14727-68-5

Basic information

• Product Name: (Z)-N,N-dimethyl-9-octadecenylamine
• Synonyms: (Z)-N,N-dimethyl-9-octadecenylamine;N,N-Dimethyloleylamine;(Z)-N,N-Dimethyl-9-octadecen-1-amine
• CAS NO: 14727-68-5
• Molecular Formula: C₂₀H₄₁N
• Molecular Weight: 295.54624
• EINECS: 238-781-7
• Mol File: 14727-68-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 376.5°Cat760mmHg
• Flash Point: 163.1°C
• Appearance: /
• Density: 0.822g/cm³
• Vapor Pressure: 7.23E-06mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: (Z)-N,N-dimethyl-9-octadecenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-N,N-dimethyl-9-octadecenylamine(14727-68-5)
• EPA Substance Registry System: (Z)-N,N-dimethyl-9-octadecenylamine(14727-68-5)

Safety Data

• Hazardous Substances Data: 14727-68-5(Hazardous Substances Data)

Usage

Description

(Z)-N,N-dimethyl-9-octadecenylamine, commonly known as stearalkonium chloride, is a quaternary ammonium salt derived from stearic acid with a long carbon chain. It is a chemical compound that serves as a surfactant and conditioning agent in hair care products, providing softness, smoothness, and reducing static in hair. Its antistatic and antimicrobial properties make it a valuable ingredient in hair care formulations.

Uses

Used in Hair Care Industry:
(Z)-N,N-dimethyl-9-octadecenylamine is used as a surfactant and conditioning agent in hair dyes, conditioners, and other hair care products for its ability to reduce static, provide softness, and smoothness to the hair.
Used in Hair Care Industry for Antistatic Properties:
(Z)-N,N-dimethyl-9-octadecenylamine is used as an antistatic agent in hair care products to minimize hair flyaways and make hair more manageable.
Used in Hair Care Industry for Antimicrobial Properties:
(Z)-N,N-dimethyl-9-octadecenylamine is used as an antimicrobial agent in hair care products to help maintain cleanliness and hygiene by inhibiting the growth of microorganisms.
However, it is important to note that (Z)-N,N-dimethyl-9-octadecenylamine has been associated with potential skin irritation and allergic reactions in some individuals. Therefore, it is crucial to use hair care products containing stearalkonium chloride with caution and consider individual sensitivities.

InChI:InChI=1/C20H41N/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(2)3/h11-12H,4-10,13-20H2,1-3H3/b12-11-

Synthetic route

N,N-dimethyl oleamide (2664-42-8) → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 6h; Heating;	36.9%

(Z)-1-bromo-9-octadecene (13044-38-7, 62871-05-0, 6110-53-8) + dimethyl amine (124-40-3) → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
In isopropyl alcohol

(Z)-9-octadecenoyl chloride (112-77-6) + (R)-O1,O2-dipalmitoyl-glycerol → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / benzene / 1 h / Ambient temperature 2: 36.9 percent / LiAlH4 / diethyl ether / 6 h / Heating View Scheme

oleoyl alcohol (143-28-2) + potassium permanganate → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) TsCl, Py, H2O, (ii) LiBr, MeCOEt 2: propan-2-ol View Scheme

oleic acid ethyl ester (111-62-6) + ClSO3Na → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4 / diethyl ether 2: (i) TsCl, Py, H2O, (ii) LiBr, MeCOEt 3: propan-2-ol View Scheme

cis-9-octadecenoamide (301-02-0) + N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide (1323108-64-0) + Palmitamide (629-54-9) + stearamide (124-26-5) → N,N-dimethylhexadecylamine (112-69-6) + N,N-dimethyl-n-octadecylamine (124-28-7) + N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine (1323108-61-7) + N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 0.5h; Reflux;

trivernolin (20449-88-1) → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol; hexane 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 24.25 h / 0 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / Reflux View Scheme

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate (2733-91-7) → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 2 h / Reflux 1.2: 24.25 h / 0 °C 2.1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / Reflux View Scheme

methanol (67-56-1) + (Z)-9-octadecen-1-amine (112-90-3) → N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
With [Ru(2-(6-methoxypyridin-2-yl)-1,10-phenanthroline)(MeCN)2Cl]Cl; sodium methylate at 110℃; for 12h; Green chemistry;	78 %Spectr.

N,N-dimethyl oleamide (2664-42-8) → oleoyl alcohol (143-28-2) + N,N-dimethyl-N-oleylamine (14727-68-5)

Conditions	Yield
With ethanol; sodium In hexane at 0℃; for 0.333333h; Inert atmosphere; Overall yield = 83 %; Overall yield = 70.7 mg; chemoselective reaction;

N,N-dimethyl-N-oleylamine (14727-68-5) + 1,5-dioxaspiro[5.5]undecane-3,3-dimethyldiglycidyl ether (364606-36-0) → 1,5-dioxaspiro[5.5]undecane-3,3-bis(1-methoxy-3-oleyldimethylammonio-propan-2-ol) dichloride

Conditions	Yield
With tetrabutylammomium bromide In ethanol at 30℃; for 20h;	61%

ethyl bromide (74-96-4) + N,N-dimethylhexadecylamine (112-69-6) + N,N-dimethyl-n-octadecylamine (124-28-7) + N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine (1323108-61-7) + N,N-dimethyl-N-oleylamine (14727-68-5) → oleyl dimethylethylammonium bromide (14351-44-1) + Br(1-)*C22H48N(1+) (111-98-8) + N,N,N-ethyl-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl ammonium bromide (1323108-68-4) + hexadecyldimethylethylammonium bromide (124-03-8)

Conditions	Yield
In ethanol for 28h; Reflux;

...Expand

Upstream product

• 13044-38-7 (Z)-1-bromo-9-octadecene 
• 124-40-3 dimethyl amine 
• 2664-42-8 N,N-dimethyl oleamide 
• 111-62-6 oleic acid ethyl ester 
• 301-02-0 cis-9-octadecenoamide 
• 1323108-64-0 N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide 
• 629-54-9 Palmitamide 
• 124-26-5 stearamide 
• 20449-88-1 trivernolin 
• 2733-91-7 methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate 
• 67-56-1 methanol 
• 112-90-3 (Z)-9-octadecen-1-amine 
• 143-28-2 oleoyl alcohol 
• 112-77-6 (Z)-9-octadecenoyl chloride 

Downstream Products

• 14351-44-1 oleyl dimethylethylammonium bromide 
• 111-98-8 Br^(1-)*C₂₂H₄₈N⁽¹⁺⁾ 
• 1323108-68-4 N,N,N-ethyl-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl ammonium bromide 
• 124-03-8 hexadecyldimethylethylammonium bromide 

Relevant articles and documents

Reduction and Reductive Deuteration of Tertiary Amides Mediated by Sodium Dispersions with Distinct Proton Donor-Dependent Chemoselectivity

A practical and scalable single electron transfer reduction mediated by sodium dispersions has been developed for the reduction and reductive deuteration of tertiary amides. The chemoselectivity of this method highly depends on the nature of the proton donor. The challenging reduction via C-N bond cleavage has been achieved using Na/EtOH, affording alcohol products, while the use of Na/NaOH/H2O leads to the formation of amines via selective C-O scission. Sodium dispersions with high specific surface areas are crucial to obtain high yields and good chemoselectivity. This new method tolerates a range of tertiary amides. Moreover, the corresponding reductive deuterations mediated by Na/EtOD-d1 and Na/NaOH/D2O afford useful α,α-dideuterio alcohols and α,α-dideuterio amines with an excellent deuterium content.

Vernonia oil: Conversion to a mixture of tertiary amines including N,N-Dimethyl-(12S,13R)-Epoxy-cis-9-Octadecenyl amine

Vernonia galamensis is a new potential industrial oilseed crop found in tropical Africa. It is the source of a naturally epoxidized oil called vernonia oil (VO) which is extracted from the seed of the plant. In this study VO was used as the starting material for the synthesis of a mixture of amines, with the major product amine being N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. VO was transesterified via a base catalyzed methanolysis using sodium methoxide to yield VO methyl esters (VOME). Aminolysis of the VOME with dimethylamine as reagent and solvent under reflux conditions afforded the tertiary amides, with N,N- dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide as the major product. The mixture was then subjected to metal hydride reduction with lithium aluminum hydride in diethylether under reflux conditions to obtain the desired amine mixture including N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. Electron impact mass spectrometry was used to characterize the mixture of amines. Additionally, proton NMR, 13C NMR, and FTIR were used for characterization of N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amine. To further confirm the conversion of VO to the amines, the quaternary ammonium salts were synthesized and characterized by matrix-assisted laser desorption ionization time-of-flight mass spectrometry.