Category: 108-41-8

Application of 108-41-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Compounds (1-27) are synthesized as described in literature [25], by Friedel-Crafts acylation of substituted benzenes with maleic acid anhydride using anhydrous AlCl3 as the catalyst in dry CH2Cl2. The 6.125 g (62.5 mmol) of maleic acid anhydride, 16.5 g (125 mmol) of anhydrous AlCl3 and 62.5 mmol of aromatic substrates were used. After 4-6 h of stirring on room temperature the reaction mixture was captured with ice/conc. HCl. The solvent was removed by steam distillation. The residuals was filtered on vacuum, or extracted by appropriate solvent. In this way obtained solids or oily substances are processed by solution of Na2CO3 to pH 8.5, filtered to remove traces of Al from catalyst, neutralized by dropwise addition of conc. HCl, filtered, than washed thoroughly by water, dried and crystallized from appropriate solvent. Yields of pure products were from 40 to 92%.

The chemical industry reduces the impact on the environment during synthesis 1-Chloro-3-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Drakuli?, Branko J.; Stanojkovi?, Tatjana P.; ?i?ak, ?eljko S.; Dabovi?, Milan M.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3265 – 3273;,
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Application of 108-41-8,Some common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a 50 mL Schlenk tube containing base (1.5 mmol) and precatalyst 4a (1 mol %, 0.0083 g) purged with N2 (three times), amine (1.2 mmol) was added via syringe, and the resulted mixture was allowed to stir at room temperature for 2-3 min. Solvent (1 mL) was then injected via syringe followed by the aryl chloride (1.0 mmol). If the aryl chloride was a solid, it was introduced into the vial prior to purging with N2. At this time, the reaction was stirred for 24 h at 100 C. After cooling to the room temperature, the reaction mixture was concentrated in vacuo and directly purified via silica gel flash chromatography. 4-(m-tolyl)morpholine (7b) ;1H NMR (CDCl3, 400 MHz, 298 K): delta=7.22 (t, J=7.2 Hz, 1H), 6.79-6.77 (m, 3H), 3.89 (m, 4H), 3.18 (m, 4H), 2.38 (s, 3H); 13C NMR (CDCl3, 100 MHz, 298 K): delta=151.22, 138.68, 128.87, 120.80, 116.38, 112.72, 66.81, 49.30, 21.64.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3-methylbenzene, its application will become more common.

Reference:
Article; Fang, Weiwei; Jiang, Jian; Xu, Yong; Zhou, Juefei; Tu, Tao; Tetrahedron; vol. 69; 2; (2013); p. 673 – 679;,
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Reference of 108-41-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

m-chlorotoluene (5.1 g, 40 mmol),sodium bromate (4.6 g, 30.6 mmol),sodium bromide (6.3 g, 61.2 mmol), 1,2-dichloroethane (25 mL) was added to a reaction flask equipped with a stirred, reflux condenser, thermometer and tail gas absorber, heated to reflux and rapidly added 1/3 of the total volume of the initiator solution (0.15 g AIBN, dissolved (5 g) was slowly added dropwise with sulfuric acid (4.6 g, 46 mmol concentrated sulfuric acid diluted with 2 mL of water) and the remaining initiator solution was followed by gas chromatography. After completion of the reaction, the reaction was cooled to At room temperature, saturated sodium bisulfite solution (10mL) was added and stirred to red to fade. The mixture was allowed to stand, and the aqueous phase was extracted twice with 1,2-dichloroethane (10 mL x 2). The organic phases were combined and washed with saturated chlorine Sodium chloride solution washing, dry.The crude product was purified by column chromatography (elution solvent as petroleum ether) to give 10.2 g of m-chlorobenzyl dibromide in 90% yield.The product was a colorless liquid

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Normal University; Xiao Xiaohui; Chen Yufeng; (12 pag.)CN107098791; (2017); A;,
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Related Products of 108-41-8, These common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

This example illustrates the tandem Ir-catalyzed borylation and catalytic amination process. [0064] 3-Aminoboronic acids and esters as shown below are of interest as evidenced by the large number of derivatives synthesized, and by several patents, which note their activity as O-lactamase inhibitors (See, for example, Shoichet et al., WO0035905). Few in number, however, are 1, 3, 5-aminoboronic acids and esters (about 25 compounds by SCIFINDER SCHOLAR). Such substrates may prove useful for further derivatization as they can possess three unique sites for diversity. Furthermore, these compounds may prove ideal as scaffolds for combinatorial libraries. The boronic acid or ester can be transformed into a myriad of functionalities including aryl or vinyl via the Suzuki-Miyuara coupling (Miyaura and Suzuki, Chem. Rev. 95: 2457-2483 (1995); Suzuki, J. Organomet. Chem. 576: 147-168 (1999); Miyaura, In Advances in Metal-Organic Chemistry: Liebeskind, Ed.: JAI: London,; Vol. 6, pp. 187-243 (1998)). If R is a halogen, then there exists a multitude of coupling opportunities (See, for examples, Metal-catalyzed Cross-coupling Reactions; Diederich and Stang, eds.: Wiley: Wienheim, 1998). [0066] Recently, a catalytic aromatic C-H activation/borylation reaction utilizing Ir- or Rh-catalysts was developed. The process is high yielding, functional group tolerant (alkyl, halo, carboxy, alkoxy, and protected amino), chemoselective (1,3-substited arenes give only the 5-boryl product), and efficient (Iverson and Smith, J. Am. Chem. Soc. 121: 7696-7697 (1999); Cho et al., J. Am. Chem. Soc. 122: 12868-12869 (2000); Tse et al., Org. Lett. 3: 2831 (2001); Chao et al., Science 295: 305-308 (2002)). Furthermore, the process allows for the direct construction of aryl boronic esters from hydrocarbon feedstocks without going through an aryl halide. Scheme 2 depicts a prototypical borylation reaction: borylation of benzene using (Ind)Ir(COD)(2 mol %), dppe (2 mol %). The borane of choice is pinacolborane (HBPin). A variety of Ir(I) catalysts can be used, including [Ir(COD)Cl]2, Ir(Indenyl)(C2H4)2, Ir(Indenyl)dppe, and (Indenyl)Ir(COD), in the presence of 2 mol equivalents of PMe3 or 1 mol equivalent of a bidentate ligand like dmpe or dppe. The catalyst system of choice is (Indenyl)Ir(COD), dppe or dmpe (2 mol % each) because of it’s cleanness of reaction and efficient TOF (24 h-1 with benzene). The reaction can be run in the neat arene or in inert solvents (e.g. cyclohexane). During our studies into tandem borylation/Suzuki coupling, we noted difficulties with the hydrolysis of the boronic ester functionality (Bpin). The robustness of the BPin group suggested that, perhaps, the pinacol might serve as a protecting group for the boron. Thus, it was deemed of interest to explore other catalytic transformations in the presence of the BPin group. One such transformation is the Buchwald-Hartwig amination of aryl halides (See, for example; Wolfe et al.,. J. Org. Chem. 65: 1158 (2000); Hartwig et al., J. Org. Chem. 64: 5575 (1999); Wolfe and Buchwald, Angew. Chem. Int. Ed. 38: 2413 (1999)). Initially, the reaction was attempted on pure 1-chloro-3-methylphenyl-5-BPin. As shown in Scheme 3 (Buchwald-Hartwig coupling of 1-chloro-3-methylphenyl-5-BPin with aniline), application of Buchwalds protocol proceeded cleanly to give the desired cross-coupling product in 64.7% and 63.8% yield. The use of PtBu3 improved the yield to 78.8%. Unfortunately, initial attempts to perform the reaction in the ?one-pot? protocol were unsuccessful. Table 1 summarizes the results. In all cases where K3PO4.nH2O was used, a significant amount of pinacol was observed by GC-FID (Entries 1-5). While this is indicative of reaction of the BPin group and is most likely a by-product of Suzuki coupling (in this case, dimerization or oligiomerization of the starting material), no dimers or oligiomers were isolated. Noteworthy, is the formation of the desired product, albeit in low yield (10% GC-FID ratio), using K3PO4.nH2O and PtBu3 when all other attempts using the base failed. With anhydrous K3PO4, results were better (Entries 6-9). Most importantly, no pinacol was formed in these reactions. Changing the base or increasing catalyst loading did not improve the results. The use of PtBu3 led to the best results and after 4 days at 100 C., 34.4% of the desired product was isolated (Entry 10). This result, however, falls short of the reaction performed on pure material and shows that the by-products from the Ir-catalyzed borylation are not completely innocuous. As was previously mentioned, a potential source of concern is the presence of free bidentate phosphines after the borylation, which may interfere with subsequent reactions. In the tandem Suzuki reactions, an aryl chloride was successfully coupled only when dmpe was used as the Ir ligand. Thus, the tandem borylation/Buchwald-Hartwig amination reaction of the present invention was attempted using the (Ind)Ir(COD)/dmpe precatalyst….

Statistics shows that 1-Chloro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 108-41-8.

Reference:
Patent; Board of Trustees of Michigan State University; US2004/24237; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 108-41-8

Example 6: 3-Chlorobenzoic Acid In a 100 ml jacketed vessel, 200 ml of acetic acid, 0.08 g of cerium(III) acetate, 4.9 g of sulfuric acid and 12.65 g of 3-chlorotoluene were initially charged. The mixture was cooled to 16 C. and 5.15 g of ozone were introduced within a period of 75 minutes. After completion of ozonolysis, the ozone present in the solvent was blown out using nitrogen. Analysis of the reaction mixture by means of HPLC or GC gave the following results: 3-chlorotoluene: >0.1%; 3-chlorobenzoic acid: 98%

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jary, Walther; Poechlauer, Peter; Ganglberger, Thorsten; US2003/216577; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 108-41-8

General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 ¡Á 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Zhao, Mengdi; Li, Meiqi; Lu, Wenjun; Synthesis; vol. 50; 24; (2018); p. 4933 – 4939;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 108-41-8.

General procedure: Under an N2 atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol %), dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol) were successively added into a Schlenk tube. The mixture was stirred vigorously at 90 C for 4 h. Then the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: PE/EA = 15:1) to give the pure products. The reported yields are the average of two runs.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Saranya, Gandhi; Viswanathamurthi, Periasamy; Bertani, Roberta; Sgarbossa, Paolo; Malecki, Jan Grzegorz; Journal of Organometallic Chemistry; vol. 831; (2017); p. 1 – 10;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 108-41-8.

General procedure: The typical procedure is as follows. Oven dried Schlenk tube was equipped with stirrer bar, was charged with aryl halides (1 mmol), acrylates (1.2 mmol), K2CO3 (2 mmol) and catalyst2 (3 mol %) in DMF medium. The reaction mixture was stirred in an oil bath at 100C under argon atmosphere for an appropriate period of time. After completion of the reaction, the reaction mixture was then cooled to room temperature and diluted with Et2O/H2O(1:1, 20 mL). The organic layer was alienated and dried with anhydrous MgSO4. The product was filtered and dried under vacuum. The resulting crude compound was purified by column chromatography on silica gel to afford the corresponding products.

The synthetic route of 1-Chloro-3-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nirmala, Muthukumaran; Arruri, Sathyanarayana; Vaddamanu, Moulali; Karupnaswamy, Ramesh; Mannarsamy, Maruthupandi; Adinarayana, Mannem; Ganesan, Prabusankar; Polyhedron; vol. 158; (2019); p. 125 – 134;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-41-8, name is 1-Chloro-3-methylbenzene, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 108-41-8

General procedure: Under an N2atmosphere, KOtBu (1.3 mmol), complex 1 (1 mol%),dioxane (2 ml), amines (1.3 mmol) and aryl chlorides (1.0 mmol)were successively added into a Schlenk tube. The mixture wasstirred vigorously at 90C for 4 h. Then the solvent was removedunder reduced pressure and the residue was purified by columnchromatography on silica gel (eluent:PE/EA = 15:1) to give the pureproducts. The reported yields are the average of two runs.The catalytic reactions have been given in Tables 4-7. The result-ing amines were identified by comparison of the1H and13C NMRdata with those previously reported (ESI).

Statistics shows that 108-41-8 is playing an increasingly important role. we look forward to future research findings about 1-Chloro-3-methylbenzene.

Reference:
Article; Nirmala, Muthukumaran; Prakash, Govindan; Ramachandran, Rangasamy; Viswanathamurthi, Periasamy; Malecki, Jan Grzegorz; Linert, Wolfgang; Journal of Molecular Catalysis A: Chemical; vol. 397; (2015); p. 56 – 67;,
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Adding some certain compound to certain chemical reactions, such as: 108-41-8, name is 1-Chloro-3-methylbenzene, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 108-41-8. 108-41-8

General procedure: (If aryl chloride is liquid) under N2 atmosphere, arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube, then aryl chloride 2 (0.5 mmol) was added. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.Comment(If aryl chloride is solid) under N2 atmosphere, aryl chloride 2 (0.5 mmol), arylboronic acid 3 (0.6 mmol), 1a (1.0 mol%), K3PO4¡¤3H2O (2.0 equiv), H2O (2.0 mL), and THF (1.0 mL) were added into a Schlenk reaction tube. The mixture was stirred at room temperature for 24 h. Then the mixture was extracted with EtOAc, dried over anhydrous Na2SO4, filtered and purified by flash column chromatography to give the pure products.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Chloro-3-methylbenzene.

Reference:
Article; Tang, Yi-Qiang; Lu, Jian-Mei; Shao, Li-Xiong; Journal of Organometallic Chemistry; vol. 696; 23; (2011); p. 3741 – 3744;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics