1234-28-2

Usage

Physical state

Yellow to orange crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Primary use

Reagent for the determination of heavy metals in various substances

Reaction with metal ions

Forms insoluble complexes

Additional uses

Synthesis of other organic compounds, photometric reagent for the determination of nitro compounds

Toxicity

Toxic if ingested or inhaled

Hazards

Can cause skin and eye irritation

Safety precautions

Handle with caution

Upstream product

• 463-71-8 thiophosgene 
• 100-01-6 4-nitro-aniline 
• 2131-61-5 p-nitrophenyl isothiocyanate 
• 103-72-0 phenyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 17356-08-0 thiourea 

Downstream Products

• 26946-76-9 (6-nitro-benzothiazol-2-yl)-(4-nitro-phenyl)-amine 
• 587-90-6 bis-N,N'-(4-nitrophenyl)urea 
• 18440-30-7 N,N',N''-tris-(4-nitro-phenyl)-guanidine 
• 36212-83-6 [4-(4-chloro-phenyl)-3-(4-nitro-phenyl)-3H-thiazol-2-ylidene]-(4-nitro-phenyl)-amine 
• 42748-48-1 [4-methyl-3-(4-nitro-phenyl)-3H-thiazol-2-ylidene]-(4-nitro-phenyl)-amine 
• 61333-96-8 5-methyl-3-(4-nitro-phenyl)-2-(4-nitro-phenylimino)-thiazolidin-4-one 
• 36220-68-5 4-[3-(4-nitro-phenyl)-2-(4-nitro-phenylimino)-2,3-dihydro-thiazol-4-yl]-phenol 
• 82686-76-8 [4-Isopropyl-3-(4-nitro-phenyl)-3H-thiazol-(2Z)-ylidene]-(4-nitro-phenyl)-amine 
• 79051-96-0 2-(p-nitrophenylimino)-3-(p-nitrophenyl)-4-(β-(p-methoxyphenyl)ethyl)-Δ4-thiazoline 
• 82844-54-0 5,5-Bis-(2-hydroxy-phenyl)-1,3-bis-(4-nitro-phenyl)-2-thioxo-imidazolidin-4-one 
• 82844-67-5 5,5-Bis-(4-hydroxy-phenyl)-1,3-bis-(4-nitro-phenyl)-2-thioxo-imidazolidin-4-one 
• 82686-60-0 [5-Isopropyl-4-methyl-3-(4-nitro-phenyl)-3H-thiazol-(2Z)-ylidene]-(4-nitro-phenyl)-amine 
• 79051-26-6 2-(p-nitrophenylimino)-3-(p-nitrophenyl)-4-(p-tolyl)-Δ4-thiazoline 
• 82694-52-8 [4,5-Dimethyl-3-(4-nitro-phenyl)-3H-thiazol-(2Z)-ylidene]-(4-nitro-phenyl)-amine 

Relevant academic research and scientific papers

Electron density distribution studies as a tool to explore the behaviour of thiourea-based anion receptors

Building on previous studies of anion-receptor complexes based on a urea scaffold substituted symmetrically with electron-withdrawing nitro groups, the electron density distribution in an analogous thiourea receptor complex and the related asymmetrically

Backscattering Interferometry: An alternative approach for the study of hydrogen bonding interactions in organic solvents

Intermolecular interactions involving hydrogen bonds are responsible for catalysis and recognition. Traditional methods used to study hydrogen-bonding interactions are generally limited to relatively large volumes and high substrate concentrations. Backscattering Interferometry (BSI) provides a microfluidic platform to study these interactions in nonaqueous media at micromolar to nanomolar concentrations in picoliter volumes by monitoring changes in the refractive index.

A thiourea-based chromoionophore for selective binding and sensing of acetate

Highly selective binding and sensing of acetate over various monovalent inorganic anions (MeCO2-?H2PO4- >Cl-, Br-, I-, SCN-, NO3-, HSO

Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water

ABATRACT: A direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.

Hydrogen-Bond Catalysis of Imine Exchange in Dynamic Covalent Systems

The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines, and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.

Synthesis, characterization, and pharmacological evaluation of thiourea derivatives

Thioureas and their derivatives are organosulfur compounds having applications in numerous fields such as organic synthesis and pharmaceutical industries. Symmetric thiourea derivatives were synthesized by the reaction of various anilines with CS2. The synthesized compounds were characterized using the UV-visible and nuclear magnetic resonance (NMR) spectroscopic techniques. The compounds were screened for in vitro inhibition of α-amylase, α-glucosidase, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) enzymes and for their antibacterial and antioxidant potentials. These compounds were fed to Swiss male albino mice to evaluate their toxicological effects and potential to inhibit glucose-6-phosphatase (G6Pase) inhibition. The antibacterial studies revealed that compound 4 was more active against the selected bacterial strains. Compound 1 was more active against 2,2-diphenyl-1-picrylhydrazyl and 2,2'-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radicals, AChE, BuChE, and α-glucosidase. Compound 2 was more potent against α-amylase and G6Pase. Toxicity studies showed that compound 4 is safe as it exerted no toxic effect on any of the hematological and biochemical parameters or on liver histology of the experimental animals at any studied dose rate. The synthesized compounds showed promising antibacterial and antioxidant potential and were very active (both in vitro and in vivo) against G6Pase and moderately active against the other selected enzymes used in this study.

A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling

Promoted by KOH under ball milling, anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly "click" with other amines to afford unsymmetrical thioureas.

An environmentally benign method for the synthesis of symmetrical N,N′-disubstituted thioureas in a water medium

An environmentally benign method for the synthesis of symmetrical N,N′-disubstituted thioureas in a water medium using poly(ethylene glycol)-400 (PEG-400) as a catalyst and a microwave as a heating source is described. Diaryl- and dialkyl-thioureas efficiently are synthesized by the reactions of thiourea with a variety of amines. This protocol has advantages of (a) no use of hazardous reagents and volatile organic solvents, (b) a rapid reaction rate, (c) a high yield, and (d) a simple work-up procedure. Copyright Taylor & Francis Inc.

Microwave-assisted synthesis of N,N′-diaryl cyanoguanidines

(Chemical Equation Presented) A mild, efficient, and high-yielding method for the synthesis of N,N′-diaryl cyanoguanidines from their corresponding thioureas under microwave-assisted conditions is described. A series of cyanoguanidines were synthesized containing both electron-donating and electron-withdrawing substituents. The reactions were facilitated by the use of polar solvents along with moderate temperatures.