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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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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)
M C Rezende et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 57(6), 1183-1190 (2001-06-23)
The preparation and the solvatochromic behavior of two dyes, obtained by condensation of N,N'-dimethylbarbituric acid with dimethylaminobenzaldehyde and with 4,4'-bis(N,N-dimethylamino)benzophenone (Michler's ketone) are described. The latter dye is rather sensitive to the polarity of the medium, and in particular, to
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)
Michler's ketone.
Report on carcinogens : carcinogen profiles, 12, 270-271 (2011-08-24)
New Push-Pull Dyes Derived from Michler?s Ketone For Polymerization Reactions Upon Visible Lights.
Tehfe M, et al.
Macromolecules, 46(10), 3761-3770 (2013)
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