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

Uses

2-Chloro-1,3,5-trimethoxybenzene is a building block. It was used as a reactant in the Pd-catalyzed borylation of sterically demanding aryl halides by bis(pinacolato)diboron to produce arylboronates.

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

Upstream product

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

Downstream Products

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

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.