100-34-5

Basic information

• Product Name: benzenediazonium chloride
• Synonyms: benzenediazonium chloride;diazobenzene chloride;Edaravone Impurity 1
• CAS NO: 100-34-5
• Molecular Formula: C₆H₅N₂*Cl
• Molecular Weight: 140.5703
• EINECS: 202-842-6
• Mol File: 100-34-5.mol

Chemical Properties

• Melting Point: 191-197 °C
• Boiling Point: 228.71°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.2625 (rough estimate)
• Refractive Index: 1.4877 (estimate)
• CAS DataBase Reference: benzenediazonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: benzenediazonium chloride(100-34-5)
• EPA Substance Registry System: benzenediazonium chloride(100-34-5)

Safety Data

• Hazardous Substances Data: 100-34-5(Hazardous Substances Data)

Usage

Uses

1. Used in Dye Industry:
Benzenediazonium chloride is used as a dye intermediate for the synthesis of various types of dyes. Its reactivity and solubility properties make it a suitable candidate for creating a range of colorants used in different industries.
2. Used in Chemical Synthesis:
As a chemical intermediate, benzenediazonium chloride is employed in the synthesis of other organic compounds, taking advantage of its reactivity and the ease with which it can be converted into different products.
3. Used in Analytical Chemistry:
Due to its ionic nature, benzenediazonium chloride can be used in analytical chemistry as a reagent for the detection and identification of certain functional groups or compounds through colorimetric or spectroscopic methods.
4. Used in Research and Development:
The unique properties of benzenediazonium chloride make it a valuable compound for research purposes, particularly in the fields of organic chemistry and materials science, where it can be used to explore new reactions and develop novel materials.

Hazard

Highly toxic. Can explode on heating.

Safety Profile

Potentially explosive when dry.Potentially explosive reaction with potassium omethyldithiocarbonate.When heated to decomposition itemits toxic fumes of Cl- and NOx.

InChI:InChI=1/C6H5N2.ClH/c7-8-6-4-2-1-3-5-6;/h1-5H;1H/q+1;/p-1

Upstream product

• 142-04-1 aniline hydrochloride 
• 59-88-1 phenylhydrazine hydrochloride 
• 75-36-5 acetyl chloride 
• 17420-03-0 N-sulphinylphenylhydrazine 
• 100-63-0 phenylhydrazine 
• 62-53-3 aniline 
• 4203-28-5 phenyl-diazenecarboxylic acid amide 
• 58364-68-4 3-methyl-2-(1Ξ,2E)-phenyltriazenylidene-2,3-dihydro-benzothiazole 
• 3768-55-6 N-trimethylsilylaniline 
• 58364-75-3 3-methyl-2-(1Ξ,2Z)-phenyltriazenylidene-2,3-dihydro-benzothiazole 
• 222851-56-1 N-phenylsulfinylamine 
• 60-11-7 methyl yellow 
• 3639-37-0 1,3-Diphenyltriazen-1-oxid 
• 128620-11-1 1-phenyl-2-bromodiazene 1-oxide 

Downstream Products

• 5371-52-8 2-hydroxytetrahydrofuran 
• 36719-71-8 1-phenyl-3,3-tetramethylenetriazene 
• 22347-47-3 1,4-dioxane-2-ol 
• 17113-33-6 2-phenylfuran 
• 2538-52-5 1,3-diphenyl-4,5-dihydro-1H-pyrazole 
• 742-01-8 1,3,5-triphenyl-4,5-dihydro-1H-pyrazole 
• 49597-17-3 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid 
• 1008-89-5 2-phenylpyridine 
• 939-23-1 p-phenylpyridine 
• 95046-97-2 5-methyl-dihydro-furan-2,3-dione-3-phenylhydrazone 
• 842-07-9 Sudan I 
• 3173-13-5 1,5,1',5'-tetraphenyl-3,3'-ethanediyl-di-formazan 
• 34938-47-1 2-(phenylazo)-1H-imidazole 
• 92184-43-5 4-phenylpyridazine 

Relevant articles and documents

Synthesis of Certain New Thiazole and 1,3,4-Thiadiazole Derivatives via the Utility of 3-Acetylindole

2-(2-(1-(1H-Indol-3-yl)ethylidene)-hydrazinyl)-4-substituted 5-(aryldiazenyl)thiazoles and 5-((1-(1H-indol-3-yl)ethylidene)hydrazono)-2-substituted-4-phenyl-4,5-dihydro-1,3,4-thiadiazoles were synthesized via reaction of hydrazonoyl halides and 2-(1-(1H-indol-3-yl)ethylidene)hydrazine-1-carbothioamide and alkyl 2-(1-(1H-indol-3-yl)ethylidene)hydrazine-1-carbodithioate in ethanolic triethylamine. Structures of the newly synthesis were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic route whenever possible.

Synthesis, in vitro and in Silico studies of some novel 5-nitrofuran-2-yl hydrazones as antimicrobial and antitubercular agents

In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06-0.98 μg/mL and antimycobacterial activity with MIC=3.9 μg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 μg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

Reaction of Triazene 1-Oxides: Novel Synthesis of Solid Arenediazonium Chlorides

Treatment of 1,3-diaryltriazene 1-oxides with oxalyl chloride in dry toluene at room temperature gives only solid arenediazonium chlorides; however, treatment with acetyl and benzoyl chlorides does not afford the corresponding diazonium chlorides.

Tetracyclic compounds from 1-oxo-1,2,3,4,5,6-hexahydrocycloocta[b]indole. Synthesis of oxazolo[4′5′:8,7]cycloocta[b]indoles

Japp-Klingmann method was used to diazotise aniline derivatives and 2-hydroxymethylenecyclooctanone 2 to obtain cyclooctan-1′,2′ -dione-1′-arylhydrazone 3 which upon acid cyclisation using kents reagent gave 1-oxo-1,2,3,4,5,6-hexahydrocycloocta[b]indole 4

New 2-pyrone-based hydrazones: Synthesis, spectral characterisation, UV–visible study and evaluation of the antiradicalar activity

The synthesis of new 2-pyrone-based hydrazones has been prepared by the coupling of 6-methyl-2H-furo[3,2-c]pyran-3,4-dione with diazonium salts, obtained by diazotization of aniline derivatives. The structure of all compounds was established by spectrosco

ASYMMETRIC SYNTHESIS OF α-AMINO β-HYDROXY PHOSPHONIC ACIDS VIA BINAP-RUTHENIUM CATALYZED HYDROGENATION

BINAP-Ru catalyzed hydrogenation of configurationally labile α-amido β-keto phosphonic esters gives the (R,R)- or (S,S)-α-amido β-hydroxy phosphonic esters in a highly enantio- and diastereoselective manner.

Electrochemical investigations of some newly synthesized arylazapyrazole derivatives

Abstract: Three derivatives of arylazapyrazole ((E)-4-(phenyldiazenyl)-3,5-dimethyl-1H-pyrazole, (E)-4-[(4-fluorophenyl)diazenyl]-3,5-dimethyl-1H-pyrazole, and (E)-4-[(4-iodophenyl)diazenyl]-3,5-dimethyl-1H-pyrazole) were synthesized, characterized, and further investigated for their electrochemical behavior at glassy carbon electrode using cyclic voltammetry. All compounds were reduced following Ei Ci mechanism giving single cathodic peak in potential range 0 to ?2?V vs. Ag/AgCl. The plots of log iP vs. log ν showed that the electrode process is mixed adsorption-diffusion controlled. The kinetic parameters such as transfer coefficient (αn), diffusion coefficients (Do), and standard heterogeneous rate constants (ks) were determined from the electrochemical data. The values of Do were determined and found greater for the smallest among the three compounds. ks values were calculated by Laviron formalism which lies in the order of 10?2?s?1. Temperature and pH effects were studied and thermodynamic parameters such as change in free energy of activation (ΔG#), apparent activation energy (Ea), enthalpy (ΔH#), and entropy (ΔS#) of activation were determined. Negative values of Ea, ΔH#, and ΔS# imply that the electrode process needs lesser over potential with temperature rise, pre-adsorption of the analyte onto the electrode surface and the activated complex has a more organized structure than the reactants, respectively. Graphical abstract: [Figure not available: see fulltext.]

3-Aminopyrazolo[4,3-c]pyridine-4,6-dione as a precursor for novel pyrazolo[4,5,1-ij][1,6]naphthyridines and pyrido[4’,3’:3,4]pyrazolo[1,5-a]pyrimidines

The versatile, 3-aminopyrazolo[4,3-c]pyridine-4,6-dione (2) was synthesized and allowed to react with aldehydes, aryldiazonium chlorides, chalcones and enaminones to afford regioselectively the novel pyrazolo[4,3-c]pyridine derivatives 4a-c, pyrazolo[4,5,

Polymer complexes. LXX. Synthesis, spectroscopic studies, thermal properties and antimicrobial activity of metal(II) polymer complexes

The monomer 3-allyl-5-(phenylazo)-2-thioxothiazolidine-4-one (HL) was prepared by the reaction of allyl rhodanine with aniline through diazo-coupling reaction. Reaction of HL with Ni(II) or Co(II) salts gave polymer complexes (1–8) with general stoichiome

Rates and mechanisms of the thermal solvolytic decomposition of arenediazonium ions

Arenediazonium tetrafluoroborates have been prepared and the kinetics of solvolysis have been investigated in water, trifluoroethanol, water-trifluoroethanol mixtures, hexafluoropropan-2-ol, trifluoroacetic acid, and ethanol by a UV method. A heterolytic mechanism involving short-lived aryl cations leads to products derived from nucleophilic capture of the aryl cations by solvent or a solute. Ionic solutes in aqueous trifluoroethanol and trifluoromethoxybenzene in trifluoroethanol have no kinetic effect and neither does replacement of the tetrafluoroborate counter-ion by chloride in trifluoroethanol. Rate constants for any one compound are not very solvent dependent, the reactions generally being characterised by high enthalpies of activation and appreciably positive entropies of activation. Compounds with 4-Cl, 4-F, 4-NO2, and 4-MeO substituents proved too unreactive for kinetic studies, but for different reasons. In ethanol, a radical reaction with characteristically different activation parameters competes with the heterolytic path and leads to hydrodediazoniation (reduction) by hydrogen atom abstraction from the CH2 group of ethanol.