This compound belongs to the class of organic compounds known as iodobenzenes. These are aromatic compounds containing one or more iodine atoms attached to a benzene.
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
Not applicable. No validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small‑molecule reagent. For chemical use, see Reaction Conditions and Synthetic Utility for general procedural guidance. For analytical internal standard use, follow your method’s specific sample preparation and calibration protocols.
Biological Roles
This product is a small halogenated aromatic used as a chemical reagent; it does not serve a biological role.
General/literature context
Iodobenzene‑d5 is employed as an isotopic internal standard in analytical chemistry (e.g., GC‑MS) to quantify related aromatic compounds in complex biological or environmental matrices because it co‑elutes similarly but is resolved by mass.
Deuterium labeling can be used in metabolism studies to trace fate of the phenyl fragment in synthetic analogues; the label is not radioactive and does not change connectivity, minimizing perturbation of biochemical properties relative to protiated analogues.
Safety note
No clinical or therapeutic claims are implied. Handle as a laboratory chemical; consult the SDS for toxicological information.
Buffer Applications
Not typically applicable. Iodobenzene‑d5 is a nonpolar organic reagent and is not used to prepare aqueous buffer systems. For practical guidance, refer instead to the Reaction & Applications, Synthetic Utility, and Solvent Selection sections.
Green Alternatives
While iodobenzene‑d5 is often uniquely required for isotopic labeling, consider greener strategic choices in the overall synthesis.
Replace aryl iodides with aryl bromides or chlorides when feasible; they are less resource‑intensive to produce, though often require more active catalysts/conditions. This may not be suitable when isotopic phenyl‑d5 transfer from the aryl halide itself is essential.
Use aryl diazonium salts or aryl sulfonates (e.g., tosylates/triflates) as alternatives in cross‑coupling; they can sometimes be generated in situ, reducing halogen waste.
Solvent and process selection
Favor bio‑derived or safer solvents (e.g., 2‑MeTHF, CPME, propylene carbonate, aqueous ethanol) over chlorinated hydrocarbons when compatible with the catalytic system.
Employ continuous flow for exotherm control and reduced solvent inventories, especially in photoredox or high‑temperature couplings.
Comparison snapshot (general; not item-specific)
Aryl iodide vs bromide: iodides enable lower temperature and higher rate but produce iodine‑containing waste; bromides may require higher energy input but reduce iodine waste.
Waste minimization
Choose ligand/catalyst systems that operate at low loadings and enable base recycling; capture/recycle iodine when feasible.
Pharmaceutical Uses
Item-specific (from Product Data)
No pharmacopeial status or excipient role is provided; For research use only.
General/process chemistry context (no therapeutic claims)
Isotopically labeled aryl halides such as iodobenzene‑d5 are valuable in tracer studies, impurity profiling, and synthesis of deuterium‑labeled API intermediates for PK/ADME investigations.
Aryl iodides are commonly used as electrophiles in C–N and C–C bond‑forming steps en route to APIs; using the d5 analogue enables incorporation of a phenyl‑d5 motif for internal standards or to modulate analytical response without significantly altering physicochemical properties.
In QC/analytical development, deuterated analogues serve as stable isotope internal standards for LC‑MS/GC‑MS assay validation and lot‑to‑lot tracking.
Practical notes
Verify isotopic enrichment and chemical purity on the CoA to ensure suitability for regulated analytical methods.
Maintain inert, light‑protected storage to preserve isotopic and chemical integrity over long projects.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature values for closely related substance (iodobenzene) and deuterated analogue guidance (not specifications)
Boiling point: iodobenzene 188–189 °C (literature); iodobenzene‑d5 expected to be very similar.
Melting point: iodobenzene −30 to −31 °C (literature); deuterated analogue expected comparable.
Density: iodobenzene ~1.83 g/mL at 25 °C (literature); deuterated analogue expected within a few percent.
Solubility: negligible in water; miscible with common organic solvents (e.g., THF, toluene, ether, dichloromethane) (literature, qualitative).
Vapor pressure: low at ambient temperature (literature, qualitative for aryl iodides).
General interpretive notes for users
Isotopic substitution (H→D) minimally affects phase behavior; expect handling similar to iodobenzene.
Due to high polarizability of iodine, the liquid is relatively high‑index and dense compared to lighter aryl halides.
For exact item specifications (e.g., water content, isotope enrichment, residual solvents), consult the CoA/Spec Sheet; they are not provided here.
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What to look for with isotopically labeled aryl iodides (general guidance)
Isotopic enrichment: For deuterated reagents, the %D at each labeled position and overall isotopic purity are critical. This product’s enrichment is not specified here; verify on the CoA.
Chemical purity: Residual unlabeled iodobenzene (C6H5I), water, and halide impurities can impact spectral clarity and coupling yields. Look for GC/LC area % and residual solvent profiles on the Spec Sheet.
Metals: Trace Pd/Cu/Ni may be relevant if the material was produced via cross‑coupling; limits are not provided here.
Stabilizers: None stated for this item. If stabilizers or antioxidants are used, they will be listed on the CoA; absence/presence can affect downstream catalysis.
Practical implications
For NMR/MS internal standard applications, higher isotopic enrichment and low protio content are essential to avoid overlap. For cross‑coupling, very high chemical purity is typically adequate even with modest residual protio content, but verify specifications.
If low UV background is important (e.g., HPLC monitoring), ensure any stabilizers or residual aromatics are reported on the CoA.
Reaction and Applications
Item-specific (from Product Data)
Manufacturer Applications: Not specified beyond listing; reagent for research use only.
Principal uses (literature/general for iodobenzene‑d5)
Isotopic labeling: Source of a phenyl‑d5 fragment for the synthesis of deuterated arenes via cross‑coupling (e.g., Suzuki–Miyaura with boronic acids/esters; Sonogashira with terminal alkynes; Heck arylation with alkenes; Negishi/Kumada with organozincs/magnesiums; Buchwald–Hartwig amination to anilines‑d5).
Analytical internal standard: Mass‑shifted standard for GC‑MS/LC‑MS quantitation of iodobenzene or related aromatics; deuterium provides +5 Da shift without changing chromatographic behavior dramatically.
Mechanistic probes: H/D kinetic isotope effect studies on electrophilic aromatic substitution of derived products or in oxidative addition steps.
Photoredox/radical chemistry: Aryl iodides undergo facile single‑electron reduction to aryl radicals; iodobenzene‑d5 enables preparation of phenyl‑d5 labeled products under Ni/photoredox dual catalysis or EDA complex activation.
Practical notes
Oxidative addition order I > Br > Cl provides high reactivity toward Pd(0)/Ni(0) catalysts; milder conditions can be used versus bromides/chlorides.
Preserve isotopic integrity: avoid strongly protic/acidic media and elevated temperatures that may promote H/D exchange in downstream intermediates.
For cross‑coupling, ensure base and solvent do not introduce protium exchange at benzylic or heteroatom‑bound positions in coupling partners.
Reaction Conditions
General literature guidance for aryl iodide couplings (for planning; not item-specific specifications). Optimize per substrate.
Suzuki–Miyaura biaryl coupling
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1 mol%) with SPhos/XPhos.
Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
Solvent: toluene, 1,4‑dioxane, or THF; often H2O (0–30%) improves rates.
Temperature/time: 50–90 °C, 1–12 h.
Notes: aryl iodides typically give high conversions at lower temperature versus bromides/chlorides.
Buchwald–Hartwig amination
Catalyst: Pd2(dba)3 (1–2 mol%) with BINAP, BrettPhos, or XPhos; or Pd(OAc)2 precatalyst systems.
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: toluene, dioxane, or t‑AmylOH.
Temperature: 60–100 °C; 2–16 h.
Sonogashira coupling
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%).
Base/Solvent: Et3N or iPr2NH as both base and solvent; or THF/amine mixtures.
Temperature: rt–60 °C; 2–8 h. Copper‑free variants use Pd with bulky ligands.
Photocatalyst: Ir(ppy)3 or [Ru(bpy)3]2+ (0.5–2 mol%); NiCl2•glyme (5–10 mol%) with bipyridine ligand.
Light: blue LEDs; solvent MeCN/DMF; rt–40 °C.
Isotopic integrity note
Avoid strong acids/protic solvents at high temperature that could enable H/D exchange in sensitive intermediates. Use dry, degassed conditions to suppress side reactions (e.g., protodeiodination).
Safety and Handling
Item-specific (from Product Data)
Storage: Store at 2–8 °C, protected from light, argon charged.
Shipping: Shipped on wet ice.
GHS/Signal word/H‑statements/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/standard practice; defer to SDS for authoritative data)
Likely hazards for aryl iodides: may cause skin/eye irritation and be harmful if swallowed or inhaled; potentially hazardous to aquatic life. Avoid aerosol formation and inhalation of vapors.
PPE: use chemical splash goggles, lab coat, and nitrile gloves; handle in a fume hood.
Incompatibilities: strong oxidizers; strong bases at elevated temperature; reactive metals in the presence of halide activation. Avoid prolonged exposure to light (product note) and heat.
Special risks/notes: Although aryl iodides are generally stable, light can promote homolysis leading to trace iodine/HI formation—hence protection from light and inert gas blanket are advisable for long‑term stability and isotopic integrity.
First‑aid overview (general)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin contact: wash with soap/water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product’s SDS for definitive hazard classification and response measures.
Solvent Selection
This product is a labeled aryl iodide reagent rather than a solvent. Solvent selection relates to dissolving and reacting iodobenzene‑d5 in synthesis or analysis.
Practically insoluble in water; readily soluble in nonpolar to moderately polar organics (toluene, hexanes, diethyl ether, THF, dioxane, dichloromethane, acetonitrile).
Choosing solvents for typical uses
Cross‑coupling (Suzuki/Heck/Buchwald–Hartwig): toluene, dioxane, THF, DMAc, DMF, or mixed aqueous alcoholic systems depending on base and catalyst.
Radical/photoredox arylations: MeCN, DMF, DMSO, or acetone are common due to polarity and photochemical transparency.
GC/LC sample prep: hexane, isooctane, or DCM for GC; acetonitrile or methanol for LC (ensure compatibility with detectors and sample cleanup).
Practical tips
Ensure solvents are anhydrous when moisture‑sensitive catalysts or boron reagents are used.
If using for isotopic internal standards, choose solvents that minimize H/D exchange risk (avoid strongly protic/acidic media and high temperatures).
Comparison (general)
Aryl iodides dissolve better in aromatic and chlorinated solvents than in highly aliphatic low‑polarity media; however, reaction rates in cross‑coupling are often optimized in ethers/dioxane due to catalyst solubility.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Store at 2–8 °C, protected from light, argon charged.
Shipping: Shipped on wet ice.
Research Use Note: For research use only.
Practical handling guidance (general)
Keep container tightly closed; maintain inert headspace (argon) to preserve long‑term stability and isotopic integrity. Minimize headspace exchanges.
Protect from light during use and storage (foil‑wrap amber bottles if aliquoted). Avoid prolonged heating.
No reconstitution is required; supplied neat. If viscosity increases or partial solidification occurs at low temperature, allow to warm gently to ambient and mix thoroughly before dispensing.
For air‑sensitive catalytic applications, transfer via syringe or cannula under inert atmosphere to avoid moisture/oxygen pickup.
After opening, consider aliquoting under argon to reduce repeated headspace exposure.
Stability notes (general)
Aryl iodides are generally stable under recommended storage; trace iodine formation can occur upon light/air exposure over extended periods—periodically verify appearance and assay if used for quantitative standards.
Avoid contact with strong oxidizers and strong bases during storage.
Refer to the product’s label and CoA/SDS for any additional, lot‑specific instructions.
Structure and Identity
Brief overview: Iodobenzene‑d5 is the deuterium‑labeled analogue of iodobenzene, consisting of a benzene ring in which five ring hydrogens are replaced by deuterium and bearing an iodine substituent. It is an isotopically enriched aryl iodide used in labeling and cross‑coupling chemistry.
Item-specific (from Product Data)
SKU: I266085
CAS: 7379-67-1
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (identity details; not item-specific specifications)
Common name: Iodobenzene‑d5 (phenyl‑d5 iodide)
Isotopic formula (literature): C6D5I
Average molecular weight (literature): ~209.0 g/mol (C6 = 72.066; D5 ≈ 10.07; I = 126.90)
Structural features: six‑membered aromatic ring bearing iodine at one ring carbon; five ring positions deuterated (D). No stereocenters; planar aromatic system.
2D structure in words: An iodine atom is bonded to a benzene ring. The remaining five ring positions carry deuterium atoms (D) rather than protium (H).
General notes
Isotopic labeling does not change connectivity but modifies mass, vibrational frequencies, and can subtly affect reaction kinetics (kinetic isotope effect).
Synthetic Utility
Iodobenzene‑d5 is a highly useful isotopically labeled electrophile for C–X activation chemistry.
Key functional handle
Aryl iodide (C–I) bond: excellent leaving group; fastest oxidative addition among aryl halides to Pd(0)/Ni(0). Enables mild conditions and broad substrate scope.
Suzuki–Miyaura: C6D5–I + Ar–B(OR)2 → C6D5–Ar under Pd(0), base (K2CO3, K3PO4, Cs2CO3), in toluene/dioxane/THF with or without H2O.
Buchwald–Hartwig amination: C6D5–I + R2NH → C6D5–NR2 (Pd/XPhos/BINAP; base NaOtBu or Cs2CO3) for anilines‑d5.
Sonogashira: C6D5–I + RC≡CH → C6D5–C≡C–R (Pd/CuI; Et3N/amine base) followed by hydrogenation to C6D5–CH2–R if desired.
Heck: arylation of alkenes (Pd, base) to give stilbenes/styrenes bearing C6D5.
Negishi/Kumada: coupling with organozinc/magnesium reagents to access C6D5‑alkyl/aryl products.
Photoredox/Ni dual catalysis: reductive arylation of radicals (e.g., with carboxylates or silicates) for labeled scaffolds.
Retrosynthetic value
Directly installs a phenyl‑d5 unit late‑stage, avoiding H/D exchange protocols that can erode labeling at sensitive positions.
Practical guidance
Choose catalysts/ligands that minimize protodehalogenation; thoroughly degas and use dry solvents. Monitor for any isotopic dilution from inadvertent H/D exchange in protic media.
Target Specificity
Not applicable. This product is a small‑molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope, species reactivity, clone, or isotype data are relevant.
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