19350-68-6

Basic information

• Product Name: p-bromobenzaldehyde tosylhydrazone
• Synonyms: p-bromobenzaldehyde tosylhydrazone
• CAS NO: 19350-68-6
• Molecular Weight: 353.239
• Mol File: 19350-68-6.mol

Chemical Properties

• CAS DataBase Reference: p-bromobenzaldehyde tosylhydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: p-bromobenzaldehyde tosylhydrazone(19350-68-6)
• EPA Substance Registry System: p-bromobenzaldehyde tosylhydrazone(19350-68-6)

Safety Data

• Hazardous Substances Data: 19350-68-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
p-Bromobenzaldehyde tosylhydrazone is used as a key intermediate in the synthesis of pharmaceuticals for its ability to facilitate the creation of complex molecular structures. Its role in the development of potential anti-tuberculosis agents highlights its importance in addressing global health challenges.
Used in Dye Industry:
In the dye industry, p-bromobenzaldehyde tosylhydrazone is employed as a precursor for the production of various dyes. Its chemical properties allow for the creation of dyes with specific characteristics, such as color intensity and stability, which are crucial for different applications.
Used in Agrochemical Industry:
p-Bromobenzaldehyde tosylhydrazone is utilized as a reagent in the synthesis of agrochemicals, contributing to the development of effective and targeted pest control solutions. Its versatility in this field aids in the creation of compounds that can address specific agricultural needs.
Used in Organic Synthesis:
As a building block in organic synthesis, p-bromobenzaldehyde tosylhydrazone is used for the preparation of a wide array of organic compounds. Its reactivity allows chemists to construct complex molecules with diverse functionalities, which can be applied across various industries and research areas.

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 87531-33-7 α-(N,N-dimethylamino)-α-phenyl-α'-(p-bromophenyl)-azine 
• 73900-14-8 1-bromo-4-(diazomethyl)benzene 
• 51554-95-1 4-pentylbromobenzene 
• 76287-54-2 1-(4-bromophenyl)pentan-1-ol 
• 2765-14-2 4,4'-dibromostilbene 
• 586-76-5 4-Bromobenzoic acid 
• 87185-13-5 2-(p-Bromophenyl)-1-isopropylidenecyclopropane 
• 65354-66-7 2-(p-Bromophenyl)-3,3-dimethylmethylenecyclopropane 
• 1224735-13-0 3-(4-bromophenyl)-[1,2,4]triazolo[4,3-a]pyridine-7-carbaldehyde 
• 26885-97-2 1-bromo-4-(p-tolylsulfonylmethyl)benzene 
• 1010691-04-9 3-(4-bromophenyl)-1H-indazole 
• 477841-90-0 2-[(4-bromophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1033053-68-7 C₁₇H₁₅BrN₂O₂S 
• 1380216-67-0 C₂₂H₂₃BrN₂O₄S 

Relevant articles and documents

Potassium tert -Butoxide Promoted Synthesis of 4,5-Diaryl-2 H -1,2,3-triazoles from Tosylhydrazones and Nitriles

Intermolecular cycloaddition of tosylhydrazones with nitriles was investigated. t -BuOK was shown to be an excellent base for increasing the effectiveness of the reaction in this protocol, and homocoupling of the tosylhydrazones was significantly inhibited by using xylene as a solvent. Through this transformation, a variety of 4,5-diaryl-2 H -1,2,3-triazoles were prepared in good to excellent yields and with high purities. The process is azide-free and transition-metal-free.

Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes

A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

[2 + 2 + 1] Cycloaddition ofN-tosylhydrazones,tert-butyl nitrite and alkenes: a general and practical access to isoxazolines

N-Tosylhydrazones have proven to be versatile synthons over the past several decades. However, to our knowledge, the construction of isoxazolines based onN-tosylhydrazones has not been examined. Herein, we report the first demonstrations of [2 + 2 + 1] cycloaddition reactions that allow the facile synthesis of isoxazolines, employingN-tosylhydrazones,tert-butyl nitrite (TBN) and alkenes as reactants. This process represents a new type of cycloaddition reaction with a distinct mechanism that does not involve the participation of nitrile oxides. This approach is both general and practical and exhibits a wide substrate scope, nearly universal functional group compatibility, tolerance of moisture and air, the potential for functionalization of complex bioactive molecules and is readily scaled up. Both control experiments and theoretical calculations indicate that this transformation proceedsviathein situgeneration of a nitronate from the coupling ofN-tosylhydrazone and TBN, followed by cycloaddition with an alkene and subsequent elimination of atert-butyloxy group to give the desired isoxazoline.

Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones

A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.

Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol

A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Photoisomerization-enhanced 1,3-dipolar cycloaddition of carbon-bridged octocyclic azobenzene with photo-released nitrile imine for peptide stapling and imaging in live cells

A photo-induced 1,3-dipolar cycloaddition between nitrile imine and highly ring-strained NN double bond as a dipolarophile was discovered. The photo-isomerization of carbon-bridged octocyclic azobenzene (CBOA) into its trans-configuration accelerates the ligation reaction at a very rapid rate (28 400 M-1 s-1). The CBOA-based photo-click reaction was proved to be bioorthogonal. In addition, the NoxaB peptide was successfully cross-linked by a CBOA stapler which plays a dual role: Photo-control of the conformation of the peptide and photo-conjugation of probes in live cells.

Copper-catalyzed cross-coupling and sequential allene-mediated cyclization for the synthesis of 1,2,3-triazolo[1,5-a]quinolines

In this paper, a tandem reaction involving copper-catalyzed cross-coupling and allene-mediated cyclization of 1-(2-ethynylaryl)-1,4-disubstituted-1,2,3-triazole withN-tosylhydrazone has been developed. This method features operational simplicity, excellen

Structure-based design and in vivo anti-arthritic activity evaluation of a potent dipeptidyl cyclopropyl nitrile inhibitor of cathepsin C

Cathepsin C (CatC)is a dipeptidyl-exopeptidase which activates neutrophil serine protease precursors (elastase, proteinase 3, cathepsin G and NSP4)by removing their N-terminal propeptide in bone marrow cells at the promyelocytic stage of neutrophil differ