(2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile

Base Information

• Chemical Name: (2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile
• CAS No.: 51325-91-8
• Deprecated CAS: 142347-86-2,80892-60-0,83404-52-8
• Molecular Formula: C19H17N3O
• Molecular Weight: 303.363
• Hs Code.: 29329990
• European Community (EC) Number: 257-137-6
• Mol file: 51325-91-8.mol

Synonyms:CCRIS 4973;EINECS 257-137-6;(2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile;Propanedinitrile, (2-(2-(4-(dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)-;Malononitrile, (2-(p-(dimethylamino)styryl)-6-methyl-4H-pyran-4-ylidene)-;(2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinit rile;(2-(2-(4-(Dimethylamino)phenyl)vinyl)-6-methyl-4H-pyran-4-ylidene)malononitrile;2-[2-[2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile;(2-(p-(Dimethylamino)styryl)-6-methyl-4H-pyran-4-ylidene)malononitrile;[2-[2-[4-(Dimethylamino)phenyl]ethenyl]-6-methyl-4H-pyran-4-ylidene]propanedinitrile;[2-[2-[4-(dimethylamino)phenyl]vinyl]-6-methyl-4H-pyran-4-ylidene]malononitrile;4-dicyanomethylene-2-methyl-6-p-dimethylaminostyryl-4H-pyran;2-[2-[2-[4-(Dimethylamino)phenyl]ethenyl]-6-methyl-4H-pyran-4-ylidene]propanedinitrile;Propanedinitrile, [2-[2-[4-(dimethylamino)phenyl]ethenyl]-6-methyl-4H-pyran-4-ylidene]-;Propanedinitrile, 2-(2-(2-(4-(dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)-;AKOS024306936;SB66796;LS-88919;FT-0616740;4-dicyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4h-pyran

Chemical Property of (2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile

Chemical Property:

• Appearance/Colour: red/brown crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 215-220 °C(lit.)
• Refractive Index: 1.689
• Boiling Point: 446.875 °C at 760 mmHg
• PKA: 5.46±0.24(Predicted)
• Flash Point: 224.062 °C
• PSA: 60.05000
• Density: 1.239 g/cm³
• LogP: 3.92746
• Storage Temp.: Flammables area
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 303.137162174
• Heavy Atom Count: 23
• Complexity: 650

Purity/Quality:

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

4-(Dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran >95.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXn
• Hazard Codes: F,Xn
• Statements: 11-20-36/37/38-20/21/22-10
• Safety Statements: 16-26-36-7/9-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=C(C#N)C#N)C=C(O1)C=CC2=CC=C(C=C2)N(C)C
• Uses: DCM can be used as a laser dye to enhance the emission of distributed feedback (DFB) device by F?rster resonance energy transfer (FRET). It may be used as a capping layer that allows the conversion of blue to red colored emission in organic light emitting diodes (OLED). DCM may also find potential applications in the enhancement of energy transfer of different devices like metal organic frameworks (MOFs), dye sensitized solar cells (DSSCs) and polarity sensors.

Technology Process of (2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile

There total 5 articles about (2-(2-(4-(Dimethylamino)phenyl)ethenyl)-6-methyl-4H-pyran-4-ylidene)propanedinitrile 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: 63.0%

2?[2?(4?bromostyryl)?6?methyl?4H?pyran?4?ylidene]propanedinitrile + dimethyl amine (124-40-3) → 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (51325-91-8)

Guidance literature:

With copper(l) iodide; potassium carbonate; L-proline; In dimethyl sulfoxide; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1007/s13738-020-01956-5

Reference yield: 57.0%

4-dicyanomethylene-2,6-dimethyl-4H-pyran (28286-88-6) + 4-dimethylamino-benzaldehyde (100-10-7) → 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (51325-91-8)

Guidance literature:

With piperidine; In propan-1-ol; for 10h; Reflux;

Reference yield:

4-bromo-benzaldehyde (1122-91-4) → 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran (51325-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol / 24 h / 20 °C

2: potassium carbonate; copper(l) iodide; L-proline / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere

With copper(l) iodide; sodium methylate; potassium carbonate; L-proline; In methanol; dimethyl sulfoxide; 1: |Knoevenagel Condensation / 2: |Ullmann Condensation;

DOI:10.1007/s13738-020-01956-5

upstream raw materials:

4-dicyanomethylene-2,6-dimethyl-4H-pyran

4-dimethylamino-benzaldehyde

dimethyl amine

4-bromo-benzaldehyde

Refernces

• 1、 Rahimpour, Keshvar,Zarenezhad, Hassan,Teimuri-Mofrad, Reza. "Transition metal-catalyzed C–N cross-coupling reaction of bromine-substituted pyranilidene derivatives: synthesis, characterization, and optical properties study of pyran-based chromophores". . p. 2627 - 2636. Retrieved 2020.
• 2、 Bourson, Jean,Valeur, Bernard. "Ion-Responsive Fluorescent Compounds, 2. Cation-Steered Intramolecular Charge Transfer in a Crowned Merocyanine". . p. 3871 - 3876. Retrieved 2007/10/02.