Michler's ketone

Michler's ketone
Names
	Preferred IUPAC name Bis[4-(dimethylamino)phenyl]methanone
	Other names 4,4'-Bis(N,N-dimethylamino)benzophenone; 4,4'-Bis(dimethylamino)benzophenone; Bis(p-(N,N-dimethylamino)phenyl)ketone; Michler ketone; Michler's Ketone
Identifiers
CAS Number	90-94-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	6764 ;
ECHA InfoCard	100.001.843
EC Number	202-027-5;
KEGG	C19266 ;
PubChem CID	7031;
UNII	3Z2SN6B347 ;
CompTox Dashboard (EPA)	DTXSID2020894 ;
	InChI 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 Key: VVBLNCFGVYUYGU-UHFFFAOYSA-N ; InChI=1/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 Key: VVBLNCFGVYUYGU-UHFFFAOYAE;
	SMILES CN(C)C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)N(C)C;
Properties
Chemical formula	C17H20N2O
Molar mass	268.360 g·mol−1
Appearance	Colorless solid
Melting point	173 °C (343 °F; 446 K)
Hazards
	GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H318, H341, H350
Precautionary statements	P201, P280, P305+P351+P338+P310, P308+P313
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	Benzophenone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Michler's ketone is an organic compound with the formula of [(CH₃)₂NC₆H₄]₂CO. This electron-rich derivative of benzophenone is an intermediate in the production of dyes and pigments, for example Methyl violet. It is also used as a photosensitizer.[2] It is named after the German chemist Wilhelm Michler.

Synthesis

The ketone is prepared today as it was originally by Michler using the Friedel-Crafts acylation of dimethylaniline (C₆H₅NMe₂) using phosgene (COCl₂) or equivalent reagents such as triphosgene[3]

COCl₂ + 2 C₆H₅NMe₂ → (Me₂NC₆H₄)₂CO + 2 HCl → salt

The related tetraethyl compound (Et₂NC₆H₄)₂CO, also a precursor to dyes, is prepared similarly.

Uses

Michler's ketone is an intermediate in the synthesis of dyes and pigments for paper, textiles, and leather. Condensation with various aniline derivatives gives several of the dyes called methyl violet, such as crystal violet.

Condensation of Michler's ketone with N-phenyl-1-naphthylamine gives the dye Victoria Blue B (CAS#2580-56-5, CI Basic Blue 26), which is used for coloring paper and producing pastes and inks for ballpoint pens.

Michler's ketone is commonly used as an additive in dyes and pigments as a sensitizer for photoreactions because of its absorption properties. Michler's ketone is an effective sensitizer provided energy transfer is exothermic and the concentration of the acceptor is sufficiently high to quench the photoreaction of Michler's ketone with itself. Specifically Michler's ketone absorbs intensely at 366 nm and effectively sensitizes photochemical reactions such as the dimerization of butadiene to give 1,2-divinylcyclobutane.[4]

Related compounds

p-Dimethylaminobenzophenone is related to Michler's ketone, but with only one amine.[5] Auramine O, a dye, is a salt of the iminium cation [(CH₃)₂NC₆H₄]₂CNH₂⁺. Michler's thione, [(CH₃)₂NC₆H₄]₂CS, is prepared by treatment of Michler's ketone with hydrogen sulfide in the presence of acid or sulfideing auramine O.[6] Hydride reduction of Michler's ketone gives 4,4'-bis(dimethylamino)benzhydrol.

References

Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
Kan, Robert O. (1966). Organic Photochemistry. New York: McGraw-Hill.
W. Michler (1876). "Synthese aromatischer Ketone mittelst Chlorkohlenoxyd". Berichte der Deutschen Chemischen Gesellschaft. 9: 716–718. doi:10.1002/cber.187600901218.
Charles D. DeBoer, Nicholas J. Turro, and George S. Hammond (1973). "cis- and trans-1,2-Divinylcyclobutane". Organic Syntheses.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 5, p. 528
Hurd, Charles D.; Webb, Carl N. (1925). "p-Dimethylaminobenzophenone". Organic Syntheses. 7: 24. doi:10.15227/orgsyn.007.0024.
Elofson, R. M.; Baker, Leslie A.; Gadallah, F. F.; Sikstrom, R. A. (1964). "The Preparation of Thiones in the Presence of Anhydrous Hydrogen Fluoride". The Journal of Organic Chemistry. 29 (6): 1355. doi:10.1021/jo01029a020.

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[1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[2] Kan, Robert O. (1966). Organic Photochemistry. New York: McGraw-Hill.

[3] W. Michler (1876). "Synthese aromatischer Ketone mittelst Chlorkohlenoxyd". Berichte der Deutschen Chemischen Gesellschaft. 9: 716–718. doi:10.1002/cber.187600901218.

[4] Charles D. DeBoer, Nicholas J. Turro, and George S. Hammond (1973). "cis- and trans-1,2-Divinylcyclobutane". Organic Syntheses.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 5, p. 528

[5] Hurd, Charles D.; Webb, Carl N. (1925). "p-Dimethylaminobenzophenone". Organic Syntheses. 7: 24. doi:10.15227/orgsyn.007.0024.

[6] Elofson, R. M.; Baker, Leslie A.; Gadallah, F. F.; Sikstrom, R. A. (1964). "The Preparation of Thiones in the Presence of Anhydrous Hydrogen Fluoride". The Journal of Organic Chemistry. 29 (6): 1355. doi:10.1021/jo01029a020.