67827-56-9

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-1,3,5-trimethoxybenzene is used as a building block for the synthesis of complex organic molecules. Its chlorinated benzene ring and methoxy substituents provide opportunities for further functionalization and modification, making it a valuable component in the creation of diverse chemical structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-1,3,5-trimethoxybenzene is used as a reactant in the Pd-catalyzed borylation of sterically demanding aryl halides by bis(pinacolato)diboron to produce arylboronates. This reaction is significant for the development of new drugs and pharmaceutical compounds, as arylboronates are key intermediates in various synthetic routes.
Used in Material Science:
2-Chloro-1,3,5-trimethoxybenzene may also find applications in material science, where its unique structure could be utilized to create novel materials with specific properties. For instance, its electronic and steric characteristics could be exploited in the design of organic semiconductors or as components in advanced polymer systems.

InChI:InChI=1/C9H11ClO3/c1-11-6-4-7(12-2)9(10)8(5-6)13-3/h4-5H,1-3H3

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 99070-92-5 3-chloro-2,4,6-trimethoxy-benzoic acid 
• 34425-71-3 1-lithium-2,4,6-trimethoxybenzene 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 3481-09-2 N-chlorophthalimide 

Downstream Products

• 99070-86-7 3-chloro-2,4,6-trimethoxybenzaldehyde 
• 77189-89-0 2-Chloro-1,3,5-trimethoxy-4-p-tolylsulfanyl-benzene 
• 77189-85-6 2-Chloro-1,3,5-trimethoxy-4-(2,4,6-trimethyl-phenylsulfanyl)-benzene 
• 77189-98-1 Bis(3-chloro-2,4,6-trimethoxyphenyl) Disulfide 
• 102333-32-4 3-chloro-2,4,6-trimethoxybenzenesulfinyl chloride 
• 77189-86-7 2-Chloro-1,3,5-trimethoxy-4-phenylsulfanyl-benzene 
• 99070-92-5 3-chloro-2,4,6-trimethoxy-benzoic acid 
• 103323-77-9 3-chloro-2,4,6-trimethoxy-toluene 
• 108476-79-5 4-((Z)-3-chloro-2,4,6-trimethoxy-benzylidene)-2-phenyl-4H-oxazol-5-one 
• 269410-04-0 4,4,5,5-tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolane 
• 1493772-41-0 (N-2,4,6-trimethoxyphenyl)-2,6-dimethyl-aniline 
• 77189-93-6 2-Chloro-4-(4-chloro-phenylsulfanyl)-1,3,5-trimethoxy-benzene 

Relevant academic research and scientific papers

Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes

A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl3 and phenyliodine diacetate. The AuIII salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C-H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C-O and C-C bonds.

Sulfoxide-Promoted Chlorination of Indoles and Electron-Rich Arenes with Chlorine as Nucleophile

An efficient chlorination of indoles and electron-rich arenes with chlorine anion as nucleophile is described. With the use of ethyl phenyl sulfoxide as the promoter, the reaction went smoothly under metal-free and mild conditions. Various indoles and electron-rich arenes are converted into the corresponding chlorinated compounds in moderate to excellent yields. A plausible interrupted Pummerer reaction mechanism was proposed without the oxidation of chloride anion. In addition, the byproduct thioether could be easily converted to the starting material sulfoxide just by a simple oxidation reaction. (Figure presented.).

Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes

Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Preparation, Characterization and Reactivity of a Bis-hypochlorite Adduct of a Chiral Manganese(IV) Salen Complex

A bis-hypochlorite adduct of a manganese(IV) salen complex having a chiral (R,R)-cyclohexane-1,2-diamine linkage (2-tBu) is successfully prepared and characterized by various spectroscopic methods. The reactions of 2-tBu with various organic substrates show that 2-tBu is capable of sulfoxidation, epoxidation, chlorination, and hydrogen abstraction reactions. However, the enantioselectivity of the epoxidation reactions by 2-tBu is much lower than that reported for the catalytic reactions by Jacobsen's catalyst. The low enantioselectivity is consistent with a planar conformation of the salen ligand, which is suggested by circular dichroism spectroscopy. This study suggests that 2-tBu is not a reactive intermediate of Jacobsen's enantioselective epoxidation catalysis.

Atom-Economic Electron Donors for Photobiocatalytic Halogenations

In vitro cofactor supply and regeneration have been a major obstacle for biocatalytic processes, in particular on a large scale. Peroxidases often suffer from inactivation by their oxidative co-factor. Combining photocatalysis and biocatalysis offers an innovative solution to this problem, but lacks atom economy due to the sacrificial electron donors needed. Herein, we show that redox-active buffers or even water alone can serve as efficient, biocompatible electron sources, when combined with photocatalysis. Mechanistic investigations revealed first insights into the possibilities and limitations of this approach and allowed adjusting the reaction conditions to the specific needs of biocatalytic transformations. Proof-of-concept for the applicability of this photobiocatalytic reaction setup was given by enzymatic halogenations.

Transition metal-free protodecarboxylation of electron rich aromatic acids under mild conditions

A mild and practical method for the transition metal-free protodecarboxylation of aromatic acids using readily available and safe sodium persulfate as initiator was described. This environment-friendly decarboxylation approach was performed at 60 °C in ethanol and could easily scale up to the gram level with a good yield. In Particular, the tandem reactions of decarboxylation and halogenation were achieved by the addition of the corresponding halogenating reagents to the reaction system.

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions

Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.