1129-69-7

Usage

Uses

Used in Organic Synthesis:
2-Hexylpyridine is used as a key intermediate for the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceuticals:
In the pharmaceutical industry, 2-Hexylpyridine serves as a crucial building block for the production of drugs, playing a significant role in the discovery and development of novel therapeutic agents.
Used in Agrochemicals:
2-Hexylpyridine is utilized as a vital component in the formulation of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Used in Dyestuff:
2-Hexylpyridine is also employed in the dyestuff industry for the production of dyes and pigments, contributing to the coloration and appearance of various products.
Used in Flavor Industry:
2-Hexylpyridine is used in the creation of flavors for vegetables, meat, and nuts, with a maximum concentration of up to 1ppm, adding unique taste profiles to these food products.

Oral/Parenteral Toxicity

oral-rat LDLo > 500 mg/kg

InChI:InChI=1/C11H17N/c1-2-3-4-5-8-11-9-6-7-10-12-11/h6-7,9-10H,2-5,8H2,1H3

Upstream product

• 110-86-1 pyridine 
• 17774-09-3 n-hexyl mercury chloride 
• 109-04-6 2-bromo-pyridine 
• 81745-81-5 ⁿhexylzinc chloride 
• 24244-60-8 2-(phenylsulfonyl)pyridine 
• 3761-92-0 n-hexylmagnesium bromide 
• 111770-81-1 5-bromo-2-(hex-1-yn-1-yl)pyridine 
• 638-45-9 1-Iodohexane 
• 109-09-1 2-chloropyridine 
• 100-69-6 2-vinylpyridine 
• 542-69-8 1-iodo-butane 
• 44767-62-6 n-hexylmagnesium chloride 
• 34039-95-7 (2-pyridyl)diethylphosphate 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 110273-87-5 2-hexyl-1-methyl-pyridinium; picrate 
• 940-53-4 2-hexylpiperidine 
• 449-41-2 1-(4-fluoro-phenacyl)-2-hexyl-pyridinium; bromide 

Relevant academic research and scientific papers

X-ray spectroscopic verification of the active species in iron-catalyzed cross-coupling reactions

X-ray absorption: The activation of the pre-catalyst as well as the catalytically active species and reaction mechanism of Fe-catalyzed cross-couplings were investigated by X-ray absorption spectroscopy. The active catalytic components are small iron clus

Odd-Even Effect on the Spin-Crossover Temperature in Iron(II) Complex Series Involving an Alkylated or Acyloxylated Tripodal Ligand

In the context of magneto-structural study, a relatively short alkyl group was introduced to anionic spin-crossover (SCO) building blocks based on [Fe(py3CR)(NCS)3]-, where py3CR stands for tris(2-pyridyl)methyl derivatives. The linear alkyl and acyloxyl derivatives of Me4N[Fe(py3CR)(NCS)3] with R = CnH2n+1 (n = 1-7) and CnH2n+1CO2 (n = 1-6) were synthesized, and the magnetic study revealed that all the compounds investigated here exhibited SCO. The SCO temperature (T1/2) varied in 289-338 K for the alkylated compounds, and those of the acyloxylated ones were lower with a narrower variation width (T1/2 = 216-226 K). The crystal structures of the former with n = 3, 4, and 5 and the latter with n = 1, 4, 5, and 6 were determined, and various molecular arrangements were characterized. There is no structural evidence for a molecular fastener effect. The plots on T1/2 against n displayed a pronounced odd-even effect; the SCO temperatures of the homologues with even n are relatively higher than those of the homologues with odd n. The odd-even effect on T1/2 may be related with the entropy difference across the SCO, rather than crystal field modification or intermolecular interaction. The present work will help molecular design to fine-tune T1/2 by means of simple chemical modification like alkylation and acyloxylation.

Stereoselective synthesis of (±)-indolizidines 167B and 209D and their trans-isomers based on the reductive allylboration of pyridine

A general method for the synthesis of 5-substituted indolizidines based on intramolecular cyclization of trans-and cis-2-allyl-6-R-1,2,3,6-tetrahydropyridines, obtained from pyridine and triallylborane, has been elaborated. The closure of the five-membered ring is carried out by hydroboration-oxidation followed by cyclization of the resulting δ-amino alcohols in the presence of the Ph3P-CBr4-Et3N system. (Pr2BH)2 and Pr3B are used as the hydroborating reagents, and H2O2 in an acid medium is used for the oxidation of 2-[3-(dipropylboryl)propyl]-Δ3-piperideines formed. This method has been used for the synthesis of two natural alkaloids: indolizidine 209D (cis-5-hexylindolizidine) and its trans-isomer were prepared from cis-and trans-2-allyl-6-hexyl-1,2,3,6-tetrahydropiridine, respectively; indolizidine 167B and trans-5-propylindolizidine were synthesized from cis-and trans-2,6-diallyl-1,2,3,6-tetrahydropyridine, respectively.

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

Unlocking the Accessibility of Alkyl Radicals from Boronic Acids through Solvent-Assisted Organophotoredox Activation

Despite their prevalence in organic synthesis, the application of boronic acids (BAs) as alkyl radical precursors in visible-light-assisted photocatalyzed reactions has been limited by their high oxidation potential. This study demonstrates the prominent

Copper-catalyzed cross-coupling of aryl-, primary alkyl-, and secondary alkylboranes with heteroaryl bromides

A method for the Cu-catalyzed cross-coupling of both aryl and alkylboranes with aryl bromides is described. The method employs an inexpensive Cu-catalyst and functions for a variety of heterocyclic as well as electron deficient aryl bromides. In addition, aryl iodides of varying substitution patterns and electronic properties work well.

Manganese-Catalyzed Kumada Cross-Coupling Reactions of Aliphatic Grignard Reagents with N-Heterocyclic Chlorides

Herein we report the use of manganese(II) chloride for the catalytic generation of C(sp 2)-C(sp 3) bonds via Kumada cross-coupling. Rapid and selective formation of 2-alkylated N-heterocyclic complexes were observed in high yields with use of 3 mol% MnCl 2 THF 1.6 and under ambient reaction conditions (21 °C, 15 min to 20 h). Manganese-catalyzed cross-coupling is tolerant toward both electron-donating and electron-withdrawing functional groups in the 5-position of the pyridine ring, with the latter resulting in an increased reaction rate and a decrease in the amount of nucleophile required. The use of this biologically and environmentally benign metal salt as a catalyst for C-C bond formation highlights its potential as a catalyst for the late-stage functionalization of pharmaceutically active N-heterocyclic molecules (e.g., pyridine, pyrazine).

Ionic iron(III) complexes bearing a dialkylbenzimidazolium cation: Efficient catalysts for magnesium-mediated cross-couplings of aryl phosphates with alkyl bromides

A series of ionic iron(III) complexes of general formula [HLn][FeX4] (HL1?=?1,3-dibenzylbenzimidazolium cation, X?=?Cl, 1; HL1, X?=?Br, 2; HL2?=?1,3-dibutylbenzimidazolium cation, X?=?Br, 3; HL3?=?1,3-bis(diphenylmethyl)benzimidazolium cation, X?=?Br, 4) were easily prepared in high yields by the direct reaction of FeX3 with 1 equiv. of [HLn]X under mild conditions. All of them were characterized using elemental analysis, Raman spectroscopy and electrospray ionization mass spectrometry, and X-ray crystallography for 1 and 4. In the presence of magnesium turnings and LiCl, these air- and moisture-insensitive complexes showed high catalytic activities in direct cross-couplings of aryl phosphates with primary and secondary alkyl bromides with broad substrate scope, wherein complex 4 was the most effective.

Alkyl Grignard cross-coupling of aryl phosphates catalyzed by new, highly active ionic iron(II) complexes containing a phosphine ligand and an imidazolium cation

A novel family of ionic iron(ii) complexes of the general formula [HL][Fe(PR′3)X3] (HL = 1,3-bis(2,6-diisopropylphenyl)imidazolium cation, HIPr, R′ = Ph, X = Cl, 2; HL = HIPr, R′ = Cy, X = Cl, 3; HL = HIPr, R′ = Ph, X = Br, 4; HL = HIPr, R′ = Cy, X = Br, 5; HL = 1,3-bis(2,4,6-trimethylphenyl)imidazolium cation, HIMes, R′ = Cy, X = Br, 6) was easily prepared via a stepwise approach in 88%-92% yields. In addition, an ionic iron(ii) complex, [HIPr][Fe(C4H8O)Cl3] (1), has been isolated from the reaction of FeCl2(THF)1.5 with one equiv. of [HIPr]Cl in 90% yield and it can further react with one equiv. of PPh3 or PCy3, affording the corresponding target iron(ii) complex 2 or 3, respectively. All these complexes were characterized by elemental analysis, electrospray ionization mass spectrometry (ESI-MS), 1H NMR spectroscopy and X-ray crystallography. These air-insensitive complexes 2-6 showed high catalytic activities in the cross-coupling of aryl phosphates with primary and secondary alkyl Grignard reagents with a broad substrate scope, wherein [HIPr][Fe(PCy3)Br3] (5) was the most effective. Complex 5 also catalyzes the reductive cross-coupling of aryl phosphates with unactivated alkyl bromides in the presence of magnesium turnings and LiCl, as well as the corresponding one-pot acylation/cross-coupling sequence under mild conditions.

Ionic iron (II) composition as well as preparation method and application thereof

The invention discloses an ionic iron (II) composition as well as a preparation method and application thereof. The ionic iron (II) composition contains phosphine ligands and imidazole (quinoline) cations, and the general formula of the ionic iron (II) is [Fe(PR3)X3][(R1NCHnCHnNR1)CH], wherein X is selected from one of chlorine or bromine. The ionic iron (II) composition containing the phosphine ligands and the imidazole (quinoline) cations can efficiently catalyze a phosphoric acid aryl diethyl ester compound and an alkyl group Grignard reagent to perform a crisscross coupling reaction, and particularly can effectively catalyze an unactivated phosphoric acid aryl diethyl ester compound and the alkyl group Grignard reagent to perform the reaction.