6311-92-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
3-N-Hexylpyridine is used as a key intermediate in the synthesis of pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its chemical properties.
Used as a Flavoring Agent in the Food Industry:
Leveraging its aromatic properties, 3-N-Hexylpyridine is utilized as a flavoring agent in the food industry, enhancing the taste and aroma of certain products.
Used in the Production of Corrosion Inhibitors:
3-N-Hexylpyridine serves as a component in the formulation of corrosion inhibitors, helping to protect materials from the damaging effects of corrosion.
Used in the Manufacturing of Lubricants and Surfactants:
This chemical compound is also employed in the production of lubricants and surfactants, where it contributes to the performance and efficiency of these products.
Safety Precautions:

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

Upstream product

• 108-99-6 3-Methylpyridine 
• 7335-01-5 1-hexylpiperidine 
• 110-89-4 piperidine 
• 111-27-3 hexan-1-ol 
• 626-55-1 3-Bromopyridine 
• 3761-92-0 n-hexylmagnesium bromide 
• 72253-33-9 diethyl pyridin-3-yl phosphate 
• 44767-62-6 n-hexylmagnesium chloride 
• 1120-90-7 3-iodopyridine 
• 1132-27-0 pyridin-3-yl dimethylsulfamate 
• 51581-40-9 3-pyridyl diethylcarbamate 
• 111-25-1 1-bromo-hexane 

Downstream Products

• 948559-97-5 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-[2-(5-hexylpyrid-2-yl)ethynyl]uracil 

Relevant academic research and scientific papers

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.

Iron-catalyzed alkylations of aryl sulfamates and carbamates

The alkylation of aryl sulfamates and carbamates using iron catalysis is reported. The method constructs sp2-sp3 carbon-carbon bonds and provides synthetically useful yields across a range of substrates (>35 examples). The directing group ability of sulfamates and carbamates, accompanied by their low reactivity toward conventional cross-couplings, renders these substrates useful for the synthesis of polyfunctionalized arenes.

Unprecedented Negishi coupling at C-Br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis

(Chemical Equation Presented) The 2-bromo-5(or 6)-tri-n- butylstannylpyridines, prepared from dibromopyridines and i-PrMgCl at room temperature, undergo Negishi coupling with either alkyl or arylzinc chlorides. The new alkyl- and aryl-substituted pyridylstannanes produced are shown to be suitable for further functionalization by Stille coupling. A group of new liquid crystalline materials with aromatic cores comprised of pyridine and thiophene rings were prepared utilizing these new pyridinylstannanes as key intermediates.

Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d] pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core

Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2′-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl dec-1-en-1-yl decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were ～20-fold more potent inhibitors of VZV than acyclovir but were ～6-fold less potent than BVDU and ～60-fold weaker than the most active 6-(4-pentylphenyl)- substituted prototype.

Preparation of 5-brominated and 5,5′-dibrominated 2,2′-bipyridines and 2,2′-bipyrimidines

Efficient syntheses of 5-brominated and 5,5′-dibrominated 2,2′-bipyridines and 2,2′-bipyrimidines, useful for the preparation of metal-complexing molecular rods, have been developed. 5-Bromo-2,2-bipyridine, 5-bromo-5′-n-butyl-2,2′-bipyridine, and 5-bromo-5′-n-hexyl-2,2′-bipyridine were obtained by Stille coupling of 2,5-dibromopyridine with 2-trimethylstannylpyridine or the requisite 5-alkyl-2-trimethylstannylpyridine, obtained via regioselective zincation of a 3-alkylpyridine. BF3 complex in the less hindered of the two reactive positions with lithium di-tert-butyl-(2,2,6,6-tetramethyl-piperidino)zincate. 5,5′-Dibromo-2,2′-bipyridine was obtained by the reductive symmetric coupling of 2,5-dibromopyridine with hexa-n-butyldistannane. The yields of these coupling reactions ranged from 70 to 90%. 5-Bromo- and 5,5′-dibromo-2,2′-bipyrimidines were obtained in yields of 30 and 15%, respectively, by bromination of 2,2′-bipyrimidine, prepared from 2-chloropyrimidine in 80% yield by an improved reductive symmetric coupling procedure.

New Synthesis of 3-Alkylpyridines

An effective method is reported for preparation of 3-alkylpyridines from piperidine and C1-C10 aliphatic alcohols at 300-500 deg C in the presence of a dehydrogenating catalyst.