This compound belongs to the class of organic compounds known as organoiodides. These are compounds containing a chemical bond between a carbon atom and an iodine atom.
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
No vendor-validated biological application protocols are provided for this small-molecule reagent.
General lab usage notes (non-validated, literature-informed):
For SN2 alkylations, prepare a dry solution of nucleophile/base, add 1-iodooctadecane under inert atmosphere, and stir at 20–60 °C until completion (TLC/GC).
For quaternizations, combine tertiary amine with excess 1-iodooctadecane in MeCN or alcohol, heat (50–100 °C) in a sealed vessel, then cool to precipitate the ammonium salt.
For photoredox, charge a dry, degassed solvent with catalyst and coupling partner, add the iodide, and irradiate with blue LEDs under N2/Ar.
These are general starting points; develop and validate conditions for your specific system. For research use only.
Biological Roles
1-Iodooctadecane is a synthetic, long-chain primary alkyl halide and does not have known endogenous biological roles.
General biochemical context (literature/general):
The C18 (stearyl) motif is common in lipids and membrane anchors; 1-iodooctadecane serves as a derivatization agent to introduce a stearyl group onto small molecules, peptides (via thiol or amine alkylation in model systems), polymers, or surfaces for research on hydrophobic interactions and self-assembly.
Quaternary ammonium salts derived from stearyl iodide are cationic surfactant precursors used in research on membrane mimetics, vesicles, and antimicrobial testing (no clinical claims).
In tracer or labeling studies, long alkyl chains can modulate partitioning into lipid phases, micelles, or lipoprotein-like systems; the iodide serves purely as a synthetic handle and is typically replaced in the final product.
Caution
Any use with biological systems should be evaluated for cytotoxicity and non-specific alkylation. This product is for research use only. No medical, diagnostic, or therapeutic uses are intended or implied.
Buffer Applications
This compound is a highly hydrophobic primary alkyl iodide and is not a buffering agent. It has no intrinsic acid–base buffering capacity and is not typically used to prepare biochemical buffers.
Practical note: In biochemical experiments, it may be dissolved in water-immiscible or water-miscible organic cosolvents (e.g., acetonitrile, DMSO) before introduction into aqueous systems, but such use is for delivery as a hydrophobic reagent rather than buffering. Choose the buffer based on the biological system (e.g., phosphate, HEPES) independently of this reagent.
Green Alternatives
When evaluating 1-iodooctadecane for synthetic steps, consider greener approaches that balance reactivity, safety, and environmental impact.
Greener leaving groups vs iodide (general considerations):
Replace iodide with mesylate/tosylate derived from octadecanol; these are less toxic and avoid heavy halogen waste but may require higher temperatures or catalysts.
1-Bromooctadecane can sometimes substitute with modest rate penalty; bromide generates less persistent halogen waste vs iodide.
Solvent substitutions (literature/general):
Prefer 2-MeTHF or cyclopentyl methyl ether (CPME) over THF/Et2O for Grignard or SN2, reducing peroxide risk and improving sustainability.
Use acetonitrile or dimethyl carbonate (where compatible) instead of DMF/DMSO for SN2 operations to ease workup and reduce environmental burden.
Process intensification:
Phase-transfer catalysis (PTC) in biphasic water/green solvent systems may allow lower temperatures and reduced solvent volumes.
Microwaves or flow photochemistry can reduce reaction times and energy usage for alkylations and radical transformations.
Comparison snapshot (general)
Iodide vs tosylate: iodide offers highest reactivity (milder, faster); tosylate offers greener profile and lower halogenated waste.
DCM vs toluene/ethyl acetate: switching away from chlorinated solvents reduces environmental and regulatory impact, with tradeoffs in solubility and temperature limits.
Note: Substituting the electrophile may alter selectivity (SN2 vs elimination) and necessitate re-optimization of bases, temperatures, and catalysts.
Pharmaceutical Uses
No pharmacopeial grade or excipient role is specified for this item. This product is intended for research use only.
General R&D relevance (non-clinical):
Synthesis of cationic lipids, quaternary ammonium salts, and hydrophobically modified polymers used in formulation research, delivery vectors, and surface coatings (laboratory studies only).
Preparation of stearyl derivatives of small molecules to study membrane affinity, self-assembly, or micelle/liposome interactions in preclinical research settings.
Compliance note:
Without explicit pharmacopeial designation (USP/EP/JP) or GMP documentation, this material should not be used in clinical manufacturing or as an excipient. For any regulated application, request appropriate grades and documentation.
Grade/Purity, stabilizers, and any low-UV/low-residue specifications are Not specified for this item; refer to CoA/Spec Sheet if considering analytical or formulation development work.
Physical Properties
The following values are general literature data for 1-iodooctadecane and are provided for reference only; they are not item-specific specifications.
Physical state/appearance (literature): waxy solid or high-melting oil near ambient temperature; becomes fully liquid slightly above room temperature.
Melting point (literature): typically in the mid-20s to low-30s °C range; reported values around ~25–33 °C depending on purity and measurement.
Boiling point (literature): very high at 1 atm (thermal decomposition likely); reported distillation typically performed under reduced pressure, e.g., ~200–230 °C at ~5–15 mmHg (literature).
Density (literature): expected >1 g/mL in the molten state due to the iodine atom (reports around ~1.10–1.20 g/mL at 25–30 °C for related long-chain iodides).
Refractive index nD (literature, molten/liquid): approximately ~1.50–1.52.
Solubility (general):
Water: essentially insoluble.
Organic: soluble in nonpolar and moderately polar aprotic media (hexane, heptane, toluene, chlorinated solvents, THF, diethyl ether, acetonitrile, DMF, DMSO); solubility increases with temperature.
Vapor pressure (literature): very low at room temperature.
Not specified for this item; refer to CoA/Spec Sheet for any lot-specific values (e.g., exact melting range, refractive index, or residual solvent content). Always verify suitability for critical applications with the Certificate of Analysis.
Quality & Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and practical notes (general guidance)
Primary alkyl iodides are sensitive to light and prolonged storage; minor iodine formation may cause yellowing. The presence of free iodine can be monitored by UV–vis or simple visual inspection; decolorizing with small amounts of sodium thiosulfate in a biphasic wash (where compatible) is a common purification step in synthetic workflows.
If an HPLC or GC assay is part of the specification (not provided here), it typically reflects the area percent of the iodide and may include limits for related long-chain halides or elimination products (alkenes). Verify with the CoA.
For applications in catalysis or surface science where trace halide or acid is critical, request metal/acid content and moisture specifications from the CoA. In the absence of item-specific limits, assume normal research-grade tolerances.
Stabilization: None stated for this item. Many iodides are supplied without stabilizer but protected from light and under inert gas to mitigate photolysis and oxidation.
Recommendation
For sensitive reactions (e.g., anionic polymerizations, air/moisture-sensitive couplings), consider pre-drying and using freshly opened material, and document lot-specific quality attributes from the CoA.
Reaction & Applications
As a primary alkyl iodide with a long hydrophobic chain, 1-iodooctadecane is a versatile C18 electrophile and radical precursor.
Nucleophilic substitutions (SN2):
Rapid quaternization of tertiary amines to give stearyl ammonium salts (phase-transfer agents, surfactant precursors).
Alkylation of thiolates/selenolates to form C18 thioethers/selenoethers; useful in surface anchors and conjugation linkers.
O-alkylation of phenoxides/carboxylates to yield aryl/alkyl stearyl ethers and esters (Williamson-type).
N-alkylation of imidazoles, pyridines, and other heterocycles to access ionic liquids and cationic amphiphiles (e.g., 1-alkyl-3-alkylimidazolium salts).
Organometallic routes:
Grignard reagent formation (stearylmagnesium iodide) in ether/THF; subsequent reactions with carbonyls or cross-couplings.
Metal–halogen exchange is less favored vs bromides/chlorides but possible under strong conditions; care to minimize elimination.
Radical chemistry:
Under photoredox (blue LEDs) or peroxide/thermal initiation, acts as a stearyl radical source for ATRA/Giese-type additions and HAT processes.
Ni/Fe-catalyzed alkyl–alkyl or alkyl–aryl cross-coupling of primary alkyl iodides is documented (literature), enabling C–C bond construction under relatively mild conditions.
Materials/surface applications (general):
Installation of C18 chains onto polymers, nanoparticles, silica, or small molecules to tune hydrophobicity, phase behavior, and self-assembly; formation of quats used as phase-transfer catalysts or antimicrobial research agents (no clinical claims).
Practical tips
Primary iodides are highly reactive; run SN2 at lower temperatures to minimize E2 elimination. Use dry, oxygen-free conditions for radical/cross-coupling and protect from light to prevent adventitious I2 formation.
Reaction Conditions
The following are general literature guidelines for primary alkyl iodides such as 1-iodooctadecane; optimize for your specific substrate and scale.
SN2 alkylation of thiolates (RS–):
Solvent: MeCN, acetone, THF, or DMF (anhydrous).
Base: NaH, K2CO3, or DBU to generate thiolate in situ (if not preformed).
Temperature: 20–60 °C; typical times 0.5–6 h; often quantitative conversion for primary iodides.
Quaternization of tertiary amines:
Solvent: MeCN, MeOH, EtOH, or acetone; sealed tube or reflux.
Temperature: 50–100 °C; 2–24 h; isolate stearyl ammonium salts by precipitation or solvent removal.
O-alkylation (phenoxides/carboxylates):
Solvent: DMF/MeCN; Base: K2CO3/Cs2CO3 or NaH (careful).
Temperature: 25–80 °C; monitor for E2 (1-octadecene) at higher temperatures.
Grignard formation:
Magnesium turnings in anhydrous Et2O or THF; initiate with iodine crystal or 1,2-dibromoethane.
Temperature: 0–reflux; post-formation use for additions or couplings.
Radical/photoredox activation:
Catalysts: Ir(ppy)3 or [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 (or organic dyes/Ni cocatalysis).
Light: blue LEDs; Solvent: MeCN, DMF, or toluene; Temperature: ambient; Times: 1–12 h.
Cross-coupling (Ni-catalyzed, literature):
Catalyst: NiCl2(dppp) or related; Base: amine or carbonate; Solvent: DMA, MeCN, or THF; Temperature: 25–80 °C.
Workup tips
Due to high hydrophobicity, product often partitions into organic phase strongly; warm hexane/toluene aids transfer and filtration. Remove traces of iodine (if present) with sodium thiosulfate wash.
Safety & Handling
Safety information below is general to primary alkyl iodides and 1-iodooctadecane. Item-specific GHS classification is not provided in the Product Data.
GHS/Classification (item-specific):
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 hazards (literature/general):
Primary alkyl iodides can be harmful if inhaled, swallowed, or upon skin contact; may irritate eyes/skin/respiratory tract; some exhibit alkylating potential.
Light-sensitive; slow photolysis may release iodine, evidenced by yellow/purple discoloration.
Recommended PPE/practices (general):
Wear lab coat, nitrile gloves (change regularly), and splash goggles; handle in a fume hood to avoid vapor/aerosol exposure during heating or weighing of melted material.
Avoid strong bases at elevated temperature (risk of E2 elimination) and strong nucleophiles in open systems (uncontrolled exotherm).
Skin: wash with soap/water; remove contaminated clothing.
Eyes: rinse cautiously with water for several minutes; seek medical attention.
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product SDS for authoritative, up-to-date hazard and response information.
Solvent Selection
1-Iodooctadecane is extremely hydrophobic and dissolves readily in nonpolar and moderately polar aprotic solvents. Choice of solvent should be guided by the intended transformation (SN2 alkylation, radical processes, Grignard formation, etc.).
Alcohols: limited solubility at ambient T; solubility improves when warm. For quaternization reactions, hot MeCN or MeOH/EtOH often used with phase-transfer or sealed-vessel heating.
Selection by reaction class (general):
SN2 alkylations of hard nucleophiles: DMF/DMSO/MeCN enhance rates for primary iodides; ensure anhydrous conditions.
Thiolate/selenolate alkylation: MeCN, acetone, or THF at RT–50 °C usually efficient.
Grignard formation: dry ether or THF under inert atmosphere; initiate with iodine or ultrasound if needed.
Radical/photoredox: nonpolar solvents (toluene, chlorobenzene) or acetonitrile; choose based on catalyst solubility.
Mini comparison (general)
MeCN vs DMF: MeCN offers easier removal and lower high-boiling residue; DMF can deliver faster SN2 but complicates workup.
Toluene vs DCM: toluene tolerates higher temperatures and is less volatile; DCM improves solubility at lower temperatures but is more regulated.
Storage: Store at 2–8 °C, protected from light, argon charged.
Shipped in: Wet ice.
General handling and preparation (literature/general):
Light sensitivity: Protect from light to limit slow photolysis to I2 (discoloration). Store in amber glass under inert gas as supplied.
Opening/transfer: Allow container to equilibrate to room temperature (to avoid moisture condensation), then open under inert atmosphere if possible. If solidified, gently warm (30–40 °C) to liquefy before dispensing; do not overheat.
Solubilization: Dissolve in anhydrous nonpolar or aprotic solvents (hexane, toluene, THF, MeCN, DCM) as required by your application. Filter through a PTFE syringe filter if particulates are present.
Stability: Primary alkyl iodides are generally stable when protected from light and air. Yellow/purple tint indicates iodine formation; a quick wash of the organic solution with dilute sodium thiosulfate can remove I2 (confirm compatibility first).
Freeze–thaw: Not typically applicable to neat liquids/solids; if preparing stock solutions, store under inert gas in amber vials at 2–8 °C and avoid repeated thermal cycling.
Always consult the product CoA/SDS for lot-specific shelf life and stability guidance.
Structure & Identity
1-Iodooctadecane (also known as stearyl iodide) is a linear, saturated C18 primary alkyl iodide useful as a highly reactive C18 electrophile for SN2 and radical chemistry.
Item identifiers (from Product Data)
SKU: I157553
CAS: 629-93-6
PubChem CID: 12402
InChIKey: 461610 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Composition (literature)
Molecular formula: C18H37I
Molecular weight: ~380.39 g/mol (literature)
Structural features (general description)
Linear n-octadecyl chain (18 carbons) bearing a terminal iodine at C1; no rings, no unsaturation, no heteroatoms besides I.
Functional group: primary alkyl iodide (R–CH2–I). Strong C–I bond polarization; excellent leaving group for bimolecular nucleophilic substitutions.
Stereochemistry: none (achiral, no stereocenters). 2D structure can be envisioned as a straight hydrocarbon “tail” with an ω-iodo substituent at the head carbon.
The identifiers listed under “Item identifiers” are taken directly from the Product Data. Any additional chemical descriptors provided above are literature/general values and not item-specific specifications.
Synthetic Utility
Key functional group: primary alkyl iodide (R–CH2–I). 1-Iodooctadecane is a robust electrophile for installing a C18 (stearyl) chain and a useful radical precursor.
Electrophilic substitutions (literature/general):
SN2 with soft nucleophiles (RS–, SeR–, I–) proceeds rapidly at mild temperatures; excellent for preparing stearyl thioethers and selenoethers.
O-alkylation of phenoxides/alcoholates and N-alkylation of tertiary amines/imidazoles/pyridines produce ethers and quaternary salts (phase-transfer catalysts, ionic liquids).
Carboxylate alkylation yields esters; the long chain imparts strong hydrophobicity to products.
Organometallic transformations:
Grignard formation (R–MgI) enables additions to carbonyls and cross-couplings (Kumada, Negishi after transmetalation).
Wurtz-type coupling with sodium can produce C36 alkanes (research context).
Radical and catalytic reactions:
Photoredox/Ni-catalyzed activation of primary iodides enables C(sp3)–C(sp2)/C(sp3) couplings under relatively mild conditions; the long chain assists phase separation during workup.
Retrosynthetic value:
Acts as a convergent handle for late-stage stearyl installation onto polar scaffolds, enhancing lipophilicity, crystallinity, or self-assembly behavior without introducing additional heteroatoms beyond the linkage.
Considerations
Competing E2 elimination to 1-octadecene can occur under strong base/heat; maintain SN2 conditions (polar aprotic, moderate T, appropriate base/nucleophile) to favor substitution.
Target Specificity
Not applicable. This product is a small-molecule alkyl halide, not a biological targeting reagent or antibody. No antigen/epitope/clone/isotype information applies.
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