75318-49-9

Basic information

• Product Name: N-[(5Z)-4-chloro-5H-1,2,3-dithiazol-5-ylidene]-4-methoxyaniline
• CAS NO: 75318-49-9
• Molecular Formula: C₉H₇ClN₂OS₂
• Molecular Weight: 258.7477
• Mol File: 75318-49-9.mol

Chemical Properties

• Boiling Point: 392.3°C at 760 mmHg
• Flash Point: 191°C
• Density: 1.48g/cm³
• Vapor Pressure: 5.25E-06mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: N-[(5Z)-4-chloro-5H-1,2,3-dithiazol-5-ylidene]-4-methoxyaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(5Z)-4-chloro-5H-1,2,3-dithiazol-5-ylidene]-4-methoxyaniline(75318-49-9)
• EPA Substance Registry System: N-[(5Z)-4-chloro-5H-1,2,3-dithiazol-5-ylidene]-4-methoxyaniline(75318-49-9)

Safety Data

• Hazardous Substances Data: 75318-49-9(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 

Downstream Products

• 939-69-5 2-cyano-6-hydroxybenzothiazole 
• 943-03-3 2-cyano-6-methoxybenzothiazole 
• 110357-57-8 N'-(4-methoxyphenyl)ethanedithioamide 
• 2591-17-5 D-luciferin 
• 4968-41-6 (4-methoxyphenyl)carbamothioyl cyanide 

Relevant articles and documents

1,2,3-Dithiazoles-new reversible melanin synthesis inhibitors: A chemical genomics study

A chemical genomic screen of an in-house library of small molecule heterocycles was carried out using Xenopus laevis embryos. This led to the identification of N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline (1c), which elicits loss of pigmenta

Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin

All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.

Rapid and scalable assembly of firefly luciferase substrates

Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is

Expedient synthesis of electronically modified luciferins for bioluminescence imaging

Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

Antibacterial evaluation of novel N-arylimino-1,2,3-dithiazoles and N-arylcyanothioformamides

N-Aryl-1,2,3-dithiazoles 2 and the corresponding N-arylcyanothioformamides 3 have been synthesized via 4,5-dichloro-1,2,3-dithiazole derivatives, and their antibacterial activity measured; the dithiazoles are significantly active against Gram-positive bacteria.

Synthesis and Reactions of 4,5-Dichloro-1,2,3-dithiazolium Chloride

Disulfur dichloride reacts with acetonitrile via chloro- and dichloroacetonitrile to give finally 4,5-dichloro-1,2,3-dithiazolium chloride (1).The reactivity of 1 with proton-active compounds is determined by the nucleophilic substitution of the chlorine at carbon atom C-5.Substrates like H2O, H2S, primary amines, and sulfonamides, having two active hydrogen atoms, form the covalent 4-chloro-5H-1,2,3-dithiazole derivatives 2, 3, 5. 1 reacts with phenols in o- or p-position by an electrophilic attack to form 4-chloro-5-(hydroxyphenyl)-1,2,3-dithiazolium chlorides 9a - d.HCl elimination from these leads to deep violet, metallic-reflecting crystals of the betaine-like neutral molecules 10a, b.X-ray analysis shows a planar structure of 10a and a molecular arrangement of a right and a left helix.Ring cleavage of 1 with chlorine gives compounds 14, 15; correspondingly, 2 reacts with chlorine to yield 2-chloro-2-(chlorothioimino)acetyl chloride (18).