2-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide

Base Information

• Chemical Name: 2-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide
• CAS No.: 2156-29-8
• Molecular Formula: C₁₆H₁₉N₂*I
• Molecular Weight: 366.245
• DSSTox Substance ID: DTXSID10944163
• ChEMBL ID: CHEMBL608857
• Mol file: 2156-29-8.mol

Synonyms:GNF-Pf-329;CHEBI:51600;GNF-Pf-5154;CHEMBL608857;DTXSID10944163;AKOS030695158;FT-0608568;2-{2-[4-(dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide

Chemical Property of 2-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide

Chemical Property:

• Vapor Pressure: 1.55E-06mmHg at 25°C
• Melting Point: 280 °C
• Refractive Index: 1.668
• Boiling Point: 397.8°C at 760 mmHg
• Flash Point: 179.3°C
• PSA: 7.12000
• Density: 1.091g/cm³
• LogP: -0.24850
• Solubility.: DMSO: soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 366.05930
• Heavy Atom Count: 19
• Complexity: 264

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-[4-(Dimethylamino)styryl]-1-methylpyridinium iodide Dye content 95 % ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+]1=CC=CC=C1C=CC2=CC=C(C=C2)N(C)C.[I-]
• Uses: DASPMI is a polar sensitive dye that measures the membrane potential of mitochondria in living cells. It may be used as a light absorber in the development of a photoinitiator based system.

Technology Process of 2-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide

There total 14 articles about 2-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridin-1-ium iodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

N-methyl-2-methylpyridinium iodide (872-73-1) + 4-dimethylamino-benzaldehyde (100-10-7) → (E)-2-[4-(dimethylamino)phenyl]vinyl-1-methylpyridinium iodide (2156-29-8,1694-49-1,1694-48-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; for 0.5h; Neat (no solvent); Grinding;

DOI:10.1080/00397911.2010.528573

Reference yield: 57.0%

N-methyl-2-methylpyridinium iodide (872-73-1) + p-dimethylaminocinnamaldehyde (6203-18-5) → 2-(4-(dimethylamino) styryl)-1-methylpyridinium iodide (1694-48-0,1694-49-1,2156-29-8)

Guidance literature:

With piperidine; In methanol; Heating;

DOI:10.1246/bcsj.65.71

Reference yield:

4-dimethylamino-benzaldehyde (100-10-7) + 1-methyl picolinium iodide → (E)-2-[4-(dimethylamino)phenyl]vinyl-1-methylpyridinium iodide (2156-29-8,1694-49-1,1694-48-0)

Guidance literature:

With piperidine; In ethanol; for 24h; Yield given; Heating;

upstream raw materials:

N-methyl-2-methylpyridinium iodide

4-dimethylamino-benzaldehyde

p-dimethylaminocinnamaldehyde

2-(dimethylamino)benzaldehyde

Downstream raw materials:

C₁₆H₁₉N₂⁽¹⁺⁾*I^(1-)

(E)-2-(4-(dimethylamino)styryl)-1-methylpyridinium 4-methoxybenzenesulfonate

(E)-2-(4-(dimethylamino)styryl)-1-methylpyridinium 4-chlorobenzenesulfonate

(E)-2-(4-(dimethylamino)styryl)-1-methylpyridinium 4-bromobenzenesulfonate

Refernces

• 1、 Tripathy, Sarita,Dash, Sukalyan. "Solvation studies of some tailor made α-N,N-dimethylaminostyryl-N-alkyl pyridinium dyes in binary solvent mixtures containing alcohols, hexane, 1,4-dioxane, DCM and acetone". . p. 29 - 38. Retrieved 2015/03/04.
• 2、 Seiad, Linda Loucif,Villemin, Didier,Bar, Nathalie,Hachemi, Messaoud. "Solvent-free condensation of methyl pyridinium and quinolinium salts with aldehydes catalyzed by DBU". experimental part. p. 650 - 657. Retrieved 2011/12/21.