7372-88-5

Basic information

• Product Name: 4-METHYLDIBENZOTHIOPHENE
• Synonyms: 4-METHYLDIBENZOTHIOPHENE;4-Methyldibenzo[b,d]thiophene;Dibenzothiophene, 4-methyl-;4-Methyldibenzothiophene ,97%;4-Methyldibenzothiophene 96%
• CAS NO: 7372-88-5
• Molecular Formula: C₁₃H₁₀S
• Molecular Weight: 198.28
• Product Categories: API intermediates;Benzothiophenes;Building Blocks;Heterocyclic Building Blocks
• Mol File: 7372-88-5.mol

Chemical Properties

• Melting Point: 64-68 °C(lit.)
• Boiling Point: 298 °C(lit.)
• Flash Point: 122.6°C
• Appearance: /
• Density: 1.1424 (rough estimate)
• Vapor Pressure: 9.74E-05mmHg at 25°C
• Refractive Index: 1.6170 (estimate)
• CAS DataBase Reference: 4-METHYLDIBENZOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLDIBENZOTHIOPHENE(7372-88-5)
• EPA Substance Registry System: 4-METHYLDIBENZOTHIOPHENE(7372-88-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 7372-88-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-METHYLDIBENZOTHIOPHENE is used as a key intermediate in the synthesis of various 2-substituted products, which have potential applications in different fields. The expression is: 4-METHYLDIBENZOTHIOPHENE is used as a chemical intermediate for the synthesis of 2-substituted products.
The 2-substituted products that can be synthesized using MDBT include:
1. 2-(3′-carboxypropanoyl)-4-methyldibenzothiophene: 4-METHYLDIBENZOTHIOPHENE can be used in the development of pharmaceuticals, agrochemicals, or other specialty chemicals, where the carboxylic acid group can be further functionalized or used for conjugation to other molecules.
2. 2-acetyl-4-methyldibenzothiophene: This derivative can be employed in the synthesis of various organic compounds, such as dyes, pigments, or pharmaceuticals, where the acetyl group can be utilized for further reactions or as a protecting group.
3. 2-nitro-4-methyldibenzothiophene: 4-METHYLDIBENZOTHIOPHENE can be used as a precursor for the synthesis of other functionalized MDBT derivatives, such as amines or nitro-containing heterocycles, which can find applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1737, 1990 DOI: 10.1002/jhet.5570270642

InChI:InChI=1/C13H10S/c1-9-5-4-7-11-10-6-2-3-8-12(10)14-13(9)11/h2-8H,1H3

Upstream product

• 144463-77-4 allyl 2-(2-methylthiophenoxy)benzoate 
• 67-56-1 methanol 
• 1207-12-1 4,6-dimethyldibenzothiophene 
• 1053361-45-7 C₂₀H₁₇NO₂S₂ 
• 139-66-2 diphenyl sulfide 
• 128916-16-5 2-Allylsulfanyl-benzoic acid o-tolyl ester 

Downstream Products

• 132-65-0 dibenzothiophene 
• 92-52-4 biphenyl 
• 644-08-6 4-Methylbiphenyl 
• 643-93-6 3-methylbiphenyl 
• 1053361-45-7 C₂₀H₁₇NO₂S₂ 
• 23985-81-1 bisbenzo[b,d]thiophene-4-carbaldehyde 
• 132034-91-4 4,6-Diethyldibenzothiophene 
• 89816-99-9 4-Ethyldibenzothiophene 
• 1207-12-1 4,6-dimethyldibenzothiophene 
• 23654-20-8 6-methyl-1,2,3,4-tetrahydro-dibenzothiophene 
• 4575-46-6 1-cyclohexyl-3-methylbenzene 
• 82388-13-4 3,4''-Dimethyl-1,1':2',1''-terphenyl 
• 2871-91-2 1-methyltriphenylene 
• 1256485-80-9 [Ni(triisopropylphosphine)(η6-toluene)] 

Relevant articles and documents

Synthesis of NiMo Catalysts Supported on Gallium-Containing Mesoporous y Zeolites with Different Gallium Contents and Their High Activities in the Hydrodesulfurization of 4,6-Dimethyldibenzothiophene

Mesoporous MY-xGa zeolites exhibiting both crystallized pore walls and narrowly dispersed mesopores with different Ga content were successfully synthesized. The synthesized samples were characterized by XRD, N2 adsorption desorption isotherms, SEM, TEM, XPS, FTIR, 29Si MAS NMR, 71Ga MAS NMR, and Py-FTIR methods. The results show that the synthesized samples exhibit unique open channel like mesopore systems and outstanding crystallite natures; no nonframework Ga species were observed over the MY-xGa series samples, and their acidic properties can be modulated by varying the Ga/Al ratio in the initial synthesis gel. The corresponding NiMo/HMY-xGa catalysts were prepared via the incipient wetness coimpregnation method; the morphologies of the sulfide catalysts were characterized by HRTEM, and the covalent states of the active metals were characterized by XPS. The catalytic activities of the investigated catalysts for the 4,6-DMDBT HDS reaction were assessed, and the collected products were analyzed by GC and GC-MS methods. The catalyst NiMo/HMY-0.5Ga showed the highest catalytic activity due to the synergistic effect of modulated acidic properties, excellent morphology, highest sulfidation degree, and proper proportion of NiMoS phase. More importantly, 4-MDBT, DBT, and BP were observed and identified as the products of the 4,6-DMDBT HDS reaction, designated as the demethylation pathway (DM) for the 4,6-DMDBT HDS reaction. Finally, a reaction network including DDS, HYD, ISO, and DM pathways for the 4,6-DMDBT HDS reaction over catalyst NiMo/HMY-0.5Ga was proposed.

Effect of the nature of sulfur compounds on their reactivity in the oxidative desulfurization of hydrocarbon fuels with oxygen over a modified CuZnAlO catalyst

The reactivity of thiophene, dibenzothiophene (DBT), and 4,6-dimethyldibenzothiophene (4,6-DMDBT), which are the representatives of the main classes of sulfur compounds that are the constituents of diesel fractions, was studied in the course of their oxidative desulfurization with oxygen on a CuO/ZnO/Al2O3 catalyst modified with boron and molybdenum additives. At T ≥ 375°C, the reactivity increased in the order thiophene 2 from hydrocarbon fuel, which was simulated by a solution of 4,6-DMDBT in toluene, was 80%. Under the assumption of a first order reaction with respect to sulfur compound and oxygen, the apparent activation energies of the test processes were calculated. An attempt was made to reveal the role of the adsorption of sulfur compounds in the overall process of oxidative desulfurization with the use of X-ray diffraction analysis, X-ray photoelectron spectroscopy, and differential thermal and thermogravimetric analysis with the massspectrometric monitoring of gas phase composition.

Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650°C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl radical. Synthetically, the procedure works well for p-substituted substrates, which lead to 2-substituted dibenzofurans 19b-f (73-90%) and dibenzothiophenes 20b-c (90-94%). Little selectivity is shown in the cyclisation of m-substituted substrates and competing interactions of the radical with the substituent - and ipso-attack - complicate the pyrolyses of o-substituted substrates. FVP of related radical precursors including 2-(allyloxy)phenyl benzoates 43 gave no dibenzofurans, whereas 2-(allyloxy-5-methyl)azobenzene 44 gave a much reduced yield. No carbazoles were obtained by FVP of 4-methylphenyl 2-(allylamino)benzoate 42.

Generation of nitrene by the photolysis of N-substituted iminodibenzothiophene

(Chemical Equation Presented) To evaluate the ability of dibenzothiophene N-substituted sulfilimines as photochemical nitrene sources, their photolyses in the presence of several trapping reagents, such as sulfides, olefins, and phosphorus compounds, were performed. In the reactions, the corresponding imino-transfer compounds, namely sulfilimines, aziridines, and iminophosphoranes, were formed in good yields, indicating dibenzothiophene N-tosyl and N-acylsulfilimines have a potent nature as nitrogen sources.

Gas phase generation and cyclisation reactions of some o-substituted phenyl radicals

Flash vacuum pyrolysis of the allyl esters 2 (X=O, S, CH2, CO) at 900°C (10-2 Torr) gives dibenzofurans, dibenzothiophenes, fluorenes, and fluorenones respectively as the major products. The mechanism involves the phenyl radical intermediates 1 which equilibrate by intramolecular hydrogen transfer via six-membered transition states, prior to cyclisation.

The Insertion and Extrusion of Heterosulfur Bridges. XI. Desulfurization of Condensed Thiophenes by Means of Methanol and a Molybdena Catalyst

Desulfurization of 2-methyl- (1b), 4-methyl- (1c), and 4,6-dimethyldibenzothiophenes (1d), benzothiophene (2), and benzonaphthothiophene (5) were effected by means of methanol and a sulfided CMA catalyst at 450 deg C.Desulfurization was accompanied by processes of demethylation and ring hydrogenation in the case of 1d and by both methylation and demethylation in the cases of 1b and 1c.Compound 2 gave ethylbenzene (80percent), while 5 produced 2-phenylnaphthalene (69percent).