4953-70-2

Upstream product

• 75318-48-8 N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitrobenzenamine 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 100-01-6 4-nitro-aniline 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 

Downstream Products

• 70742-41-5 N-Cyanocarbothioyl-2,2,2-trifluoro-N-(4-nitro-phenyl)-acetamide 
• 7724-12-1 2-cyano-6-aminobenzothiazole 
• 188672-83-5 6-nitro-1,3-benzothiazole-2-carbonitrile 
• 70612-15-6 N-(-4-Nitrophenyl)cyanoformamide 

Relevant academic research and scientific papers

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.

A "caged" Luciferin for Imaging Cell-Cell Contacts

Cell-cell interactions underlie fundamental biological processes but remain difficult to visualize over long times and large distances in tissues and live organisms. Bioluminescence imaging with luciferase-luciferin pairs is sufficiently sensitive to imag

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

Conversion of imino-1,2,3-dithiazoles into 2-cyanobenzothiazoles, cyanoimidoyl chlorides and diatomic sulfur

Primary aromatic amines condense with 4,5-dichloro-1,2,3-dithiazolium chloride 1 to give high yields of the N-aryl imines 2 which on heating give 2-cyanobenzothiazoles 3, thus providing a simple two-step route to these heterocycles from the appropriate aniline. This thermolysis is favoured by electron donating substituents in the aniline ring, and retarded by electron withdrawing groups in favour of a second pathway in which both dithiazole sulfur atoms are lost to form cyanoimidoyl chlorides 4. This is the sole pathway when both aniline ortho positions are substituted. Analogous N-alkyl imines 5, prepared from the salt 1 and the bis(trimethylsilyl) derivatives of the amine, also decompose with loss of both sulfur atoms as singlet diatomic sulfur, S2. 4-Chloro-5-methylimino-5H-1,2,3-diathiazole 5a does this at 140-150°C and the S2 generated is intercepted with 2,3-diphenylbutadiene, 2,3-dimethylbutadiene and norbornene to give 16a, 16b and 17 respectively.

Reactions of 5-Arylimino-4-chloro-5H-1,2,3-dithiazoles with Stable Phosphoranes: Novel Preparation of Dithiomethylenephosphoranes

The reactions of 5-arylimino-4-chloro-5H-1,2,3-dithiazoles with 2 equivalents of stable phosphoranes such as carboethoxymethylene-, acetylmethylene-, 4-chlorobenzoylmethylene-, and cyanomethylenetriphenylphosphoranes in the presence of pyridine in CH2Cl2 at room temperature gave a new type of the corresponding phosphoranes with aryliminocyanomethyldithiomethylene moiety as a major product.