Names | |
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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 | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.001.843 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C17H20N2O | |
Molar mass | 268.360 g·mol−1 |
Appearance | Colorless solid |
Melting point | 173 °C (343 °F; 446 K) |
Hazards | |
Safety data sheet | External MSDS |
GHS labelling: [1] | |
Warning | |
H318, H341, H350 | |
P201, P280, P305+P351+P338+P310, P308+P313 | |
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.
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]
The related tetraethyl compound (Et2NC6H4)2CO, also a precursor to dyes, is prepared similarly.
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]
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.
In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
In chemistry thioesters are compounds with the functional group R–S–CO–R'. They are analogous to carboxylate esters with the sulfur in the thioester playing the role of the linking oxygen in the carboxylate ester. They are the product of esterification between a carboxylic acid and a thiol. In biochemistry, the best-known thioesters are derivatives of coenzyme A, e.g., acetyl-CoA.
In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -COCl. Their formula is usually written RCOCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.
Azo compounds are compounds bearing the functional group diazenyl R−N=N−R′, in which R and R′ can be either aryl or alkyl.
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
Trimethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2(CH3)6 (abbreviated as Al2Me6 or TMA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially important compound, closely related to triethylaluminium.
A sulfoxide is a chemical compound containing a sulfinyl (SO) functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are the oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.
Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.
Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.
Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl. They are a commercially important family of azo compounds, i.e. compounds containing the linkage C-N=N-C. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related to azo dyes are azo pigments, which are insoluble in water and other solvents.
Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.
Methyl isothiocyanate is the organosulfur compound with the formula CH3N=C=S. This low melting colorless solid is a powerful lachrymator. As a precursor to a variety of valuable bioactive compounds, it is the most important organic isothiocyanate in industry.
Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.
Thioureas are members of a family of organosulfur compounds with the formula SC(NR2)2. The parent member of this class of compounds is thiourea SC(NH2)2. The thiourea functional group has a planar CSN2 core.
Benzylideneacetone is the organic compound described by the formula C6H5CH=CHC(O)CH3. Although both cis- and trans-isomers are possible for the α,β-unsaturated ketone, only the trans isomer is observed. Its original preparation demonstrated the scope of condensation reactions to construct new, complex organic compounds. Benzylideneacetone is used as a flavouring ingredient in food and perfumes.
1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.
Triarylmethane dyes are synthetic organic compounds containing triphenylmethane backbones. As dyes, these compounds are intensely colored. They are produced industrially as dyes.
Pigment violet 23 is an organic compound that is a commercial pigment. It is member of the dioxazine family of heterocyclic compounds, but derived from carbazoles. It is prepared by condensation of chloranil and 3-amino-N-ethylcarbazole. It has a centrosymmetric angular structure. For many years, the structure was assigned, incorrectly, as having a "linear structure" which differ in terms of the carbazole ring fusion.
4,4′-Bis(dimethylamino)benzhydrol is an organic compound with the formula (Me2NC6H4)2CH(OH), where Me is methyl. It is a white solid that is soluble is a variety of organic solvents. The compound is notable as the reduced derivative of Michler's ketone. It is a precursor to triarylmethane dyes.