71215-89-9

Basic information

• Product Name: 2-Methyl-5-phenylbenzothiazole
• Synonyms: 2-methyl-5-phenyl-benzothiazol;Benzothiazole, 2-methyl-5-phenyl- (7CI,9CI);2-Methyl-5-phenylbenzo[d]thiazole;2-METHYL-5-PHENYL-BENZOTHIAZOLE;2-methyl-5-phenyl-1,3-benzothiazole
• CAS NO: 71215-89-9
• Molecular Formula: C₁₄H₁₁NS
• Molecular Weight: 225.31
• Product Categories: BENZOTHIAZOLE
• Mol File: 71215-89-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 89 °C
• Boiling Point: 379.3 °C at 760 mmHg
• Flash Point: 187 °C
• Appearance: white to light yellow solid
• Density: 1.199 g/cm³
• Vapor Pressure: 1.29E-05mmHg at 25°C
• Refractive Index: 1.667
• Storage Temp.: 2-8°C
• PKA: 1.62±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-5-phenylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-5-phenylbenzothiazole(71215-89-9)
• EPA Substance Registry System: 2-Methyl-5-phenylbenzothiazole(71215-89-9)

Safety Data

• Hazardous Substances Data: 71215-89-9(Hazardous Substances Data)

Usage

General Description

2-Methyl-5-phenylbenzothiazole is a chemical compound belonging to the class of organic compounds known as benzothiazoles, which are polycyclic aromatic compounds containing a benzene fused to a thiazole ring. 2-Methyl-5-phenylbenzothiazole has a distinct aromatic smell and is generally used in organic synthesis while also being used as an intermediate for the production of other chemicals. The chemical formula for 2-Methyl-5-phenylbenzothiazole is C15H13NS and it appears as a slightly yellow crystalline powder. Even though this compound is not as common as other benzothiazoles, it is essential for the syntheses of specific commercial products.

InChI:InChI=1/C14H11NS/c1-10-15-13-9-12(7-8-14(13)16-10)11-5-3-2-4-6-11/h2-9H,1H3

Upstream product

• 63837-11-6 5-bromo-2-methylbenzothiazole 
• 98-80-6 phenylboronic acid 
• 1006-99-1 2-methyl-5-chloro-benzothiazole 
• 100-58-3 phenylmagnesium bromide 
• 76209-05-7 4,4′-dibromo-2,2′-dinitrodiphenyl disulfide 
• 98-13-5 Phenyltrichlorosilane 
• 934-56-5 trimethyl(phenyl)stannane 
• 28557-00-8 phenylzinc chloride 
• 95943-07-0 C₂₄H₁₆N₂O₄S₂ 

Downstream Products

• 951122-54-6 2-bromomethyl-5-phenylbenzothiazole 
• 104852-82-6 (1-ethyl-6-methoxy-[2]quinolyl)-[3-(2-carboxy-ethyl)-5-phenyl-benzothiazol-2-yl]-methinium ; iodide 

Relevant articles and documents

Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction

The Kumada-Corriu reaction is a powerful tool for C-C bond formation, but is seldom utilized due to perceived chemoselectivity issues. Herein, we demonstrate that high-yielding couplings can occur in the presence of many electrophilic and heterocyclic functional groups. Our strategy is mechanically based, matching oxidative addition rates with the rate of syringe pump addition of the Grignard reagent. The mechanistic reason for the effectiveness of this strategy is uncovered by continuous-infusion ESI-MS studies.

Creating an antibacterial with in vivo efficacy: Synthesis and characterization of potent inhibitors of the bacterial cell division protein FTSZ with improved pharmaceutical properties

3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure-activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.

Cross-coupling of triallyl(aryl)silanes with aryl bromides and chlorides: An alternative convenient biaryl synthesis

Cross-coupling of a diverse range of aryl bromides with triallyl(aryl)silanes is effective in the presence of PdCl2/PCy 3 and tetrabutylammonium fluoride (TBAF) in DMSO-H2O to give various biaryls in good yields. It is worthwhile to note that the all-carbon-substituted arylsilanes, stable towards moisture, acid, and base and easily accessible, serve as a highly practical alternative to their aryl(halo)silane counterparts. A catalyst system consisting of [η3-C3H5)PdCl]2 and 2-[2,4,6-(i-Pr)3C6Ha]-C6H4PCy 2 and use of TBAF· 3 H2O in THF-H2O are effective especially for the cross-coupling with aryl chlorides. Both of the catalyst systems tolerate a broad spectrum of common functional groups. The high efficiency of reactions is presumably due to the ready cleavage of the allyl groups upon treatment with TBAF·3 H2O and an appropriate amount of water. Diallyl(diphenyl)silane also cross-couples with various aryl bromides and chlorides in good yields, whereas allyl(triphenyl)silane gives the cross-coupled products in only moderate yields. Through sequential cross-coupling of bromochlorobenzenes with different arylsilanes, a range of unsymmetrical terphenyls are accessible in good overall yields.