4-Iodophenyl isocyanate - ≥97% , CAS No.15845-62-2

CAS: 15845-62-2 Cat. No.: I352477 Fórmula: C₇H₄INO Peso molecular: 245.019 Número EC: 627-308-3

GRADE & PURITY ≥97%

Synonyms

Benzene, 1-iodo-4-isocyanato- | MFCD00013875 | EN300-148306 | 1-iodo-4-isocyanatobenzene | 1-iodo-4-isocyanato-benzene | FT-0618793 | SCHEMBL93320 | AS-59984 | DTXSID60392135 | KVMKUTIUJGYHBA-UHFFFAOYSA-N | AKOS005207128 | Benzene,1-iodo-4-isocyanato- | G

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Application：

4-Iodophenyl isocyanate may be used in the preparation of: silicon-stereogenic silicon-bridged arylpyridinones; N-(4-iodophenyl)cholesteryl-3-carbamate; N-(4-iodophenyl)pregnenolone-3-carbamate

Specifications

Sinónimos

Benzene, 1-iodo-4-isocyanato- | MFCD00013875 | EN300-148306 | 1-iodo-4-isocyanatobenzene | 1-iodo-4-isocyanato-benzene | FT-0618793 | SCHEMBL93320 | AS-59984 | DTXSID60392135 | KVMKUTIUJGYHBA-UHFFFAOYSA-N | AKOS005207128 | Benzene,1-iodo-4-isocyanato- | G

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥97%

Nombres e identificadores

Pubchem Sid

504762552

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504762552

Sonrisas canónicas

C1=CC(=CC=C1N=C=O)I

IUPAC Name

1-iodo-4-isocyanatobenzene

InChIKey

KVMKUTIUJGYHBA-UHFFFAOYSA-N

INCHI

1S/C7H4INO/c8-6-1-3-7(4-2-6)9-5-10/h1-4H

Isómeros SMILES

C1=CC(=CC=C1N=C=O)I

Peso molecular

245.019

Reaxy-Rn

2716151

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2716151&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Clase Benzene and substituted derivatives
      • Subclass Halobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Clase: Benzene and substituted derivatives
• Subclass: Halobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Iodobenzenes
• Alternative Parents: Aryl iodides Isocyanates Propargyl-type 1,3-dipolar organic compounds Organopnictogen compounds Organooxygen compounds Organoiodides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Iodobenzene - Aryl halide - Aryl iodide - Isocyanate - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organic nitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organoiodide - Organohalogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Descripción: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Punto de inflamación (°F): >230°F
• Punto de inflamación (°C): >110°C
• Punto de fusión (°C): 43-45°C
• Peso molecular: 245.020 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 244.934 Da
• Monoisotopic Mass: 244.934 Da
• Topological Polar Surface Area: 29.400 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 146.000
• 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

Application Protocols

Not applicable. This listing is a chemical reagent rather than an antibody, enzyme, or kit. There are no validated WB/IHC/IF/FC protocols or recommended dilutions. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general procedures and optimization guidance.

Biological Roles

This product is intended strictly for research use; no clinical or in vivo use is implied. 4-Iodophenyl isocyanate does not have a native biological role. The following points describe how aryl isocyanates interact with biomolecules in laboratory contexts (general literature information):

• Reactivity with biomacromolecules: Isocyanates react with nucleophilic residues (e.g., lysine ε-NH2, cysteine thiols, and N-terminal amines) to give ureas or thiocarbamates. This property is exploited for covalent tagging/derivatization of proteins/peptides in vitro.
• Derivatization in analytical chemistry: Aryl isocyanates can be used to derivatize primary/secondary amines to ureas, improving chromatographic retention, UV response, or MS detectability of small molecules.
• Probe and materials precursor: The para-iodo substituent enables subsequent cross-coupling to append reporter groups or affinity handles onto a urea/urethane-modified biomolecular scaffold prepared in vitro.
• Stability considerations: In aqueous buffers, free isocyanates hydrolyze; therefore, any bioconjugation is performed in aprotic, anhydrous organic solvents or microemulsions, followed by quench/purification before exposure to water.

Caveat: Exposure of living systems to isocyanates is hazardous due to sensitization potential; all uses should be confined to controlled laboratory settings with proper containment. No physiological, metabolic, or therapeutic roles are claimed or implied.

Buffer Applications

Not typically applicable. 4-Iodophenyl isocyanate is moisture-sensitive and reacts with water and protic buffers, forming ureas/carbamates and decomposing the –NCO functionality. Consequently, it is not used to prepare or stabilize aqueous buffers.

Practical note for related workflows:

• If derivatizing amines in biomolecules, perform reactions in anhydrous organic media (e.g., dry DMSO, DMF, or acetonitrile) with strictly controlled addition to the biomaterial, then immediately quench and transfer to aqueous buffers only after the –NCO has been fully consumed and excess reagent removed.
• Any required pH control is managed in the subsequent aqueous workup, not during the isocyanate reaction step.

Green Alternatives

Greener choices can be made at two levels: solvent selection and functional-group strategy to avoid handling free isocyanates.

1. Solvent substitution (literature-based comparison):

• Replace halogenated solvents (e.g., DCM) with greener ethers or esters when feasible.

| Use case | Conventional | Greener alternative | Pros | Trade-offs | |---|---|---|---|---| | Urea formation (amines) | DCM, THF | 2-MeTHF, CPME, EtOAc | Lower toxicity/volatility, better EHS | Ensure anhydrous; potential rate changes | | Urethane formation (alcohols) | Toluene, DCM | 2-MeTHF, propylene carbonate (if compatible) | Reduced environmental impact | Viscosity/temperature adjustments needed | | Cross-coupling | Toluene, dioxane | 2-MeTHF, CPME, green anisole | Sustainability, often similar performance | Catalyst/ligand re-optimization |

2. Isocyanate-free routes (strategy-level):

• Curtius/DPPA or acyl azide routes generate carbamates/ureas in situ, avoiding isolated isocyanates—though they introduce azide hazards.
• CDI-mediated coupling of amines with carbonates/carbamic acids to ureas/carbamates without free –NCO.
• Carbonylation strategies (CO/CO2) with amines/alcohols under catalysis to build urea/carbamate frameworks.

Risk reduction practices even when –NCO is used:

• Microscale screening, closed transfers (syringe/Schlenk), LEL-reducing ventilation, and rigorous drying minimize waste and exposure.

Note: Select alternatives must be vetted for reaction compatibility with the aryl iodide and target functional tolerance.

Pharmaceutical Uses

No therapeutic or clinical uses are claimed or supported for this product. For research and process-development contexts, 4-iodophenyl isocyanate may serve as:

• Intermediate for urea/carbamate formation: The isocyanate facilitates rapid assembly of urea motifs frequently encountered in small-molecule APIs and screening compounds (research use only). Para-iodo substitution provides a handle for late-stage diversification.
• Building block in linker design: The –NCO group can cap amines to give aryl ureas that modulate polarity and H-bonding; the aryl iodide allows subsequent palladium-catalyzed cross-coupling to append solubilizing groups or pharmacophore fragments in medicinal chemistry campaigns.
• Materials and excipient-adjacent research: Aryl isocyanate chemistry underpins polyurethane/urea networks; para-iodo substitution can impart X-ray contrast in materials testing. This product itself is not an excipient and has no pharmacopeial monograph to our knowledge (verify per project requirements).

Manufacturing/formulation notes (general):

• Isocyanates must be rigorously excluded from final drug product; when used as intermediates, robust purge and analytical controls (IR for –NCO, LC for residual isocyanate/aniline) are necessary.
• Selection of solvent systems should align with ICH Q3C guidance; greener ethers/esters are preferred when compatible.

Always confirm regulatory suitability and impurity clearance in your specific workflow; this item is sold for research use only.

Physical Properties

Item-specific specifications for this listing:

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general reference values (for context; not product specifications):

• Empirical formula: C7H4INO (literature)
• Formula weight: ~245.02 g/mol (literature, calculated from elemental composition)
• Physical state: typically a low-melting solid or high-boiling liquid among para-halophenyl isocyanates (literature trend); exact MP/BP for this material should be verified on CoA.
• Solubility profile (qualitative, literature):
  • Reacts with water; therefore “solubility in water” is not meaningful—hydrolyzes to corresponding amine/urea/CO2.
  • Soluble in common aprotic organic solvents (e.g., dichloromethane, toluene, THF, acetonitrile); miscibility depends on temperature and purity.
• Density, refractive index, UV cutoff, residual peroxides/metals: Not specified for this item; refer to CoA/Spec Sheet.

Interpretive notes for practitioners:

• The isocyanate group is moisture-sensitive; any measured MP/BP or density can shift with trace hydrolysis or oligomerization. Confirm freshly with a well-sealed, dry sample.
• For quantitative work, measure concentration by NMR (e.g., integrate Ar–H vs. internal standard) or IR (–NCO stretch ~2260–2275 cm−1, literature) to assess integrity before use.

Always consult the product CoA/Spec Sheet for definitive lot-specific physical data.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Interpretive guidance for this compound class:

• Aryl isocyanates are sensitive to moisture and can slowly trimerize (to isocyanurates) or form ureas upon adventitious water exposure. Lots that are “stabilized” may contain trace acid scavengers or inhibitors; absence/presence of stabilizers affects downstream reactivity (e.g., catalytic coupling, urea/urethane formation) and may necessitate pre-purification.
• For synthesis targeting high-purity ureas/carbamates or cross-coupling on the aryl iodide, choose material with:
  • Low hydrolysis byproducts (anilines/ureas) and minimal oligomers (check by 1H NMR/IR: loss of –NCO stretch).
  • Low UV background and non-absorbing stabilizers if the product will be used in photochemical or analytical applications.

Recommended quality checks before use (general best practice):

• IR quick check for –NCO band (~2260–2275 cm−1, literature). Significant attenuation indicates degradation.
• 1H/13C NMR in dry CDCl3 or CD2Cl2 to verify purity and absence of para-iodoaniline/urea impurities.
• KF (Coulometric) moisture determination to ensure anhydrous handling; specification threshold should be defined internally if not provided on CoA.

Documentation:

• When Grade/Purity are not listed, rely on the provided CoA/Spec Sheet for lot-specific assay, residual solvent/metals, and stabilizer disclosure, and adjust purification/drying protocols accordingly.

Reaction and Applications

As a bifunctional building block, 4-iodophenyl isocyanate participates in two main reactivity manifolds: (1) electrophilic isocyanate additions to heteroatom nucleophiles, and (2) cross-coupling chemistry at the aryl iodide.

Isocyanate electrophile chemistry (literature):

• Amines → ureas: Primary/secondary amines react rapidly at 0–25°C in aprotic solvents to furnish mono- or N,N′-disubstituted ureas. Tertiary amines serve as bases/catalysts when needed.
• Alcohols → urethanes (carbamates): Often require base catalysis (e.g., DBU, tertiary amines) or mild heating. Beneficial for installing protecting groups or linkers.
• Thiols → thiocarbamates: Typically very fast at ambient temperature; minimal base required.
• Water → amines/ureas: Hydrolysis with CO2 evolution; important as a decomposition pathway.

Aryl iodide cross-coupling (literature):

• Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig (less common due to NCO sensitivity), and Heck couplings can be achieved under controlled, anhydrous, and base-moderated conditions. The isocyanate must be preserved—choose milder catalysts/ligands and lower temperatures.

Representative applications:

• Rapid synthesis of para-iodophenyl ureas/carbamates as pharmacophore surrogates and linkers in materials and probe chemistry (research use only).
• Late-stage diversification: first couple at iodine (e.g., Suzuki with boronic acids) to access substituted aryl isocyanates, then trap the –NCO with amines/alcohols; or vice versa.

Practical tips:

• Titrate –NCO content by IR prior to stoichiometric reactions.
• Add nucleophile to isocyanate slowly at low temperature to control exotherm.
• For cross-couplings, minimize strong bases and avoid free water; consider base-free or carbonate systems and bulky, electron-rich phosphines to lower required temperature.

Reaction Conditions

General, literature-based conditions for common transformations of 4-iodophenyl isocyanate (guidance only; optimize per substrate):

1. Urea formation (amine + –NCO → urea):

• Solvent: dry DCM, THF, or EtOAc.
• Temperature: 0–25°C (cool initial charge to manage exotherm).
• Stoichiometry: 1.0–1.1 equiv isocyanate to 1.0 equiv amine; tertiary amine base (0–0.5 equiv) as needed.
• Time: 10 min to 4 h depending on nucleophile.
• Workup: quench excess –NCO with MeOH, then standard aqueous wash; monitor by IR (disappearance of ~2260–2275 cm−1 band) and TLC/LC.
• Typical isolated yields (literature): 70–95% for unhindered amines.

2. Carbamate (urethane) formation (alcohol + –NCO):

• Solvent: dry toluene, THF, 2-MeTHF.
• Catalyst/base: DBU, TBD, or tertiary amines (5–20 mol%).
• Temperature: ambient to 60°C.
• Time: 1–12 h.
• Yields (literature): 60–90% depending on sterics and catalyst.

3. Thiocarbamate formation (thiol + –NCO):

• Solvent: dry DCM/THF.
• Conditions: often base-free; 0–25°C.
• Time: minutes to 2 h; typically high yields.

4. Suzuki–Miyaura coupling at aryl iodide (preserving –NCO):

• Solvent: dry toluene, dioxane, or 2-MeTHF.
• Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI-type; base: K2CO3/K3PO4; H2O minimized.
• Temperature: 25–60°C (lower than typical to protect –NCO).
• Time: 2–24 h.
• Notes: Monitor for –NCO degradation; inert and anhydrous setup critical.

All data above are general literature norms and should not be construed as product specifications. Validate conditions on small scale before scale-up.

Safety and Handling

Item-specific hazard fields in Product Data are not populated (GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS). The guidance below is general for aryl isocyanates and does not replace the SDS.

General hazards (literature/industry practice):

• Isocyanates are potent electrophiles; many are skin/respiratory sensitizers and irritants. Aryl iodides may add irritancy.
• Hydrolysis with moisture releases CO2 and forms amines/ureas; exothermic on scale.

PPE and engineering controls:

• Handle in a chemical fume hood. Wear nitrile gloves (double-gloving recommended for extended contact), lab coat, splash goggles/face shield for transfers.
• Use dry, inert gas-blanketed techniques to minimize inhalation/dermal exposure and moisture ingress.

Storage and incompatibilities:

• Storage per Product Data: Store at 2–8°C. Keep container tightly closed under dry inert atmosphere with desiccant. Avoid light/heat which can promote trimerization/polymerization.
• Incompatible with: water/alcohols/amines (nucleophiles), strong bases/acids (can accelerate polymerization), active hydrogen compounds, and oxidizers.

First aid overview (consult SDS for details):

• Skin/eye contact: Immediate decontamination with copious water for 15+ minutes; remove contaminated clothing. Seek medical attention.
• Inhalation: Move to fresh air; obtain medical attention. Provide oxygen if breathing difficulty occurs.
• Ingestion: Rinse mouth, do not induce vomiting; seek medical attention.

Waste and spill response:

• Absorb small spills with dry, inert material (avoid moisture). Quench cautiously with anhydrous alcohol/amine only in a controlled hood after containment; then neutralize and dispose per regulations. For significant releases, evacuate and follow institutional EHS procedures.

Always defer to the official SDS for authoritative, product-specific safety information.

Solvent Selection

Role and polarity considerations:

• 4-Iodophenyl isocyanate is a neutral, moderately nonpolar aryl compound bearing a polar –NCO group that does not hydrogen bond as a donor. It dissolves well in many aprotic organic solvents; it reacts with protic media.

Preferred solvent classes (general guidance):

• Chlorinated: dichloromethane (DCM), chloroform—excellent solubility, low basicity; minimize moisture content.
• Aromatic: toluene, chlorobenzene—good for higher-temperature reactions and cross-couplings on the aryl iodide.
• Ethers: THF, MTBE, CPME—use rigorously anhydrous grades; THF enables low-temperature additions to amines/thiols.
• Polar aprotic: acetonitrile, DMF, DMSO—use only when necessary; basicity/polarity can accelerate side reactions or polymerization.

Avoid/limit:

• Water and protic solvents (MeOH, EtOH, t-BuOH): they consume isocyanates to give carbamates; only use intentionally for urethane formation.

When to choose among options:

• For rapid urea formation with amines: anhydrous DCM/EtOAc/THF at 0–25°C; DCM often provides optimal control with minimal side reactions.
• For cross-coupling (e.g., Suzuki/Sonogashira) on the aryl iodide while preserving –NCO: non-protic solvents like toluene, dioxane, or CPME under carefully dried conditions.

Small comparison (general):

• DCM: excellent control, easy removal; environmental concerns (halogenated waste).
• 2-MeTHF/CPME: greener ether alternatives; ensure low water content.
• Toluene: robust at elevated temperatures; slower dissolution at low temp.

Always dry solvents (molecular sieves, >3 Å) and use inert atmosphere to maintain isocyanate integrity.

Storage and Reconstitution

• Storage conditions (from Product Data): Store at 2–8°C. Shipped on wet ice.
• Container and atmosphere: Keep tightly closed under dry inert gas (nitrogen or argon). Include desiccant where possible. Use amber glass if prolonged light exposure is expected.
• Moisture sensitivity: Isocyanates react with water to form ureas and CO2; even trace moisture shortens shelf life. Open only in a dry box or under a dry nitrogen blanket and promptly reseal.
• Handling practices:
  • Pre-dry syringes/needles/vials and solvents (3Å sieves or distillation).
  • Minimize headspace and transfer times; consider septum-capped bottles for syringe withdrawal.
  • Record the date of first opening; consider aliquoting to reduce repeated exposures.
• Reconstitution: Not required; supplied neat. If dilution is needed, prepare an anhydrous stock solution (e.g., in dry DCM, THF, toluene, or acetonitrile) immediately before use. Store solutions at 2–8°C under inert gas and use within the same day for best integrity.
• Stability indicators: Monitor by IR for the –NCO stretch (~2260–2275 cm−1, literature). Loss or significant shift indicates hydrolysis/oligomerization.
• Disposal: Quench residual reagent with a controlled addition of anhydrous alcohol or dilute amine in an appropriate solvent in a fume hood, then dispose according to institutional and regulatory guidelines.

Always consult the product CoA and SDS for definitive storage and handling instructions for the specific lot.

Structure and Identity

Brief description: 4-Iodophenyl isocyanate is a para-iodo substituted aryl isocyanate comprising an electrophilic –N=C=O group on a phenyl ring that also bears an iodine atom at the para position. This dual functionality (isocyanate + aryl iodide) makes it a versatile bifunctional building block.

• Item-specific identifiers (from Product Data):

  • SKU: I352477
  • CAS: 15845-62-2
  • CID: 3399787
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature structural identifiers (for reference only):

  • Preferred SMILES (literature): O=C=Nc1ccc(I)cc1
  • Molecular formula (literature): C7H4INO
  • Molecular weight (literature): ~245.02 g/mol

• 2D structural features (general description):

  • Aromatic ring: monosubstituted phenyl bearing two para-disposed substituents.
  • Functional groups: aryl isocyanate (–N=C=O) para to an aryl iodide (–I).
  • Connectivity: the isocyanate nitrogen is bonded directly to the aromatic carbon (Ar–N=C=O). Iodine is para to the isocyanate on the ring (1,4-relationship).
  • Stereochemistry: none (achiral, planar aromatic core). No E/Z or chiral centers.

• Category path (from Product Data): 全部 / 可售 / 化学和生化试剂

Note: All identity data not explicitly listed under Product Data should be confirmed against the product’s CoA/Spec Sheet for this specific lot.

Synthetic Utility

Key reactive motifs:

• Electrophilic –N=C=O enables rapid formation of ureas (amines), carbamates (alcohols), and thiocarbamates (thiols). These transformations often proceed under mild, base-catalyzed or even base-free conditions.
• Aryl iodide is a highly activating leaving group for cross-coupling (Suzuki, Sonogashira, Heck) and metal–halogen exchange, permitting orthogonal manipulation to introduce diverse functionality.

Strategic uses in synthesis (literature):

• Divergent synthesis: Sequentially address iodine then –NCO, or vice versa. Example sequences:
  1. Suzuki coupling with a boronic acid to install a substituent, followed by urea formation with a specific amine to furnish a target library.
  2. Trap –NCO with an amine to set a urea pharmacophore, then use Sonogashira to append an alkynyl tag for conjugation or materials applications.
• Protecting-group logic: The isocyanate can be temporarily converted to a carbamate/urea as a handle, then manipulated; however, reversibility is limited compared to classic protecting groups.
• Directed assembly of bifunctional linkers: The para relationship of I and –NCO offers predictable substitution patterns and minimized steric clash.

Operational guidance:

• Maintain anhydrous, oxygen- and moisture-free conditions. Verify –NCO content by IR before scale-up.
• For sensitive substrates, perform cross-couplings using milder bases (e.g., K3PO4/K2CO3) and lower temperatures with electron-rich ligands to preserve –NCO.
• Quench excess isocyanate with a benign nucleophile (e.g., aniline or MeOH) before aqueous workup to simplify purification.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.