3,4,5-Triiodobenzaldehyde - ≥95% , CAS No.1083181-39-8

CAS: 1083181-39-8 Cat. No.: T1014076 Formula: C₇H₃I₃O Peso molecolare: 483.81 PubChem CID: 71463636

QUALITÀ & PUREZZA ≥95%

Storage

Room temperature

Specifiche

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1=C(C=C(C(=C1I)I)I)C=O

IUPAC Name

3,4,5-triiodobenzaldehyde

InChIKey

HMOZUVUNDIAPAH-UHFFFAOYSA-N

INCHI

1S/C7H3I3O/c8-5-1-4(3-11)2-6(9)7(5)10/h1-3H

Isomeri SMILES

C1=C(C=C(C(=C1I)I)I)C=O

PubChem CID

71463636

Peso molecolare

483.81

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Benzoyl derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzoyl derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoyl derivatives
• Alternative Parents: Benzaldehydes Iodobenzenes Aryl iodides Organoiodides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzoyl - Benzaldehyde - Aryl-aldehyde - Iodobenzene - Halobenzene - Aryl iodide - Aryl halide - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organoiodide - Organohalogen compound - Aldehyde - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 483.810 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 483.732 Da
• Monoisotopic Mass: 483.732 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 139.000
• 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 application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions tab for representative procedures and to current literature for scale-up and optimization.

Manufacturer applications: Not specified for this item; refer to the catalog page and CoA/Spec Sheet. Research Use Only.

Biological Roles

Item-specific biological roles: Not applicable; this is a synthetic building block for research use only.

General context (literature):

• 3,4,5-Triiodobenzaldehyde is not known as a natural metabolite or biochemical cofactor. The aldehyde functionality can form reversible Schiff bases with primary amines in biomolecules, but such reactions are nonspecific and typically of analytical or conjugation interest rather than intrinsic biology.
• Heavily iodinated aromatics are of interest in imaging and materials research due to high atomic number (X-ray attenuation) and polarizability; however, these are application concepts, not biological functions.
• In bioconjugation method development, the aldehyde can be used to create imines/oximes/hydrazones with aminooxy or hydrazide reagents under mild aqueous-organic conditions, followed by reduction if stable linkages are desired.

Compliance note: No medical, diagnostic, or therapeutic uses are claimed or supported for this product. For research use only.

Buffer Applications

This compound is a hydrophobic aromatic aldehyde and is not used as a buffering agent. It lacks acid/base pairs in the physiological pH range suitable for buffering.

Practical note: If used in biomolecule conjugation method development, reactions are typically run in acetate, phosphate, or anilinium-catalyzed buffers with organic co-solvent (e.g., 10–30% DMF/DMSO) to solubilize the aldehyde. Select the buffer based on the nucleophile (aminooxy/hydrazide) and desired pH (commonly pH 4–6 for oxime/hydrazone formation).

Green Alternatives

Greener strategy revolves around solvent and catalyst choices; the substrate itself is a heavily halogenated aromatic and not inherently “green.” The aim is to reduce process mass intensity and hazardous solvent use in its transformations.

Greener options (literature/general):

• Replace polar aprotic solvents: Use 2-MeTHF, CPME, or toluene instead of DMF/DMAc/NMP when feasible in cross-couplings or Wittig-type steps.
• Aqueous micellar catalysis: Employ surfactant media (e.g., TPGS-750-M) for Suzuki/Sonogashira at room temperature to 45 C with ppm-level Pd, reducing solvent and metal load.
• Base and oxidant choices: Use carbonate or phosphate bases over hydroxides; prefer TEMPO/bleach or O2 for oxidations rather than chromium(VI).
• Workup minimization: Telescoping coupling and carbonyl steps to reduce solvent exchanges and silica waste.

Concise comparison (general, not item-specific):

• DMF/DMSO/NMP: excellent solvation; regulatory and workup burdens.
• 2-MeTHF/CPME: renewable/low peroxide tendency (CPME) with good hydrophobicity; sometimes lower solubility, may require heat.
• Toluene/EtOH/water systems: greener profile and facile separations; may demand careful base and ligand selection to maintain activity.

Trade-offs: Greener media can slow reactions or require re-optimization of ligand/base; ensure adequate mixing and oxygen control for O2/TEMPO oxidations.

Pharmaceutical Uses

Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

General, non-clinical context:

• 3,4,5-Triiodobenzaldehyde may serve as a synthetic intermediate in API research, enabling rapid diversification via its three aryl iodides and subsequent manipulation of the aldehyde to alcohols, acids, or olefins.
• The dense iodination can be leveraged to build radiopaque motifs or as a strategic handle for late-stage cross-coupling diversification in medicinal chemistry platforms.
• No direct therapeutic, diagnostic, or clinical claims are made. This product is sold strictly for research and process development uses (Research Use Only).

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations (for professional planning only; not item specifications):

• Physical state: typically a high-melting crystalline solid for tri-iodinated aromatics.
• Color/appearance: off-white to pale yellow crystals are common for polyiodo aromatics (literature/experience); actual appearance may vary by lot.
• Solubility profile: sparingly soluble in nonpolar hydrocarbons; more soluble in moderately polar organics (CH2Cl2, THF, toluene when warm), and in polar aprotics (DMF, DMSO). Very low expected aqueous solubility.
• LogP: high, driven by three iodines (qualitative, literature expectation).
• UV-vis: aromatic π–π* absorption typical near 200–280 nm (literature, qualitative).

Handling-relevant traits (general):

• The aldehyde can slowly oxidize to the corresponding carboxylic acid on prolonged air exposure, especially in moist conditions.
• The aryl iodides enhance molecular polarizability; materials can be dense relative to unsubstituted aromatics.

If exact BP/MP, density, refractive index, UV cutoff, water/peroxide/metal limits are needed: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity information: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and implications (general guidance):

• For cross-coupling and carbonyl transformations, trace metal content, halide integrity (no deiodination), and low moisture are critical. If “high-purity” or “anhydrous” grades are offered, they help minimize side-reactions (e.g., aldehyde hydration/oxidation) and catalyst poisoning.
• If an HPLC grade or “low UV absorbance” solvent is ever referenced, that pertains to solvents, not this solid; for this aldehyde, purity is usually assessed by HPLC/GC and NMR.
• Stabilizers: Not typically required for this compound; any stabilizer or inhibitor would be disclosed on the CoA/Spec Sheet. If present, understand its potential to interfere (e.g., residual acid/base affecting condensations).

What to check on receipt (practical QA):

• Visual inspection for discoloration (browning can indicate oxidation to acid or iodine release).
• Rapid ID/purity check by 1H NMR (distinct aldehyde proton ~9.8–10.3 ppm, literature) and LC/HPLC.
• Water content by Karl Fischer is useful when performing moisture-sensitive reactions (no item-specific spec provided here).

Reaction and Applications

Functional handles:

• Three aryl iodides (C–I) are exceptionally reactive in oxidative addition, enabling diverse cross-couplings.
• One aldehyde (–CHO) supports classic carbonyl chemistry (reductions, oxidations, condensations, olefinations).

Representative reaction families and use-cases (literature/general):

• Cross-couplings at aryl iodide sites: Suzuki–Miyaura (biaryls/arylated motifs), Sonogashira (alkynylation), Heck (vinylation), and Buchwald–Hartwig (amination). Triiodo substitution allows sequential or convergent installation of three substituents to assemble 3,4,5-trisubstituted benzaldehydes and star-shaped π-systems.
• Carbonyl transformations: Wittig/Horner–Wadsworth–Emmons to install alkenes; Knoevenagel condensations with active methylenes; reductive amination to benzylamines; NaBH4/DIBAL/LAH reductions to the corresponding benzyl alcohol; Pinnick/TEMPO or Jones oxidation to the benzoic acid.
• Orthogonal strategies: Couple on C–I sites first (Pd catalysis tolerated by –CHO under mild base), then manipulate the aldehyde; or protect –CHO as acetal/oxime if harsh conditions are planned.
• Materials/medchem applications: Dense iodination is useful for high-atom-number building blocks in imaging probes, conjugated materials, or as a handle for late-stage diversification.

Practical tips:

• Use degassed solvents and inert atmosphere for Pd/Cu-catalyzed couplings; iodides typically react at lower temperatures than bromides/chlorides.
• Monitor for adventitious deiodination under strongly reducing or high-temperature conditions; choose ligands/catalysts that minimize β-hydride pathways.
• If sequential couplings are planned, leverage steric/electronic differentiation or temporary directing/blocking strategies to control order of substitution.

Reaction Conditions

General literature conditions (guidance only; optimize per substrate and scale):

• Suzuki–Miyaura coupling (aryl iodide): Pd(PPh3)4 (1–2 mol%) or Pd-PEPPSI-type NHC catalysts; base K2CO3 or Cs2CO3 (2–3 equiv); solvent toluene/dioxane/H2O or DMF/H2O; 60–90 C, 2–12 h. For micellar media, use ppm Pd with aqueous surfactant at 25–45 C. Iodides typically exhibit high conversions under mild conditions.
• Sonogashira alkynylation: PdCl2(PPh3)2 (1–2 mol%) with CuI (2–5 mol%); Et3N, i-Pr2NH, or Cs2CO3 as base; THF, DMF, or toluene; 25–80 C, 1–8 h. Copper-free protocols with bulky ligands can suppress Glaser homocoupling.
• Buchwald–Hartwig amination: Pd2(dba)3 (1 mol%) with dialkylbiaryl phosphine (e.g., XPhos, BrettPhos); NaOtBu or Cs2CO3; toluene/dioxane; 70–100 C, 4–16 h. Iodoaryl substrates typically outperform bromo/chloro analogs at lower temperatures.
• Wittig/HWE olefination (aldehyde): THF or toluene; ylide generated from Ph3P=CHR or phosphonate with NaH/KOtBu; 0–25 C to reflux, 1–6 h. Control E/Z via reagent choice and temperature.
• Reduction to benzyl alcohol: NaBH4 (1.5–2.0 equiv) in MeOH/THF, 0–25 C, 0.5–2 h; or DIBAL-H in toluene at 0 C. Work up under mildly acidic conditions to avoid hydrolysis of sensitive substituents.
• Oxidation to acid: Pinnick (NaClO2, NaH2PO4, t-BuOH/H2O) at 0–25 C; or TEMPO/bleach in MeCN/H2O. Avoid over-oxidation of iodides (rare but monitor).

Notes: In sequential couplings, adjust ligand/electronic bias to control order. Protect –CHO if strong base/heat is required to prevent aldol-type side reactions.

Safety and Handling

Authoritative classification for this specific item: Not specified for this item; refer to SDS for complete and current GHS details (signal word, hazard statements, pictograms, and precautionary statements).

General hazards (aromatic aldehydes and aryl iodides; literature/experience):

• Irritation: may cause skin/eye irritation; aldehydes can be respiratory irritants.
• Sensitization: some aldehydes sensitize on repeated exposure.
• Environmental: heavy halogen content can pose aquatic toxicity concerns—avoid release.

PPE and engineering controls (good laboratory practice):

• Wear safety glasses or face shield, lab coat, and appropriate chemical-resistant gloves (nitrile or equivalent). Use in a fume hood to control vapors/dust.
• Avoid inhalation of dust; minimize skin contact. Wash thoroughly after handling.

Incompatibilities and reactivity (general):

• Avoid strong oxidizers (risk of rapid oxidation of the aldehyde), strong bases in the presence of nucleophiles (aldol-type side reactions), and strong reducing agents that may dehalogenate aryl iodides.
• Light and air/moisture can promote slow oxidation of –CHO; store tightly closed, desiccated.

First-aid overview (non-authoritative; consult SDS):

• Inhalation: move to fresh air; seek medical attention if symptoms persist.
• Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation continues.
• Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Waste: Collect halogenated organic waste in designated containers; follow institutional and local regulations.

Solvent Selection

Context: This product is a solid aromatic aldehyde/aryl iodide used as a substrate or building block. Solvent choice affects solubility, coupling efficiency, and carbonyl reactivity.

General solubility/miscibility guidance (literature/experience):

• Good: DCM, chloroform, THF, toluene/xylene (often with heating), DMF, DMAc, DMSO, NMP.
• Limited: Hexanes, heptane (sparingly soluble at RT).
• Aqueous: Negligible without co-solvent or surfactant systems.

Choosing a solvent by application:

• Pd-catalyzed cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig): toluene, dioxane, or DMF/DMAc with water or alcohol co-solvent, depending on base. For aqueous/micellar systems, add minimal organic co-solvent.
• Wittig/olefinations: THF or toluene under anhydrous conditions.
• Reductions to benzyl alcohol: MeOH, EtOH, or THF with NaBH4/DIBAL; ensure controlled addition to manage exotherm.
• Oxidations to benzoic acid derivative: Acetonitrile, acetone, or t-BuOH/water for TEMPO/bleach or Pinnick-type protocols.

Comparison notes (general):

• DMF/DMSO maximize solubility but complicate workup and green metrics.
• Toluene/2-MeTHF balance solubility and greener profiles; reflux temperatures aid dissolution.
• For chromatographic handling, DCM/EtOAc mixtures typically elute efficiently; avoid strong basic eluents that can cause side reactions.

Storage and Reconstitution

Item-specific storage/shipping:

• Storage conditions: Room temperature (per Product Data). Protect from moisture and air exposure to minimize slow oxidation of the aldehyde (general best practice).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance (literature/experience):

• Keep tightly closed in a dry, inert atmosphere (desiccator or nitrogen/argon). Consider amber glass to limit light exposure.
• For long-term storage, periodic QC (e.g., 1H NMR for aldehyde proton) can detect onset of oxidation.

Reconstitution/stock solutions (general):

• Prepare concentrated stock solutions in dry DMSO, DMF, THF, toluene, or DCM depending on downstream use. Typical ranges: 10–200 mg/mL for DMSO/DMF; lower in less polar solvents.
• Filter (PTFE, 0.2–0.45 µm) if particulate is present. Use dry, oxygen-free solvents for moisture-sensitive steps.

Freeze–thaw: Not typically required for solids. If storing solutions, aliquot and store under inert gas at low temperature (e.g., 2–8 C for DMSO/DMF stocks) and minimize freeze–thaw cycles.

Research Use Only: For laboratory research use; not for human or veterinary use.

Structure and Identity

Brief overview: 3,4,5-Triiodobenzaldehyde is a heavily iodinated aromatic aldehyde bearing three aryl iodides (at the 3-, 4-, and 5-positions) ortho/meta to the formyl group, providing a dual-function handle: a reactive aldehyde and highly activatable C–I bonds for cross-coupling.

Item-specific identifiers (Product Data):

• SKU: T1014076
• Product name: 3,4,5-Triiodobenzaldehyde
• CAS: 1083181-39-8
• PubChem CID: 71463636
• InChIKey: 125538
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structure description (general/literature):

• Core: benzene ring bearing an aldehyde at C-1 (–CHO) and three iodine substituents at C-3, C-4, C-5 (contiguous tri-iodo array para/meta to –CHO).
• Functional groups: aromatic aldehyde (electrophilic carbonyl), aryl iodides (excellent leaving groups/reaction handles for Pd- and Cu-catalyzed couplings).
• Symmetry/features: dense halogenation increases polarizability and facilitates oxidative addition at C–I; the –CHO is deactivating/Meta-directing in SEAr but orthogonal to cross-coupling reactivity.

Computed/literature identifiers (not item-specific):

• Molecular formula (literature): C7H3I3O
• Formula weight (literature): ~483.81 g/mol

2D structure in words: A benzene ring with –CHO at the top (C-1). Moving clockwise, positions 2 (H), 3 (I), 4 (I), 5 (I), 6 (H); thus three adjacent iodines occupy the 3–5 arc opposite the aldehyde.

Synthetic Utility

Key reactivity elements:

• Aryl iodides (3×): Most reactive aryl halides in oxidative addition; compatible with low catalyst loadings and mild conditions.
• Aldehyde (–CHO): Electrophilic carbonyl amenable to protection (acetals), reductions, oxidations, condensations, and C=C installation.

Strategic value in synthesis (literature/general):

• Convergent assembly: Introduce three distinct substituents on the 3,4,5-positions via orthogonal couplings to build densely substituted benzaldehydes, triaryl cores, or dendrons.
• Chemoselectivity: Conduct Pd-catalyzed couplings under conditions that leave –CHO intact (mild base, controlled temperature), or protect –CHO as a dimethyl acetal before strong base/heat.
• Retrosynthesis: Many 3,4,5-trisubstituted benzaldehydes trace back to this node, after which –CHO can be transformed to alcohols, acids, or alkenes, or used for imine-derived diversification.
• Late-stage diversification: Iodides enable rapid SAR scanning by amination, etherification (via borylation then Chan–Lam), or alkynylation.

Common manipulations:

• Stepwise Suzuki couplings with aryl/heteroaryl boronic acids to build π-extended systems.
• Sonogashira couplings to install ethynyl units, followed by hydrofunctionalization or cycloadditions.
• Wittig/HWE on the aldehyde to produce styrenyl motifs after (or before) aryl substitutions.

Notes: Monitor for partial deiodination and over-reaction of –CHO in strongly nucleophilic/basic media; protect if necessary.

Target Specificity

Not applicable. This product is a small-molecule building block and does not have biological target specificity, antigen/epitope reactivity, clone, or isotype. No item-specific target data are provided.