Misplaced Pages

Michler's ketone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Michler's ketone
Names
Preferred IUPAC name Bismethanone
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.843 Edit this at Wikidata
EC Number
  • 202-027-5
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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,1-4H3Key: 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,1-4H3Key: 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
Appearance Colorless solid
Melting point 173 °C (343 °F; 446 K)
Hazards
GHS labelling:
Pictograms GHS05: Corrosive GHS08: Health hazard
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Michler's ketone is an organic compound with the formula of 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. 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

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.

Related compounds

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

References

  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); Collected Volumes, 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.
Categories: