67827-56-9

Basic information

• Product Name: 2-Chloro-1,3,5-trimethoxybenzene
• Synonyms: 2-Chloro-1,3,5-trimethoxybenzene;1-CHLORO-2,4,6-TRIMETHOXYBENZENE
• CAS NO: 67827-56-9
• Molecular Formula: C₉H₁₁ClO₃
• Molecular Weight: 202.6348
• Mol File: 67827-56-9.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 288°Cat760mmHg
• Flash Point: 112.8°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 0.00416mmHg at 25°C
• Refractive Index: 1.502
• CAS DataBase Reference: 2-Chloro-1,3,5-trimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,3,5-trimethoxybenzene(67827-56-9)
• EPA Substance Registry System: 2-Chloro-1,3,5-trimethoxybenzene(67827-56-9)

Safety Data

• Hazardous Substances Data: 67827-56-9(Hazardous Substances Data)

Usage

Description

2-Chloro-1,3,5-trimethoxybenzene is an organic compound characterized by its chlorinated benzene ring with three methoxy groups attached at the 1st, 3rd, and 5th positions. It is a versatile intermediate in the synthesis of various organic molecules and has potential applications in the pharmaceutical and chemical industries due to its unique structural features.

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 
• 77189-93-6 2-Chloro-4-(4-chloro-phenylsulfanyl)-1,3,5-trimethoxy-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 

Relevant articles and documents

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.

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.

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.