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147834

Sigma-Aldrich

Michler′s ketone

98%

Synonym(s):

4,4′-Bis(dimethylamino)benzophenone

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About This Item

Linear Formula:
[(CH3)2NC6H4]2CO
CAS Number:
90-94-8
Molecular Weight:
268.35
Beilstein:
790733
EC Number:
202-027-5
MDL number:
MFCD00008312
UNSPSC Code:
12162002
PubChem Substance ID:
24848830
NACRES:
NA.23

Assay

98%

form

powder

mp

174-176 °C (lit.)

SMILES string

CN(C)c1ccc(cc1)C(=O)c2ccc(cc2)N(C)C

InChI

1S/C17H20N2O/c1-18(2)15-9-5-13(6-10-15)17(20)14-7-11-16(12-8-14)19(3)4/h5-12H,1-4H3

InChI key

VVBLNCFGVYUYGU-UHFFFAOYSA-N

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General description

Michler′s ketone (MK) is a derivative of benzophenone that shows temperature dependent phosphorescence. It also exhibits triplet-triplet absorption spectra at a lower temperature.

Application

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).

Pictograms

Health hazardCorrosion
GHS08,GHS05

Signal Word

Danger

Hazard Statements

H318,H341,H350

Hazard Classifications

Carc. 1B - Eye Dam. 1 - Muta. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis of a novel addition-fragmentation agent based on Michler's ketone and its use as photo-initiator for cationic polymerization
Onen A and Yagci Y
Polymer, 42(16), 6681-6685 (2001)
Excited state dynamics of Michler's ketone: a laser flash photolysis study
Singh AK, et al.
Research on Chemical Intermediates, 27(1-2), 125-136 (2001)
R F Struck et al.
Xenobiotica; the fate of foreign compounds in biological systems, 11(8), 569-567 (1981-08-01)
1. Studies on the metabolism of 14C-Michler's ketone (4,4'-bis-(dimethylamino)[carbonyl- 14C]benzophenone) in rats have revealed that this carcinogen is subject to demethylation, ring-hydroxylation and N-acetylation after adjacent methyl groups have been removed. 2 As identified by mass spectral analysis, microsomal metabolites
A Lafi et al.
Mutagenesis, 1(1), 17-20 (1986-01-01)
The industrial chemical Michler's ketone (MK) has been examined for its ability to induce abnormalities of mitotic cell division and the production of chromosomal aberrations and aneuploidy. MK was shown to produce aberrant cell division stages in cultured mammalian cells
L Castle et al.
Food additives and contaminants, 14(1), 45-52 (1997-01-01)
A survey of retail samples was conducted in two phases with 50 general paper and board food contact materials and articles analysed in 1992, and 121 samples, specifically of printed cartonboard, analysed in 1995. Packaging samples were extracted with ethanol
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