Ipodate - ≥95% , CAS No.5587-89-3

CAS: 5587-89-3 Cat. No.: I1072979 Formula: C12H14ClI3N2O2 Molecular Weight: 634.42 EC Number: 226-992-7 PubChem CID: 5241

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

CN(C)C=NC1=C(C=C(C(=C1I)CCC(=O)O)I)I

IUPAC Name

3-[3-(dimethylaminomethylideneamino)-2,4,6-triiodophenyl]propanoic acid

InChIKey

YQNFBOJPTAXAKV-UHFFFAOYSA-N

INCHI

1S/C12H13I3N2O2/c1-17(2)6-16-12-9(14)5-8(13)7(11(12)15)3-4-10(18)19/h5-6H,3-4H2,1-2H3,(H,18,19)

Isomeric SMILES

CN(C)C=NC1=C(C=C(C(=C1I)CCC(=O)O)I)I

PubChem CID

5241

Molecular Weight

634.42

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Phenylpropanoic acids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Phenylpropanoic acids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpropanoic acids
• Alternative Parents: Iodobenzenes Aryl iodides Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Formamidines Carboxylic acids Carboxamidines Organopnictogen compounds Organoiodides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: 3-phenylpropanoic-acid - Halobenzene - Iodobenzene - Aryl halide - Aryl iodide - Monocyclic benzene moiety - Benzenoid - Amidine - Formamidine - Carboxylic acid amidine - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Organohalogen compound - Organoiodide - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
• 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

Chemical and Physical Properties

• Molecular Weight: 597.960 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 597.811 Da
• Monoisotopic Mass: 597.811 Da
• Topological Polar Surface Area: 52.900 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 339.000
• 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

No vendor‑validated application protocols are provided for this SKU.

General laboratory handling suggestions (non‑validated):

• Prepare a small test solution to determine solubility: start with DMSO or DMF (10–50 mg/mL), then dilute into the working medium.
• For aqueous systems (if provided as a salt): dissolve in deionized water or buffer, adjusting pH if needed to maintain solubility and stability; filter sterilize (0.22 µm) for cell‑free assays.
• For synthetic use: dry the material under vacuum before air‑/moisture‑sensitive reactions; use anhydrous, degassed solvents for cross‑couplings.

For any specific analytical, biological, or materials protocols related to this SKU: Not specified for this item; refer to CoA/Spec Sheet or validate in‑house.

Biological Roles

Item-specific biological data are not provided for this SKU.

General context (literature/general knowledge, no clinical claims):

• Heavily iodinated small molecules interact primarily through hydrophobic and halogen‑bonding interactions; the iodine atoms increase polarizability and can modulate binding to proteins via halogen bonds with Lewis basic sites.
• The high electron density of iodine confers strong X‑ray attenuation; in laboratory research settings, iodine‑rich organic compounds are studied as radiodense standards or components in imaging phantoms and materials designed to interact with ionizing radiation.
• Metabolism/biotransformation of iodinated aromatics depends on the specific scaffold; deiodination, conjugation (e.g., glucuronidation, sulfation), and oxidative pathways have been reported for related compounds. Exact pathways for this specific material should not be assumed without experimental verification.
• Biological buffer compatibility and osmolarity can be significantly affected by salt forms and concentration; verify compatibility empirically if using in biochemical assays.

Note: Aladdin supplies this product strictly for research and laboratory use. No medical, diagnostic, or clinical application is intended or supported.

Buffer Applications

This compound is not a conventional buffering agent. It does not define a physiologically relevant pKa range suitable for pH buffering in typical biochemical systems (information specific to this SKU is not provided).

Practical guidance:

• If the material is supplied or converted to a salt form and must be prepared in aqueous media for assays, dissolve it in an appropriate buffer selected for your biological system (e.g., phosphate, HEPES, Tris) and confirm that the compound is chemically stable at that pH and ionic strength.
• Prepare concentrated stocks in DMSO or DMF and dilute into buffered aqueous media to the desired final concentration, ensuring that the final organic cosolvent content is compatible with your assay.

For any buffer recipes, pKa values, or ionic strength adjustments specific to this SKU: Not specified for this item; refer to CoA/Spec Sheet and perform small‑scale solubility/stability trials.

Green Alternatives

Ipodate is a heavily halogenated organic compound. While powerful for certain research applications, halogenated substrates can carry environmental burdens.

General green chemistry considerations (literature/general knowledge):

• Avoid unnecessary halogen load: If radiodensity or heavy-atom effects are not required, consider non‑halogenated scaffolds or lighter‑halogen analogs.
• Solvent selection: Favor greener solvents (MeOH, EtOH, 2‑MeTHF, CPME, water) when compatible with stability and performance. Replace DMF/NMP with safer alternatives such as propylene carbonate or Cyrene in appropriate transformations.
• Catalysis: Use ligand/catalyst systems that operate at lower loadings, lower temperatures, and in greener media (e.g., aqueous micellar catalysis for cross‑couplings of aryl iodides).
• Waste minimization: Iodinated waste streams require segregated disposal; design reactions with high atom economy and easy workup (e.g., telescoped couplings, flow chemistry) to reduce waste volume.

Illustrative comparison (informational; not product specifications):

• Objective: radiodensity for phantom/materials research
  • Conventional: iodine‑rich aromatics (e.g., ipodate‑type) — high X‑ray attenuation, halogenated waste.
  • Alternative: bismuth‑ or tantalum‑containing inorganic fillers (e.g., Bi2O3 nanoparticles) — comparable radiopacity; different handling/tox profile; not organic.
• Objective: aryl functionalization platform
  • Conventional: multi‑iodo aromatics — high reactivity in cross‑coupling.
  • Alternative: bromides/chlorides with enabling ligands or C–H activation — lower halogen mass, may need more forcing conditions.

Always evaluate alternatives with life‑cycle and performance trade‑offs in mind.

Pharmaceutical Uses

Aladdin supplies this product for research use only; it is not intended for human or veterinary use, diagnostics, or clinical applications.

Non‑clinical, laboratory‑oriented context (general):

• Reference/standard: Iodine‑rich aromatics are sometimes used as laboratory reference materials in analytical method development where radiodensity or heavy atom content is relevant (e.g., imaging phantom calibration, non‑clinical materials studies).
• Formulation R&D: When exploring radiopaque materials or contrast in preclinical device/materials testing, such compounds can be incorporated into polymer matrices or suspensions to tailor X‑ray attenuation properties for in‑lab evaluation.

Regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet.

Note: No therapeutic or clinical formulation guidance is provided or implied for this SKU.

Physical Properties

Item-specific data

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Storage Conditions (from Product Data): Room temperature

Literature/general expectations for highly iodinated aromatic salts (informational; not product specifications):

• Physical state: typically solid at ambient conditions due to high molecular weight and strong intermolecular interactions.
• Density: often higher than typical organics because of iodine content.
• Solubility: neutral iodinated aromatics tend to be sparingly soluble in water but soluble in polar aprotic solvents (e.g., DMSO, DMF). When provided as an alkali metal salt, aqueous solubility can be appreciable, particularly in mildly basic media.
• Thermal behavior: aryl iodides can decompose on strong heating; melting points are often high and may be accompanied by decomposition.
• UV–Vis: heavy-atom substituted aromatics exhibit strong UV absorption; exact cutoff depends on substituents and conjugation.
• LogP: heavily iodinated aromatics are generally lipophilic unless ionized; salt formation decreases apparent logP in water.

For precise numerical values (bp, mp, density, refractive index, pKa, logP, UV cutoff) specific to this SKU: Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Research Use Note: For research use only.

How to interpret quality for this material (general guidance for professional users):

• Identity confirmation: Verify by NMR, MS, and, for iodinated aromatics, iodine content assay can be informative. For salts, confirm counter‑ion by elemental analysis or ion chromatography.
• Purity assessment: HPLC/UPLC or LC–MS for organic impurities; ion chromatography for inorganic halides/iodide if relevant; water content by Karl Fischer if the material is hygroscopic.
• Absorbance profile: If the compound is to be used in optical applications, request a UV–Vis scan to ensure low background at analytical wavelengths.
• Residual solvents/metals: If using in catalysis or materials research, you may require ICP‑MS for metal traces or GC for residual solvents—request on the CoA when critical.
• Stabilizers: None specified for this item. If stabilizers are present in a particular lot, they will be declared on the CoA; consider implications for downstream reactions or analytics.

Choosing the right grade (general):

• Synthetic research: standard research grade is typically sufficient.
• Analytical reference or high‑sensitivity imaging materials work: consider higher purity/trace analysis data (low UV background, known residual metals/solvents), and documented water content.

Reaction & Applications

Applications below are general to iodinated aromatic scaffolds and intended for research contexts; they are not item-specific specifications.

• Cross-coupling platform: Aryl iodides are among the most reactive substrates in Pd‑ and Ni‑catalyzed cross-couplings. Dense iodination enables selective mono‑ or polysubstitution strategies.
  • Suzuki–Miyaura: install aryl/alkenyl/alkyl groups with boron reagents under mild conditions.
  • Sonogashira: append alkynes; useful for conjugated materials or probes.
  • Buchwald–Hartwig: form C–N bonds with amines; heavy-atom scaffold can tune electronics.
• Deiodination/iodine–halogen exchange: chemoselective reduction (e.g., Bu3SnH/AIBN alternatives, or catalytic hydrogenation) or exchange to aryl bromide/chloride under halogenation protocols provides access to derivative libraries.
• Electrophilic substitution and late-stage diversification: Remaining positions (if any) can be functionalized via nitration, sulfonylation, or directed metalation (with care due to iodine lability).
• Materials/analytical research: High iodine content confers X‑ray opacity; ipodate‑type scaffolds are investigated as standards or building blocks in radiodense materials and imaging phantom research (non-clinical, in‑lab studies only).
• Ionizable functionality: If a carboxylate is present, salt formation can modulate solubility and processability; esterification/amidation provides pro‑scaffolds or handles for conjugation.

Practical tips:

• Protect iodine substituents from strong nucleophiles/bases when not intended to couple.
• Use anhydrous, degassed solvents for Pd/Ni catalysis; monitor by LC–MS to track sequential deiodinations.
• Consider stepwise coupling with orthogonal reactivity (I > Br > Cl) if mixed halides are present.

Reaction Conditions

General conditions commonly employed for aryl iodide transformations (literature guidance; optimize for your substrate):

• Suzuki–Miyaura coupling:

  • Catalyst: Pd(PPh3)4 (0.5–2 mol%) or Pd2(dba)3 with appropriate phosphine/biarylphosphine ligand.
  • Base: K2CO3, Cs2CO3, K3PO4, or NaOtBu (1.5–3.0 equiv).
  • Solvent: dioxane/water, toluene/water, DMF, or MeOH/H2O; 60–90 °C.
  • Notes: Aryl iodides generally react faster than bromides/chlorides; aqueous co‑solvent assists boronate transmetalation.

• Sonogashira coupling (terminal alkynes):

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) with CuI (2–5 mol%) or copper‑free systems with bulky phosphines.
  • Base: Et3N, iPr2NH, or K2CO3; solvents such as THF, DMF, or acetonitrile; rt–60 °C.
  • Notes: Exclude oxygen/moisture for copper‑mediated variants to minimize Glaser homocoupling.

• Buchwald–Hartwig amination:

  • Catalyst: Pd2(dba)3 or Pd(OAc)2 with ligands (e.g., BINAP, XPhos, BrettPhos).
  • Base: NaOtBu, Cs2CO3; solvents: toluene, dioxane, or DMAc; 60–110 °C.

• Reductive deiodination:

  • Methods: catalytic hydrogenation (Pd/C, H2), transfer hydrogenation (ammonium formate/Pd–C), or metal hydrides (carefully chosen to avoid overreduction). Solvents: EtOH, THF, or DMF.

• Ester/amide interconversions (if a carboxyl function is present):

  • Esterification via Fischer or coupling reagents (DIC/DMAP); amidation via EDCI/HOBt, HATU, or CDI in DMF/DCM.

These are starting points; substrate‑specific optimization, careful monitoring (LC–MS/GC), and control experiments are essential.

Safety & Handling

Authoritative safety guidance must be taken from the product’s SDS.

Item-specific hazard information

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for iodinated aromatic salts (literature/general knowledge):

• Likely hazards: may cause irritation to eyes, skin, and respiratory tract. Combustion can release hydrogen iodide and iodine vapors along with carbon oxides.
• Handling: use in a chemical fume hood. Avoid dust generation and inhalation. Employ standard laboratory PPE: lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Wash thoroughly after handling.
• Incompatibilities: strong reducing agents (risk of dehalogenation or halide release), strong bases/acids depending on functional groups, and strong oxidizers (may promote oxidative degradation). Avoid contact with finely divided reactive metals.
• Fire response: use CO2, dry chemical powder, or alcohol-resistant foam; cool containers with water spray. Decomposition products may include iodine/HI—wear self-contained breathing apparatus in a fire scenario.
• First aid (overview): if inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously for several minutes; if ingested, rinse mouth. Seek medical attention if symptoms occur.

Storage (from Product Data): Store at room temperature in a tightly closed container, protected from light and moisture as good laboratory practice.

Solvent Selection

This product is a small organic molecule rather than a solvent; however, solvent choice is important for handling, dissolution, and reaction use.

General guidance (literature/general knowledge for heavily iodinated aromatics):

• Polarity/miscibility: neutral iodinated aromatics often dissolve well in polar aprotic solvents (DMSO, DMF, NMP, acetone, acetonitrile) and in some chlorinated solvents (DCM, chloroform). Alcohols may be modestly effective. Water solubility is typically low unless the compound is provided as a salt; alkali metal salts may be soluble in water and buffered aqueous systems.
• pH effects: if a carboxylate is present, deprotonation increases aqueous solubility; acidification reduces it and can aid crystallization.
• Selection tips for analytics: for LC–MS, acetonitrile/water with 0.1% formic acid or ammonium formate often provides good peak shape; DMSO stock solutions can be diluted into aqueous mobile phase.
• Selection tips for synthesis: use dry, oxygen‑free polar aprotic solvents (e.g., anhydrous DMF, DMAc, dioxane) for cross‑coupling on aryl iodides; consider solvent/ligand compatibility with the catalytic system.

Small comparison (general):

• DMSO: highest solvating power; miscible with water; high bp may complicate workup.
• DMF/DMAc: good balance of polarity and volatility; handle with care for toxicity and residuals.
• ACN: lower viscosity/volatility; may have limited solubility for very heavy substrates.
• Water (for salts): viable if provided as a water‑soluble salt; adjust ionic strength/pH as needed.

Storage & Reconstitution

Item-specific storage

• Storage Conditions: Room temperature (per Product Data). Store in a tightly closed container, protected from moisture and excessive light. Keep in a dry, well‑ventilated place.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution (general guidance; verify experimentally):

• Stock solutions for analytical/screening work: Dissolve in DMSO or DMF to 10–100 mg/mL, then dilute into aqueous buffers or organic media as required. Filter through 0.22 µm if particulate is present.
• Aqueous preparation (if salt form and water‑soluble): Dissolve in deionized water or buffer; gentle warming and stirring can aid dissolution. Adjust pH to favor ionized state if a carboxylate is present.
• Stability of solutions: Prepare fresh as needed or aliquot and store at 2–8 °C for short term. For longer storage, freeze aliquots (−20 °C) to minimize degradation; avoid repeated freeze–thaw cycles.

Labeling note: Exact solubility limits, solution stability, and reconstitution recipes are Not specified for this item; refer to CoA/Spec Sheet and SDS. Always confirm by small‑scale trials before committing valuable samples.

Structure & Identity

• SKU: I1072979
• Product Name: Ipodate
• CAS: 5587-89-3
• InChIKey (as provided): 444265
• SMILES: 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.

General identity notes (literature/general knowledge):

• Ipodate refers to a highly iodinated organic anion (commonly encountered as an alkali metal salt in practice). The scaffold is an aromatic system densely substituted with iodine atoms, contributing to its high electron density and X‑ray opacity.
• Structural features typically include: multiple aryl–I bonds on an aromatic ring system and a carboxylate/ester functionality that can exist as a salt. No stereocenters are expected; structure is predominantly aromatic and planar around the ring systems.
• 2D depiction (in words): an iodine-rich aromatic core bearing several iodo substituents and a carboxyl-derived group capable of forming a salt; the heavy iodine atoms dominate the periphery of the aromatic ring(s).

Synthetic Utility

From a synthetic perspective, iodine‑rich aromatic scaffolds provide versatile handles for diversification (general literature guidance):

• Multiple aryl–I bonds: Highest reactivity among aryl halides in oxidative addition enables stepwise or convergent functionalization via Pd/Ni catalysis.
  • Orthogonal strategies: Selectively transform iodides in the presence of bromides/chlorides to build complexity.
• Carboxylate/ester functionality (if present): Allows interconversion among acid, ester, and amide derivatives. Useful for attaching linkers, polymers, or targeting moieties in probe/materials design.
• Heavy‑atom effect: Facilitates incorporation of X‑ray attenuating units or enhancement of spin–orbit coupling in photophysical systems.
• Late‑stage editing: Deiodination or halogen exchange enables access to less halogenated analogs after key bond constructions, streamlining SAR or property tuning.
• Conjugation chemistry: Activation of the carboxyl group (e.g., as acid chlorides, NHS esters, or via coupling reagents like EDC/HOBt) provides routes to bioconjugates for in‑vitro research.

Workflow tips:

• Sequence planning is critical to manage selectivity among multiple iodides; employ steric/electronic bias or ligand control.
• Monitor metal contamination and remove Pd/Ni residues (e.g., scavenger resins, activated carbon) if the product is destined for sensitive studies.
• Protect potential hydrolyzable moieties during prolonged basic or high‑temperature steps.

Target Specificity

This product is a small molecule, not a biological targeting reagent or antibody. No antigen, epitope, clone, isotype, or species reactivity data apply to this SKU.

Item-specific targeting data: Not applicable.