21572-61-2

Basic information

• Product Name: (2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium
• CAS NO: 21572-61-2
• Molecular Formula: C₅Cl₄N₂
• Molecular Weight: 230.8863
• Mol File: 21572-61-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium(CAS DataBase Reference)
• NIST Chemistry Reference: (2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium(21572-61-2)
• EPA Substance Registry System: (2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium(21572-61-2)

Safety Data

• Hazardous Substances Data: 21572-61-2(Hazardous Substances Data)

Usage

General Description

(2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium is a chemical compound that belongs to the class of diazeniumdiolate compounds. It is characterized by a cyclopentadienyl ring with four chlorine atoms and a diazenium moiety attached to it. These compounds are known to be potential sources of nitric oxide (NO), a signaling molecule in the human body that plays a crucial role in various physiological processes. Due to their ability to release NO, (2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-ylidene)diazenium compounds have been investigated for their potential use in medical applications, such as vasodilation and cancer therapy. Additionally, they have also been studied for their antimicrobial and anti-inflammatory properties. These compounds hold promise for the development of new therapeutic agents and have therefore garnered significant interest in the scientific community.

Upstream product

• 17581-52-1 2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-one hydrazone 
• 77-47-4 hexachlorocyclopentadiene 

Downstream Products

• 72749-20-3 trans-bis(triphenylphosphine)(tetrachlorodiazocyclopentadiene)chloroiridium(I)*toluene 
• 1807-65-4 α-Diphenylmethylen-β-tetrachlor-cyclopentadienyliden-hydrazin 
• 13736-99-7 N,N'-Bis-(2,3,4,5-tetrachloro-cyclopenta-2,4-dienylidene)-hydrazine 
• 10269-62-2 tetrachloro-α-pyrone 
• 4723-74-4 tetrachlorocyclopentadienone 
• 5216-72-8 Norcaran-7-spiro-5'-(tetrachlor-cyclopenta-1',3'-dien) 
• 6693-51-2 --hydrazin 
• 5216-71-7 5-Cyclohexyl-tetrachlor-cyclopentadien-(1,3) 
• 17581-52-1 2,3,4,5-tetrachlorocyclopenta-2,4-dien-1-one hydrazone 
• 114663-28-4 4,4,6,6-tetramethyl-2,2-diphenyl-5-(2,3,4,5-tetrachlorcyclopenta-2,4-dien-1-yliden)-1-thiaspiro<2.3>hexan 

Relevant articles and documents

The reaction of cyclopentadienylidine, fluorenylidene and tetrachlorocyclopentadienylidene with alcohols. A laser flash photolysis study

Rate constants of reaction of cyclopentadienylidene, fluorenylidene and tetrachlorocyclopentadienylidene with alcohols and other quenchers were determined by laser flash photolysis methods. The rate constants of reaction of cyclopentadienylidene and fluorenylidene with various alcohols were determined and found to increase with increasing alcohol acidity. Alcohols as a group reacted faster with cyclopentadienylidene and fluorenylidene than likely ylide formers such as pyridine, ethyl acetate and tetrahydrofuran. Bronsted plots of the reaction of cyclopentadienylidene and fluorenylidene with alcohols are linear with slopes of 0·061 and 0·082, respectively. In the case of tetrachlorocyclopentadienylidene, an ylide type of reaction mechanism with alcohols is indicated. Tetrachlorocyclopentadienylidene reacts most rapidly with the least acidic alcohol studied and this carbene reacts more rapidly with tetramethylurea, pyridine and tetrahydrofuran than with methanol.

Isolation of an Antiaromatic Singlet Cyclopentadienyl Zwitterion

The reaction of triplet tetrachlorocyclopentadienylidene with BF3 in rare gas matrices yields a zwitterion consisting of a cyclopentadienyl cation bearing a positive charge and a negatively charged BF3 unit. IR and UV-vis spectra as well as the absence of EPR signals demonstrate a singlet ground state of the zwitterion, and its calculated geometry and magnetic properties clearly reveal a strong antiaromatic character. The zwitterion is highly labile and by visible or IR irradiation rearranges via a 1,2-fluorine migration from boron to carbon. Interaction with a second molecule of BF3 stabilizes the zwitterion and suppresses the fluorine migration, thus providing a convenient and efficient synthesis of an antiaromatic molecule under very mild conditions.

Pentachlorocyclopentadienyl derivatives of manganese and rhodium

Reaction of diazotetrachlorocyclopentadiene, I, with di-μ-chloro-bis(1,5-cyclooctadienerhodium), [RhCl(1,5-C8H12)]2, gives high yields of (η5-pentachlorocyclopentadienyl)(1,5-cyclooctadiene)rhodium, Rh(η5-C5Cl5)(COD), II. A similar reaction between I and pentacarbonylchloromanganese, MnCl(CO)5, gave two products: pentacarbonyl(η1-pentachlorocyclopentadienyl)manganese, Mn(η1-C5Cl5)(CO)5, III, and tricarbonyl(η5-pentachlorocyclopentadienyl)manganese, Mn(η5-C5Cl5)(CO)3, IV. III is the first transition metal complex containing a η1-C5Cl5- ring and for which there is no analog in C5H5--Mn chemistry. These compounds and other polychloro-substituted cyclopentadienyl complexes have been characterized by infrared, Raman, 13C nuclear magnetic resonance, and 35Cl nuclear quadrupole resonance spectroscopy. Qualitative results from investigations into the mechanism of the insertion reactions of diazocyclopentadienes into manganese-halogen bonds are discussed.