4314-19-6

Basic information

• Product Name: BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97
• Synonyms: BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97;bis(1H-benzo[d][1,2,3]triazol-1-yl)Methanethione;1,1′-(Thiocarbonyl)bis-1H-benzotriazole;Bis(1-benzotriazolyl)methanethione 97%
• CAS NO: 4314-19-6
• Molecular Formula: C₁₃H₈N₆S
• Molecular Weight: 280.314
• Product Categories: C-C Bond Formation;Others;Synthetic Reagents
• Mol File: 4314-19-6.mol

Chemical Properties

• Melting Point: 170-174 °C(lit.)
• Boiling Point: 509.1 °C at 760 mmHg
• Flash Point: 261.7 °C
• Appearance: /
• Density: 1.58 g/cm³
• Vapor Pressure: 1.75E-10mmHg at 25°C
• Refractive Index: 1.859
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97(4314-19-6)
• EPA Substance Registry System: BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97(4314-19-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 4314-19-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BIS(1-BENZOTRIAZOLYL)METHANETHIONE 97 is used as a thioacylating agent for the synthesis of various organic compounds. Its ability to form thioacyl derivatives makes it a valuable tool in the development of new chemical entities.
Used in Multicomponent Heterocyclization Reactions:
In the field of heterocyclic chemistry, BBTM is employed as a reactant in multicomponent reactions, which are essential for the synthesis of complex heterocyclic structures with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in the Synthesis of Substituted Thiosemicarbazides and N-Hydroxythioureas:
BBTM is utilized in the preparation of substituted thiosemicarbazides and N-hydroxythioureas, which are important classes of compounds with diverse biological activities, including antimicrobial, antiviral, and anticancer properties.
Used in Guanylation of Amines:
BBTM is also used in the guanylation of amines, a reaction that involves the formation of guanidine derivatives. These compounds have a wide range of applications, including their use as pharmaceuticals, agrochemicals, and synthetic intermediates.

InChI:InChI=1/C13H8N6S/c20-13(18-11-7-3-1-5-9(11)14-16-18)19-12-8-4-2-6-10(12)15-17-19/h1-8H

Upstream product

• 463-71-8 thiophosgene 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 

Downstream Products

• 18792-49-9 pyrrolidine-1-carbothioic acid phenylamide 
• 36903-85-2 (cyclohexylamino)morpholin-4-ylmethane-1-thione 
• 85557-18-2 morpholine-4-carbothioic acid 4-methoxyphenylamide 
• 690634-07-2 benzotriazole-1-carbothioic acid (thiazol-2-yl)amide 
• 690634-08-3 benzotriazole-1-carbothioic acid [(furan-2-yl)methyl]amide 
• 690634-04-9 benzotriazole-1-carbothioic acid cyclohexylamide 
• 690634-10-7 benzotriazole-1-carbothioic acid 4-methoxybenzylamide 
• 722-04-3 N-(3-dimethylaminopropyl)-N’-phenylthiourea 
• 690634-09-4 benzotriazole-1-carbothioic acid [(R)-1-phenylethyl]amide 
• 690634-06-1 benzotriazole-1-carbothioic acid allylamide 
• 690634-11-8 benzotriazole-1-carbothioic acid benzylamide 
• 1212-30-2 1,3-di-pyridin-2-yl-thiourea 
• 865075-54-3 N-(2-phenethyl)-1H-benzotriazole-1-carbothioamide 
• 24694-06-2 1-(N-phenylthiocarbamoyl)-1H-benzotriazole 

Relevant articles and documents

Urea and thiourea based anion receptors in solution and on polymer supports

Herein we report the development of a new series of surface bound anion sensors exploiting the urea or thiourea motif capable of binding anions through hydrogen bonding interactions. The use of high resolution magic angle spinning 1H NMR allows the direct comparison of the anion binding properties of these receptors in solution versus those tethered to polymer resins. Some intramolecular hydrogen bonding and solvent effects were observed at the solution:surface interface however in general the anion binding properties of the polymer bound urea and thiourea receptors were maintained.

Mechanism-Based Inhibitors of the Human Sirtuin 5 Deacylase: Structure–Activity Relationship, Biostructural, and Kinetic Insight

The sirtuin enzymes are important regulatory deacylases in a variety of biochemical contexts and may therefore be potential therapeutic targets through either activation or inhibition by small molecules. Here, we describe the discovery of the most potent inhibitor of sirtuin 5 (SIRT5) reported to date. We provide rationalization of the mode of binding by solving co-crystal structures of selected inhibitors in complex with both human and zebrafish SIRT5, which provide insight for future optimization of inhibitors with more “drug-like” properties. Importantly, enzyme kinetic evaluation revealed a slow, tight-binding mechanism of inhibition, which is unprecedented for SIRT5. This is important information when applying inhibitors to probe mechanisms in biology.

Trapping Reactive Intermediates by Mechanochemistry: Elusive Aryl N-Thiocarbamoylbenzotriazoles as Bench-Stable Reagents

Monitoring of mechanochemical thiocarbamoylation by in situ Raman spectroscopy revealed the formation of aryl N-thiocarbamoylbenzotriazoles, reactive intermediates deemed unisolable in solution. The first-time isolation and structural characterization of these elusive molecules demonstrates the ability of mechanochemistry to access otherwise unobtainable intermediates and offers a new range of masked isothiocyanate reagents.