Michler's ketone

Base Information

• Chemical Name: Michler's ketone
• CAS No.: 90-94-8
• Deprecated CAS: 1817604-20-8
• Molecular Formula: C17H20N2O
• Molecular Weight: 268.359
• Hs Code.: 29223990
• European Community (EC) Number: 202-027-5
• NSC Number: 9602
• UN Number: 3143
• UNII: 3Z2SN6B347
• DSSTox Substance ID: DTXSID2020894
• Nikkaji Number: J4.330C
• Wikipedia: Michler%27s_ketone,Michler's_ketone
• Wikidata: Q418109
• NCI Thesaurus Code: C44403
• Metabolomics Workbench ID: 123575
• ChEMBL ID: CHEMBL15137
• Mol file: 90-94-8.mol

Synonyms:4,4'-bis(dimethylamino)benzophenone;Michler's ketone

Chemical Property of Michler's ketone

Chemical Property:

• Appearance/Colour: white to light greenish crystals
• Melting Point: 174 -176 °C(lit.)
• Refractive Index: 1.5486 (estimate)
• Boiling Point: 427.7 °C at 760 mmHg
• PKA: 2.55±0.12(Predicted)
• Flash Point: 183.9 °C
• PSA: 23.55000
• Density: 1.101 g/cm³
• LogP: 3.04960
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: 5 mg/mL, clear
• Water Solubility.: 400 mg/L (20 ºC)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 268.157563266
• Heavy Atom Count: 20
• Complexity: 281
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

4,4''-Bis(dimethylamino)benzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 45-41-68-36/37/38
• Safety Statements: 53-45-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CN(C)C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)N(C)C
• Uses: MK can be used as an additive that acts as a photoinitiator in the preparation of dyes. It can also be used as a precursor material in the synthesis of 4,4′-bis{N,N,dimethyl, N (2-ethoxy carbonyl-1-propenyl) ammonium hexafluoro antimonate}benzophenone (MKEA). In manufacture of dyes and pigments.

Technology Process of Michler's ketone

There total 82 articles about Michler's ketone 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%

4,4'-bis(dimethylamino)benzhydrol (119-58-4) → bis(p-dimethylaminophenyl)methanone (90-94-8)

Guidance literature:

With potassium phosphate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In tetrahydrofuran; at 65 ℃; for 12h;

DOI:10.1002/adsc.200600394

Reference yield: 94.0%

2,2'-bis(4-dimethylaminophenyl)-1,3-dioxane → bis(p-dimethylaminophenyl)methanone (90-94-8)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.3987/COM-95-7375

Reference yield: 93.0%

4,4'-bis(dimethylamino)benzophenone 1,2-phenylene acetal (95430-30-1) → bis(p-dimethylaminophenyl)methanone (90-94-8)

Guidance literature:

With hydrogenchloride; In acetonitrile; for 0.0833333h;

DOI:10.3987/COM-95-7375

upstream raw materials:

methanol

sodium methylate

hexa-N-methyl-4,4'-carbonyl-di-anilinium; dichloride

ethanol

Downstream raw materials:

p-N,N-dimethylaminobenzoic acid

1,1-bis(4-dimethylaminophenyl)-2,2-diphenylethene

2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-quinoline

2-[2]quinolyl-1,1-bis-(4-dimethylamino-phenyl)-ethanol

Refernces

Features of the Quantum Chain Process in the Photochemical One-Way Isomerization of 2-Anthrylethylenes

10.1246/bcsj.67.3030

The research focuses on the photochemical one-way isomerization of 2-anthrylethylenes, specifically investigating the preparative methods and the quantum chain process involved in the cis-to-trans isomerization. The study aims to understand the high efficiency of this process and the factors contributing to it. The researchers used various chemicals, including 2-anthrylethylenes (la-d), Michler's ketone, biacetyl, and a range of dyes with different triplet energies, such as Rose Bengal, Eosin Y, erythrosine, fluorescein, Acridine Orange, and proflavine. The conclusions drawn from the research indicate that the isomerization efficiently proceeds through a quantum chain process, with the efficiency being slightly higher for 1b and 1c than for la. The high efficiency is attributed to the long lifetime of the triplet state, which enables its nearly thermoneutral energy transfer to take place effectively, competing with its relatively slow decay.