57155-63-2

Basic information

• Product Name: (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE
• Synonyms: DODECYL(2-HYDROXY-1-METHYL-2-PHENYLETHYL)DIMETHYLAMMONIUM BROMIDE;(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE;[R-(R*,S*)]-dodecyldimethyl(α-methylphenacyl)ammonium bromide;[R-(R*,S*)]-dodecyldimethyl(alpha-methylphenacyl)ammonium bromide;(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE 99+%;(-)-DMEB, (1R,2S)-Dodecyl(2-hydroxy-1-methyl-2-phenylethyl)dimethylammonium bromide;(1R,2S)-(-)-N-Dodecyl-N-methylephedrinium bromide;[(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl](dodecyl)dimethylaminium·bromide
• CAS NO: 57155-63-2
• Molecular Formula: Br*C₂₃H₄₂NO
• Molecular Weight: 428.49
• EINECS: 260-596-5
• Mol File: 57155-63-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• BRN: 5421952
• CAS DataBase Reference: (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE(57155-63-2)
• EPA Substance Registry System: (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE(57155-63-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 57155-63-2(Hazardous Substances Data)

Usage

Description

(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE is a quaternary ammonium compound that serves as a surfactant and an ionic liquid. It is known for its ability to act as a phase transfer catalyst in organic reactions, enabling the transfer of reactants between immiscible phases. This chemical is also recognized for its potential antiviral and antibacterial properties, making it a versatile and significant compound in various industries.
Used in Chemical Industry:
(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE is used as a phase transfer catalyst for facilitating the transfer of reactants between immiscible phases in organic reactions.
Used in Pharmaceutical Industry:
(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE is used as an emulsifier in different formulations, which helps in the dispersion of substances to create stable mixtures.
Used in Corrosion Prevention:
(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE is used as a corrosion inhibitor in various applications to protect materials from degradation and wear.
Used in Antimicrobial Applications:
(-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE is studied for its potential antiviral and antibacterial properties, making it a candidate for use in sanitizing and disinfecting products.

InChI:InChI=1/C23H40NO.BrH/c1-5-6-7-8-9-10-11-12-13-17-20-24(3,4)21(2)23(25)22-18-15-14-16-19-22;/h14-16,18-19,21H,5-13,17,20H2,1-4H3;1H/q+1;/p-1/t21-;/m1./s1

Upstream product

• 552-79-4 (-)-N-methylephedrine 
• 143-15-7 1-dodecylbromide 
• 1201-56-5 (1S,2S)-N-Methylpseudoephedrine 
• 90-82-4 pseudoephedrine 

Downstream Products

• 14212-54-5 (+)-(R,R)-β-methylstyrene oxide 
• 1261244-80-7 CHO₃^(1-)*C₂₃H₄₂NO⁽¹⁺⁾ 
• 1261244-81-8 C₃H₅O₃^(1-)*C₂₃H₄₂NO⁽¹⁺⁾ 
• 1357498-62-4 C₃H₅O₃^(1-)*C₂₃H₄₂NO⁽¹⁺⁾ 

Relevant articles and documents

Spectral and physicochemical characterization of dysprosium-based multifunctional ionic liquid crystals

We report on the synthesis and characterization of multifunctional ionic liquid crystals (melting points below 100 °C) which possess chirality and fluorescent behavior as well as mesomorphic and magnetic properties. In this regard, (1R,2S)-(-)-N-methylephedrine ((-)MeEph), containing a chiral center, is linked with variable alkyl chain lengths (e.g., 14, 16, and 18 carbons) to yield liquid crystalline properties in the cations of these compounds. A complex counteranion consisting of trivalent dysprosium (Dy3+) and thiocyanate ligand (SCN-) is employed, where Dy3+ provides fluorescent and magnetic properties. Examination of differential scanning calorimetry (DSC) and hot-stage polarizing optical microscopy (POM) data confirmed liquid crystalline characteristics in these materials. We further report on phase transitions from solid to liquid crystal states, followed by isotropic liquid states with increasing temperature. These compounds exhibited two characteristic emission peaks in acetonitrile solution and the solid state when excited at ex = 366 nm, which are attributed to transitions from 4F9/2 to 6H15/2 and 4F9/2 to 6H13/2. The emission intensities of these compounds were found to be very sensitive to the phase.

Chiral ammonium-capped rhodium(0) nanocatalysts: Synthesis, characterization, and advances in asymmetric hydrogenation in neat water

Optically active amphiphilic compounds derived from N-methylephedrine, N-methylprolinol, or cinchona derivatives possessing bromide or chiral lactate counterions were efficiently used as protective agents for rhodium(0) nanoparticles. The full characterization of these surfactants and the obtained nanocatalysts was performed by means of different techniques. These spherical nanoparticles, with sizes between 0.8-2.5 nm depending on the stabilizer, were evaluated in the hydrogenation of model substrates in neat water as a green solvent. The rhodium catalysts showed relevant kinetic properties, but modest enantiomeric excess values of up to 13 % in the hydrogenation of ethyl pyruvate. They were also investigated in the hydrogenation of disubstituted arenes, such as m-methylanisole, providing interesting catalytic activities and a preferential cis selectivity of around 80 %; however, no asymmetric induction was observed. Green nanocatalysts: Optically active compounds derived from N-methylephedrine, N-methylprolinol, or cinchona derivatives with bromide or chiral lactate counterions are used as protective agents for rhodium(0) nanoparticles in asymmetric catalysis of the hydrogenation of ethyl pyruvate and m-methylanisole in water as a green solvent. Copyright