621-83-0

Basic information

• Product Name: BENZYLTHIOUREA
• Synonyms: Thiourea, (phenylmethyl)-;BENZYLTHIOUREA;1-BENZYL-2-THIOUREA;N-BENZYLTHIOUREA;1-BENZYLTHIOUREA;(phenylmethyl)-Thiourea;1-(Phenylmethyl)thiourea
• CAS NO: 621-83-0
• Molecular Formula: C₈H₁₀N₂S
• Molecular Weight: 166.24
• EINECS: 210-709-9
• Mol File: 621-83-0.mol

Chemical Properties

• Melting Point: 163-165°C
• Boiling Point: 300.9 °C at 760 mmHg
• Flash Point: 135.8 °C
• Appearance: /
• Density: 1.189 g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.77±0.29(Predicted)
• BRN: 972372
• CAS DataBase Reference: BENZYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYLTHIOUREA(621-83-0)
• EPA Substance Registry System: BENZYLTHIOUREA(621-83-0)

Safety Data

• Statements: 22
• Safety Statements: 22-36/37
• RIDADR: UN 2811 6.1/PG III
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 621-83-0(Hazardous Substances Data)

Usage

Uses

Used in Rubber Industry:
Benzylthiourea is used as a rubber accelerator for the production of tires and other rubber products. It functions as a vulcanization agent, promoting the cross-linking of rubber molecules, which enhances the strength and elasticity of the final product.
Used in Pharmaceutical Research:
Benzylthiourea is studied for its potential anticancer and antifungal properties. It is being investigated for its possible use in medicine, although further research is required to fully understand its pharmacological applications and ensure its safety and efficacy.

InChI:InChI=1/C8H10N2S/c9-8(11)10-6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,9,10,11)

Upstream product

• 6630-99-5 1,2,3,4-thiatriazole-5-amine 
• 100-46-9 benzylamine 
• 3287-99-8 benzylamine hydrochloride 
• 333-20-0 potassium thioacyanate 
• 1147550-11-5 ammonium thiocyanate 
• 622-78-6 Benzyl isothiocyanate 
• 51571-89-2 benzylammonium thiocyanate 
• 107-21-1 ethylene glycol 
• 625-57-0 O-ethyl thiocarbamate 
• 4921-91-9 N-benzoyl-N'-benzylthiourea 
• 14327-01-6 1-t-butyl-3-benzylthiocarbamide 
• 14294-17-8 N-Benzyl-N'-(tert-pentyl)-thioharnstoff 
• 43009-20-7 triethylammonium N-benzyldithiocarbamate 
• 76746-68-4 1-amidino-3-benzyl-1-phenylthiourea hydrochloride 

Downstream Products

• 115541-09-8 2-(benzylamino)-4-(2'-pyrazinyl)thiazole 
• 7664-41-7 ammonia 
• 108-88-3 toluene 
• 74-89-5 methylamine 
• 41249-63-2 3-benzylamino-6-phenyl-4H-[1,2,4]triazin-5-one 
• 15087-97-5 N-benzyl-4-phenyl-1,3-thiazol-2-amine 
• 538-32-9 benzylurea 
• 111427-08-8 3-benzyl-4,5-dimethyl-1,3-thiazol-2(3H)-imine 
• 132666-79-6 N‐benzyl‐4‐methylthiazol‐2‐amine 
• 16914-30-0 3-benzyl-4-methyl-1,3-thiazol-2(3H)-imine 
• 5667-47-0 phenacyldimethylsulfonium bromide 
• 6343-54-0 N-benzylformamide 

Relevant articles and documents

Derivatization of isothiocyanates and their reactive adducts for chromatographic analysis

Isothiocyanates form adducts with a multitude of biomolecules, and these adducts need analytical methods. Likewise, analytical methods for hydrophilic isothiocyanates are needed. We considered reaction with ammonia to form thiourea derivatives. The hydrophilic, glycosylated isothiocyanate moringin, 4-(α-l-rhamnopyranosyloxy)benzyl isothiocyanate, was efficiently derivatized to the thiourea derivative by incubation with ammonia. The hydrophobic benzyl isothiocyanate was also efficiently derivatized to the thiourea derivative. The thiourea group provided a UV absorbing chromophore, and the derivatives showed expectable sodium and hydrogen adducts in ion trap mass spectrometry and were suitable for liquid chromatography analysis. Reactive dithiocarbamate adducts constitute the major type of reactive ITC adduct expected in biological matrices. Incubation of a model dithiocarbamate with ammonia likewise resulted in conversion to the corresponding thiourea derivative, suggesting that a variety of matrix-bound reactive isothiocyanate adducts can be determined using this strategy. As an example of the application of the method, recovery of moringin and benzyl isothiocyanate applied to cabbage leaf discs was studied in simulated insect feeding assays. The majority of moringin was recovered as native isothiocyanate, but a major part of benzyl isothiocyanate was converted to reactive adducts.

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

ANTIVIRAL COMPOUNDS AND USE THEREOF

The present invention relates to compounds of formula (I), their use as medicaments, in particular as broad spectrum antiviral agents, their combination with a further antiviral agent and relative pharmaceutical compositions. In particular, the compounds of the invention are useful in the treatment of a disease caused by an enveloped virus.

CuBr2 mediated synthesis of 2-Aminothiazoles from dithiocarbamic acid salts and ketones

In a one-pot procedure, CuBr2 has been used as a efficient desulfurizing agent in the synthesis of 2-aminothiazoles by the condensation of in situ-generated 1-substituted thioureas from their dithiocarbamic acid salts, with in situ-generated α-bromoketones from ketones. All reactions were carried out under optimized reaction conditions and gave the target products in 61–95% yield.

Novel broad spectrum virucidal molecules against enveloped viruses

Viral infections are an important cause of death worldwide. Unfortunately, there is still a lack of antiviral drugs or vaccines for a large number of viruses, and this represents a remarkable challenge particularly for emerging and re-emerging viruses. For this reason, the identification of broad spectrum antiviral compounds provides a valuable opportunity for developing efficient antiviral therapies. Here we report on a class of rhodanine and thiobarbituric derivatives displaying a broad spectrum antiviral activity against seven different enveloped viruses including an HSV-2 acyclovir resistant strain with favorable selectivity indexes. Due to their selective action on enveloped viruses and to their lipid oxidation ability, we hypothesize a mechanism on the viral envelope that affects the fluidity of the lipid bilayer, thus compromising the efficiency of virus-cell fusion and preventing viral entry.

Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles

[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.

Aminoguanidine hydrazone derivatives as non-peptide NPFF1 receptor antagonists reverse opioid induced hyperalgesia

Neuropeptide FF receptors (NPFF1R and NPFF2R) and their endogenous ligand Neuropeptide FF have been shown previously to display anti-opioid properties and to play a critical role in the adverse effects associated with chronic administrations of opiates including the development of opioid-induced hyperalgesia and analgesic tolerance. In this work, we sought to identify novel NPFF receptors ligands by focusing our interest on a series of heterocycles as rigidified non-peptide NPFF receptor ligands, starting from already described aminoguanidine hydrazones (AGH's). Binding experiments and functional assays highlighted AGH 1n and its rigidified analog 2-amino-dihydropyrimidine 22e for in vivo experiments. As earlier shown with the prototypical dipeptide antagonist RF9, both 1n and 22e reduced significantly the long lasting fentanyl-induced hyperalgesia in rodents. Altogether these data indicate that AGH rigidification maintains nanomolar affinities for both NPFF receptors, while improving antagonist character towards NPFF1R.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids

The catalytic asymmetric α-functionalization of prochiral barbituric acids, a subtype of pseudosymmetric 1,3-diamides, to yield the corresponding 5,5-disubstituted (quaternary) derivatives remains essentially unsolved. In this study 2-alkylthio-4,6-dioxopirimidines are designed as key 1,3-diamide surrogates that perform exceedingly in amine-squaramide catalyzed C-C bond forming reactions with vinyl ketones or Morita-Baylis-Hillmann-type allyl bromides as electrophiles. Mild acid hydrolysis of adducts affords barbituric acid derivatives with an in-ring quaternary carbon in unprecedented enantioselectivity, offering valuable materials for biological evaluations.

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide

A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.