This compound belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
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
308.120 g/mol
XLogP3
4.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
307.981 Da
Monoisotopic Mass
307.981 Da
Topological Polar Surface Area
24.700 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
204.000
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
No item-specific application protocols are provided for this product. As a general chemical building block, procedures depend on the intended synthetic transformation (e.g., Suzuki, Sonogashira, Heck). Consult standard literature protocols and adapt catalyst/solvent/base to the coupling partner. Refer to the product’s CoA/SDS for handling guidance.
Biological Roles
No biological activity or roles are specified for this catalog item. The following points are general literature context for azobenzene scaffolds used in research; they are not product claims.
Photoswitchable motif: Azobenzenes act as reversible E/Z photoswitches. Upon UV/visible irradiation they can modulate conformation, polarity, and steric profile—tools exploited in photopharmacology and optochemical genetics.
Conjugation handles: The aryl iodide facilitates coupling of azobenzene units to peptides, nucleic acids, and small molecules, creating photoresponsive conjugates that alter binding or structure upon isomerization (e.g., peptide stapling or DNA crosslinking, literature).
Biophysical probes: Derivatives serve as chromophores in materials and membrane studies to interrogate microenvironments via absorbance changes.
Caveats:
Hydrophobicity and limited aqueous solubility generally require co-solvents or delivery systems for biological assays.
No clinical or therapeutic claims are made; this product is for research use only, as noted by the manufacturer.
Buffer Applications
This compound is a hydrophobic aryl iodide and is not a buffering agent. It does not participate in defined acid/base buffer systems for pH control.
Practical note:
If used in biochemical settings, dissolve in a compatible co-solvent (e.g., DMSO, DMF, or ethanol) before dilution into buffered aqueous media. Keep final co-solvent content low (often ≤1–2% v/v) to avoid perturbing biological systems. Verify solubility and photostability in the selected buffer by small-scale tests.
Green Alternatives
Greener strategy focuses on solvent and catalyst systems rather than replacing the aryl iodide (which is itself high-reactivity but iodine-intensive).
Options and trade-offs (literature/guidance):
Greener solvents for cross-coupling: 2-MeTHF, CPME, EtOAc, propylene carbonate, or water/micellar media (e.g., TPGS-750-M) can replace dioxane/DMF in many Pd-catalyzed couplings of aryl iodides.
Ligand/catalyst economy: Modern bulky biaryl phosphines (XPhos, SPhos) or NHC–Pd precatalysts enable lower Pd loadings and room-temperature couplings, reducing energy demand.
Base selection: K3PO4 or carbonate bases in aqueous/biobased solvents can be preferable to strong inorganic bases in polar aprotics.
One-pot telescoping: Use the high reactivity of the iodide to shorten sequences and reduce solvent exchanges (e.g., in situ borylation–Suzuki sequences).
Small comparison (illustrative; not product spec):
Conventional: Pd(PPh3)4 (2–5 mol%), 1,4-dioxane, 80–100 °C.
Greener alternative: Pd-precatalyst (0.1–1 mol%), 2-MeTHF/H2O or micellar H2O, 25–60 °C.
Considerations:
Waste: Iodide-containing waste requires appropriate handling; coupling byproducts (borates, halides) should be minimized by stoichiometric control.
Photochemistry: If photoswitch properties are central, ensure chosen green solvent does not strongly quench or alter isomerization kinetics—verify by UV–Vis/kinetic tests.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item. The notes below are general, literature-based considerations relevant to discovery and formulation research only.
Discovery building block: 4-Iodoazobenzene provides a handle to append azobenzene photoswitches onto drug-like scaffolds using Pd-catalyzed couplings, enabling light-controlled ligand conformation (research context).
Conjugation to carriers: The aryl iodide allows late-stage diversification to affinity tags, polymers, or lipids to study delivery and photoresponsive behavior.
Formulation aspects: Due to hydrophobicity, formulations typically require organic co-solvents, cyclodextrins, or nanosuspension strategies for in vitro work. Photostability must be assessed; protect from UV/blue light during preparation if E/Z ratio is critical.
Important: No therapeutic, diagnostic, or clinical use is claimed or implied for this product. It is supplied strictly for research use only.
Appearance: 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.
Melting point, boiling point, density, refractive index, water/peroxide/metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
General/literature characterization (for context; not product specification):
Empirical formula (literature): C12H9IN2.
Formula mass (literature): ~308.12 g/mol.
Physical state: Typically an orange to red crystalline solid for many para-substituted azobenzenes; exact color and habit can vary by lot and purity.
Solubility profile: Sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, dioxane, acetonitrile, and hot alcohols (literature trends for aryl iodide azobenzenes). Solubility increases with temperature and in aromatic/chlorinated media.
Photophysical note: Exhibits π–π* and n–π* transitions characteristic of azobenzenes; para-iodo substitution typically red-shifts and enhances spin–orbit coupling relative to unsubstituted azobenzene (literature). Exact λmax and ε are system- and solvent-dependent and are not specified for this item.
Important: Use literature data only as planning guidance; consult the item’s CoA/SDS for lot-specific physical data prior to process qualification.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
Guidance on grades and what to expect:
Research-grade aryl iodides are typically supplied with HPLC/GC purity sufficient for synthesis and method development; low-level iodide/iodobenzene/byproduct content and E/Z isomer ratio may be reported on the CoA.
Chromatographic suitability: If using for photochemical/mechanistic studies, low UV background and defined E/Z ratio can matter; request or review UV–Vis and HPLC traces where relevant.
Stabilizers: Azobenzenes can be shipped without stabilizers; when present, stabilizers are listed on the CoA. Absence or presence of stabilizer affects photophysics and purification.
Trace inorganics/halides: For cross-coupling, trace metal content is usually not critical, but for sensitive catalysis or materials applications, consult the Spec Sheet for metals/halide content if provided.
Recommendation: Match grade to application—e.g., standard research grade for routine cross-couplings; higher assay and documented E/Z ratio for photophysics or photoswitching studies. Always verify lot-specific data on the CoA.
Reaction and Applications
4-Iodoazobenzene is a versatile building block that merges a highly reactive aryl iodide handle with a photoswitchable azobenzene core.
Synthetic and materials applications (literature/guidance):
Cross-coupling platform: The para-iodo site undergoes rapid oxidative addition, enabling high-yielding Suzuki–Miyaura (biaryls), Sonogashira (aryl–alkynes), Heck (aryl–alkenes), and Negishi/Stille couplings under comparatively mild conditions.
Heteroatom arylation: Ullmann-type or Pd-catalyzed N-/O-/S-arylations to append donors/acceptors onto the azobenzene framework, tuning photophysical properties.
Metal–halogen exchange: Fast I/Li exchange (e.g., n-BuLi, –78 °C) to access para-lithiated azobenzene, enabling formylation, carboxylation, borylation (via quench with B(OMe)3) or other electrophile traps.
Photoswitch studies: As a parent scaffold for push–pull azobenzenes, enabling red-shifted switching, altered Z→E thermal half-lives, and surface/ polymer attachment via coupling from the aryl iodide terminus.
Surface/conjugate fabrication: Site-specific coupling onto nanoparticles, metal–organic frameworks, and polymers for light-responsive materials and valves.
Practical tips:
Light control: Work under ambient lab light for routine synthesis, but protect from intense UV/blue light when E/Z ratio matters (wrap glassware or use amberware).
Catalyst choice: Aryl iodides generally allow lower Pd loadings (≤1–2 mol%) and milder temperatures than bromides/chlorides; base and ligand choice controls selectivity and rate.
Purification: Silica gel chromatography under minimized light; add 0.1–1% triethylamine to suppress adsorption if tailing observed. Monitor E/Z ratio by 1H NMR or HPLC if relevant.
Reaction Conditions
The following are literature-style, general conditions for aryl iodide couplings and related transformations. They are not product specifications.
Suzuki–Miyaura coupling:
Catalyst: Pd(PPh3)4 (0.5–2 mol%) or Pd-precatalyst with XPhos/SPhos (0.2–1 mol%).
Base: K2CO3, K3PO4, Cs2CO3 (2–3 equiv).
Solvent: 1,4-dioxane/H2O, THF/H2O, 2-MeTHF/H2O, or toluene/H2O.
Temperature/time: 25–80 °C, 1–12 h depending on partner reactivity.
Notes: Aryl iodides generally couple faster than bromides/chlorides; minimize light if E/Z ratio matters.
Sonogashira coupling:
Catalyst/co-catalyst: PdCl2(PPh3)2 (1–2 mol%) + CuI (5–10 mol%).
Base/solvent: Et3N, DIPEA, or i-Pr2NH; or THF/amine mixtures.
Temperature/time: 20–60 °C, 1–8 h.
Notes: Copper-free variants with bulky ligands reduce Glaser homocoupling.
Heck reaction:
Catalyst: Pd(OAc)2 (1–3 mol%) + PPh3 or modern ligands.
Base: Et3N, K2CO3.
Solvent: DMF, NMP, toluene.
Temperature: 80–120 °C.
Buchwald–Hartwig amination:
Catalyst: Pd2(dba)3 or Pd(OAc)2 (1–2 mol%) + XPhos/BrettPhos.
Base: NaOtBu, Cs2CO3.
Solvent: Toluene, dioxane.
Temperature: 60–100 °C.
I/Li exchange and electrophile trapping:
Base: n-BuLi or t-BuLi (1.1–1.5 equiv) at –78 °C in anhydrous THF or Et2O.
Quench: DMF (formyl), CO2 (carboxyl), B(OMe)3 then work up to boronate.
Always optimize conditions for the specific coupling partner and scale; confirm that the azo unit remains intact under chosen conditions.
Safety and Handling
Item-specific hazard classification:
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 considerations for aryl iodide azobenzenes (guidance only; defer to SDS):
Likely hazards: May cause skin/eye irritation and respiratory irritation upon dust generation; avoid inhalation/ingestion and contact. Handle under adequate ventilation.
Photosensitivity: Azobenzenes undergo E/Z photoisomerization. Minimize unnecessary light exposure during analytical measurements or when isomer ratio matters.
Incompatibilities: Strong reducing agents (may affect the azo linkage), strong oxidizers, and strong bases/acids under forcing conditions. Avoid sodium/alkali metals unless intentional for metal–halogen exchange.
PPE: Lab coat, safety glasses or goggles, nitrile gloves. Use a fume hood when weighing or dissolving.
First aid (overview; follow institutional protocols):
Inhalation: Move to fresh air, seek medical attention if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; seek medical advice if irritation continues.
Ingestion: Rinse mouth; seek medical attention.
Fire response: Many organic solids are combustible. Use CO2, dry chemical, or foam. Avoid water streams that may spread contamination.
Spills: Avoid dust; collect mechanically and place in a suitable container for disposal per regulations.
Always consult the product SDS for authoritative, current hazard and response information.
Solvent Selection
This product is a solid aryl iodide, not a solvent. Selection of dissolution and reaction media should consider both the azobenzene chromophore and the aryl iodide reactivity.
General solvent compatibility (literature/guidance):
Preferred dissolution media: Aromatic (toluene, xylene), chlorinated (CH2Cl2, CHCl3), and polar aprotic solvents (THF, dioxane, acetonitrile, DMF, DMSO). Solubility in alcohols increases with temperature.
Poor media: Water and highly protic, strongly basic aqueous systems (low solubility; risk of azo reduction under harsh conditions).
Choosing a reaction solvent:
Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig): 1,4-dioxane, THF, toluene, MeCN, or greener options like 2-MeTHF/CPME; often with an aqueous base component for Suzuki.
Sonogashira/Heck: Triethylamine or DIPEA as both solvent and base, or polar aprotic solvents with added base.
Metal–halogen exchange: Anhydrous ethers (THF, Et2O) at low temperature.
Comparison notes:
2-MeTHF vs THF: 2-MeTHF offers higher hydrophobicity and better phase separation in Suzuki couplings; THF is more polar and can improve solvation of bases/boronates.
Toluene vs dioxane: Toluene tolerates higher temperatures; dioxane enhances solubility for some substrates but carries safety considerations.
Always assess photostability in chosen solvent and minimize unnecessary light during spectral measurements.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store in a tightly closed container in a dry place.
Light sensitivity: As with many azobenzenes, minimize prolonged exposure to strong UV/blue light to avoid altering E/Z composition; amber glass or foil-wrapped containers are recommended for long-term storage.
Atmosphere: Keep container tightly sealed; for long-term storage, an inert headspace (e.g., nitrogen) is prudent to limit oxidative processes, although not strictly required unless specified on the CoA.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution/use:
This is a solid reagent; dissolve in a suitable organic solvent (e.g., DCM, toluene, THF, MeCN, DMF, or DMSO) appropriate for the intended application. Filter if necessary to remove particulates.
For spectroscopic/photochemical work, prepare solutions under reduced light and record the preparation conditions to ensure reproducibility of E/Z ratios.
Freeze–thaw: Not applicable to the solid; for prepared solutions, avoid repeated freeze–thaw cycles that may introduce moisture and affect concentration.
Always consult the CoA/SDS for any lot-specific storage or handling instructions.
Structure and Identity
4-Iodoazobenzene is a para-iodinated azobenzene scaffold combining an electrophilic aryl iodide with a photoswitchable azo (–N=N–) linkage.
Item-specific identifiers from Product Data:
CAS: 6639-27-6
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity (for reference; not item specification):
Molecular formula (literature): C12H9IN2 (para-iodo substitution on azobenzene)
Molecular weight (literature): ~308.12 g/mol
Representative SMILES (literature): Ic1ccc(cc1)N=Nc2ccccc2 (para-iodo on one phenyl ring of azobenzene)
Structural features (general description):
Core: An azobenzene (diphenyldiazene) framework consisting of two phenyl rings linked by an azo (–N=N–) unit.
Substitution pattern: Iodine at the para position of one ring; the other ring is unsubstituted (in the parent 4-iodoazobenzene).
Functional groups: Aryl iodide (excellent leaving group for cross-coupling), azo group (E/Z photoisomerizable chromophore), aromatic rings.
Stereochemistry: Typically exists predominantly as the E (trans) isomer across the –N=N– bond under ambient light; the Z (cis) isomer can be generated photochemically and thermally relaxes back depending on substitution and conditions (literature).
Synthetic Utility
Key reactive elements and their value (literature/guidance):
Aryl iodide (para): Highest oxidative-addition propensity among aryl halides enables mild and rapid Pd-catalyzed coupling. Facilitates late-stage diversification to tune azobenzene electronics (push–pull systems) and photoisomerization kinetics.
Azo group (–N=N–): Serves as a robust, conjugated linker that can be spectroscopically monitored; its photochemistry permits dynamic control over conformation in target molecules and materials.
Representative transformations:
Suzuki–Miyaura: Rapid biaryl formation with aryl/alkenyl/heteroaryl boron partners, enabling diverse substitution on the iodinated ring.
Sonogashira/Heck: Construction of alkyne- and alkene-linked azobenzenes for extended conjugation and surface attachment.
Buchwald–Hartwig/Ullmann-type: N-/O-/S-arylation to install heteroatom substituents (anilides, phenols, thiols) influencing λmax and Z→E half-lives.
Halogen–metal exchange: I/Li exchange at cryogenic temperature followed by electrophile trapping (CHO, CO2, B(OR)3, Me3SiCl, etc.).
Borylation: Pd- or lithiation-based routes to the corresponding pinacol boronate for iterative coupling campaigns.
Practical considerations:
Protect from intense light when maintaining a defined E/Z ratio is needed (analytics, materials alignment).
For scale-up couplings, aryl iodide allows reduced catalyst loadings; verify catalyst/ligand to minimize dehalogenation or azo reduction.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity, epitope, clone, isotype, or species reactivity. No item-specific targeting data are provided.
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