120-75-2

Basic information

• Product Name: 2-Methylbenzothiazole
• Synonyms: 2-methylbenzothiazol;2-methyl-benzothiazol;Benzothiazole,2-methyl-;USAF ek-1853;usafek-1853;2-METHYLBENZOTHIAZOLE;METHYLBENZOTHIAZOLE;2-methylbenzo[d]thiazole
• CAS NO: 120-75-2
• Molecular Formula: C₈H₇NS
• Molecular Weight: 149.21
• EINECS: 204-423-3
• Product Categories: Industrial/Fine Chemicals;BENZOTHIAZOLE;Building Blocks;Heterocyclic Building Blocks;Thiazoles
• Mol File: 120-75-2.mol

Chemical Properties

• Melting Point: 11-14 °C(lit.)
• Boiling Point: 238 °C(lit.)
• Flash Point: 216 °F
• Appearance: slightly yellow/Liquid
• Density: 1.173 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0669mmHg at 25°C
• Refractive Index: n20/D 1.617(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 1.65±0.10(Predicted)
• Water Solubility: Not miscible or difficult to mix with water.
• BRN: 112427
• CAS DataBase Reference: 2-Methylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzothiazole(120-75-2)
• EPA Substance Registry System: 2-Methylbenzothiazole(120-75-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 23-24/25
• WGK Germany: 3
• RTECS: DL5600000
• TSCA: Yes
• Hazardous Substances Data: 120-75-2(Hazardous Substances Data)

Usage

Chemical Description

2-methylbenzothiazole is a derivative of benzothiazole with a methyl group attached to the second carbon atom.

Uses

Used in Biomedical Research:
2-Methylbenzothiazole is used as a reagent for the development of fluorescent probes for RNA G quadruplex imaging, which is crucial for studying the structure and function of RNA molecules in various biological processes.
Used in Chemical Synthesis:
2-Methylbenzothiazole is used as a building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals, due to its unique chemical properties and reactivity.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 1349, 1987 DOI: 10.1002/jhet.5570240523

InChI:InChI=1/C8H7NS/c1-6-9-7-4-2-3-5-8(7)10-6/h2-5H,1H3

Upstream product

• 6310-41-4 N-(2-methylsulfanyl-phenyl)-acetamide 
• 72687-34-4 2-methyl-2,3-dihydrobenzo[d]thiazole 
• 615-22-5 2-methylmercaptobenzothiazole 
• 56278-50-3 2-cyanomethylbenzothiazole 
• 36874-53-0 1,3-benzothiazol-2-ylacetone 
• 6270-76-4 2-methyl-2-phenyl-2,3-dihydrobenzo[d]thiazole 
• 29182-45-4 2-(benzo[d]thiazol-2-yl)acetic acid 
• 637-53-6 thioacetanilide 
• 60419-67-2 benzothiazol-2-yl-cyano-acetic acid ethyl ester 
• 29198-44-5 1,3-diethyl 2-(1,3-benzothiazol-2-yl)propanedioate 
• 25115-98-4 acetic acid-(2-methanesulfinyl-anilide) 
• 100559-86-2 (2-nitrophenylthio)acetonitrile 
• 108-24-7 acetic anhydride 
• 137-07-5 2-amino-benzenethiol 

Downstream Products

• 55526-95-9 N-(δ-sulfonatobutyl)-2-methyl-benzothiazole 
• 5132-05-8 2-(4-phenyl-1E,3E-butadienyl)benzothiazole 
• 61414-22-0 N-methyl-1,3-benzothiazole-2-carbothioamide 
• 52625-67-9 (Benzothiazolyl-2)-2 indanedione-1,3 
• 46055-91-8 2-benzothiazol-2-yl-ethanol 
• 68006-75-7 (3-ethyl-benzothiazol-2-yl)-(3-ethyl-benzoxazol-2-yl)-methinium ; iodide 
• 106167-09-3 benzothiazole-2-carbaldehyde (4-nitro-phenyl)-hydrazone 
• 20614-71-5 2-pentylbenzo[d]thiazole 
• 37859-37-3 2-(cyclohexylmethyl)benzo[d]thiazole 
• 66838-67-3 2-benzothiazol-2-yl-1-(4-chloro-phenyl)-ethanone 
• 101273-93-2 2-(benzo[d]thiazol-2-yl)-1-(4-methoxyphenyl)ethan-1-one 
• 64873-75-2 2,2'-dimethyl-3,3'-ethane-1,2-diyl-bis-benzothiazolium; bis-(toluene-4-sulfonate) 
• 100734-73-4 3-benzothiazol-2-ylmethyl-2-methyl-benzothiazolium; toluene-4-sulfonate 
• 346-63-4 2,3-dimethyl-benzothiazolium; 2-nitro-4-trifluoromethyl-benzenesulfonate 

Relevant articles and documents

INTRAMOLECULAR AROMATIC SUBSTITUTION (SRN1) REACTIONS: USE OF ENTRAINMENT FOR THE PREPARATION OF BENZOTHIAZOLES

The process of entrainment (catalytic chain initiation) with the enolate-anion of acetone has been used in intramolecular aromatic SRN1 substitution for the preparation of 2-phenyl- and 2-methyl-1,3-benzothiazole in high yield from o-iodothiobenzanilide and o-iodothioacetanilide.

Transforming LiTMP Lithiation of Challenging Diazines through Gallium Alkyl Trans-Metal-Trapping

This study establishes a new trans-metal-trapping (TMT) procedure based on a mixture of LiTMP (the base) and tris(trimethylsilylmethyl)gallium [Ga(CH2SiMe3)3, GaR3] (the trap) that, operating in a tandem manner, is effective for the regioselective deprotonation of sensitive diazines in hydrocarbon solution, as illustrated through reactions of pyrazine, pyridazine, and pyrimidine, as well as through the N-S heterocycle benzothiazole. The metallo-activated complexes of all of these compounds were isolated and structurally defined.

Novel hemicyanine sensitizers based on benzothiazole-indole for dye-sensitized solar cells: Synthesis, optoelectrical characterization and efficiency of solar cell

Synthesis, characterization, and photovoltaic properties of three new hemicyanine sensitizers based benzothiazole-indoline (HC-TH, HC-IND1 and HC-IND2) were tested in DSSC with TiO2 film. These sensitizers have a higher molar absorption coefficient, and thus have better light harvesting properties. Electrochemical, theoretical, and spectroscopic methods were used to calculate energy levels of the dye molecules both in the excited state and in the ground state. The results obtained from the spectroscopy and Tafel studies show a marked increase in overall photoelectro-chemical cell output with Br-substitute at p-position in the hemicyanine sensitizer. Interestingly, HC-IND2 showed absorption of UV–Vis at a longer wavelength than HC-IND1 and HC-TH. This structural feature, as well as optical properties, would result in an improved efficiency of DSSC with a better photovoltaic output (4.01percent) solar to electricity conversion efficiency compared to HC-IND1 and HC-TH.

A novel practical synthesis of benzothiazoles via Pd-catalyzed thiol cross-coupling

A convenient synthesis of substituted benzothiazoles from 2-bromoanilides has been accomplished. The various 2-bromoanilides were reacted with an alkyl thiolate in high yields using a palladium catalyst. The resulting sulfides were easily converted to the corresponding benzothiazoles via the simultaneous generation of thiols and condensation under basic or acidic conditions.

Synthesis of novel colorants for DSSC to study effect of alkyl chain length alteration of auxiliary donor on light to current conversion efficiency

Five (MA1-MA5) hemicyanine based sensitizer having N, N-diethyl aniline as a primary donor and hydroxy or alkoxy as an auxiliary donor have been synthesized to establish a correlation between amphiphilic nature of the sensitizer and charge recombination. A strong electron withdrawing 3-(carboxymethyl)-2-methylbenzo[d]thiazol-3-ium bromide has been explored as an acceptor. All the dyes were characterized by 1H-NMR, 13C-NMR and CHN analysis. The photophysical properties of these dyes were recorded in seven different solvents which do not show any significant impact on absorption and emission maxima while molar absorptivity coefficient decreases with increase in alkyl chain length. These dyes show very poor emission in all the solvents. Nano-crystalline mesoporous TiO2 based dye-sensitized solar cells were fabricated using MA1 to MA5 sensitizers to evaluate their photovoltaic performance. MA5 having six carbon alkyl chain shows maximum efficiency of 4.97% while MA1 without any alkyl chain shows the lowest efficiency of 3.40%. As the length of alkyl chain increase efficiency increase due to increment in short circuit current (Jsc) and retardation in the recombination process. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) were explored to obtain vertical excitation, HOMO-LUMO energy and electron density distribution.

A simple and efficient route for synthesis of 2-alkylbenzothiazoles

The condensation of 2-aminothiophenol with aliphatic aldehydes in the presence of 4? molecular sieves, followed by oxidation with silica gel supported pyridinium chlorochromate offers a simple and efficient route to 2-alkylbenzothiazoles.

THERMOLYSIS AND MASS SPECTROMETRY OF meso-SUBSTITUTED THIACARBOCYANINES

The pathways of fragmentation of thiacarbocyanine dyes with various electron-donor substituents in the meso position of the polymethine chain under the influence of high temperatures and electron impact were investigated.The results of thermolysis of the dyes are compared with the results of quantum-chemical calculations of the labilities of the bonds in the molecules.

Ligand exchange reactions of NiCl2(PPh3)2 with O(S)∩N∩S ligands

Ligand exchange reactions of NiCl2(PPh3)2 with O(S)∩N∩S ligands were studied. Oxidation products of O∩N∩S ligands have been characterized and their structures determined: 3-methyl-4H-benzo[b][1,4]thiazin-2-yl-phenylmethanone / 2-methyl-benzo[d][1,3]thiazole (mixed crystal); [2-iminoisopropyl-thiophenolato(2-)](triphenyl-phosphane)-nickel(II); 1-phenyl-3-methyl-4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thione; [1-phenyl-3-methyl-4-(benzoyl-thiobenzoylhydrazono)-pyrazol-5-thionato] (triphenyl-phosphane)-nickel(II).

One-pot preparation of 2 (alkly)arylbenzothiazoles from the corresponding o-halobenzanilides

Thionation of o-halobenzanilides was carried out in the presence of Lawesson's reagent. Subsequently, the formed thioamides reacted with cesium carbonate to give the corresponding benzothiazole derivatives in the same pot. Georg Thieme Verlag Stuttgart.

A ball-milling strategy for the synthesis of benzothiazole, benzimidazole and benzoxazole derivatives under solvent-free conditions

A convenient solvent-free method for the synthesis of benzothiazole, benzimidazole, and benzoxazole derivatives has been developed using recyclable ZnO-NPs via a ball-milling strategy. The method affords environmentally friendly reaction conditions that score high on the ecoscale with the low E-factor. The process is also highly efficient even on a multi-gram scale and provides easy product isolation.