4292-19-7

Usage

Uses

Used in Chemical Synthesis:
1-Iodododecane is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity with other molecules makes it a valuable building block in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Material Science:
1-Iodododecane is used in the preparation of dodecylated graphite and alkyl functionalized single-walled carbon nanotubes (SWNTs). The dodecyl groups attached to the graphite or SWNTs enhance their solubility and dispersibility in organic solvents, making them suitable for applications in nanocomposites, energy storage, and electronic devices.
Used in Surface Modification:
1-Iodododecane can be used for surface modification of various materials, such as metals, polymers, and nanoparticles. The attachment of dodecyl groups to the surface can improve the material's hydrophobicity, biocompatibility, and stability, which is beneficial for applications in coatings, sensors, and drug delivery systems.

InChI:InChI=1/C12H25I/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2-12H2,1H3

Upstream product

• 143-15-7 1-dodecylbromide 
• 112-53-8 1-dodecyl alcohol 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 83486-10-6 C₁₈H₃₀I₂Te 
• 51323-71-8 dodecyl mesylate 
• 112-40-3 dodecane 
• 177035-82-4 2-dodecyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 112-55-0 1-dodecylthiol 
• 112-52-7 1-chlorododecane 
• 75250-42-9 n-dodecyl(phenyl)telluride 
• 94435-41-3 1-(dodecylsulfonyl)-4-methylbenzene 
• 6222-00-0 dodecyl 2,2,2-trifluoroacetate 
• 112-41-4 1-dodecene 

Downstream Products

• 5917-47-5 1-dodecylpiperidine 
• 82394-21-6 1,4-didodecylpiperazine 
• 14402-22-3 N-lauryl-α-methylpyridinium iodide 
• 70710-07-5 N-(2-dodecane)-4-methylpyridinium iodide 
• 112-40-3 dodecane 
• 112-41-4 1-dodecene 
• 646-31-1 tetracosane 
• 102-87-4 tridodecylamine 
• 53685-77-1 heptadecan-4-one 
• 18276-99-8 octadecan-5-one 
• 854306-07-3 4,N-didodecyl-aniline 
• 874514-21-3 toluene-4-sulfonic acid-[N-dodecyl-4-(4-nitro-benzenesulfonyl)-anilide] 
• 83027-71-8 dodecyl 2-nitrophenyl ether 
• 5303-25-3 dodecyl stearate 

Relevant academic research and scientific papers

Self-assembled ionophores as phase transfer catalysts

The nucleoside, 5'-(t-butyl-dimethylsilyl)-2',3'-O-isopropylidene isoG 1, catalyzes the S(N)2 reactions of alkali and ammonium iodides with dodecyl mesylate 2 under both liquid-liquid and solid-liquid phase transfer conditions. IsoG 1 self-associates to give a complex that extracts the salts into CDCl3 solution. Sodium iodide, in the presence of isoG 1, reacts faster with 2 than the other iodides under solid-liquid conditions. This reactivity difference is attributed to the open-faced structure of the ionophore-M+ complex under solid-liquid conditions.

Activity and behavior of imidazolium salts as a phase transfer catalyst for a liquid-liquid phase system

The structure-activity relationship and behavior of N,N′-dialkylimidazolium salts as a phase transfer and/or ion-exchange catalyst in a liquid-liquid phase system were investigated for the reactions such as β-elimination reaction of alkyl halides, nucleophilic epoxidation of α,β-unsaturated carbonyl compounds, alkylation of active methylenes, and nucleophilic substitution reaction.

Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration

We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.

NUCLEOSIDE PRODRUGS AND USES RELATED THERETO

Disclosed are acyclic nucleoside prodrugs with improved metabolic stability and oral bioavailability. In general, the prodrugs are derivatives of acyclic nucleoside phosphonates containing a lipid-like moiety that can increase oral absorption and subsequent stability in the liver and plasma. Preferably, the lipid-like moiety can resist enzyme-mediated ω-oxidation, such as ω -oxidation catalyzed by cytochrome P450 enzymes. Also disclosed are pharmaceutical formulations of the acyclic nucleoside prodrugs. The acyclic nucleoside prodrugs and pharmaceutical formulations thereof can be used to treat viral infections, such as HIV infections, and/or viral-associated cancer, such as HPV-associated cancers.

ω-Functionalized Lipid Prodrugs of HIV NtRTI Tenofovir with Enhanced Pharmacokinetic Properties

Tenofovir (TFV) is the cornerstone nucleotide reverse transcriptase inhibitor (NtRTI) in many combination antiretroviral therapies prescribed to patients living with HIV/AIDS. Due to poor cell permeability and oral bioavailability, TFV is administered as one of two FDA-approved prodrugs, both of which metabolize prematurely in the liver and/or plasma. This premature prodrug processing depletes significant fractions of each oral dose and causes toxicity in kidney, bone, and liver with chronic administration. Although TFV exalidex (TXL), a phospholipid-derived prodrug of TFV, was designed to address this issue, clinical pharmacokinetic studies indicated substantial hepatic extraction, redirecting clinical development of TXL toward HBV. To circumvent this metabolic liability, we synthesized and evaluated ω-functionalized TXL analogues with dramatically improved hepatic stability. This effort led to the identification of compounds 21 and 23, which exhibited substantially longer t1/2 values than TXL in human liver microsomes, potent anti-HIV activity in vitro, and enhanced pharmacokinetic properties in vivo.

Quinim: A New Ligand Scaffold Enables Nickel-Catalyzed Enantioselective Synthesis of α-Alkylated ?-Lactam

Herein, we report a nickel-catalyzed reductive cross-coupling reaction of easily accessible 3-butenyl carbamoyl chloride with primary alkyl iodide to access the chiral α-alkylated pyrrolidinone with broad substrate scope and high enantiomeric excess. The current art of synthesis still remains challenging on the enantioselective α-monoalkylation of pyrrolidinones. The newly designed chiral 8-quinoline imidazoline ligand (Quinim) is crucial for maintaining the reactivity and enantioselectivity to ensure the reductive cyclization of monosubstituted alkenes for unprecedented synthesis of chiral non-aromatic heterocycles.

Photocatalytic Aerobic Phosphatation of Alkenes

A catalytic regime for the direct phosphatation of simple, non-polarized alkenes has been devised that is based on using ordinary, non-activated phosphoric acid diesters as the phosphate source and O2 as the terminal oxidant. The title method enables the direct and highly economic construction of a diverse range of allylic phosphate esters. From a conceptual viewpoint, the aerobic phosphatation is entirely complementary to traditional methods for phosphate ester formation, which predominantly rely on the use of prefunctionalized or preactivated reactants, such as alcohols and phosphoryl halides. The title transformation is enabled by the interplay of a photoredox and a selenium π-acid catalyst and involves a sequence of single-electron-transfer processes.

A mild and highly chemoselective iodination of alcohol using polymer supported DMAP

The synthesis of organic compounds using polymer supported catalysts and reagents, where the required product is always in solution, has been of great interest in recent years, both in industries and academia especially in pharmaceutical research. Here, a simple and efficient method for conversion of alcohols into their iodides in high yield using polymer supported 4-(Dimethylamino)pyridine (DMAP) is described. Polymer supported DMAP is used in catalytic amount and is recovered and reused several times. Additionally, this method is highly chemoselective. [Figure not available: see fulltext.]

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Ruthenium bipyridyl tethered porous organosilica: A versatile, durable and reusable heterogeneous photocatalyst

A versatile heterogeneous photocatalysis protocol was developed by using ruthenium bipyridyl tethered porous organosilica (Ru-POS). The versatility of the Ru-POS catalyst in organo-photocatalysis was explored by (i) oxidative aromatization of Hantzsch ester, (ii) reductive dehalogenation of alkyl halides, and (iii) functional group interconversion (FGI) of alcohols to alkyl halides. This journal is