20199-06-8

Basic information

• Product Name: 4-methyl-N-phenylbenzenecarbothioamide
• CAS NO: 20199-06-8
• Molecular Formula: C₁₄H₁₃NS
• Molecular Weight: 227.3247
• Mol File: 20199-06-8.mol

Chemical Properties

• Boiling Point: 343.6°C at 760 mmHg
• Flash Point: 161.6°C
• Density: 1.181g/cm³
• Vapor Pressure: 6.95E-05mmHg at 25°C
• Refractive Index: 1.682
• CAS DataBase Reference: 4-methyl-N-phenylbenzenecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-N-phenylbenzenecarbothioamide(20199-06-8)
• EPA Substance Registry System: 4-methyl-N-phenylbenzenecarbothioamide(20199-06-8)

Safety Data

• Hazardous Substances Data: 20199-06-8(Hazardous Substances Data)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 108-88-3 toluene 
• 2168-80-1 4-methyldithioic acid 
• 62-53-3 aniline 
• 104-87-0 4-methyl-benzaldehyde 
• 103-70-8 Formanilid 
• 622-47-9 4-tolylacetic acid 
• 98-95-3 nitrobenzene 
• 874-60-2 4-methyl-benzoyl chloride 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 97270-47-8 4-(methyl)thiobenzoyl diphenylphosphino sulfide 
• 74670-57-8 cesium 4-methylbenzenecarbodithioate 
• 53724-36-0 sodium 4-(methyl)dithiobenzoate 
• 42967-76-0 piperidinium 4-methylbenzenecarbodithiolate 

Downstream Products

• 16112-21-3 2-(4-methylphenyl)-1,3-benzothiazole 
• 133218-28-7 p-Methyl-N-(3-phenylpropionyl)thiobenzanilide 
• 83078-39-1 4-methyl-thiobenzoic acid O-benzyl ester 
• 136169-27-2 C₁₅H₁₆N₄S 
• 6833-18-7 4-methyl-N-phenylbenzamide 
• 20199-07-9 Thio-p-toluylanilin-S-oxyd; N-(4-Methyl-thiobenzoyl)-anilin-S-oxyd 

Relevant articles and documents

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson's reagent

After completing the thio-substitution with Lawesson's reagent, ethanol was found to be effective in the decomposition of the inherent stoichiometric six-membered-ring byproduct from the Lawesson's reagent to a highly polarized diethyl thiophosphonate. The treatment significantly simplified the following chromatography purification of the desired thioamide in a small scale preparation. As scaling up the preparation of two pincer-type thioamides, we have successfully developed a convenient process with ethylene glycol to replace ethanol during the workup, including a traditional phase separation, extraction, and recrystallization. The newly developed chromatography-free procedure did not generate P-containing aqueous waste, and only organic effluents were discharged. It is believed that the optimized procedure offers the great opportunity of applying the Lawesson's reagent for various thio-substitution reactions on a large scale.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Method for promoting elemental sulfur to synthesize thioamide by mixed alkali in water phase

The invention provides a method for promoting elemental sulfur to synthesize a thioamide compound by a mixed alkali in a water phase, and belongs to the field of organic synthesis. According to the method, an aldehyde compound and an amide compound are us

Mixed bases mediated synthesis of thioamides in water

A mixed bases mediated protocol is developed to synthesize thioamides from N-aryl or N-alkylamide, aldehyde and elemental sulfur in water. This reaction requires no addition of external oxidant and avoids large excess of amides. Various functional groups

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Functionalization of activated methylene C-H bonds with nitroarenes and sulfur for the synthesis of thioamides

We report a method to obtain arylthioamides by the functionalization of sp3 C-H bonds in phenylacetic acids and benzyl alcohols. Reactions proceeded without the use of any solvents and were compatible with many functionalities and heterocycles. These conditions allow for a rapid synthesis of thioamides from simple, commercial substrates.

Transition metal-free α-Csp3-H oxidative sulfuration of benzyl thiosulfates with anilines to form N-aryl thioamides

A metal-free approach to N-aryl thioamides from Bunte salts and anilines in DMSO has been developed. This method tolerated a wide range of functional groups on the aromatic ring, providing an ideal way to N-aryl thioamides in good to excellent yields from cheap and easily available starting materials. A plausible mechanism was also proposed based on the X-ray single crystal diffraction, NMR and MS analyses of DMSO-concerning intermediates.

Thioamide derivative and preparation method thereof

The invention discloses a thioamide derivative. The structural formula of the thioamide derivative is represented by the formula (I) or the formula (II). The invention also provides a preparation method of the thioamide derivative. According to the preparation method, alkali metal salts are taken as the alkalis, amines are directly coupled with alkenes and sulfur, and by selecting the alkali, twodifferent thioamide derivatives represented by the formula (I) and the formula (II) can be prepared from same raw materials. The provided preparation method has the advantages that the raw materials are cheap and easily available, the synthesis method is simple, and the cost is largely reduced. The provided thioamide derivatives can be used in fields such as bioactive molecules, drug synthesis, and the like, and has a wide application range.

Base-Controlled Three Component Reactions of Amines, Elemental Sulfur, and Styrenes: Synthesis of Thioamides under Metal-Free Conditions

Three component reactions of olefins, amines, and sulfur were studied. Thioamidation of styrenes is base-controlled, and 2-phenylethanethioamides and benzothioamides were obtained selectively in the presence of two different bases. This protocol offers a simple and efficient procedure for the synthesis of thioamides.

Photochemical δ-Hydrogen Abstraction from Acyclic and Semicyclic Monothioimides

Photochemical δ-hydrogen abstraction from acyclic and semicyclic monothioimides have been studied.Photolysis of acyclic monothioimides possessing a benzylic hydrogen atom at the δ-position gave γ-lactams, via a 1,5-diradical intermediate, accompanied by thioamides were generated by γ-hydrogen abstraction.Irradiation of the five-membered semicyclic monothioimide, N-(3-phenylpropionyl)pyrrolidine-2-thione, yielded 5-mercapto-4-phenyl-1-azabicyclooctan-2-one.For N-(3-phenylbutyryl)pyrrolidine-2-thione, disproportionation, involving 1,6-hydrogen migration, was the main path.Photolysis of the six-membered semicyclic monothioimide, N-(3-phenylbutyryl)piperidine-2-thione, gave an unsaturated thiol, via a 1,4-hydrogen shift of a 1,5-diradical intermediate, accompanied by cyclisation product and piperidine-2-thione.