75318-48-8

Basic information

• Product Name: Benzenamine, N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitro-
• CAS NO: 75318-48-8
• Molecular Formula: C8H4ClN3O2S2
• Molecular Weight: 273.724
• Mol File: 75318-48-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitro-(75318-48-8)
• EPA Substance Registry System: Benzenamine, N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitro-(75318-48-8)

Safety Data

• Hazardous Substances Data: 75318-48-8(Hazardous Substances Data)

Upstream product

• 27691-52-7 S,S-dimethyl-N-(p-nitrophenyl)sulfilimine 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 7724-12-1 2-cyano-6-aminobenzothiazole 
• 188672-83-5 6-nitro-1,3-benzothiazole-2-carbonitrile 

Relevant articles and documents

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.

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).