4-[2-(1-Methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one

Base Information

• Chemical Name: 4-[2-(1-Methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one
• CAS No.: 23302-83-2
• Molecular Formula: C₁₄H₁₃NO
• Molecular Weight: 211.263
• European Community (EC) Number: 821-112-3
• NSC Number: 87344
• UNII: K765RJZ7AS
• DSSTox Substance ID: DTXSID70293129
• Nikkaji Number: J1.019.018E,J621.006F,J621.007D
• Wikipedia: Brooker%27s_merocyanine,Brooker's_merocyanine
• Wikidata: Q4974520
• ChEMBL ID: CHEMBL1564141
• Mol file: 23302-83-2.mol

Synonyms:23302-83-2;Brooker's merocyanine;4-[2-(1-methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one;MOED;MLS000737143;4-[2-(1-methylpyridin-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one;NSC-87344;K765RJZ7AS;4-(2-(1-Methylpyridin-4(1H)-ylidene)ethylidene)cyclohexa-2,5-dienone;MFCD00010099;4'-Hydroxy-1-methylstilbazolium betaine;SMR000528389;1-Methyl-4-[(4-oxocyclohexadienylidene)ethylidene]-1,4-dihydropyridine;2,5-Cyclohexadien-1-one, 4-((1-methyl-4(1H)-pyridinylidene)ethylidene)-;2,5-Cyclohexadien-1-one, 4-(2-(1-methyl-4(1H)-pyridinylidene)ethylidene)-;4-((1-Methyl-4(1H)-pyridinylidene)ethylidene)-2,5-cyclohexadien-1-one;4-(2-(1-Methylpyridin-4(1H)-ylidene)ethylidene)cyclohexa-2,5-dien-1-one;4-[2-(1-methyl-1,4-dihydropyridin-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one;4-[(1-methyl-4(1h)-pyridinylidene)ethylidene]-2,5-cyclohexadien-1-one;NSC87344;Brooker/'s merocyanine;UNII-K765RJZ7AS;NCIOpen2_005368;cid_258436;SCHEMBL1454345;CHEMBL1564141;BDBM88937;DTXSID70293129;HMS2885L12;STL297673;AKOS001645091;CCG-108816;1-Methyl-4-(4-oxylatostyryl)pyridinium;NCGC00246890-01;NS-02376;1-Methyl-4-[(E)-4-oxylatostyryl]pyridinium;V10002;SR-01000081589;Q4974520;SR-01000081589-1;4-[2-(1-methyl-4-pyridylidene)ethylidene]cyclohexa-2,5-dien-1-one;4-[2-(1-Methyl-4(1H)-pyridinylidene)ethylidene]-2,5-cyclohexadien-1-one;4-[2-(1-methyl-4-pyridinylidene)ethylidene]-1-cyclohexa-2,5-dienone;4-[2-[1-Methyl-4(1H)-pyridylidene]ethylidene]-2,5-cyclohexadien-1-one

Chemical Property of 4-[2-(1-Methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one

Chemical Property:

• Vapor Pressure: 2.19E-05mmHg at 25°C
• Melting Point: 220℃
• Boiling Point: 360.6°Cat760mmHg
• PKA: 4.41±0.20(Predicted)
• Flash Point: 141.5°C
• PSA: 22.00000
• Density: 1.268g/cm³
• LogP: 1.70820
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 211.099714038
• Heavy Atom Count: 16
• Complexity: 439

Purity/Quality:

99% ^*data from raw suppliers

4-[2-(1-methyl-1,4-dihydropyridin-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=CC(=CC=C2C=CC(=O)C=C2)C=C1
• Uses: Brooker's merocyanine dye is used as solvent polarity indicators. It is used as pH sensors and transition metal cation indicators.

Technology Process of 4-[2-(1-Methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one

There total 10 articles about 4-[2-(1-Methylpyridin-4(1h)-ylidene)ethylidene]cyclohexa-2,5-dien-1-one 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: 98.0%

1-methyl-4-[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide (95495-28-6,138001-62-4,20288-72-6,95495-31-1) → 4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one (23302-83-2,67106-77-8,67106-80-3,148904-15-8)

Guidance literature:

1-methyl-4-[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide; With potassium hydroxide; In ethanol; at 70 ℃; for 2h;

In ethanol; at 4 ℃; for 16h;

DOI:10.1016/j.saa.2007.10.017

Reference yield: 85.0%

N-methyl-4-methylpyridinium iodide (2301-80-6) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → 4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one (23302-83-2,67106-77-8,67106-80-3,148904-15-8)

Guidance literature:

With piperidine; In ethanol; for 4h; Heating;

Reference yield:

→ 4-[(1-methyl-4(1H)-pyridinylidene)-ethylidene]-2,5-cyclohexadiene-1-one (23302-83-2,67106-77-8,67106-80-3,148904-15-8)

Guidance literature:

γ-Picolinmethiodid, p-Hydroxybenzaldehyd;

DOI:10.1039/f29726800137

upstream raw materials:

N-methyl-4-methylpyridinium iodide

4-hydroxy-benzaldehyde

1-methyl-4-[2-(4-hydroxyphenyl)ethenyl]pyridinium iodide

(E)-4-[2-(1-methylpyridinium-4-yl)ethenyl]phenolate

Downstream raw materials:

(E)-4-[2-(1-methylpyridinium-4-yl)ethenyl]phenolate

cis-1-methyl-4-(4'-hydroxystyryl)pyridinium betaine

1-methyl-4-[2-(4-hydroxyphenyl)ethenyl]pyridinium hydrogensquarate

C₁₄H₁₃NO*C₄₂H₇₀O₃₅

Refernces

• 1、 Kolev, Tsonko,Koleva, Bojidarka B.,Stoyanov, Stanimir,Spiteller, Michael,Petkov, Ivan. "The aggregation of the merocyanine dyes, depending of the type of the counterions". experimental part. p. 1087 - 1096. Retrieved 2009/02/02.
• 2、 Asano, Tsutomu,Okada, Toshio. "Kinetic Effects of Pressure on Thermal Z-E Isomerization of a Stilbazolium Betaine. Dependence of Activation Volume on Reaction Conditions". . p. 3606 - 3607. Retrieved 2007/10/02.