16738-20-8

Basic information

• Product Name: 1-(2,4-DIMETHYLPHENYL)-2-THIOUREA
• Synonyms: (2,4-xylyl)thiourea;2,4-xylylthiourea;2-thio-1-(2,4-xylyl)-ure;2-thio-1-(2,4-xylyl)urea;2,4-DIMETHYLPHENYLTHIOUREA;1-(2,4-DIMETHYLPHENYL)-2-THIOUREA;AKOS BBS-00000747;1-(2,4-Dimethylphenyl)thiourea
• CAS NO: 16738-20-8
• Molecular Formula: C₉H₁₂N₂S
• Molecular Weight: 180.27
• EINECS: -0
• Mol File: 16738-20-8.mol

Chemical Properties

• Melting Point: 177-179°C
• Boiling Point: 290.7°Cat760mmHg
• Flash Point: 129.6°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.00203mmHg at 25°C
• Refractive Index: 1.674
• PKA: 13.40±0.70(Predicted)
• BRN: 2639862
• CAS DataBase Reference: 1-(2,4-DIMETHYLPHENYL)-2-THIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIMETHYLPHENYL)-2-THIOUREA(16738-20-8)
• EPA Substance Registry System: 1-(2,4-DIMETHYLPHENYL)-2-THIOUREA(16738-20-8)

Safety Data

• Statements: 25
• Safety Statements: 22-36/37-45
• RIDADR: 2811
• RTECS: YU3675000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 16738-20-8(Hazardous Substances Data)

Usage

Uses

(2,4-Dimethylphenyl)thiourea

InChI:InChI=1/C9H12N2S/c1-6-3-4-8(7(2)5-6)11-9(10)12/h3-5H,1-2H3,(H3,10,11,12)

Upstream product

• 39842-01-8 2,4-dimethylphenylisothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 21436-96-4 2,4-xylidine hydrochloride 
• 83697-77-2 N-(2,4-dimethylphenyl)-N′-benzoylthiourea 
• 95-68-1 2,4-Xylidine 
• 56615-73-7 C₆H₁₅N*C₉H₁₁NS₂ 

Downstream Products

• 64036-71-1 2-amino-4,6-dimethylbenzothiazole 
• 500586-75-4 1-(2,4-dimethylphenyl)-5-amino-1H-tetrazole 
• 71232-25-2 2,4-dimethylphenyl cyanamide 
• 154371-23-0 2-(2,4-Dimethyl-phenylamino)-1-thia-3,9,10-triaza-anthracen-4-one 
• 94646-85-2 1-(2,4-Dimethyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 133890-02-5 4,6-diamino-1-(2,4-dimethylphenyl)-2(1H)-pyrimidinethione 
• 119155-48-5 N-(2,4-Dimethyl-phenyl)-pyrrolidine-1-carboxamidine; hydriodide 
• 119155-49-6 N-(2,4-Dimethyl-phenyl)-morpholine-4-carboxamidine; hydriodide 
• 71018-87-6 1-(2,4-dimethylphenyl)-5-methyl-tetrahydro-s-triazin-2[1H]-thione 
• 1267448-30-5 6,8-dimethyl-4-phenyl-2H-pyrimido[2,1-b]benzothiazol-2-one 
• 2295-31-0 thiazoline-2,4-dione 
• 2990-02-5 1-(2,4-dimethylphenyl)urea 

Relevant articles and documents

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].

Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene

A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.

The in vivo antinociceptive and μ-opioid receptor activating effects of the combination of N-phenyl-2′,4′-dimethyl-4,5′-bi-1,3-thiazol-2-amines and naloxone

Morphine is widely used for the treatment of severe pain. This analgesic effect is mediated principally by the activation of μ-opioid receptors (MOR). However, prolonged activation of MOR also results in tolerance, dependence, addiction, constipation, nau

Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water

In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.

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.

OPIOID RECEPTOR MODULATORS AND USE THEREOF

Disclosed is an in vitro screening method for identifying an antagonist-to-agonist allosteric modifier of a mu-opioid receptor and an in vivo method for confirming that a test compound is such a modifier of a mu-opioid receptor. Also disclosed is a method

Synthesis and antitumor evaluation of 5-(benzo[: D] [1,3]dioxol-5-ylmethyl)-4-(tert -butyl)- N -arylthiazol-2-amines

A series of novel N-aryl-5-(benzo[d][1,3]dioxol-5-ylmethyl)-4-(tert-butyl)thiazol-2-amines (C1-C31) were synthesized and evaluated for their antitumor activities against HeLa, A549 and MCF-7 cell lines. Some tested compounds showed potent growth inhibition properties with IC50 values generally below 5 μM against the three human cancer cells lines. Compound C27 showed potent activities against HeLa and A549 cell lines with IC50 values of 2.07 ± 0.88 μM and 3.52 ± 0.49 μM, respectively. Compound C7 (IC50 = 2.06 ± 0.09 μM) was the most active compound against A549 cell line, while compound C16 (IC50 = 2.55 ± 0.34 μM) showed the best inhibitory activity against the MCF-7 cell line. The preliminary mechanism of the inhibitory effect was investigated via further experiments, such as morphological analysis by dual AO/EB staining and Hoechst 33342 staining, and cell apoptosis and cycle assessment by FACS analysis. The results illustrated that compound C27 could induce apoptosis and cause both S-phase and G2/M-phase arrests in HeLa cell line. Therefore, compound C27 could be developed as a potential antitumor agent.

An efficient methodology for the synthesis of thioureas from amine mediated by a cobalt source

The cheap, readily available and air stable cobalt catalyst was used as the desulfurization agent for the conversion of aniline to thioureas in one pot three step reaction under mild reaction conditions. The reactions are rapid and facile and accomplished at room temperature.

Synthesis and Cytotoxicity in Vitro of N-Aryl-4-(Tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine

A series of novel N-aryl-4-(tert-butyl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines were synthesized in a green way. H2O2-NaBr Brominating circulatory system was used in the synthesis of the key intermediate in a mild condition. All of the target compounds were confirmed by1H NMR and elemental analysis and tested for their cytotoxicity against two different human cancer cell lines. The cytotoxicity assay revealed that some of the title compounds showed moderate to strong cytotoxic activities. Compound 2i was the most potent compound with the IC50 values of 9 μMagainst Hela cells and 15 μMagainst Bel-7402 cells, respectively.

Design, synthesis and investigation on the structure-activity relationships of N-substituted 2-aminothiazole derivatives as antitubercular agents

Tuberculosis (TB) is one of the deadliest infectious diseases of all times, and its recent resurgence is a supreme matter of concern. Co-infection with HIV and, in particular, the continuous isolation of new resistant strains, makes the discovery of novel anti-TB agents a strategic priority. The research of novel agents should be driven by the accessibility of the synthetic procedure and, in particular, by the lack of cross-resistance with the drugs already marketed. Moreover, in order to shorten the duration of the therapy, and therefore decrease the rate of resistance, these molecules should be active also against the nonreplicating persistent form (NRP-TB) of the infection. The availability of an in-house small library of compounds prompted us to investigate their anti-TB activity. Two compounds, embodying a 2-aminothiazole scaffold, were found to possess a certain inhibitory activity toward Mycobacterium tuberculosis H37Rv, and therefore a medicinal chemistry campaign was initiated in order to increase the activity of the hit compounds and, especially, construct a plausible body of structure-activity relationships. The potency of the hit compound was successfully improved, and, much more importantly, some of the molecules synthesized were found to be active toward the persistent phenotype, and, also, toward a panel of resistant strains. These findings encourage further investigations around this interesting antitubercular chemotype.