538-71-6

Usage

Uses

Used in Synthetic Chemistry:
Domiphen bromide is used as a phase transfer catalyst, facilitating reactions in synthetic chemistry by promoting the transfer of reactants between different phases, thus enhancing the efficiency and yield of chemical processes.
Used in Industrial Applications:
As a cationic surfactant with antimicrobial properties, Domiphen bromide is utilized in various industrial applications, such as in the formulation of antiseptics, disinfectants, and biocides. Its broad-spectrum activity against bacteria and yeast makes it a valuable component in maintaining cleanliness and preventing the spread of microorganisms in industrial settings.
Used in Agricultural Applications:
In agriculture, Domiphen bromide is employed as a biocide to control the growth of harmful microorganisms that can negatively impact crop yields and quality. Its antimicrobial activity helps protect plants from diseases and pests, contributing to a more sustainable and efficient agricultural system.
Used in Veterinary Applications:
Domiphen bromide is also used in the veterinary industry as an antiseptic and disinfectant, helping to maintain hygiene and prevent the spread of infections in animals. Its effectiveness against a wide range of bacteria and yeast makes it a valuable tool in ensuring the health and well-being of animals in veterinary care.
Used in Clinical Applications:
In the clinical setting, Domiphen bromide is used as an active pharmaceutical ingredient, leveraging its antimicrobial properties to treat various infections. Its ability to inhibit the hERG channel also makes it a potential candidate for further research and development in the pharmaceutical industry, with the potential to contribute to the treatment of various medical conditions.

Originator

Bradosol,Ciba,US,1958

Manufacturing Process

7 parts of β-phenoxyethyl-dimethylamine are heated for 2 hours on the boiling water-bath with 11 parts of dodecyl bromide. A good yield of β-phenoxy-ethyldimethyl-dodecyl-ammonium bromide is obtained which, after recrystallization from acetone, melts at 112°C. It is a white crystalline powder which dissolves easily in water to give a neutral reaction.

Safety Profile

Poison by intraperitoneal and intravenous routes. hfutauon data reported. When heated to decomposiuon it emits very toxic fumes of NOx, NH3, and Br-. See also BROMIDES.

InChI:InChI=1/C22H40NO.BrH/c1-4-5-6-7-8-9-10-11-12-16-19-23(2,3)20-21-24-22-17-14-13-15-18-22;/h13-15,17-18H,4-12,16,19-21H2,1-3H3;1H/q+1;/p-1

Synthetic route

dimethyl(2-phenoxyethyl)amine (13468-02-5) + 1-dodecylbromide (143-15-7) → domiphen brominde (538-71-6)

n-Dodecylamine (124-22-1) + phenoxyethyl bromide (589-10-6) → domiphen brominde (538-71-6)

Conditions	Yield
With methyl bromide; formaldehyd; formic acid

N,N-dimethylaminododecane (112-18-5) + phenoxyethyl bromide (589-10-6) → domiphen brominde (538-71-6)

Conditions	Yield
With ethyl acetate
With acetone
With water

domiphen brominde (538-71-6) + 3,6-dichloro-2-methoxybenzoate sodium salt (1918-00-9) → dodecyldimethylphenoxyethylammonium 3,6-dichloro-2-methoxybenzoate

Conditions	Yield
In water	99.5%

(R)-Mecoprop (16484-77-8) + domiphen brominde (538-71-6) → domiphen (+)-(R)-2-(4-chloro-2-methylphenoxy)propionate (1354725-99-7)

Conditions	Yield
Stage #1: (R)-Mecoprop With potassium hydroxide In water at 39.84℃; Stage #2: domiphen brominde In water for 24h;	99%

MCPA (94-74-6) + domiphen brominde (538-71-6) → domiphen (4-chloro-2-methylphenoxy)acetate (1082249-07-7)

Conditions	Yield
With sodium hydroxide In water for 2h;	98%

domiphen brominde (538-71-6) + L-proline (147-85-3) → C22H40NO(1+)*C5H8NO2(1-)

Conditions	Yield
With potassium hydroxide In water at 59.84℃; for 12h;	92%

N-(phosphonemethyl)glycine (1071-83-6) + domiphen brominde (538-71-6) → bis(N,N-dimethyl-N-dodecyl-N-phenoxyethylammonium) glyphosate

Conditions	Yield
Stage #1: domiphen brominde With potassium hydroxide In 1,4-dioxane at 25℃; for 6h; Stage #2: N-(phosphonemethyl)glycine In 1,4-dioxane at 25℃; for 6h;	92%

Upstream product

• 13468-02-5 dimethyl(2-phenoxyethyl)amine 
• 143-15-7 1-dodecylbromide 
• 124-22-1 n-Dodecylamine 
• 589-10-6 phenoxyethyl bromide 
• 112-18-5 N,N-dimethylaminododecane 

Downstream Products

• 1082249-07-7 domiphen (4-chloro-2-methylphenoxy)acetate 
• 1354725-99-7 domiphen (+)-(R)-2-(4-chloro-2-methylphenoxy)propionate 

Relevant academic research and scientific papers

Dentifrice containing a poly(hydroxypropyl ether) non-ionic surfactant and a specified cationic polymer

Dentifrice containing, in combination, (A) a poly(hydroxypropyl ether) nonionic surfactant, and (B) a cationic polymer selected from the group consisting of (i) a vinylpyrrolidone/dialkylaminoalkyl or -hydroxyalkyl acrylate or methacrylate, quaternized or nonquaternized and (ii) a cationic polysaccharide. This dentifrice is characterized by good foamability, pleasant taste and it does not attack the buccal mucosae and the gums.