1226-46-6

Basic information

• Product Name: 4,4'-Bis(dimethylamino)thiobenzophenone
• Synonyms: Benzophenone, 4,4'-bis(dimethylamino)thio-;bis[4-(dimethylamino)phenyl]-methanethion;Methanethione, bis[4-(dimethylamino)phenyl]-;Michler's thioketone;Michler's thione;p,p'-bis(Dimethylamino)thiobenzophenone;THIOMICHLER,SKETONE(SENSITIVESPEC;THIOMICHLER'S KETONE
• CAS NO: 1226-46-6
• Molecular Formula: C₁₇H₂₀N₂S
• Molecular Weight: 284.42
• EINECS: 214-962-6
• Product Categories: Intermediates of Dyes and Pigments;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 1226-46-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 202-206 °C(lit.)
• Boiling Point: 429.958 °C at 760 mmHg
• Flash Point: 213.831 °C
• Appearance: /
• Density: 1.131 g/cm³
• Storage Temp.: Store below +30°C.
• PKA: 3.05±0.24(Predicted)
• CAS DataBase Reference: 4,4'-Bis(dimethylamino)thiobenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Bis(dimethylamino)thiobenzophenone(1226-46-6)
• EPA Substance Registry System: 4,4'-Bis(dimethylamino)thiobenzophenone(1226-46-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 3
• Hazardous Substances Data: 1226-46-6(Hazardous Substances Data)

Usage

Chemical Properties

Purple crystal

Purification Methods

Purify the thioketone by recrystallisation from hot EtOH or by trituration with a small volume of CHCl3, followed by filtration and washing with hot EtOH [Terbell & Wystrade J Phys Chem 68 2110 1964]. Also it recrystallises from CHCl3/ MeOH. [Beilstein 14 H 101, 14 I 395, 14 II 60.]

Upstream product

• 6483-79-0 dichloro-bis-(4-dimethylamino-phenyl)-methane 
• 90-94-8 bis(p-dimethylaminophenyl)methanone 
• 10025-87-3 trichlorophosphate 
• 463-71-8 thiophosgene 
• 121-69-7 N,N-dimethyl-aniline 
• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 
• 492-80-8 auramine O 
• 7783-06-4 hydrogen sulfide 
• 64-17-5 ethanol 
• 26514-42-1 N-methylene>aniline 
• 75-15-0 carbon disulfide 
• 25642-42-6 N-allyl-N'-(4,4'-bis-dimethylamino-benzhydrylidene)-thiourea 
• 25642-44-8 N-(4,4'-bis-dimethylamino-benzhydrylidene)-N'-phenyl-thiourea 
• 2123-34-4 4,4'-(aminomethylene)bis(N,N-dimethylaniline) 

Downstream Products

• 101796-83-2 difluoren-9-yl disulfide 
• 4364-32-3 9-(4,4'-bis-dimethylamino-benzhydrylidene)-fluorene 
• 83463-89-2 bis-(4,4'-bis-dimethylamino-benzhydryl)-disulfide 
• 103268-58-2 1-biphenyl-4-yl-2,2-bis-(4-dimethylamino-phenyl)-1-phenyl-ethene 
• 26514-42-1 N-methylene>aniline 
• 59260-77-4 1,1-bis(4-dimethylaminophenyl)-2,2-diphenylethene 
• 1261-86-5 tetrakis(p-dimethylaminophenyl)ethylene 
• 25843-98-5 Bis-(p-dimethylaminophenyl)-methyl-phenyl-sulfid 
• 51953-62-9 N-[Bis-(4-dimethylamino-phenyl)-methylene]-4-methyl-benzenesulfonamide 
• 85556-26-9 2-[2,2-bis-(4-dimethylamino-phenyl)-vinyl]-1-methyl-quinolinium; iodide 
• 103397-74-6 2,2-bis-(4-dimethylamino-phenyl)-3,3-di-p-tolyl-thiirane 

Relevant articles and documents

A new, efficient and simple method for the thionation of ketones to thioketones using P4S10/Al2O3

A simple, efficient and new method has been developed for the synthesis of thioketones by thionation of ketones using P4S10/Al 2O3 in acetonitrile. It has been found that the P 4S10/Al2O3 combination provides a simple and convenient method for the synthesis of thioketones.

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.