614-78-8

Basic information

• Product Name: N-(2-Methylphenyl)thiourea
• Synonyms: (2-methylphenyl)-thioure;1-(2-methylphenyl)thiourea;1-o-Tolyl-2-thiourea;2-thio-1-o-tolyl-ure;2-tolylthiourea;N-(o-Tolyl)thiourea;ortho-Tolylthiourea;Thiourea, (2-methylphenyl)-
• CAS NO: 614-78-8
• Molecular Formula: C₈H₁₀N₂S
• Molecular Weight: 166.24
• EINECS: 210-395-3
• Product Categories: API intermediates
• Mol File: 614-78-8.mol

Chemical Properties

• Melting Point: 149 °C
• Boiling Point: 275.5 °C at 760 mmHg
• Flash Point: 120.4 °C
• Appearance: Crystalline solid
• Density: 1.1332 (rough estimate)
• Vapor Pressure: 0.00506mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 2086802
• CAS DataBase Reference: N-(2-Methylphenyl)thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Methylphenyl)thiourea(614-78-8)
• EPA Substance Registry System: N-(2-Methylphenyl)thiourea(614-78-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39
• RIDADR: 2811
• RTECS: YU2975000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 614-78-8(Hazardous Substances Data)

Usage

General Description

Crystalline solid.

Reactivity Profile

When heated to decomposition, N-(2-Methylphenyl)thiourea emits very toxic fumes of oxides of nitrogen and sulfur. [EPA, 1998]. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Health Hazard

The material is highly toxic if orally ingested.

Fire Hazard

When heated to decomposition, N-(2-Methylphenyl)thiourea emits very toxic fumes of oxides of nitrogen and sulfur.

InChI:InChI=1/C8H10N2S/c1-6-4-2-3-5-7(6)10-8(9)11/h2-5H,1H3,(H3,9,10,11)

Upstream product

• 14185-60-5 N-acetyl-N'-o-tolyl-thiourea 
• 636-21-5 o-toluidine hydrochloride 
• 333-20-0 potassium thioacyanate 
• 17356-08-0 thiourea 
• 95-53-4 o-toluidine 
• 113815-92-2 bis(1-isothiocyanoethyl) ether 
• 1147550-11-5 ammonium thiocyanate 
• 614-69-7 2-tolyl isothiocyanate 
• 4949-88-6 N-benzoyl-N'-(2-methylphenyl)thiourea 
• 14327-05-0 1-tert-butyl-3-o-tolylthiourea 
• 540-72-7 sodium thiocyanide 
• 14185-59-2 N-propionyl-N'-o-tolyl-thiourea 
• 45892-06-6 N-(o-tolyl)dithiocarbamic acid 
• 7732-18-5 water 

Downstream Products

• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 21344-75-2 4-phenyl-N-(2-methylphenyl)thiazol-2-amine 
• 1477-42-5 4-methyl-1,3-benzothiazol-2-amine 
• 38338-21-5 6-chloro-4-methylbenzo[d]thiazol-2-amine 
• 681126-45-4 6-bromo-4-methyl-1,3-benzothiazol-2-amine 
• 10532-63-5 N-(o-tolyl)cyanamide 
• 14185-60-5 N-acetyl-N'-o-tolyl-thiourea 
• 63082-66-6 (5-imino-4-o-tolyl-4,5-dihydro-[1,2,4]thiadiazol-3-yl)-otolyl-amine 
• 80306-60-1 N-(2-methylphenyl)-S-methylisothiourea 
• 37394-99-3 2-(2-methyl-anilino)-thiazol-4-one 
• 37394-95-9 o-tolylcarbamimidoylmercapto-acetic acid 
• 20943-24-2 5-(2-methyl-anilino)-3H-thiazolo[4,5-d]thiazol-2-one 
• 61108-39-2 (4'-methyl-2'-phenyl-[4,5']bithiazolyl-2-yl)-o-tolyl-amine 
• 61108-53-0 [2'-(4-chloro-phenyl)-4'-methyl-[4,5']bithiazolyl-2-yl]-o-tolyl-amine 

Relevant articles and documents

Synthesis of 4-acetyl-2(3H)-benzothiazolone: Sulfur bioisostere of benzoxazolone allelochemicals

A multi-step methodology for the synthesis of 4-acetyl-2(3H)-benzothiazolone was developed in order to prepare a new biomimetic analogue of benzoxazolone allelochemicals. The compound was prepared from commercially available o-toluidine in 23% overall yield. The structure of 4-acethyl-2(3H)-benzothiazolone was confirmed by NMR spectroscopy and X-ray crystallography.

Discovery of aminothiazole derivatives as novel human enterovirus A71 capsid protein inhibitors

Enterovirus A71 (EV-A71), one of the major pathogens that causes hand, foot and mouth disease (HFMD), has seriously threatened the health and safety of young children. In this study, aminothiazole derivatives were synthesized and screened against EV-A71 in Rhabdomyosarcoma (RD) cells. The best compound (12s), with a biphenyl group, showed activity against EV-A71 (EC50: 0.27 μM) but also against a series of different human enteroviruses without significant cytotoxicity (CC50 > 56.2 μM). Mechanistic studies including time-of-drug-addition assays, viral entry assays and microscale thermophoresis (MST) experiments, showed that 12s binds to EV-A71 capsid and blocks the binding between the viral protein VP1 and the relevant human scavenger receptor class B member 2 (hSCARB2).

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.

Method for synthesizing 4-methyl-2-benzothiazolehydrazine

The invention discloses a method for synthesizing 4-methyl-2-benzothiazolehydrazine. The method comprises the following steps: carrying out synthesis reaction on o-toluidine and thiocyanate in acid toobtain o-tolylthiourea; carrying out a synthesis reaction on the o-tolylthiourea and a catalyst in water to obtain 2-amino-4-methylbenzothiazole; and carrying out a synthesis reaction on the 2-amino-4-methylbenzothiazole in hydrazine hydrate, so as to obtain the 4-methyl-2-benzothiazolehydrazine. The method for synthesizing the 4-methyl-2-benzothiazolehydrazine, provided by the invention, is simple to operate, less in three wastes, capable of repeatedly applying wastewater, high in product content, good in quality and suitable for industrial mass production.

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.

Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles

A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2–0.25 μg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).

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.

Production process for 4-methyl-2-hydrazinobenzothiazole

4-methyl-2-hydrazinobenzothiazole is an important intermediate for synthesis of tricyclazole, and the tricyclazole is a main drug for preventing and controlling rice blast and a high-efficiency systemic fungicide, and has high biological activity, a unique action mechanism and special effects on preventing and controlling the rice blast. A current synthetic technology has low reaction efficiency and not high product purity, and produces more three industrial waste (waste water, waste gas and solid waste). The invention overcomes the above disadvantages to provide a production process for the 4-methyl-2-hydrazinobenzothiazole; and the process is realized through the following steps: 1, weighing raw materials for standby application; 2, performing an addition reaction to synthesize o-methylphenyl-thiourea; 3, performing a ring-closure reaction to synthesize 4-methyl-2-aminobenzothiazole hydrochloride; 4, performing a substitution reaction to synthesize the 4-methyl-2-hydrazinobenzothiazole; and 5, performing drying and performing packaging.

A COLORANT COMPOUND, AND A COLORANT MATERIAL COMPRISING THE SAME

A disclosure of the present invention includes novel colorant compounds based on triarylmethane structure, methods for preparing the same, and colorant materials comprising the same.

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).