor pressure), generate internal measurements under your lab conditions.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet for assay, residual solvent profile, and impurity limits.
Understanding grades (general guidance)
Research grade: suitable for most synthetic applications; typical assay ≥95%, but verify on the CoA.
High-purity/97–99%: preferred for catalysis (e.g., Pd-couplings) to minimize catalyst poisoning from halides, metals, or oxidized byproducts.
Low-residual-water/low-UV grades: relevant if using in photochemistry or analytical applications; check UV cutoff and residual solvent/moisture on the CoA when critical.
Stabilizers/additives
None specified for this item. If stabilizers are present in a particular lot, they will be declared on the CoA/SDS. 2‑Iodobenzonitrile is generally stable and not typically stabilized.
Quality considerations specific to aryl iodides
Oxidative impurities (iodinated phenols/iodobenzenes), dehalogenation products, and isomeric nitriles (meta/para) are the most common related substances; confirm identity by 1H/13C NMR, IR (sharp CN stretch ~2225 cm⁻¹, literature), and MS (M+ at ~229, literature).
Trace iodine/iodide can affect cross-couplings; a prewash with aqueous sodium thiosulfate during workup can reduce free iodine if observed.
For coupling chemistry, ensure low water and amine impurities; dry the solid under vacuum before charging to air/moisture-sensitive reactions.
Reaction and Applications
2‑Iodobenzonitrile is a versatile bifunctional synthon where the aryl iodide drives cross-couplings while the ortho nitrile serves as a latent handle and directing group.
Cross-couplings (literature)
Suzuki–Miyaura: rapid oxidative addition from Ar–I enables low Pd loadings and mild temperatures to forge biaryls adjacent to a nitrile (useful for pharmaceutical scaffolds). The CN group is typically tolerated.
Sonogashira: terminal alkynes couple efficiently to give o‑alkynyl benzonitriles; copper-assisted conditions are classical, copper-free systems minimize Glaser byproducts.
Buchwald–Hartwig amination: amines can replace iodine to give o‑aminobenzonitriles; ligand choice (e.g., XPhos/BrettPhos) tunes scope.
Carbonylative couplings: under CO, access o‑cyanobenzoyl derivatives or amides.
Nitrile transformations (orthogonal to C–I chemistry)
Reduction: DIBAL‑H (to aldehyde) or LiAlH4/catalytic hydrogenation (to benzylamine), preserving or following modifications at the iodo site.
Hydrolysis: acidic or basic conditions to amide/acid; can be sequenced after cross-coupling to introduce carboxamide/acid functionality ortho to the new substituent.
Directed metalation/annulation
The ortho CN is a strong directing group for lithiation, enabling further substitution or intramolecular cyclizations (e.g., to indoles/quinazolines after appropriate functionalization).
Applications
Assembly of heteroaryl‑biaryl motifs, alkynylated nitriles, and ortho‑functionalized benzo‑fused scaffolds prevalent in agrochemicals, OLED materials, and medicinal chemistry intermediates.
Practical tip: Exploit the differential reactivity—perform Pd coupling at the iodide first, then manipulate the nitrile; or invert the sequence via DoM if the iodide must be retained.
Reaction Conditions
The following conditions are representative literature guidance for aryl iodides bearing nitriles; optimize for your substrate set. Values are not product specifications.
Suzuki–Miyaura coupling (Ar–I + Ar′–B(OH)2)
Catalyst: Pd(PPh3)4 (0.5–2 mol%) or Pd–XPhos/XantPhos systems.
Temperature/time: 25–80 °C, 1–8 h; aryl iodides often couple at the low end.
Sonogashira coupling (to alkynes)
Catalyst: PdCl2(PPh3)2 (1–2 mol%) + CuI (2–5 mol%) or copper‑free Pd–XPhos.
Base/solvent: Et3N or iPr2NEt in THF, toluene, or DMF; 25–60 °C, 1–6 h.
Buchwald–Hartwig amination
Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) with BINAP, XPhos, or BrettPhos.
Base: NaOtBu or K3PO4.
Solvent: toluene, dioxane, or 2‑MeTHF; 60–110 °C.
Nitrile reductions/hydrolysis
DIBAL‑H (to aldehyde): 1.5–2.5 equiv in toluene/THF at −78 to 0 °C; careful quench to avoid over‑reduction.
LiAlH4 (to amine): 2–4 equiv in THF/Et2O, 0–25 °C, then hydrolytic workup.
Hydrolysis: H2SO4/H2O (reflux) to amide/acid; or NaOH/KOH aq. (reflux) to amide/acid over hours to overnight.
Directed ortho‑metalation (DoM)
Base: s‑BuLi or n‑BuLi (1.1–1.5 equiv) ± TMEDA at −78 to −40 °C in THF/toluene; quench with electrophiles (I2, DMF, CO2, MeI, etc.).
Tips
Exclude oxygen/moisture for Pd couplings when sensitive nucleophiles are present.
CN group is generally robust; strong bases/acids for extended times may hydrolyze—sequence steps accordingly.
Safety and Handling
Follow good industrial hygiene and standard precautions for halogenated aromatics and nitriles. Always consult the SDS for authoritative, item-specific information.
Item-specific hazard data (from Product Data)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/typical for aryl iodides/nitriles)
Likely hazards: skin/eye irritation; harmful if swallowed or inhaled; possible aquatic toxicity. Avoid dust generation and inhalation of particulates.
PPE: lab coat, safety glasses or splash goggles, nitrile gloves; use in a fume hood to minimize exposure to vapors or dust.
Incompatibilities: strong bases/acids for prolonged contact (can induce hydrolysis or side reactions of the nitrile), strong oxidizers, and strong reducing agents. Avoid reactive metals unless intentionally performing metalation.
Thermal considerations: avoid overheating; decompose with release of irritating fumes may occur on thermal stress. Use heat-resistant setup and local exhaust if heating.
First aid (overview): in case of skin contact, wash with soap and water; for eye contact, rinse cautiously with water for several minutes and seek medical attention; if inhaled, move to fresh air; if ingested, rinse mouth—do not induce vomiting; obtain medical advice.
For 2‑iodobenzonitrile as a solid building block, solvent choice governs dissolution, reaction kinetics, and selectivity in cross-couplings or functional group interconversions.
Polarity/miscibility (literature, qualitative)
Poorly soluble in water; readily soluble in mid‑polarity organic solvents: THF, dioxane, EtOAc, toluene, MeCN, DCM; highly soluble in polar aprotics (DMF, DMSO, NMP).
For biphasic couplings (e.g., Suzuki), dioxane/H2O or toluene/EtOH/H2O mixtures are common.
Selection by application
Pd-catalyzed couplings: 1,4‑dioxane, toluene, THF, CPME, or green alternatives like 2‑MeTHF/EtOH/H2O. DMF/NMP enable high solubility at lower temperature but consider workup and EHS.
Nucleophilic substitutions on the nitrile are rare; for nitrile transformations (hydrolysis/reduction), use protic (AcOH, aqueous mineral base/acid) or hydride-compatible media (toluene/THF for DIBAL‑H; Et2O/THF for LiAlH4).
Directed ortho‑metalation (DoM): anhydrous ethers (THF, TBME, 2‑MeTHF) or toluene under cryogenic control; avoid donor solvents that over-stabilize lithiates when high reactivity is needed.
Practical tips
Start with 5–20 mL solvent per gram to establish solubility, warming gently if needed.
For crystallizations, toluene or EtOAc/hexanes often give good morphology; seed if oils persist near the literature mp.
If LC quantitation is planned, prefer HPLC‑grade MeCN/MeOH for sample prep to reduce baseline noise.
Small comparison (literature, qualitative)
THF/dioxane: good for Pd couplings; peroxide monitoring needed.
DMF/DMSO: maximal solubility, harder workups.
2‑MeTHF/CPME: greener ethers with water tolerance and facile phase splits.
Storage and Reconstitution
Storage (from Product Data)
Store protected from light at room temperature.
Shipped under normal conditions.
Container/atmosphere (general good practice)
Keep tightly closed in an amber glass bottle with a PTFE-lined cap. Protect from prolonged humidity; while the solid is not strongly hygroscopic, dryness benefits sensitive transformations.
Shelf life and specifications
Not specified for this item; refer to CoA/Spec Sheet for retest date and acceptance criteria.
Preparing solutions (general guidance)
Weigh quickly and cap promptly to minimize ambient moisture uptake. Dissolve in dry, oxygen-free solvent (e.g., THF, toluene, DMF, DMSO) if required. For air/moisture-sensitive steps, sparge solvents and maintain inert atmosphere.
Typical stock concentrations: 10–100 mg/mL depending on solvent and application. Warm gently to aid dissolution; avoid exceeding the literature melting point to prevent oiling during transfers.
Freeze–thaw
Not generally necessary for the solid. If storing solutions, aliquot into amber vials and store under inert gas at 2–8 °C or −20 °C, protected from light; allow to equilibrate to room temperature before opening to prevent condensation.
Disposal
Dispose of residues/solutions as halogenated organic waste per institutional and regulatory guidelines.
Structure and Identity
A bifunctional aryl building block combining an activated aryl iodide with an ortho nitrile, enabling orthogonal transformations on the ring.
Item-specific identifiers (from Product Data)
CAS: 4387-36-4
SKU: I130037
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Note: the short token “157247” provided is not a standard InChIKey.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (general reference, not item-specific)
Common name: 2-Iodobenzonitrile (o-iodobenzonitrile)
Molecular formula (literature): C7H4IN
Molecular weight (literature): ~229.01 g/mol
Representative SMILES (literature): Ic1ccccc1C#N (one of several valid depictions of the ortho isomer)
Typical InChIKey (literature): often a 27-character hash; consult reference databases for the canonical string.
Structural features (general chemistry)
Functional groups: aryl iodide (Ar–I), nitrile (–C≡N) in the ortho relationship.
Ring system: substituted benzene; the nitrile is a strong π-acceptor and ortho/para director for further electrophilic substitution, while also serving as a directing group for ortho metalation.
Reactivity handles: C–I is highly reactive in cross-coupling (oxidative addition-favorable). The nitrile can undergo hydrolysis (to amide/acid), reduction (to aldehyde or primary amine), and cycloaddition-type transformations.
2D description: A benzene ring bearing an iodine substituent adjacent (ortho) to a linear –C≡N group; the proximity of I and CN enables chemoselective, sequential functionalization strategies.
Synthetic Utility
The ortho juxtaposition of iodine and nitrile offers orthogonal handles that enable convergent route design.
Electrophilic platform (Ar–I)
Rapid oxidative addition with Pd(0) unlocks Suzuki, Sonogashira, Heck, and carbonylative couplings. The CN substituent often survives these transformations, allowing sequential functionalization.
Copper-mediated reactions (e.g., Ullmann-type N/O couplings) are feasible, though iodides favor Pd-catalyzed manifolds for milder conditions.
Nitrile as a latent function and director
Transformations: hydrolysis to amide/acid; reduction to aldehyde (DIBAL‑H) or primary amine (LiAlH4 or catalytic hydrogenation). Pinner and related reactions open access to imidates and amidines.
Directing group: promotes ortho-metalation enabling subsequent quench with electrophiles (halogens, carbonyls), cyclizations (e.g., to quinazolinones after amination), or intramolecular annulations once the iodide or an appended handle is engaged.
Retrosynthetic leverage
Biaryl synthesis via Suzuki at iodine, followed by nitrile editing (hydrolysis/reduction) yields ortho‑substituted benzoic acid/benzamide motifs common in medicinal chemistry.
Alkyne installations (Sonogashira) set up downstream heterocycle formation (e.g., annulations to indoles/isoquinolines depending on partners).
Chemoselectivity strategy
Sequence couplings at Ar–I before harsher nitrile chemistry; alternatively, perform DoM under cryogenic conditions, then functionalize iodine under milder cross-couplings to retain integrity of sensitive installs.
Analytical note: Monitor reactions by GC or LC–MS; the CN group affords a distinctive IR band (~2220–2240 cm⁻¹, literature) to track consumption/formation.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent. No antigen, epitope, species reactivity, clone, or isotype information applies.
Häufig gestellte Fragen
What is the purity of this product?
This product is supplied at ≥97% 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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