Basic information
- CAS
538-71-6- Standard SMILES
CCCCCCCCCCCC[N+](C)(C)CCOc1ccccc1.[Br-]- InChIKey
OJIYIVCMRYCWSE-UHFFFAOYSA-M- Molecular formula
- C22H40NO.Br
- Average molar mass
- 414.5 g/mol
- Monoisotopic mass
- 413.229327
Overview
Domiphen bromide is an aromatic ether.
Names & identifiers
- Preferred name
- Domiphen Bromide
- IUPAC
- dodecyl-dimethyl-(2-phenoxyethyl)azanium bromide
- English name
- Domiphen bromide
- Molecular formula
- C22H40BrNO
- Molecular weight
- 414.46
Names & synonyms
domiphen bromide538-71-6OradolPhenododecinium bromideNSC-39415Bromuro de domifenoBromure de domiphene1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromideDomipheni bromidumDTXSID5033468R4CY19YS7CDodecyldimethyl(2-phenoxyethyl)ammonium bromide
Show more names
DOMIPHENDomiphenbromide,97%pddbMr C mbradosolbradoralbradonitfungitex
DTXCID3013468domifene bromuroRefChem:590363A01AB06NSC39415208-702-0Domiphen (bromide)Bradasol
Database identifiers
- CAS
538-71-6- PubChem CID
- 10866
- DTXSID
DTXSID5033468- ChEMBL
CHEMBL486696- ChEBI
CHEBI:31514- UNII
- R4CY19YS7C
- EC Number
- 208-702-0
Properties
Computed structural properties
- Topological polar surface area
- 9.2 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 15
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 271
Experimental & physicochemical properties
CosmeticsAntiplaque; Oral care; Deodorant; Antimicrobial
pHpH of 10% solution: 6.42; 1% commercial product @ 25 °C: 5.5; of 0.1%: 6.8
LogPlog Kow = 4.20 /Estimated/
OdorMild characteristic odor
TasteBitter
Color/FormCrystals
SolubilityFreely soluble in water (100 g/100 mL), much less sol at low temps. Soluble in ethanol, acetone, ethyl acetate, chloroform; very slightly soluble in benzene
Melting Point112-113 °C
Vapor Pressure3.1X10-11 mm Hg @ 25 °C /Estimated/
Surface Tension... by the capillary rise method, range from 36.75 dynes/cm (10% soln) to 22.08 dynes/cm (0.1% soln).
Henry's Law ConstantHenry's Law constant = 4.3X10-13 atm-cu m/mole @ 25 °C /Estimated/
Other Experimental Properties
Aqueous solutions are clear, colorless, and foam profusely on shaking. ... Incompatible with soap
Hydroxyl radical reaction rate constant = 8.6X10-11 cu cm/molec-sec @ 25 °C /Estimated/
Physicochemical properties
- Melting point
- 117 · 117-119 °C (lit.)
- Density
- 1.1411 · 1.1411 (rough estimate)
- refractive index
- 1.557 · 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 · 14,3415
- BRN
- 3922742 · 3922742
- Cosmetics Ingredients Functions
- ANTIMICROBIALDEODORANTANTIPLAQUEORAL 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 · 538-71-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 4 CY19YS7C · R4CY19YS7C
- ATC code
- 1 AB06 · A01AB06
- EPA Substance Registry System
- 1 · 1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromide (1:1) (538-71-6)
- UNSPSC Code
- 12352112 · 12352112
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 2030000 · BQ2030000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 538 · 538-71-6(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (16.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: 1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromide
Hazard Classes and CategoriesAcute Tox. 4 (16.3%)
Safety & protection
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Toxicology
Probable Routes of Human ExposureNIOSH (NOES Survey 1981-1983) has statistically estimated that 853 workers (209 of these are female) are potentially exposed to domiphen bromide in the US(1).
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BQ2030000
- ridadr
- UN 2811 6.1/PG 3
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 538-71-6(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of ActionDomiphen bromide is a quaternary antiseptic with actions and uses similar to those of cationic surfactants.
Uses & manufacturing
Uses
Medication
Anti-infective (topical)
Formulations/PreparationsTrade names: Bradosol Bromide, Oradol, Modicare, Neo-Bradoral
Household ProductsInformation on 15 consumer products that contain Domiphen bromide in the following categories is provided:
Use ClassificationCosmetics -> Antiplaque; Oral care; Deodorant; Antimicrobial
General Manufacturing Information
1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromide (1:1): ACTIVE
Prepared by heating phenoxyethyldimethylamine with dodecyl bromide
Applications
DescriptionDomiphen 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.
UsesAntiinfective, topical.
UsesDomiphen 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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Domiphen bromide is an aromatic ether.
Related reactions
1 records
Compound notes
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