5351-69-9

Basic information

• Product Name: 4-PHENYL-3-THIOSEMICARBAZIDE
• Synonyms: 4-phenyl-3-thio-semicarbazid;n-phenyl-hydrazinecarbothioamid;usafek-5426;N1-PHENYLHYDRAZINE-1-CARBOTHIOAMIDE;TIMTEC-BB SBB007538;4-PHENYL-3-THIOSEMICARBAZIDE;4-PHENYLTHIOSEMICARBAZIDE;AKOS B001502
• CAS NO: 5351-69-9
• Molecular Formula: C₇H₉N₃S
• Molecular Weight: 167.23
• EINECS: 226-329-1
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 5351-69-9.mol
• Article Data: 104

Chemical Properties

• Melting Point: 138-140 °C(lit.)
• Boiling Point: 281.3°Cat760mmHg
• Flash Point: 123.9°C
• Appearance: /
• Density: 1.1960 (rough estimate)
• Vapor Pressure: 0.00248mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store at +15°C to +25°C.
• Solubility: methanol: 50 mg/mL, clear
• PKA: 11.01±0.70(Predicted)
• BRN: 608285
• CAS DataBase Reference: 4-PHENYL-3-THIOSEMICARBAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYL-3-THIOSEMICARBAZIDE(5351-69-9)
• EPA Substance Registry System: 4-PHENYL-3-THIOSEMICARBAZIDE(5351-69-9)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: VT4025000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5351-69-9(Hazardous Substances Data)

Usage

Description

4-PHENYL-3-THIOSEMICARBAZIDE is an organic compound with the molecular formula C7H9N3S. It is a derivative of thiosemicarbazide, which is a heterocyclic compound known for its various applications in chemical synthesis and pharmaceuticals. It possesses a phenyl group attached to the thiosemicarbazide structure, which may contribute to its reactivity and potential uses in different industries.

Uses

Used in Chemical Synthesis:
4-PHENYL-3-THIOSEMICARBAZIDE is used as a synthetic intermediate for the production of various organic compounds, including amberlite XAD resins and a series of thiosemicarbazones. Its unique structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-PHENYL-3-THIOSEMICARBAZIDE is used as a building block for the development of new drugs, particularly those with potential therapeutic applications. Its ability to form thiosemicarbazones, which are known for their diverse biological activities, makes it an important compound in the search for new medications.
Used in Material Science:
4-PHENYL-3-THIOSEMICARBAZIDE is also used in the development of advanced materials, such as amberlite XAD resins. These resins are high-capacity, nonionic adsorbents used in various applications, including water treatment, food processing, and chromatography. The incorporation of 4-PHENYL-3-THIOSEMICARBAZIDE into the synthesis process can enhance the properties of these resins, making them more effective for their intended uses.

Purification Methods

Crystallise it from EtOH. [Beilstein 12 IV 827.]

InChI:InChI=1/C7H9N3S/c8-10-7(11)9-6-4-2-1-3-5-6/h1-5H,8H2,(H2,9,10,11)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 102-08-9 N,N-diphenylthiourea 
• 1074-52-8 ammonium N-phenyldithiocarbamate 
• 103-85-5 monophenylthiourea 
• 40231-24-1 N-phenyldithiocarbamic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 18418-42-3 phenyl-dithiocarbamic acid; sodium salt 
• 118-48-9 isatoic anhydride 
• 13220-57-0 tryptanthrine 
• 79-19-6 thiosemicarbazide 
• 28492-94-6 isatin-3-(N⁴-benzylthiosemicarbazone) 
• 49645-33-2 phenyl thioisocyanate 
• 53278-51-6 S-(phenylthiocarbamoyl)thioglycolic acid 
• 62-53-3 aniline 

Downstream Products

• 67526-44-7 (E)-N-phenyl-2-(pyridin-4-ylmethylene)hydrazine-1-carbothioamide 
• 67526-46-9 (E)-N-phenyl-2-(pyridin-3-ylmethylene)hydrazine-1-carbothioamide 
• 31397-09-8 furan-2-carbaldehyde N¹-phenylthiosemicarbazone 
• 83796-44-5 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-phenylhydrazinecarbothioamide 
• 38110-48-4 3-phenylthiocarbamoyl-carbazic acid ethyl ester 
• 80269-69-8 2-cyclohexylidene-N-phenyl(hydrazinecarbothioamide) 
• 13153-00-9 N⁴-phenyl acetic acid thio-semicarbazide 
• 35559-25-2 3-nitro-benzaldehyde 4-phenyl-thiosemicarbazone 
• 13456-63-8 1-benzylidene-4-phenylthiosemicarbazide 
• 74959-64-1 2-(4-methoxybenzylidene)-N-phenylhydrazinecarbothioamide 
• 14938-70-6 2-hydroxybenzaldehyde 4-phenylthiosemicarbazone 
• 101878-82-4 2-benzoyl-1-isopropylidene-4-phenyl thiosemicarbazide 
• 13153-01-0 1-benzoyl-4-phenyl-3-thiosemicarbazide 
• 861564-09-2 1,2-dibenzoyl-4-phenyl thiosemicarbazide 

Relevant articles and documents

Novel, green and sustainable route for synthesis of 5-aryl-4-phenyl-1,2,4-triazolidine-3-thiones

A highly efficient, one-pot, novel and greener straightforward multi-component approach has been disclosed for the facile synthesis of 5-aryl-4-phenyl-1,2,4-triazolidine-3-thiones from reaction of phenyl isothiocyanate, hydrazine hydrate and diverse aromatic aldehydes/cyclic ketones/isatins in the presence of a novel Lewis acid-surfactant-combined catalyst. High yields, use of ambient temperature and water as a universally accepted green solvent, simple work-up procedure, easy isolation of product, high atom economy makes the present method attractive, sustainable and economical.

Structural and spectral perspectives of a novel thiosemicarbazone synthesized from di-2-pyridyl ketone and 4-phenyl-3-thiosemicarbazide

A new thiosemicarbazone, HL is synthesized from di-2-pyridyl ketone and 4-phenyl-3-thiosemicarbazide and structurally and spectrochemically characterized. 1H NMR, 13C NMR, COSY, HMQC and IR spectra of the compound are studied and the proton magnetic resonance spectrum reveals some unprecedented observations. The thione form is predominant in the solid state, as supported by the crystal structure and IR data, while a thiol-thione equilibrium is proposed in the solution state by NMR studies. The compound crystallizes into a monoclinic lattice with space group C2/c and the ZE conformation is exhibited by the thiosemicarbazone. Intra- and intermolecular hydrogen-bonding interactions give rise to a two-dimensional packing in the crystal lattice.

Pyridoxal hydrochloride thiosemicarbazones with copper ions inhibit cell division via Topo-I and Topo-IIɑ

Topoisomerase (Topo) accelerates cell growth and division, and has been a theoretical target for anti-cancer drugs for decades. A series of pyridoxal thiosemicarbazone (PLT) ligands were designed and synthesized, and the dependence of their antiproliferative activity on copper was investigated. The insertion of N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride (compound 9) and Chlorido(N-cyclohexyl-2-((3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene)-N-methylhydrazinecarbothioamide hydrochloride-O,N,S)?copper(II) nitrate (9-Cu complex) into Topo-I and Topo-II prevented uncoiling of DNA through hydrogen bonds and intermolecular forces. The combination of PLT derivatives and copper gluconate (CuGlu) improved their anti-tumour activity against a cell line with high expression of topoisomerase (SK-BR-3). The non-linear regression equations of the inhibitory activity and anti-tumour activity of Topo-I and Topo-IIɑ in SK-BR-3 cells had R2 values of 0.93 and 0.94, respectively. In addition to lipophilicity, inhibition of topoisomerase also affected the activity of PLT ligands by coordinating with copper ions. At the cellular level, PLTs and CuGlu penetrate the cell membrane to form metabolites in the cell, thus selectively inhibiting the activity of Topo-I and Topo-IIɑ, and ultimately inhibiting cell division. These findings will inform the design of future anti-cancer thiosemicarbazone drugs.

Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents

With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.

Electrochemical characterization of isatin-thiosemicarbazone derivatives

Abstract: Herein, we have notably described the electrochemical behavior of four isatin-thiosemicarbazone derivatives. In this regard, cyclic voltammograms of isatin-3-thiosemicarbazone (ITSC), isatin-3-(N4-benzylthiosemicarbazone) (ITSC-Ph), 1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide (NO2-ITSC) and 1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide (NO2-ITSC-Ph) have demonstrated an irreversible oxidation process. More specifically, the generation of isatin and thiourea moieties as the final oxidation products was proposed. The cyclic voltammograms also demonstrate irreversible reduction processes of ITSC and ITSC-Ph in three steps. The proposed final products are 3-aminoindolin-2-one and thiourea moieties. In the cyclic voltammograms of NO2-ITSC and NO2-ITSC-Ph, five reduction processes were observed: three of them due to reduction of the nitro group. It was proposed that the formation of 5-hydroxyamino-3-iminoindolin-2-one and the thiourea moieties would be the final products. Graphic abstract: [Figure not available: see fulltext.] Electrochemical characterization of four isatin thiosemicarbazone derivatives is described. The compounds are irreversibly oxidized and reduced. Isatin moieties and thiourea are proposed to be the products generated after oxidation. Considering the reduction processes, the nitro group present at the isatin moiety is also reduced and influences the reduction products generated.