This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
333.120 g/mol
XLogP3
3.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
332.965 Da
Monoisotopic Mass
332.965 Da
Topological Polar Surface Area
40.900 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
332.000
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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Recensioni
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Application Protocols
Not applicable. No immunoassay or bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.
Biological Roles
This compound is a synthetic aromatic building block and is not typically used to probe endogenous biological pathways.
No inherent biological role is established for 3-cyano-3′-iodobenzophenone itself (literature/general). Any biological relevance would derive from its transformation into bioactive analogs during medicinal chemistry campaigns.
For in vitro use, it may serve as a hydrophobic scaffold or photoactive motif in materials/photochemistry studies, but such applications are outside physiological function.
Note: For research use only. Not for human or veterinary use.
Buffer Applications
Not typically applicable. 3-Cyano-3′-iodobenzophenone is a hydrophobic organic building block and is not used to prepare aqueous buffer systems.
If aqueous work is required (e.g., bioconjugation after derivatization), dissolution generally proceeds via organic cosolvents (DMSO, DMF) followed by dilution into buffered media with surfactants or co-solvent, validated by solubility tests.
Green Alternatives
While the substrate itself is a halogenated aromatic (iodide), greener choices can be made in process design and solvent/catalyst selection.
Solvent choices (comparison, general)
2-MeTHF vs THF: 2-MeTHF (bio-based, higher bp, easier phase separation) can replace THF in many couplings/additions
CPME vs toluene/dioxane: CPME offers low peroxide propensity and broad applicability in Pd couplings
Water/EtOH mixtures: effective for Suzuki couplings with appropriate ligands/bases; minimize dipolar aprotics
Catalysis
Use precatalysts/ligands enabling low catalyst loadings at lower temperatures (e.g., Pd-PEPPSI, Buchwald biaryl phosphines)
Base selection: K3PO4, K2CO3 in aqueous media to reduce hazardous solvents
Alternative coupling handles (strategy level)
Where feasible, prepare/convert to less halogenated partners (e.g., boronates, diazonium salts) to curtail iodinated waste; recognize trade-offs in step count and overall E-factor
Trade-offs
Aryl iodides provide superior reactivity (lower energy input, higher yields) but generate iodide-containing waste. Greener solvent matrices and efficient catalysis can offset environmental impact through shorter reaction times and reduced energy use.
Pharmaceutical Uses
As supplied, this material is a research-grade synthetic intermediate and is not an approved excipient or API.
Potential roles in pharma R&D (general)
Intermediates for SAR exploration, enabling installation of diverse substituents via cross-coupling through the aryl iodide
Scaffold for photoresponsive or high-aromaticity motifs in discovery chemistry
Pharmacopeial status, residual solvent limits, and excipient monographs: Not applicable/not specified for this item; refer to CoA/Spec Sheet if required for GMP-adjacent research.
Use is restricted to laboratory research settings only.
Physical Properties
Item-specific physical constants are not provided in the product data. The following are general/literature-based expectations for closely related benzophenone derivatives; verify with the item’s CoA/Spec Sheet before use.
State/appearance: Not specified for this item; refer to CoA/Spec Sheet. (Many substituted benzophenones are off-white to pale solids.)
Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general guidance for aryl iodide benzophenones)
Water: very low solubility (literature, qualitative)
Organic solvents: typically soluble in chlorinated solvents (CH2Cl2, CHCl3), moderately soluble in THF, toluene, acetone, ethyl acetate; high solubility in polar aprotics (DMF, DMSO) (literature, qualitative)
Lipophilicity: expected high aromatic character implies moderate-to-high logP (literature expectation for benzophenone derivatives)
UV-vis: benzophenone chromophore absorbs in near-UV; substituents may shift intensity/wavelength (literature, qualitative)
Note: Do not treat these as product specifications. For exact values (mp, purity, residual solvents, elemental analysis), consult the lot-specific CoA.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What grade implies (general guidance)
For synthetic building blocks, common grades include research grade (general synthesis), ≥95–98% purity (NMR/GC/HPLC), or higher for sensitive transformations. Lower UV background is relevant mainly for analytical applications; for coupling chemistry, residual halides/iodide and metal traces can impact catalysis.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. (Aryl iodides are typically offered neat without stabilizers.)
Documentation to review per lot
Assay/purity and identification (1H NMR, 13C NMR, HPLC/GC)
Mass spectrum (HRMS/ESI), IR (CN stretch ~2220–2240 cm−1 (literature)), and compliance with appearance/spec range
Residual solvents, water (KF), metals (if relevant to catalytic use) — Not specified for this item; refer to CoA
Recommendation: For Pd-catalyzed couplings, select lots with low metal contaminants and verify iodide integrity (absence of dehalogenated impurities) by HPLC or LC–MS.
Reaction and Applications
This substrate integrates three orthogonal handles—aryl iodide, aryl ketone, and nitrile—enabling rich diversification and convergent synthesis.
Cross-coupling via aryl iodide (literature)
Suzuki–Miyaura: install aryl/heteroaryl/alkenyl partners under Pd(0) catalysis; iodide ensures high reactivity and milder conditions
Sonogashira: form aryl–alkynes; Pd/Cu with amine base or Cu-free systems using modern ligands
Buchwald–Hartwig amination: introduce anilines/anilides; XPhos/BrettPhos-type ligands often effective with aryl iodides
Carbonylative couplings: CO or CO surrogates to expand the carbonyl framework
Ketone chemistry (literature)
Nucleophilic additions (RMgX, RLi, organozincs) to give tertiary carbinols; stereocontrol via chiral aux/catalysts
Reductions: NaBH4/L-Selectride/DIBAL-H to secondary alcohol; Wolff–Kishner/Clemmensen for deoxygenation as needed
Photochemistry: benzophenone chromophore can act as triplet sensitizer; substituents modulate photoreactivity (evaluate case-by-case)
Nitrile transformations (literature)
Hydrolysis: to amide (mild) or acid (vigorous) under acidic or basic conditions
Reductions: to primary amine (e.g., catalytic hydrogenation, BH3) or to aldehyde (DIBAL-H, controlled)
Cyclizations: as a cyano handle for heterocycle assembly (imidates, amidines)
Orthogonal strategies
Sequence selectivity: exploit iodide (most reactive) first, then manipulate nitrile/ketone; or protect/convert the ketone to an oxime/ketal to steer chemoselectivity
Late-stage diversification of aryl iodide into libraries while retaining CN/CO for further elaboration
Applications span medicinal chemistry SAR, materials/aromatic scaffolds, and labeled intermediates preparation (research use only).
Reaction Conditions
General literature-guided conditions for typical transformations of aryl iodide benzophenones; optimize per substrate and scale.
Suzuki–Miyaura coupling (Ar–I → Ar–Ar)
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-PEPPSI-type (0.5–1 mol%)
Base: K2CO3/K3PO4/Cs2CO3 (2–3 equiv)
Solvent: toluene/EtOH/H2O or 1,4-dioxane/H2O; 2-MeTHF/H2O as greener option
Temp/time: 60–100 C, 2–12 h; aryl iodides often couple at lower temperatures
Solvent: toluene, tBuOH, CPME, or dioxane; 80–110 C, 6–16 h
Sonogashira coupling (Ar–I → Ar–C≡C–R)
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%) or Cu-free systems with bulky ligands
Base/solvent: iPr2NH, Et3N, or NEt3 in THF/DMF; rt–60 C, 2–8 h
Nucleophilic addition to ketone
RMgX or RLi (1.2–2.0 equiv) in dry THF/Et2O at −78 to 0 C; quench with NH4Cl; beware competitive halogen–metal exchange
Ketone reduction
NaBH4 (1.5–2.0 equiv) in MeOH/EtOH or THF/H2O at 0–25 C to give benzhydrol derivatives
Nitrile transformations
Hydrolysis: H2SO4/H2O (reflux) → amide/acid; or NaOH/H2O/EtOH (reflux)
Reduction: H2, Pd/C (3–10 bar) in EtOH/THF; or BH3·THF; DIBAL-H (−78 to −20 C) for partial reduction to aldehyde
Notes
Protect the ketone (as ketal/oxime) if performing lithium–halogen exchange at the iodide
Monitor for dehalogenation under forcing Pd conditions; use mild bases and lower temperatures when feasible
Always run small-scale screens to identify chemoselective windows with this multifunctional substrate
Safety and Handling
Authoritative safety information is provided in the SDS. The following are general precautions for aryl iodide benzophenone derivatives.
GHS/Classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
Likely hazards (general): May cause skin/eye irritation and respiratory irritation if dust is formed; harmful if swallowed. Avoid inhalation of dust and contact with skin/eyes.
Handle solids in a fume hood to avoid dust inhalation
Handling
Avoid exposure to heat sources and strong light; benzophenone chromophores can be photosensitive in some contexts (general precaution)
Prevent contact with strong oxidizers; avoid strong bases/acids during storage
First aid (overview; follow site SOP/SDS)
Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists
Inhalation: move to fresh air; seek medical attention if symptoms occur
Ingestion: rinse mouth; do not induce vomiting; seek medical attention
Fire
Use CO2, dry chemical, or foam; combustion may produce COx, NOx, hydrogen iodide/iodine vapors
Spills/Waste
Avoid dust; collect by gentle sweeping or HEPA vacuum; dispose of as halogenated organic waste per institutional and regulatory guidelines
Always defer to the SDS for this specific SKU for definitive hazard and response instructions.
Solvent Selection
As a nonpolar-to-moderately polar aromatic ketone with an aryl iodide and nitrile, 3-cyano-3′-iodobenzophenone dissolves in many aprotic organic solvents but poorly in water.
Cross-coupling (Suzuki/Sonogashira/Buchwald): toluene, 1,4-dioxane, CPME, 2-MeTHF, THF, or mixed EtOH/H2O with a polar cosolvent; DMF/DMAc for high-temperature operations
Nucleophilic additions/reductions to the ketone: THF, Et2O, or toluene for organometallics; MeOH/EtOH typically avoided with highly basic reagents
Nitrile transformations (hydrolysis/reduction): alcoholic solvents or mixed aqueous-organic systems depending on catalyst/base/acid
Practical tips
For heterogeneous bases (K2CO3, Cs2CO3), mixed biphasic systems (toluene or dioxane with H2O) can accelerate Suzuki couplings
Ensure dryness for moisture-sensitive steps (e.g., Grignard additions to the ketone)
Quick comparison (general)
Toluene: high bp, low polarity; ideal for Pd couplings at 100–120 C
THF/2-MeTHF: good solvation of organometallics; 2-MeTHF offers greener profile
DMF/DMAc: excellent solubility; high boiling but challenging workup; consider greener alternatives where possible
Storage and Reconstitution
Storage conditions (item-specific)
Storage: Room temperature (product data)
Shipped: Normal (ambient) (product data)
General handling guidance
Keep container tightly closed in a dry place; use desiccant to minimize moisture uptake
Store away from strong light and heat sources as a general precaution for aryl iodides and benzophenone chromophores
If long-term storage is planned, consider inert-atmosphere packaging after opening to limit oxidative degradation
Reconstitution/solution preparation
Not applicable to solids per se; dissolve for use in a suitable dry organic solvent (e.g., DCM, THF, toluene, DMF, DMSO), filtered through PTFE if particulate is present
Prepare stock solutions freshly or store aliquots at 2–8 C or −20 C, protected from light and moisture, based on solvent stability (general guidance; verify solubility and stability empirically)
Always consult the lot-specific CoA/SDS for definitive storage limitations and stability information. Research use only.
Structure and Identity
A bifunctional benzophenone building block featuring an aryl iodide and a meta-cyano substituent, useful for cross-coupling and late-stage diversification.
Names
Product name: 3-Cyano-3'-iodobenzophenone (meta-cyano on one ring; meta-iodo on the other)
Planar, conjugated biaryl carbonyl system; no stereocenters
2D structure in words
Two benzene rings linked by a carbonyl carbon. On ring A (relative to the carbonyl ipso), a –CN at position 3. On ring B, an –I at position 3′. The carbonyl is para to neither substituent, giving a meta/meta pattern across the two rings.
Synthetic Utility
The combination of an aryl iodide, a benzophenone carbonyl, and a meta-cyano group affords multiple, orthogonal disconnections.
Aryl iodide handle
High reactivity in Pd-catalyzed cross-couplings (Suzuki, Sonogashira, Heck, Buchwald–Hartwig) facilitates rapid diversification of ring B
Enables metal–halogen exchange (I/Li) at low temperatures for directed lithiation, followed by trapping with electrophiles (requires careful control to avoid ketone/nitrile attack)
Benzophenone carbonyl
Accepts nucleophiles (RMgX/RLi) to form tertiary alcohols; can be protected as ketals/oximes to modulate chemoselectivity during metalation steps
Reductive manipulations (NaBH4/L-Selectride) and deoxygenation strategies furnish diarylmethanes
Meta-cyano group
Robust under many coupling conditions; later convertible to amide/acid (hydrolysis), amine (reduction), or aldehyde (DIBAL-H)
Serves as a directing/withdrawing group, tuning reactivity and electronics for electrophilic/nucleophilic aromatic substitution on the opposite ring
Strategic sequencing (examples)
First, cross-couple the iodide to install complexity; second, chemoselective reduction or hydrolysis of CN; third, manipulate the carbonyl as needed
Alternatively, protect the ketone, perform halogen–lithium exchange, introduce an electrophile, then deprotect
These orthogonal operations support convergent assembly of advanced intermediates in medicinal and materials chemistry.
Target Specificity
Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, enzyme, or biologic. No target, epitope, or species reactivity is defined.
Domande frequenti
How should this product be stored?
Store at room temperature.
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 890098-71-2, the molecular formula is C14H8INO, and the molecular weight is 333.128 g/mol. InChIKey JKUXYTLWFOTEFJ-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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