64690-19-3

Basic information

• Product Name: N-octylpyridin-4-amine
• Synonyms: N-octylpyridin-4-amine;4-(OCTYLAMINO)PYRIDINE;N-Octyl-4-pyridinamine;N-Octylpyridine-4-amine;N-oCLylpyridin-4-aMine;4-(Octylamino)pyridine/N-Octyl-4-pyridinamine
• CAS NO: 64690-19-3
• Molecular Formula: C₁₃H₂₂N₂
• Molecular Weight: 206.32718
• EINECS: 265-019-0
• Product Categories: Amines;Aromatics;Heterocycles;Heterocycle-Pyridine series
• Mol File: 64690-19-3.mol

Chemical Properties

• Melting Point: 70-73 °C(Solv: hexane (110-54-3))
• Boiling Point: 327.3 °C at 760 mmHg
• Flash Point: 151.7 °C
• Appearance: /
• Density: 0.947 g/cm³
• Vapor Pressure: 0.000204mmHg at 25°C
• Refractive Index: 1.521
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.32±0.26(Predicted)
• CAS DataBase Reference: N-octylpyridin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-octylpyridin-4-amine(64690-19-3)
• EPA Substance Registry System: N-octylpyridin-4-amine(64690-19-3)

Safety Data

• Hazardous Substances Data: 64690-19-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-octylpyridin-4-amine is used as a chelating agent for the synthesis of antimicrobial agents. Its ability to form complexes with metal ions makes it a valuable component in the development of new antimicrobial compounds with enhanced efficacy and reduced toxicity.
Used in Chemical Synthesis:
N-octylpyridin-4-amine is used as a key intermediate in the synthesis of Octenidine (O239150), a broad-spectrum antimicrobial agent. Octenidine is known for its rapid action against a wide range of microorganisms, including bacteria, fungi, and viruses. It is used in various applications, such as disinfectants, antiseptics, and preservatives, due to its effectiveness and low toxicity.

InChI:InChI=1/C13H22N2/c1-2-3-4-5-6-7-10-15-13-8-11-14-12-9-13/h8-9,11-12H,2-7,10H2,1H3,(H,14,15)

Synthetic route

n-Octylamine (111-86-4) + 2-chloropyridine hydrochloride (36316-71-9) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 8h;	93%

n-octylamine hydrochloride (142-95-0) + 4-chlorpyridine hydrochloride (7379-35-3) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
at 120 - 200℃; for 7h;	93%
With sodium hydroxide In water

n-Octylamine (111-86-4) + 4-bromopyridine hydrochloride (19524-06-2) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 36h;	93%
With [(CyPF-tBu)PdCl2]; sodium t-butanolate In 1,2-dimethoxyethane at 100℃; for 30h; Inert atmosphere; Sealed vial;	88%

4-aminopyridine (504-24-5) + Octanal (124-13-0) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 70 - 90℃; under 2327.2 Torr; for 4.5h;	88%
With palladium 10% on activated carbon; hydrogen In ethanol at 80℃; under 2625.26 Torr; Solvent; Pressure; Reagent/catalyst;	74.1%
palladium

n-Octylamine (111-86-4) + 4-chlorpyridine hydrochloride (7379-35-3) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 90℃; for 24h;	83%
With sodium fluoride at 130℃; for 2h; Large scale;	78.5%

4-phenoxypyridine (4783-86-2) + n-octylamine hydrochloride (142-95-0) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
at 180 - 200℃; for 4h;	80%

4-Chloropyridine (626-61-9) + n-Octylamine (111-86-4) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With sodium hydroxide; water In 1,4-dioxane at 100℃; under 6000480 Torr; for 36h; Substitution;	80%

4-iodopyridine (15854-87-2) + n-Octylamine (111-86-4) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 48h;	80%

4-methyl-N-octyl-N-(pyridin-4-yl)benzenesulfonamide → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry;	79%

4-aminopyridine (504-24-5) + 1-Iodooctane (629-27-6) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
Stage #1: 4-aminopyridine With sodium amide In 1,4-dioxane Stage #2: 1-Iodooctane

4-aminopyridine (504-24-5) + Octanoic acid (124-07-2) → 4-(octylamino)pyridine (64690-19-3)

Conditions	Yield
Stage #1: Octanoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 110℃; for 3h; Stage #2: 4-aminopyridine With triethylamine In dichloromethane at 40℃; for 2h; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran at 66℃; for 6h;

2-ethylhexyl bromide (18908-66-2) + 4-(octylamino)pyridine (64690-19-3) → [1-(2-Ethyl-hexyl)-1H-pyridin-4-ylidene]-octyl-amine; hydrobromide (103923-28-0)

Conditions	Yield
Heating;	94%

1-Chlorooctane (111-85-3) + 4-(octylamino)pyridine (64690-19-3) → N-<1-octyl-4(1H)-pyridinylidene>octanamine monohydrochloride (100227-05-2)

Conditions	Yield
at 180℃; for 2h;	94%

1-Chlorooctane (111-85-3) + pyrographite (7440-44-0) + 4-(octylamino)pyridine (64690-19-3) → N-<1-octyl-4(1H)-pyridinylidene>octanamine monohydrochloride (100227-05-2)

Conditions	Yield
In dichloromethane	93%
In dichloromethane	93%

1-bromo-hexane (111-25-1) + 4-(octylamino)pyridine (64690-19-3) → (1-Hexyl-1H-pyridin-4-ylidene)-octyl-amine; hydrobromide (103923-38-2)

Conditions	Yield
Heating;	92%

1,10-dichlorodecane (2162-98-3) + 4-(octylamino)pyridine (64690-19-3) → octenidine dihydrochloride (70775-75-6)

Conditions	Yield
In acetic acid butyl ester for 12h; Reflux;	85.1%
In N,N-dimethyl-formamide at 120 - 180℃;	39%
In water

benzyl chloride (100-44-7) + 4-(octylamino)pyridine (64690-19-3) → (1-Benzyl-1H-pyridin-4-ylidene)-octyl-amine; hydrochloride (103923-43-9)

Conditions	Yield
Heating;	85%

1-bromo-octane (111-83-1) + 4-(octylamino)pyridine (64690-19-3) → N-(1-octyl-4(1H)-pyridinylidene)octanamine monohydrobromide

Conditions	Yield
In tetrahydrofuran; ether-tetrahydrofuran	83%

2,2-bis(chloromethyl)-1,3-propanediol (2209-86-1) + 4-(octylamino)pyridine (64690-19-3) → 1,1-[2,2-bis(hydroxymethyl)propane-1,3-diyl]bis(4-octylaminopyridinium) dichloride

Conditions	Yield
With 4-methyl-2-pentanone for 24h; Reflux;	71%

1-Chloro-4-(chloromethyl)benzene (104-83-6) + 4-(octylamino)pyridine (64690-19-3) → [1-(4-Chloro-benzyl)-1H-pyridin-4-ylidene]-octyl-amine; hydrochloride (103923-46-2)

Conditions	Yield
Heating;	43%

1-Chlorononane (2473-01-0) + 4-(octylamino)pyridine (64690-19-3) → Heptyl-(1-nonyl-1H-pyridin-4-ylidene)-amine; hydrochloride (103923-37-1)

Conditions	Yield
Heating;	37%

4-(octylamino)pyridine (64690-19-3) + p-toluenesulfonyl chloride (98-59-9) → 4-methyl-N-octyl-N-(pyridin-4-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;

1,3,5-tri(2-chloroethyl)-1,3,5-triazine-2,4,6-trione (6299-37-2) + 4-(octylamino)pyridine (64690-19-3) → C48H78N9O3(3+)*3Cl(1-)

Conditions	Yield
In butan-1-ol at 117℃; for 72h;

Upstream product

• 4783-86-2 4-phenoxypyridine 
• 142-95-0 n-octylamine hydrochloride 
• 626-61-9 4-Chloropyridine 
• 111-86-4 n-Octylamine 
• 36316-71-9 2-chloropyridine hydrochloride 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 15854-87-2 4-iodopyridine 
• 19524-06-2 4-bromopyridine hydrochloride 
• 504-24-5 4-aminopyridine 
• 629-27-6 1-Iodooctane 
• 124-07-2 Octanoic acid 
• 124-13-0 Octanal 

Downstream Products

• 103923-43-9 (1-Benzyl-1H-pyridin-4-ylidene)-octyl-amine; hydrochloride 
• 103923-46-2 [1-(4-Chloro-benzyl)-1H-pyridin-4-ylidene]-octyl-amine; hydrochloride 
• 100227-05-2 N-<1-octyl-4(1H)-pyridinylidene>octanamine monohydrochloride 
• 70775-75-6 octenidine dihydrochloride 

Relevant articles and documents

Effect of 4(2)-Octylaminopyridine Distribution in a Water (HCl)/Chloroform System on the Extraction of Metal Ions from Chloride Solutions

Abstract: Distributions of 4(2)-octylaminopyridines (4(2)-OAPs) as extractants in an H2O(HCl)/CHCl3 system were studied by UV and IR spectroscopy and potentiometry. The ionization constant of monoprotonated 4-OAP, the logarithmic distribution constant of 4-OAP and its chloride, and the logarithmic extraction constant of hydrochloric acid were calculated. These values were compared with those for 2-OAP. The isotherm (20 ± 2°C) of HCl extraction with 0.1 M 4-OAP in chloroform is given. The difference in the extraction chemistry of hydrochloric acid with 2- and 4-OAPs and specific application features of these reagents for extraction of metals from chloride solutions are discussed.

PROCESS FOR THE SYNTHESIS OF N-ALKYL-4-PYRIDINAMINES

The present invention relates to an improved process for the synthesis of N-alkyl-4-pyridinamines comprising the catalytic hydrogenation of a precursor compound which is carried out in the presence of an acid.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

Synthesis and biological evaluation of novel cyanuric acid-tethered tris-pyridinium derivatives

Novel tris(4-alkylaminopyridin-1-ium) trichlorides with alkylcyanuric spacer were synthesized by quaternization of 4-alkylaminopyridines with tris(2-chloroethyl) cyanurate. The obtained compounds were evaluated for microbiological activity against five pathogenic bacterial strains (Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Acinobacter baumannii, Pseudomonas aeruginosa). The results indicate the presence of pronounced antibacterial properties in this group of compounds.

The improved method for preparing octenidine dihydrochloride and the method for preparing a pharmaceutical composition containing the octenidine dihydrochloride

The present invention relates to an improved novel method for preparing octenidine dihydrochloride which has chemical name 1 of 10-bis-[4-(octylamino)-1-pyridinium]-decane dichloride, is represented by chemical formula, C_36H_64Cl_2N_4, and has MW of 623.84 and MP of 215~217anddeg;C. The octenidine dihydrochloride is used widely in hospitals and in the general public as an agent for skin sterilization and disinfection. The method according to the present invention can reduce the preparation cost and decrease impurities generated during the preparation process. In addition, the present invention relates to a novel composite and formulation for use in skin sterilization and disinfection, which comprise octenidine dihydrochloride. When using the sterilizing and disinfecting agent according to the present invention, it is possible to provide a method for preparing a safe sterilizing and disinfecting agent which can prevent skin infection, respiratory infection, and hospital infection that becomes a problem recently in relation to a sterilizing and disinfecting agent used in hospitals.COPYRIGHT KIPO 2017

Method of synthesizing 4-alkylamino pyridine in mild condition

The invention discloses a method of synthesizing 4-alkylamino pyridine in a mild condition, and belongs to the technical field of organic synthesis. The method comprises performing a nucleophilic substitution reaction on 4-chloropyridine hydrochloride with alkyl amine in the presence of an inhibitor to prepare the 4-alkylamino pyridine, wherein the reaction temperature is in a range of 30-150 DEG C, the reaction time is in a range of 1-10 hours, the inhibitor is a fluoride salt, and the mass ratio of the inhibitor to the 4-chloropyridine hydrochloride is (0.1-1):1. In order to solve the problem of production safety hidden danger caused by a sharp rise of temperature in such kind of nucleophilic substitution reactions, the method provided by the invention introduces the inhibitor to control the reaction speed. With the addition of the inhibitor, the rise of the reaction temperature is effectively controlled, the reaction temperature and reaction speed are reduced to a controllable range, and thus the method provides possibility for safe production and is suitable for large-scale production. In addition, the synthetic reaction has only one step, the yield can reach 80%, and compared with the products of nucleophilic substitution reactions with no inhibitors, the product purity is increased and can reach 99% or more.

Highly reactive, general and long-lived catalysts for palladium-catalyzed amination of heteroaryl and aryl chlorides, bromides, and iodides: Scope and structure-activity relationships

We describe a systematic study of the scope and relationship between ligand structure and activity for a highly efficient and selective class of catalysts containing sterically hindered chelating alkylphosphines for the amination of heteroaryl and aryl chlorides, bromides, and iodides. In the presence of this catalyst, aryl and heteroaryl chlorides, bromides, and iodides react with many primary amines in high yields with part-per-million quantities of palladium precursor and ligand. Many reactions of primary amines with both heteroaryl and aryl chlorides, bromides, and iodides occur to completion with 0.0005-0.05 mol % catalyst. A comparison of the reactivity of this catalyst for the coupling of primary amines at these loadings is made with catalysts generated from hindered monophosphines and carbenes, and these data illustrate the benefits of chelation. Studies on structural variants of the most active catalyst indicate that a rigid backbone in the bidentate structure, strong electron donation, and severe hindrance all contribute to its high reactivity. Thus, these complexes constitute a fourth-generation catalyst for the amination of aryl halides, whose activity complements catalysts based on monophosphines and carbenes.

[(CyPF-Bu)PdCI2]: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides

(Chemical Equation Presented) An air- and moisture-stable palladium catalyst, [(CyPF-1Bu)PdCI2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.

Highly reactive, general, and long-lived catalysts for coupling heteroaryl and aryl chlorides with primary nitrogen nucleophiles

Resisting pathways for decomposition followed by palladium complexes of monodentate ligands is one characteristic of the highly reactive but long-lived catalyst generated from the Josiphos ligand L and palladium. It catalyzes under mild conditions the coupling of primary amines with chloropyridines and chloroarenes in high yield with low catalyst loadings (see scheme).

A new facile method for the synthesis of 4-dialkylaminopyridine derivatives by high-pressure-promoted amination of 4-chloropyridine

A new method for synthesizing 4-(di)alkylaminopyridine derivatives in high yield was established by the high-pressure-promoted nucleophilic aromatic substitution of 4-chloropyridine with various primary/secondary amines.