638-45-9

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

1-Iodohexane (cas# 638-45-9) is a compound useful in organic synthesis.

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 2384, 1969 DOI: 10.1021/ja01037a040

General Description

1-Iodohexane undergoes palladium-catalyzed cross-coupling reaction with 9-octyl-9-borabicyclo[3.3.l]nonane to give tetradecane. Thermal reactions of 1-iodohexane on Ni (100) single crystal surfaces has been studied using temperature-programmed desorption and X-ray photoelectron spectroscopy.

InChI:InChI=1/C6H13I/c1-2-3-4-5-6-7/h2-6H2,1H3

Upstream product

• 1132-66-7 1-phenoxyhexane 
• 20633-11-8 n-hexyl nitrate 
• 111-27-3 hexan-1-ol 
• 592-41-6 1-hexene 
• 373-14-8 1-fluorohexane 
• 629-05-0 n-octyne 
• 18379-62-9 dihexylboron chloride 
• 1003-38-9 2,5-dimethyltetrahydrofuran 
• 10034-85-2 hydrogen iodide 
• 472960-23-9 2-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 74-85-1 ethene 
• 75-03-6 ethyl iodide 
• 16156-50-6 n-hexyl methanesulfonate 
• 861571-88-2 (5-iodo-hexyl)-phenyl ether 

Downstream Products

• 85389-87-3 4-Methyl-7-O-hexylcoumarin 
• 117408-74-9 1,4-Dihexyloxy-2,3,5,6-tetramethylbenzol 
• 148081-72-5 2,3,5-trimethylhydroquinone-1-hexyl ether 
• 142-92-7 1-hexyl acetate 
• 94259-20-8 1,2-dihexyloxybenzene 
• 67285-54-5 1-(hexyloxy)-2-nitrobenzene 
• 3460-37-5 hexyl stearate 
• 29214-60-6 ethyl 2-acetyloctanoate 
• 5463-91-2 acetylamino-hexyl-malonic acid diethyl ester 
• 15586-23-9 n-hexyl isocyanide 
• 629-08-3 heptanenitrile 
• 4746-32-1 N-hexylaniline 
• 60948-91-6 α-hexyloctyl acid 
• 63067-61-8 docosan-7-one 

Relevant academic research and scientific papers

Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non-Activated Aliphatic C?H Bonds via Metallocarbene Intermediates

Combining an electrophilic iron complex [Fe(Fpda)(THF)]2 (3) [Fpda=N,N′-bis(pentafluorophenyl)-o-phenylenediamide] with the pre-activation of α-alkyl-substituted α-diazoesters reagents by LiAl(ORF)4 [ORF=(OC(CF3)3] provides unprecedented access to selective iron-catalyzed intramolecular functionalization of strong alkyl C(sp3)?H bonds. Reactions occur at 25 °C via α-alkyl-metallocarbene intermediates, and with activity/selectivity levels similar to those of rhodium carboxylate catalysts. Mechanistic investigations reveal a crucial role of the lithium cation in the rate-determining formation of the electrophilic iron-carbene intermediate, which then proceeds by concerted insertion into the C?H bond.

Exploring the effect of chirality on the therapeutic potential of N-alkyl-deoxyiminosugars: anti-inflammatory response to Pseudomonas aeruginosa infections for application in CF lung disease

In the frame of a research program aimed to explore the relationship between chirality of iminosugars and their therapeutic potential, herein we report the synthesis of N-akyl L-deoxyiminosugars and the evaluation of the anti-inflammatory properties of selected candidates for the treatment of Pseudomonas aeruginosa infections in Cystic Fibrosis (CF)lung disease. Target glycomimetics were prepared by the shortest and most convenient approach reported to date, relying on the use of the well-known PS-TPP/I2 reagent system to prepare reactive alkoxyalkyl iodides, acting as key intermediates. Iminosugars ent-1-3 demonstrated to efficiently reduce the inflammatory response induced by P. aeruginosa in CuFi cells, either alone or in synergistic combination with their D-enantiomers, by selectively inhibiting NLGase. Surprisingly, the evaluation in murine models of lung disease showed that the amount of ent-1 required to reduce the recruitment of neutrophils was 40-fold lower than that of the corresponding D-enantiomer. The remarkably low dosage of the L-iminosugar, combined with its inability to act as inhibitor for most glycosidases, is expected to limit the onset of undesired effects, which are typically associated with the administration of its D-counterpart. Biological results herein obtained place ent-1 and congeners among the earliest examples of L-iminosugars acting as anti-inflammatory agents for therapeutic applications in Cystic Fibrosis.

Aliphatic C-H Bond Iodination by a N-Iodoamide and Isolation of an Elusive N-Amidyl Radical

Contrary to C-H chlorination and bromination, the direct iodination of alkanes represents a great challenge. We reveal a new N-iodoamide that is capable of a direct and efficient C-H bond iodination of various cyclic and acyclic alkanes providing iodoalkanes in good yields. This is the first use of N-iodoamide for C-H bond iodination. The method also works well for benzylic C-H bonds, thereby constituting the missing version of the Wohl-Ziegler iodination reaction. Mechanistic details were elucidated by DFT computations, and the N-centered radical derived from the used N-iodoamide, which is the key intermediate in this process, was matrix-isolated in a solid argon matrix and characterized by UV-vis as well as IR spectroscopy.

PROCESS FOR THE PREPARATION OF N-IODOAMIDES

The present invention provides new stable crystalline N-iodoamides - 1-iodo- 3,5,5-trimethylhydantoin (1-ITMH) and 3-iodo-4,4-dimethyl-2-oxazolidinone (IDMO). The present invention further provides a process for the preparation of organic iodides using N-iodoamides of this invention and recovery of the amide co-products from waste water.

Synthesis of σ receptor ligands with unsymmetrical spiro connection of the piperidine moiety

The symmetrically connected spiro[[2]benzopyran-1,4′-piperidines] 1 are highly potent and selective σ1 receptor ligands. Changing the position of the spirocyclic nitrogen atom led to the unsymmetrically connected spiro[[2]benzopyran-1,3′-piperidines] 2 with a reduced distance between the aromatic system and the basic nitrogen atom. The synthesis of 2 was performed by halogen-metal exchange at the aryl bromide 3 followed by addition to the piperidone 5 and intramolecular transacetalization. The yield of 2a was considerably improved by transmetallation of the aryllithium intermediate 4a with CeCl3 (4c). The cis and trans diastereomers cis-2 and trans-2 were separated and characterized by nuclear Overhauser effect. After removal of the benzyl group, the secondary amine 2b was alkylated with various alkyl and arylalkyl halides. The σ1 and σ2 receptor affinity of the spirocyclic piperidines 2 were determined with receptor binding studies. Compared with the spirocyclic piperidines 1, the unsymmetrically connected piperidines 2 show remarkably reduced σ1 receptor affinities, whereas the selectivity over σ2 and NMDA receptors was retained. A stereoselective interaction of the σ1 receptor protein with the cis- or trans-configured spirocyclic compounds 2 was not observed. It was shown that alkyl residues at the N-atom can replace the lipophilic N-arylalkyl groups and interact with the primary hydrophobic binding site of the σ1 receptor protein.

Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid

A simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid (HI) is reported. The alkyl iodides were obtained in quick and easy work-up with good to excellent yields (66-94%) and very high purities (97-99%). Freshly prepared iodomethane and 1-iodobutane were applied to synthesize biologically relevant 3,7-dimethyladenine and 9-butyladenine, which were characterized thoroughly using 1D and 2D NMR, individually.

Reactivity of anionic nucleophiles in ionic liquids and molecular solvents

The nucleophilic reactivity of a representative series of anions has been measured in [hmim][ClO4] 3i, [hm2im][ClO4] 3′i, and [hmim][PF6] 3l ILs in the reaction with n-alkyl methanesulfonates and compared with that found in common molecular solvents (MeOH, DMSO, PhCl). The reactivity is found to depend on both the imidazolium cation-anion interaction and the specific solvation by water present in the IL, the water playing the main effect, in particular with hydrophilic anions. Removal of the largest quantity of water remarkably increases the ion pair reactivity in the IL up to rate constant value k comparable with those obtained in DMSO and in low polarity media (PhCl).

Spiro[benzopyran] or spiro[benzofuran] derivatives which inhibit the sigma receptor

The present invention relates to compounds (I) having pharmacological activity towards the sigma (σ) receptor, and more particularly to spiro[benzopyran] or spiro[benzofuran] derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis. wherein m is selected from 1 or 2, p is selected from 1 or 2, and m + p is either 2 or 3; n is selected from 0 or 1; R1, R2 are as defined in the application.

Methods for producing acetic acid

A method produces acetic acid by continuously reacting methanol with carbon monoxide in the presence of a rhodium catalyst, an iodide salt, methyl iodide, methyl acetate, and water; and thereby producing acetic acid at a production rate of 11 mol/L·hr or more while keeping the acetaldehyde content of a reaction mixture to 500 ppm or less, in which the reaction is carried out at a carbon monoxide partial pressure in a gaseous phase of a reactor of 1.05 MPa or more and/or at a methyl acetate content of the reaction mixture of 2 percent by weight or more to thereby keep the production rate of acetaldehyde to 1/1500 or less that of acetic acid. This method can reduce production of by-products without reducing the reaction rate of acetic acid even at a low water content and a low hydrogen partial pressure in a reaction system.