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.
The related tetraethyl compound (Et2NC6H4)2CO, also a precursor to dyes, is prepared similarly.
Usesedit
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 compoundsedit
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.
^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.
December 20, 2023
michler, ketone, organic, compound, with, formula, 2nc6h4, this, electron, rich, derivative, benzophenone, intermediate, production, dyes, pigments, example, methyl, violet, also, used, photosensitizer, named, after, german, chemist, wilhelm, michler, namespre. 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 Michler s ketone NamesPreferred IUPAC name Bis 4 dimethylamino phenyl methanoneOther names 4 4 Bis N N dimethylamino benzophenone4 4 Bis dimethylamino benzophenoneBis p N N dimethylamino phenyl ketoneMichler ketoneMichler s KetoneIdentifiersCAS Number 90 94 8 Y3D model JSmol Interactive imageChemSpider 6764 NECHA InfoCard 100 001 843EC Number 202 027 5KEGG C19266 YPubChem CID 7031UNII 3Z2SN6B347 YCompTox Dashboard EPA DTXSID2020894InChI 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 NKey VVBLNCFGVYUYGU UHFFFAOYSA N NInChI 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 UHFFFAOYAESMILES CN C C1 CC C C C1 C O C2 CC C C C2 N C CPropertiesChemical formula C 17H 20N 2OMolar mass 268 360 g mol 1Appearance Colorless solidMelting point 173 C 343 F 446 K HazardsGHS labelling 1 PictogramsSignal word WarningHazard statements H318 H341 H350Precautionary statements P201 P280 P305 P351 P338 P310 P308 P313Safety data sheet SDS External MSDSRelated compoundsRelated compounds BenzophenoneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Uses 3 Related compounds 4 ReferencesSynthesis editThe 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 saltThe related tetraethyl compound Et2NC6H4 2CO also a precursor to dyes is prepared similarly Uses editMichler 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 editp 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 edit 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 a href Template Cite journal html title Template Cite journal cite journal a 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 Retrieved from https en wikipedia org w index php title Michler 27s ketone amp oldid 1060802927, wikipedia, wiki, book, books, library,
