ChemicalBook CAS DataBase List 538-71-6

538-71-6

Name	Domiphen bromide
CAS	538-71-6
EINECS(EC#)	208-702-0
Molecular Formula	C22H40BrNO
MDL Number	MFCD00011769
Molecular Weight	414.46
MOL File	538-71-6.mol

Synonyms

(DODECYLDIMETHYL-2-PHENOXYETHYL)-AMMONIUM BROMIDE DOMIPHEN DOMIPHEN BROMIDE LABOTEST-BB LT00847867 beta-phenoxyethyldimethyldodecylammoniumbromide bradasol bradonit bradoral bradosol bradosolbromide dimethyldodecyl(2-phenoxyethyl)-ammoniubromide dodecyldimethyl(2-phenoxyethyl)-ammoniubromide dodecyldimethyl(2-phenoxyethyl)-ammoniumbromid fungitex fungitexr n,n-dimethyl-n-(2-phenoxyethyl)-1-dodecanaminiubromide nsc-39415 oradol pddb DOMOPHEN BROMIDE

Chemical Properties

Melting point	117-119 °C (lit.)
density	1.1411 (rough estimate)
refractive index	1.5570 (estimate)
storage temp.	Inert atmosphere,Room Temperature
solubility	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form	Solid
color	White to Off-White
Water Solubility	Soluble in ethanol, acetone, ethyl acetate, chloroform and water. Slightly soluble in benzene.
Sensitive	Hygroscopic
Merck	14,3415
BRN	3922742
Cosmetics Ingredients Functions	ANTIMICROBIAL DEODORANT ANTIPLAQUE ORAL CARE
InChI	1S/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
InChIKey	OJIYIVCMRYCWSE-UHFFFAOYSA-M
SMILES	[Br-].CCCCCCCCCCCC[N+](C)(C)CCOc1ccccc1
CAS DataBase Reference	538-71-6(CAS DataBase Reference)
EPA Substance Registry System	538-71-6(EPA Substance)

Safety Data

Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	BQ2030000
TSCA	Yes
HazardClass	6.1
PackingGroup	III
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
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. less more
Hazardous Substances Data	538-71-6(Hazardous Substances Data)

Hazard Information

Description

Domiphen is a quaternary ammonium compound and cationic surfactant with antimicrobial activity. It is active against A. viscosus, A. naeslundii, S. mutans, E. coli, and L. monocytogenes bacteria and inhibits C. neoformans yeast growth and spore germination. It also inhibits the human-ether-a-go-go-related gene (hERG) channel (IC₅₀ = 1.5 μM in a whole-cell patch-clamp assay). Formulations containing domiphen have been used as antiseptics, disinfectants, and biocides in industrial, agricultural, veterinary, and clinical applications.

Originator

Bradosol,Ciba,US,1958

Uses

Antiinfective, topical.

Uses

Domiphen bromide is employed as a phase transfer catalyst in synthetic chemistry. It is used as a quaternary ammonium cation with cationic surfactant properties. Further, it is used as an antiseptic and an active pharmaceutical ingredient.

Definition

ChEBI: Domiphen bromide is an aromatic ether.

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.

Therapeutic Function

Topical antiinfective

References

[1] P. J. BAKER. The in vitro inhibition of microbial growth and plaque formation by surfactant drugs[J]. Journal of periodontal research, 1978, 13 5: 474-485. DOI: 10.1111/j.1600-0765.1978.tb00200.x
[2] ANNELIESE MüLLER. The Listeria monocytogenes transposon Tn6188 provides increased tolerance to various quaternary ammonium compounds and ethidium bromide[J]. Fems Microbiology Letters, 2014, 361 2: 166-173. DOI: 10.1111/1574-6968.12626
[3] SCARLETT R HOLDSWORTH Christopher J L. The major facilitator superfamily transporter MdtM contributes to the intrinsic resistance of Escherichia coli to quaternary ammonium compounds.[J]. Journal of Antimicrobial Chemotherapy, 2013, 68 4: 831-839. DOI: 10.1093/jac/dks491
[4] SéBASTIEN C ORTIZ Christina M H Mingwei Huang. Spore Germination as a Target for Antifungal Therapeutics.[J]. Antimicrobial Agents and Chemotherapy, 2019, 63 12. DOI: 10.1128/aac.00994-19
[5] MENGHANG XIA . Identification of quaternary ammonium compounds as potent inhibitors of hERG potassium channels[J]. Toxicology and applied pharmacology, 2011, 252 3: Pages 250-258. DOI: 10.1016/j.taap.2011.02.016

Material Safety Data Sheet(MSDS)

Spectrum Detail

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