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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 414534712 |
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| Watchedfields = changed |
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| Name = Michler's Ketone |
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| verifiedrevid = 433524550 |
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| ImageFile = Michler's ketone.png |
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| Name = Michler's ketone |
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| ImageSize = 200px |
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| ImageFile = Michler's ketone.png |
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| OtherNames = 4,4'-bis(''N,N''-dimethylamino)benzophenone, 4,4'-bis(Dimethylamino)benzophenone; bis(p-(''N'',''N''-dimethylamino)phenyl)ketone; Michler ketone; Michler's Ketone |
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| PIN = Bismethanone |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 4,4'-Bis(''N,N''-dimethylamino)benzophenone<br />4,4'-Bis(dimethylamino)benzophenone<br />Bis(''p''-(''N'',''N''-dimethylamino)phenyl)ketone<br />Michler ketone<br />Michler's Ketone |
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| SMILES = |
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|Section1={{Chembox Identifiers |
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| CASNo = 90-94-8 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = |
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| CASNo = 90-94-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3Z2SN6B347 |
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| RTECS = |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C19266 |
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| KEGG = C19266 |
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| EINECS = 202-027-5 |
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}} |
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| PubChem = 7031 |
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| Section2 = {{Chembox Properties |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Formula = C<sub>17</sub>H<sub>20</sub>N<sub>2</sub>O |
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| ChemSpiderID = 6764 |
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| MolarMass = 268.36 g/mol |
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| SMILES = CN(C)C1=CC=C(C=C1)C(=O)C2=CC=C(C=C2)N(C)C |
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| Appearance = colorless solid |
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| 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 |
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| Density = |
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| InChIKey = VVBLNCFGVYUYGU-UHFFFAOYAE |
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| Melting point = 173 °C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| BoilingPt = |
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| StdInChI = 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 |
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| Viscosity = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| RefractIndex = |
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| StdInChIKey = VVBLNCFGVYUYGU-UHFFFAOYSA-N |
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| Section3 = {{Chembox Structure |
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|Section2={{Chembox Properties |
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| Dipole = |
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| C=17 | H=20 | N=2 | O=1 |
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}} |
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| Appearance = Colorless solid |
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| Section7 = {{Chembox Hazards |
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| Density = |
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| ExternalMSDS = |
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| MeltingPtC = 173 |
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| EUClass = not listed |
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| NFPA-H = |
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| BoilingPt = |
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| NFPA-F = |
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| Viscosity = |
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| RefractIndex = |
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| NFPA-R = |
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| FlashPt = |
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|Section3={{Chembox Structure |
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| Dipole = |
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| Section8 = {{Chembox Related |
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| Function = |
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|Section7={{Chembox Hazards |
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| OtherFunctn = |
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| ExternalSDS = |
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| OtherCpds = ] |
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| GHS_ref = <ref>{{GESTIS|ZVG=510783}}</ref> |
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}} |
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| GHSPictograms = {{GHS05}} {{GHS08}} |
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| GHSSignalWord = warning |
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| HPhrases = {{HPhrases|H318|H341|H350}} |
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| PPhrases = {{PPhrases|P201|P280|P305+P351+P338+P310|P308+P313}} |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-R = |
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| FlashPt = |
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|Section8={{Chembox Related |
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| OtherFunction_label = |
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| OtherCompounds = ] |
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'''Michler’s ketone''' is an ] with the formula of <sub>2</sub>CO. This electron-rich derivative of ] is an intermediate in the production of dyes and pigments, for example ]. It is also used as a ].<ref>Kan, Robert O. "Organic Photochemistry" McGraw-Hill, New York, 1966.</ref> It is named after the German chemist ]. |
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'''Michler's ketone''' is an ] with the formula of <sub>2</sub>CO. This electron-rich derivative of ] is an intermediate in the production of dyes and pigments, for example ]. It is also used as a ]{{Broken anchor|date=2024-07-01|bot=User:Cewbot/log/20201008/configuration|target_link=Photosensitizer#Photosensitization|reason= }}.<ref>{{cite book | author = Kan, Robert O. | title = Organic Photochemistry | publisher = McGraw-Hill | location = New York | year = 1966}}</ref> It is named after the German chemist ]. |
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==Synthesis== |
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==Synthesis== |
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The ketone is prepared today as it was originally by Michler<ref>{{cite journal |
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The ketone is prepared today as it was originally by Michler using the ] ] of ] (C<sub>6</sub>H<sub>5</sub>NMe<sub>2</sub>) using ] (COCl<sub>2</sub>) or equivalent reagents such as ]<ref>{{cite journal |
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| title = Synthese aromatischer Ketone mittelst Chlorkohlenoxyd |
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| title = Synthese aromatischer Ketone mittelst Chlorkohlenoxyd |
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| author = W. Michler |
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| author = W. Michler |
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| journal = Berichte der deutschen chemischen Gesellschaft |
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| journal = Berichte der Deutschen Chemischen Gesellschaft |
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| volume = 9 |
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| volume = 9 |
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| issue = |
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| issue = |
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| pages = 716–718 |
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| pages = 716–718 |
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| year = 1876 |
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| year = 1876 |
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| url = https://zenodo.org/record/1425100 |
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| url = |
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| doi = 10.1002/cber.187600901218}}</ref> |
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| doi = 10.1002/cber.187600901218}}</ref> using the ] ] of ] (C<sub>6</sub>H<sub>5</sub>NMe<sub>2</sub>) using ] (COCl<sub>2</sub>) or equivalent reagents such as ] (Me = methyl): |
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:COCl<sub>2</sub> + 2 C<sub>6</sub>H<sub>5</sub>NMe<sub>2</sub> → (Me<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO + 2 HCl |
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:COCl<sub>2</sub> + 2 C<sub>6</sub>H<sub>5</sub>NMe<sub>2</sub> → (Me<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO + 2 HCl → salt |
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The related tetraethyl compound (Et<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO, also a precursor to dyes, is prepared similarly. |
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The related tetraethyl compound (Et<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>)<sub>2</sub>CO, also a precursor to dyes, is prepared similarly. |
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==Uses== |
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==Uses== |
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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 ], such as ]. |
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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 ], such as ]. |
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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. |
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Condensation of Michler's ketone with ''N''-phenyl-1-naphthylamine gives the dye ] (CAS#2580-56-5, CI Basic Blue 26), which is used for coloring paper and producing pastes and inks for ballpoint pens. |
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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 ] 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 ] to give 1,2-divinylcyclobutane.<ref>{{OrgSynth | author = Charles D. DeBoer, Nicholas J. Turro, and George S. Hammond | title = cis- and trans-1,2-Divinylcyclobutane| collvol = 5 | collvolpages = 528 | year = 1973 | prep = CV5P0528}}</ref> |
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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 ] 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 ] to give 1,2-divinylcyclobutane.<ref>{{OrgSynth | author = Charles D. DeBoer, Nicholas J. Turro, and George S. Hammond | title = cis- and trans-1,2-Divinylcyclobutane| collvol = 5 | collvolpages = 528 | year = 1973 | prep = CV5P0528}}</ref> |
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==Related compounds== |
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==Related compounds== |
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], a dye, is a salt of the iminium cation <sub>2</sub>CNH<sub>2</sub><sup>+</sup>. Michler's thione, <sub>2</sub>CS, is prepared by treatment of Michler's ketone with ] in the presence of acid or sulfideing auramine O.<ref>R. M. Elofson, Leslie A. Baker, F. F. Gadallah, R. A. Sikstrom "The Preparation of Thiones in the Presence of Anhydrous Hydrogen Fluoride" J. Org. Chem., 1964, volume 29, pp 1355–1357. {{DOI|10.1021/jo01029a020}}</ref> |
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''p''-Dimethylaminobenzophenone is related to Michler's ketone, but with only one amine.<ref>{{cite journal|first1=Charles D.|last1=Hurd|first2=Carl N.|last2=Webb|year=1925|title=''p''-Dimethylaminobenzophenone|journal=Organic Syntheses|volume=7|pages=24|doi=10.15227/orgsyn.007.0024}}</ref> ], a dye, is a salt of the iminium cation <sub>2</sub>CNH<sub>2</sub><sup>+</sup>. Michler's thione, <sub>2</sub>CS, is prepared by treatment of Michler's ketone with ] in the presence of acid or ] auramine O.<ref>{{cite journal | doi = 10.1021/jo01029a020 | title = The Preparation of Thiones in the Presence of Anhydrous Hydrogen Fluoride | year = 1964 | last1 = Elofson | first1 = R. M. | last2 = Baker | first2 = Leslie A. | last3 = Gadallah | first3 = F. F. | last4 = Sikstrom | first4 = R. A. | journal = The Journal of Organic Chemistry | volume = 29 | issue = 6 | pages = 1355}}</ref> Hydride reduction of Michler's ketone gives ]. |
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==References== |
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==References== |
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