This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
313.130 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
5
Exact Mass
312.996 Da
Monoisotopic Mass
312.996 Da
Topological Polar Surface Area
40.900 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
248.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
No assay-specific protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule building block.
General laboratory usage tips (literature-based, not product-specific):
Preparing stock solutions: dissolve in dry DMSO, DMF, acetonitrile, or dichloromethane to prepare 10–100 mM stocks; filter through a PTFE syringe filter (0.22 µm) if particulates are present.
Cross-coupling setup: dry glassware, degassed solvent, inert atmosphere (N2/Ar); add base and catalyst last; monitor by LC-MS or HPLC.
Workup: quench with water/brine; extract into EtOAc or MTBE; wash with sodium thiosulfate if iodine-containing byproducts are suspected; dry (Na2SO4/MgSO4) and concentrate under reduced pressure.
Purification: flash chromatography on silica; gradients of hexanes/EtOAc or toluene/EtOAc are typical. Avoid excessive light/heat during purification to limit deiodination.
For any biological testing, confirm solubility and stability in the chosen assay media, and keep final organic co-solvent below assay limits to prevent nonspecific effects.
Biological Roles
This compound is a synthetic organic intermediate and is not a natural metabolite or cofactor.
Item-specific (Product Data)
Intended use: For research use only.
General context (literature)
Aryl iodides with carbonyl and nitrile functions have no established endogenous biological roles. They are employed as building blocks in medicinal chemistry programs to access libraries of arylated scaffolds via cross-coupling and to modulate polarity through conversion of the nitrile to amides/acids/amines.
Any interaction with biological systems would be incidental and assay-dependent; physicochemical features (hydrophobic aryl iodide, polar CN/C=O) can influence membrane permeability and binding in exploratory SAR but confer no inherent biological function.
No clinical or therapeutic claims are made. Usage should be limited to in vitro/in vivo research consistent with institutional approvals, with appropriate handling and disposal practices.
Buffer Applications
Not typically applicable. 6-(4-Iodophenyl)-6-oxohexanenitrile is a neutral, poorly water-soluble organic building block and is not used to prepare aqueous buffer systems. For experimental work requiring this compound in aqueous media, dissolve first in a miscible organic co-solvent (e.g., DMSO or ethanol) and then dilute into buffer while monitoring for precipitation.
Green Alternatives
While the molecule itself is a halogenated aryl building block (iodide is often chosen for reactivity), greener choices can be made in its use-phase.
Greener solvent/catalyst choices for typical transformations (literature guidance)
Suzuki–Miyaura: replace DMF/dioxane with 2-MeTHF, CPME, or water/ethanol biphasic systems; use aqueous bases (K2CO3, K3PO4). Ligand systems like SPhos/XPhos with Pd can operate in greener media at lower loadings.
Sonogashira: employ copper-free protocols to reduce metal waste; use ethanol/2-MeTHF as solvent; consider nickel catalysis where feasible.
Reductive amination/carbonyl chemistry: ethanol or isopropanol as solvent and hydrogen as reductant (transfer hydrogenation) in place of dichlorinated solvents and borohydrides.
Nitrile hydrolysis: aqueous media with catalytic acid/base under microwave or flow conditions to reduce energy input.
Substrate-level alternatives (context)
Aryl bromides/boronates may be greener from a halogen and resource-criticality perspective than aryl iodides; however, iodides offer superior reactivity at lower temperatures. Balance energy savings vs material footprint.
Comparison snapshot (general, not product-specific)
Greener: 2-MeTHF/H2O or EtOH/H2O, supported Pd or low-Pd nanocatalysts (≤0.1–0.5 mol%), 50–80 C, heptane/EtOAc for extraction.
Operational tips
Minimize halogenated waste by selecting nonchlorinated extraction solvents (EtOAc, MTBE) when compatible.
Use reusable heterogeneous catalysts and flow chemistry to reduce solvent/catalyst inventories and improve safety.
Pharmaceutical Uses
Item-specific (Product Data)
No pharmacopeial status or excipient grade is provided. Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context
Role: synthetic intermediate for discovery chemistry. The aryl iodide enables late-stage diversification via cross-coupling to generate analogs; the nitrile can be transformed into amides/acids/amines for property tuning; the ketone allows reductive amination to introduce amine vectors.
Formulation relevance: if used in screening, stock solutions are commonly prepared in DMSO or DMF due to solubility; compatibility with assay buffers must be verified to avoid precipitation or nonspecific binding.
Manufacturing/process chemistry: iodides can be leveraged for convergent coupling, but supply chain and cost of iodine should be considered; bromide or triflate surrogates may be used upstream with iodination reserved for late-stage steps when necessary.
No therapeutic, diagnostic, or clinical claims are made. This material is supplied strictly for research and laboratory use.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
BP/MP/Density/Refractive Index/UV Cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed expectations for this chemotype (for planning only; not product specifications)
Phase/appearance (literature expectation): para-iodoaryl alkyl ketone–nitriles of comparable size commonly isolate as off-white crystalline solids or low-melting solids; however, oils are possible depending on purity and crystallinity.
Solubility profile: typically soluble in polar aprotic organic solvents (DMSO, DMF, NMP, acetone, acetonitrile, ethyl acetate, dichloromethane, THF) and aromatic hydrocarbons (toluene); sparingly soluble to insoluble in water.
Polarity/logP: the combination of aryl iodide and aliphatic chain with one carbonyl and one nitrile generally imparts moderate to high hydrophobicity (logP often in the ~2.5–4 range for analogs; verify experimentally for this compound).
pKa: no ionizable centers in water under neutral conditions; nitrile and ketone are non-ionizing. No acidic/basic pKa relevant to aqueous buffering expected.
Practical notes
Hygroscopicity/peroxide formation: no known peroxide-forming tendency. Not expected to be hygroscopic; nonetheless, keep tightly closed to avoid moisture uptake and contamination.
Thermal behavior: aryl iodides can undergo homolytic cleavage at elevated temperature; avoid unnecessary overheating and intense UV exposure during storage and handling.
Always consult the item’s CoA/SDS for authoritative physical data before scale-up.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Additives: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research grade: typical for synthetic building blocks; suitable for most discovery chemistry and method development.
High-purity/analytical grades (if specified on CoA): indicate tighter controls on organic/metallic residues and lower non-volatile matter. For cross-coupling chemistry, lower trace metals/halide impurities can improve catalyst performance.
HPLC grade (solvents) vs reagent grade: not applicable to this solid building block; if a solution form is offered, “HPLC grade” refers to solvent quality, not the solute.
Characterization best practices (applicable generally)
Identity confirmation: 1H/13C NMR (diagnostic signals for aryl protons, carbonyl carbon ~195–200 ppm, nitrile carbon ~115–120 ppm), HRMS (M+ or [M+H]+ with characteristic iodine isotopic pattern), IR (sharp CN stretch ~2220–2260 cm−1; C=O stretch ~1680–1710 cm−1; aryl C–I ~500–600 cm−1).
Purity assessment: HPLC/UPLC with diode-array detection; GC may be limited if compound is non-volatile.
Water/peroxide/metal specs: Not specified for this item; refer to CoA/Spec Sheet.
Request the lot-specific CoA to review exact assay, residual solvents, and any stabilizers used for this SKU (I947380).
Reaction and Applications
As a multifunctional building block, 6-(4-iodophenyl)-6-oxohexanenitrile integrates an aryl iodide, a benzoyl carbonyl, and a terminal nitrile, enabling orthogonal diversification.
Aryl iodide reactivity (literature)
Cross-coupling: highly reactive in Pd-catalyzed Suzuki–Miyaura (to aryl/alkenyl substituents), Sonogashira (to alkynes), Heck (to alkenes), and Buchwald–Hartwig amination (to anilines). The iodo handle offers lower activation barriers vs bromo/chloro.
Metal–halogen exchange: iodide facilitates rapid lithium–halogen exchange at low temperature (e.g., with n-BuLi), enabling subsequent electrophile capture; exercise chemoselectivity to protect the ketone/nitrile if needed (e.g., use non-nucleophilic bases, low T).
Carbonyl reactivity (literature)
Nucleophilic additions: organometallic additions to the ketone (Grignard/organolithium) form tertiary or secondary alcohols; nitrile and iodide may require protecting or chemoselective conditions.
Condensation/derivatization: oximes, hydrazones, semicarbazones for characterization or further transformation (e.g., Beckmann rearrangement of oximes).
Reductive amination: formation of benzylic tertiary amines when combined with amines and hydride/H2 catalysis.
Nitrile reactivity (literature)
Hydrolysis: to amide (mild) or carboxylic acid (vigorous acidic or basic conditions).
Reduction: to primary amine (e.g., Raney Ni/H2, borane) or to aldehyde (DIBAL-H, controlled).
Nucleophilic addition: to generate imidates/amidines under Pinner/related conditions.
Application domains (general)
Medicinal chemistry SAR: rapid diversification at the aryl position (via I), linker modulation via carbonyl chemistry, and terminal-group interconversion from CN to amide/acid/amine.
Materials/intermediates: precursor to iodinated aromatics for subsequent functional materials or radiolabel exchange (non-clinical research).
Note: selectivity between the aryl iodide, ketone, and nitrile functions should guide protecting-group strategy and reagent choice.
Reaction Conditions
General literature guidance for the three principal reactivity manifolds of this substrate (not product specifications):
Notes: Avoid strong base/heat that might promote side reactions on the carbonyl.
Buchwald–Hartwig amination (Ar–I → Ar–NR2)
Catalyst/ligand: Pd2(dba)3 (1 mol%) + BrettPhos or RuPhos (2–4 mol%).
Base: NaOtBu, Cs2CO3.
Solvent: toluene, tAmOH, dioxane.
Temperature: 60–100 C.
Ketone reductive amination
Conditions: amine (1.2–2.0 equiv), AcOH (0.2–0.5 equiv), NaBH3CN or H2/Pd-C.
Solvent: MeOH/EtOH or DCE/MeOH mixtures.
Temperature: 0–25 C (imine formation) then rt.
Nitrile transformations
Hydrolysis: H2SO4(aq) or NaOH(aq), reflux (amide) to extended reflux (acid).
Reduction: BH3•THF (1–3 equiv) or H2 (50–60 psi) with Raney Ni/Pd-C, rt–50 C.
Yields vary with substrates and conditions; consult primary literature and run small-scale scouting before scale-up.
Safety and Handling
Item-specific (Product Data)
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aryl iodide–ketone–nitriles (literature/general guidance; not product-specific)
Likely hazards: organic compounds of this class are commonly classified as irritants; avoid inhalation of dust/vapors, skin/eye contact, and ingestion. Combustible; keep away from ignition sources.
Incompatibilities: strong oxidizers (risk of exotherm); strong bases with iodinated aromatics under high heat may promote elimination/iodide release; strong reducing agents can dehalogenate. Avoid reactive metals in the presence of halogens.
PPE: lab coat, safety glasses or splash goggles, and chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood.
First aid (consult SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Spill/cleanup: absorb small spills with inert material (vermiculite, sand), collect for disposal; avoid dust generation; ventilate area.
Firefighting: use CO2, dry chemical, or foam; combustion may produce hydrogen iodide, iodine, carbon oxides, and nitrogen oxides—wear self-contained breathing apparatus.
Waste disposal: dispose of halogenated organic waste according to institutional and local regulations.
Always defer to the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
This product is a neutral, moderately polar organic building block (aryl iodide–aryl ketone–aliphatic nitrile). Solvent choice is typically driven by the transformation being performed rather than by dissolution alone.
Limited to poor: water; alcohols vary (MeOH/EtOH may dissolve upon heating or with co-solvents).
Choosing solvents by application
Cross-coupling (Suzuki/Sonogashira/Buchwald): toluene, dioxane, THF/2-MeTHF, or DMF/DMAc; aqueous cosolvent (K2CO3 base) often used for Suzuki.
Nitrile reductions to amines/amides: protic solvents (MeOH/EtOH/iPrOH) or ethereal solvents with added hydrogen source; for catalytic hydrogenation, alcohols or ethyl acetate are common.
Carbonyl chemistry (oxime/hydrazone formation, reductive amination): alcohols (MeOH/EtOH) or aprotic polar media (MeCN, DCM) with acid catalysis.
Practical tips
If low solubility is encountered at room temperature, warm gently (30–50 C) or use a cosolvent system (e.g., toluene/DMF, DCM/MeOH).
For photolabile iodine functionality, avoid high-energy UV exposure during prolonged operations in transparent solvents; amber glassware is recommended if storing solutions.
Small comparison (general)
DMF/DMAc: high solvency, excellent for couplings; environmental and work-up burdens are higher.
2-MeTHF/CPME: greener ethers, good for organometallics/couplings, easier separation from water.
Toluene/dioxane: thermally robust, common in Pd chemistry; dioxane has regulatory concerns.
Storage and Reconstitution
Item-specific (Product Data)
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance (literature, not product-specific)
Container: store in a tightly closed, light-protective container (amber glass) to minimize photodeiodination and oxidation.
Atmosphere: keep under dry air or inert gas if storing for extended periods; include desiccant if humidity is a concern.
Stability: aryl iodides are generally stable under ambient conditions when protected from light and moisture; avoid prolonged exposure to elevated temperatures.
Reconstitution and solution handling
Solvents: dissolve in dry DMSO, DMF, acetonitrile, dichloromethane, THF, or ethyl acetate. Water solubility is expected to be low; use co-solvent strategies for aqueous applications.
Stock solutions: prepare at 10–100 mM; store aliquots at 2–8 C or −20 C (as appropriate for solvent) to limit freeze–thaw; allow to equilibrate to room temperature before opening to reduce moisture condensation.
Freeze–thaw: minimize cycles; aliquot upon first dissolution. Inspect for precipitation or discoloration before use.
Refer to the lot-specific CoA/SDS for definitive storage recommendations and any stability or impurity profile notes relevant to SKU I947380.
Structure and Identity
Brief overview: 6-(4-Iodophenyl)-6-oxohexanenitrile is an aryl iodide bearing a para-iodophenyl group conjugated to an acyl function, with a five-methylene spacer terminating in a nitrile. The scaffold combines three highly useful handles: an aryl iodide (cross-coupling), a ketone (carbonyl chemistry), and a nitrile (nucleophilic and reductive transformations).
Item-specific (Product Data)
SKU: I947380
Product Name: 6-(4-Iodophenyl)-6-oxohexanenitrile
CAS: 898767-86-7
InChIKey: 17656 (as provided)
Storage Conditions: Room temperature
Category Path: 全部 / 可售 / 生命科学
Research Use Note: For research use only
Computed/literature structural information (general; not item-specific specs)
Preferred line notation (SMILES): Not specified for this item; refer to CoA/Spec Sheet.
Likely constitutional formula (from the name): p-iodophenyl–C(=O)–(CH2)4–C≡N (i.e., an aryl–acyl moiety attached to a pentamethylene nitrile chain)
Ring systems: single benzene ring (para-substituted)
Stereochemistry: none (achiral, no stereocenters implied by the name)
2D structure described in words (literature): A para-iodophenyl ring bonded via its ipso carbon to a carbonyl carbon; the carbonyl is connected to a straight four-methylene chain ending in a cyano group. The aryl iodine is para to the acyl linkage. This places the iodo substituent on the ring, the ketone adjacent to the ring (aryl alkyl ketone), and a terminal nitrile at the opposite end of the aliphatic spacer.
Molecular formula and weight: Not specified for this item; refer to CoA/Spec Sheet. (Approximate formula/mass may be derived from literature interpretation of the name; users should confirm via CoA.)
Synthetic Utility
This scaffold offers orthogonal, sequential diversification routes:
Aryl iodide handle (most reactive aryl halide)
Cross-coupling platform: install aryl, heteroaryl, alkenyl, alkynyl, or amino substituents under Pd catalysis (Suzuki, Sonogashira, Heck, Buchwald–Hartwig). Iodide’s superior leaving-group ability often permits milder conditions and broader substrate scope.
Directed lithiation/iodine–lithium exchange: generate aryllithium at low temperature and trap with electrophiles (e.g., carbonyls, CO2, B(OMe)3) to refunctionalize the ring. Protect/consider the ketone/nitrile to avoid side reactions.
Ketone functionality adjacent to aryl
Nucleophilic additions (Grignard/R2CuLi) to form tertiary alcohols; 1,2-addition can be tuned by solvent/temperature.
Condensations: oxime/hydrazone formation (precursors to Beckmann rearrangement or Wolff–Kishner reduction to methylene), enamine formation (with secondary amines) for alpha-functionalization.
Reductive amination: introduces a benzylic amine vector while retaining the distal nitrile for further derivatization.
Terminal nitrile
Hydrolysis to primary amide (controlled) or carboxylic acid (vigorous), enabling synthesis of ω-acyl derivatives.
Reduction to primary amine (e.g., catalytic hydrogenation or borane), furnishing diamine-like motifs after subsequent carbonyl transformations.
Partial reduction (DIBAL-H) to aldehyde, unlocking further chain elaboration.
Retrosynthetic perspective
The target can arise from coupling of p-iodobenzoyl chloride (or acid) with 6-aminohexanenitrile equivalents, or via acylation of a pentanenitrile Grignard/cuprate with p-iodobenzoyl derivatives, providing flexible entry points for analog generation.
Target Specificity
Not applicable. This product is a small-molecule synthetic building block and is not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
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