2521-24-6

Basic information

• Product Name: 4-Chlorothiobenzamide
• Synonyms: Benzamide, p-chlorothio-;Benzenecarbothioamide, 4-chloro-;p-Chlorobenzothiamide;p-Chlorothiobenzamide;OTAVA-BB BB7020331320;4-CHLOROTHIOBENZAMIDE;4-CHLOROBENZENE-1-CARBOTHIOAMIDE;4-CHLOROBENZENECARBOTHIOAMIDE
• CAS NO: 2521-24-6
• Molecular Formula: C₇H₆ClNS
• Molecular Weight: 171.65
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 2521-24-6.mol

Chemical Properties

• Melting Point: 127-130 °C
• Boiling Point: 275.6 °C at 760 mmHg
• Flash Point: 120.5 °C
• Appearance: solid
• Density: 1.341 g/cm₃
• Vapor Pressure: 0.00503mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Refrigerator (+4°C)
• PKA: 12.28±0.29(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 606603
• CAS DataBase Reference: 4-Chlorothiobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chlorothiobenzamide(2521-24-6)
• EPA Substance Registry System: 4-Chlorothiobenzamide(2521-24-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/22-43-22
• Safety Statements: 37/39-26-36/37
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2521-24-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
4-Chlorothiobenzamide is used as a catalytic agent for facilitating various chemical reactions. Its ability to act as a catalyst makes it a valuable component in the production of different chemicals and compounds.
Used in Petrochemical Industry:
In the petrochemical industry, 4-Chlorothiobenzamide is utilized as an additive to enhance the performance and quality of petroleum products. Its addition can improve the efficiency, stability, and other properties of the final products, making it an essential component in the petrochemical sector.

InChI:InChI=1/C7H6ClNS/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H2,9,10)

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 4486-44-6 O,O-diisopropylphosphorothioic acid 
• 619-56-7 4-chlorobenzamide 
• 104-88-1 4-chlorobenzaldehyde 
• 144-55-8 sodium hydrogencarbonate 
• 62-55-5 thioacetamide 
• 3848-36-0 4-chlorobenzaldoxime 
• 122-01-0 4-chloro-benzoyl chloride 
• 45709-05-5 4-chlorobenzylideneimine 
• 7047-12-3 5-(4-Chlorphenyl)-1,2,4-dithiazol-3-on 
• 74-11-3 para-chlorobenzoic acid 

Downstream Products

• 25100-91-8 2-(4-chlorophenyl)-4-methylthiazole 
• 27149-26-4 2-(4-chlorophenyl)thiazole 
• 29947-35-1 2-[2-(4-chloro-phenyl)-thiazol-4-yl]-benzothiazole 
• 23821-73-0 [2-(4-chloro-phenyl)-4-thiophen-2-yl-thiazol-5-yl]-acetic acid 
• 65823-54-3 2'-(4-chloro-phenyl)-4-phenyl-[2,4']bithiazolyl 
• 62925-33-1 6-(4-chloro-phenyl)-2r-methyl-2,4t-diphenyl-4H-[1,3,5]dithiazine 
• 59824-79-2 5-benzylidene-2-(4-chloro-phenyl)-4-phenyl-4,5-dihydro-thiazole 
• 54665-83-7 2-(4-chlorophenyl)-4,6-diphenyl-4H-1,3-thiazine 
• 54665-85-9 2-(4-chloro-phenyl)-4,5-diphenyl-6H-[1,3]thiazine 
• 54665-84-8 2-(4-chloro-phenyl)-4,5-diphenyl-4H-[1,3]thiazine 
• 56472-13-0 2,6-bis-(4-chloro-phenyl)-4-phenyl-4H-[1,3,5]thiadiazine 
• 15965-41-0 3-(p-chlorophenyl)-1,4,2-dithiazole-5-thione 
• 4115-17-7 3,5-bis-(4-chloro-phenyl)-[1,2,4]thiadiazole 
• 62925-41-1 6-(4-chloro-phenyl)-2,2-diphenyl-4-propyl-4H-[1,3,5]dithiazine 

Relevant articles and documents

Alternative solvents for elevated-temperature solid-phase parallel synthesis. Application to thionation of amides

(Matrix presented) A new class of higher-boiling solvents was investigated for elevated-temperature solid-phase parallel synthesis. Extremely low vapor pressures at high temperature and a broader range of solvent effect tuning make this new class of solvents an ideal choice for high-temperature parallel solid-phase synthesis. Benzyl benzoate is identified as a superior high-boiling solvent for parallel solid-phase Lawesson's thionation reactions.

Substituted pyrimidine compound and application thereof

The present invention discloses a substituted pyrimidine compound, which has a structure represented by a general formula I, wherein each substituent is defined in the specification. According to thepresent invention, the compound has a broad-spectrum bactericidal activity, can provide excellent prevention and control effects on cucumber downy mildew, wheat powdery mildew, corn rust disease, riceblast, cucumber anthracnose and the like, and particularly can provide good prevention effects on powdery mildew, corn rust disease and rice blast.

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.

COMPOUNDS FOR THIOL-TRIGGERED COS AND/OR H2S RELEASE AND METHODS OF MAKING AND USING THE SAME

Disclosed herein are embodiments of a compound that is capable of releasing COS and/or H2S upon reaction with a thiol-containing compound. The compound embodiments also can produce a detectable signal (e.g., a fluorescent signal) substantially concomitantly with COS and/or H2S release and/or can release an active agent, such as a therapeutic agent. Methods of making and using the compound embodiments also are disclosed.

Synthesis of imidazo[1,2-: C] thiazoles through Pd-catalyzed bicyclization of tert-butyl isonitrile with thioamides

Building new biological molecules is challenging. Herein, imidazo[1,2-c]thiazoles were synthesized as a new class of heterobicyclic analogs through Pd-catalyzed cascade bicyclization from isonitriles with thioamides. The bicyclic scaffolds were constructed by inserting three molecules of isonitrile into two molecules of thioamide and then cyclizing them in a one-pot procedure. In vitro antitumor studies of these new compounds were conducted by using the MTT assay, and compound 3c showed excellent inhibitory effects against HepG2 at 7.06 ± 0.68 μM.

Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives

The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.

A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature

A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.

A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles

A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.

Design, synthesis and Structure-activity relationship studies of new thiazole-based free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

The free fatty acid receptor 1 (FFA1/GPR40) has attracted interest as a novel target for the treatment of type 2 diabetes. Several series of FFA1 agonists including TAK-875, the most advanced compound terminated in phase III studies due to concerns about liver toxicity, have been hampered by relatively high molecular weight and lipophilicity. Aiming to develop potent FFA1 agonists with low risk of liver toxicity by decreasing the lipophilicity, the middle phenyl of TAK-875 was replaced by 11 polar five-membered heteroaromatics. Subsequently, systematic exploration of SAR and application of molecular modeling, leads to the identification of compound 44, which was an excellent FFA1 agonist with robustly hypoglycemic effect both in normal and type 2 diabetic mice, low risks of hypoglycemia and liver toxicity even at the twice molar dose of TAK-875. Meanwhile, two important findings were noted. First, the methyl group in our thiazole series occupied a small hydrophobic subpocket which had no interactions with TAK-875. Furthermore, the agonistic activity revealed a good correlation with the dihedral angle between thiazole core and the terminal benzene ring. These results promote the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists.