55752-58-4

Basic information

• Product Name: 2,3-DIMETHYLPHENYLTHIOUREA
• Synonyms: 1-(2,3-DIMETHYLPHENYL)-2-THIOUREA;2,3-DIMETHYLPHENYLTHIOUREA;2,3-DIMETHYLPHENYLTHIOUREA, 98+%;N-(2,3-Dimethylphenyl)thiourea, 98+%;1-(2,3-dimethylphenyl)thiourea
• CAS NO: 55752-58-4
• Molecular Formula: C₉H₁₂N₂S
• Molecular Weight: 180.27
• Mol File: 55752-58-4.mol

Chemical Properties

• Melting Point: 202-204°C (dec.)
• Boiling Point: 294.3°Cat760mmHg
• Flash Point: 131.8°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.00164mmHg at 25°C
• Refractive Index: 1.674
• BRN: 3249041
• CAS DataBase Reference: 2,3-DIMETHYLPHENYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYLPHENYLTHIOUREA(55752-58-4)
• EPA Substance Registry System: 2,3-DIMETHYLPHENYLTHIOUREA(55752-58-4)

Safety Data

• Statements: 25
• Safety Statements: 22-36/37-45
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 55752-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-DIMETHYLPHENYLTHIOUREA is used as a synthetic intermediate for the production of 2-Amino-4,5-dimethylbenzothiazole (A605060), a compound with potential applications in the pharmaceutical industry. It is particularly useful in the synthesis of a series of substituted pyrimido[2,1-b]benzothiazoles, which have been found to exhibit antimicrobial activity. This makes 2,3-DIMETHYLPHENYLTHIOUREA an essential component in the development of new antimicrobial agents to combat drug-resistant infections.
Used in Ion Channel Modulation:
2,3-DIMETHYLPHENYLTHIOUREA is also used as a precursor in the synthesis of 2-Amino-4,5-dimethylbenzothiazole, which has been identified as a potential modulator of small-conductance calcium-activated potassium (SKCa), intermediate-conductance calcium-activated potassium (IKCa), and large-conductance calcium-activated potassium (BKCa) channels. Modulating these channels can have therapeutic benefits in various conditions, such as neurological disorders and smooth muscle dysfunction. As a result, 2,3-DIMETHYLPHENYLTHIOUREA contributes to the development of novel treatments targeting ion channelopathies.

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

Upstream product

• 1539-20-4 1-isothiocyanato-2,3-dimethylbenzene 
• 83697-76-1 1-benzoyl-3-(2,3-dimethylphenyl)thiourea 
• 532-55-8 Benzoyl isothiocyanate 
• 87-59-2 2,3-Dimethylaniline 
• 1147550-11-5 ammonium thiocyanate 
• 5417-45-8 2,3-dimethylaniline hydrochloride 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 79050-49-0 2-amino-4,5-dimethylbenzothiazole 
• 102612-85-1 1-(2,3-Dimethyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 102612-85-1 1-(2,3-Dimethyl-phenyl)-2-methyl-isothiourea; hydriodide 
• 100601-31-8 2-amino-3,4-dimethylbenzenethiol 
• 139331-48-9 2-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propyl}-5,6-dimethyl-4H-benzo[1,4]thiazin-3-one 
• 119155-47-4 N-(2,3-Dimethyl-phenyl)-morpholine-4-carboxamidine; hydriodide 
• 774544-65-9 N-(2,3-dimethylphenyl)thiazol-2-amine 

Relevant articles and documents

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

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).

A poised fragment library enables rapid synthetic expansion yielding the first reported inhibitors of PHIP(2), an atypical bromodomain

Research into the chemical biology of bromodomains has been driven by the development of acetyl-lysine mimetics. The ligands are typically anchored by binding to a highly conserved asparagine residue. Atypical bromodomains, for which the asparagine is mutated, have thus far proven elusive targets, including PHIP(2) whose parent protein, PHIP, has been linked to disease progression in diabetes and cancers. The PHIP(2) binding site contains a threonine in place of asparagine, and solution screening have yielded no convincing hits. We have overcome this hurdle by combining the sensitivity of X-ray crystallography, used as the primary fragment screen, with a strategy for rapid follow-up synthesis using a chemically-poised fragment library, which allows hits to be readily modified by parallel chemistry both peripherally and in the core. Our approach yielded the first reported hit compounds of PHIP(2) with measurable IC50 values by an AlphaScreen competition assay. The follow-up libraries of four poised fragment hits improved potency into the sub-mM range while showing good ligand efficiency and detailed structural data.

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Optimization of 2-aminothiazole derivatives as CCR4 antagonists

A series of 2-aminothiazole-derived antagonists of the CCR4 receptor has been synthesized and their affinity for the receptor evaluated using a [125I]TARC (CCL17) displacement assay. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent, orally bioavailable antagonists.

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.

Synthesis and biological activities of new 1,4-benzothiazine derivatives

New 2H-1,4-benzothiazin-3(4H)-one derivatives possessing (4-phenyl-1-piperazinyl)alkyl moieties at the 2-position were synthesized and tested for calcium antagonistic and calmodulin antagonistic activities. Antihypertensive effects in spontaneously hypertensive rats were also evaluated. In general, these compounds were rather weak calcium channel blockers, although, in contrast, many of them had moderate to potent calmodulin antagonistic activity, and 2-[3-(4-(4-fluorophenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazin-3(4H )-one derivatives 45, 74 and 75 showed potent antihypertensive effects.

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.