1666-17-7

Basic information

• Product Name: BENZALDEHYDE TOSYLHYDRAZONE
• Synonyms: BENZALDEHYDE TOSYLHYDRAZONE;N-benzylideneamino-p-toluenesulfonamide;BENZALDEHYDE TOSYLHYDRAZONE 98%;Benzaldehyde p-Toluenesulfonylhydrazone;Benzaldehyde [(4-methylphenyl)sulfonyl]hydrazone;N2-Benzylidene-4-methylbenzenesulfonic acid hydrazide;N2-Benzylidene-4-methylbenzenesulfonohydrazide;N'-Benzylidene-p-toluenesulfonic acid hydrazide
• CAS NO: 1666-17-7
• Molecular Formula: C₁₄H₁₄N₂O₂S
• Molecular Weight: 274.34
• Product Categories: B;Stains and Dyes;Stains&Dyes, A to
• Mol File: 1666-17-7.mol

Chemical Properties

• Melting Point: 130 °C
• Boiling Point: 431.8°C at 760 mmHg
• Flash Point: 214.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.17E-07mmHg at 25°C
• Refractive Index: 1.59
• PKA: 9.71±0.40(Predicted)
• CAS DataBase Reference: BENZALDEHYDE TOSYLHYDRAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZALDEHYDE TOSYLHYDRAZONE(1666-17-7)
• EPA Substance Registry System: BENZALDEHYDE TOSYLHYDRAZONE(1666-17-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1666-17-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Benzaldehyde tosylhydrazone is used as a reagent for the determination of aldehydes and ketones, playing a crucial role in the identification and analysis of these organic compounds.
Used in Pharmaceutical Synthesis:
It serves as a reagent in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Analytical Chemistry:
Benzaldehyde tosylhydrazone is used as a reagent for the detection and quantification of metal ions, thanks to its ability to form stable complexes with these ions, which aids in their analysis.
Used in Research and Development:
It is utilized in the study of its potential anti-inflammatory and antibacterial properties, indicating its possible applications in the medical and pharmaceutical industries for the treatment of various conditions.

InChI:InChI=1/C14H14N2O2S/c1-12-7-9-14(10-8-12)19(17,18)16-15-11-13-5-3-2-4-6-13/h2-11,16H,1H3/b15-11+

Upstream product

• 100-52-7 benzaldehyde 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 100-47-0 benzonitrile 
• 98-59-9 p-toluenesulfonyl chloride 
• 60-29-7 diethyl ether 
• 2327-99-3 1-phenylpropadiene 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 100-42-5 styrene 
• 2700-22-3 Benzylidenemalononitrile 

Downstream Products

• 908094-04-2 phenyldiazomethane 
• 622-08-2 2-Benzyloxyethanol 
• 5395-20-0 1-methyl-4-(benzylsulfonyl)benzene 
• 896-65-1 (1,2-diphenylcyclopropyl)benzene 
• 2978-75-8 7-Phenyl-2,3:4,5-dibenzo-norcaradien-2,4 
• 2978-77-0 7-Phenyl-2,3:5,6-dibenzo-norbornadien-2,5 
• 31910-69-7 (N'-[chloro(phenyl)methylene]-4-methylbenzenesulfonohydrazide) 
• 22959-81-5 1,2-dihydro-1-hydroxy-2-(4-methylbenzenesulfonyl)-2,3,1,-benzodiazaborine 
• 788-98-7 2-p-Toluolsulfonyl-1-benzyl-hydrazin 
• 6840-29-5 N-phenyl-N-benzylacetamide 
• 18440-50-1 N-benzyl-N'-benzylidene-4-methylbenzenesulfonohydrazide 
• 63007-13-6 C₁₆H₂₁N₂O₅PS 
• 538-86-3 benzyl methyl ether 
• 87531-36-0 α-morpholino-α,α'-diphenylazine 

Related news

Reaction of phenylcarbene formed from BENZALDEHYDE TOSYLHYDRAZONE (cas 1666-17-7) in certain solvents09/24/2019

Treatment of benzaldehyde tosylhydrazone (I) with sodium methoxide in various solvents under irradiation and/or heating yields products arising from phenylcarbene (IV) which is produced by photolytic or pyrolytic decomposition of initially formed phenyldiazomethane (III). Reaction products origi...detailed

Relevant articles and documents

Palladium-catalyzed insertion of N-tosylhydrazones and trapping with carbon nucleophiles

A Pd-catalyzed three-component cross-coupling reaction of vinyl iodide, N-tosylhydrazone, and carbon nucleophiles is reported, and a one-pot procedure is also developed. The cross-coupling is proposed to proceed through a palladium-carbene migratory inser

Synthesis of Densely Substituted Conjugated Dienes by Transition-Metal-Free Reductive Coupling of Allenylboronic Acids and Tosylhydrazones

Tosylhydrazones and allenylboronic acids underwent a transition-metal-free reductive coupling reaction. This process is suitable for synthesis of tetra- and pentasubstituted conjugated dienes. The corresponding allenyl-Bpin substrate showed a very poor re

Green-light induced cycloadditions

We introduce a red-shifted tetrazole that is able to undergo efficient nitrile imine-mediated tetrazole-ene cycloaddition (NITEC) under blue and green light irradiation. We provide a detailed wavelength-dependent reactivity map, and employ a number of LEDs for high-conversion small molecule and polymer end-group modification.

Photomechanical response of sulfonylhydrazone molecular crystals

Sulfonylhydrazones are a novel hydrazone-based organic molecular photoswitch. The four derivatives with unsubstituted ando-,m- andp-nitro substituted sulfonylhydrazone (SH-1,SH-2,SH-3, andSH-4, respectively) derived fromp-toluenesulfonyl hydrazide and corresponding benzaldehydes were examined with respect to their solution state photoswitching and photomechanical response in the crystalline state. All the compounds displayed UV-inducedE→Zisomerization in the solution state, whereas the back conversion was slow. Single crystals ofSH-3displayed rapid and large photomechanical bending, whereasSH-1andSH-4crystals underwent slow bending to a comparatively lesser extent. On the contrary,SH-2crystals did not show any photomechanical effects. The photomechanical deflection of the crystal tip ofSH-1increased linearly; forSH-3, the deflection increased in a sub-linear manner for few seconds, after which it started to revert towards the light source. ForSH-4crystals, the photo-induced tip deflection initially increased in a sub-linear fashion, after which no motion was observed even after continuous exposure to UV light irradiation. The photomechanical behavior of the crystals was also inspected with the aid of velocity-time and acceleration-time plots that unravelled the instantaneous photomechanical motion at various time intervals.

Direct Access for the Regio- And Stereoselective Synthesis of N-Alkenylpyrazoles and Chromenopyrazoles

A highly regio- and stereoselective method was developed for the preparation of N-alkenylpyrazoles and chromenopyrazoles by the reaction of N-tosylhydrazones and salicyl N-tosylhydrazones with alkynes under neat conditions in the presence of La(OTf)3. The present study was found to be efficient and convenient for direct access to N-alkenylpyrazoles and chromenopyrazoles through C-C, C-N, and C-O bond forming reactions. Structure assignment of N-alkenylpyrazole compound 5c was confirmed by X-ray analysis.

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.

Pd-Catalyzed Cascade Metallo-Ene Cyclization/Metallo-Carbene Coupling of Allenamides

A highly efficient palladium-catalyzed cascade metallo-ene/metallo-carbene coupling reaction was developed to produce 2,3-dihydropyrrole derivatives in high yields. In this transformation, two new Csp3?Csp2 and Csp2?Cspsu

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.

Copper-Catalyzed Regioselective Coupling of Tosylhydrazones and 2-Pyridones: A Strategy for the Production of N-Alkylated Compounds

The highly regioselective N-alkylation reaction of 2-pyridones was achieved through hydrazone chemistry, especially for substrates with bulky secondary alkyl groups. Described herein is a copper-catalyzed coupling reaction of pyridone derivatives with tosylhydrazones.

Diversity-Oriented Synthesis of 1,2,4-Triazols, 1,3,4-Thiadiazols, and 1,3,4-Selenadiazoles from N-Tosylhydrazones

The diversity-oriented synthesis of 1,2,4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones was developed, and the reactions were general for a wide range of substrates, in which NH2CN, KOCN, KSCN, and KSeCN were used as odorless sources. Two different pathways were proposed, and N-tosylhydrazonoyl chlorides were formed in situ in the presence of NCS.