2100-42-7

Basic information

• Product Name: 2-Chloro-1,4-dimethoxybenzene
• Synonyms: Monochloro-1,4-dimethoxybenzene;O-CHLORO-P-DIMETHOXYBENZENE;CHLORO-2,5-DIMETHOXYBENZENE;CHLOROHYDROQUINONE DIMETHYL ETHER;2,5-DIMETHOXYCHLOROBENZENE;2-CHLORO-1,4-DIMETHOXYBENZENE;1-CHLORO-2,5-DIMETHOXYBENZENE;2-Chloro-1,4-dimethoxybenzene, 99+%
• CAS NO: 2100-42-7
• Molecular Formula: C₈H₉ClO₂
• Molecular Weight: 172.61
• EINECS: 218-267-9
• Product Categories: Pesticide Intermediate
• Mol File: 2100-42-7.mol

Chemical Properties

• Melting Point: 8.1 °C
• Boiling Point: 247 °C (759.8513 mmHg)
• Flash Point: 117 °C
• Appearance: clear light pink to green or blue liquid
• Density: 1.21
• Vapor Pressure: 0.0661mmHg at 25°C
• Refractive Index: 1.5452-1.5472
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: practically insoluble
• CAS DataBase Reference: 2-Chloro-1,4-dimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,4-dimethoxybenzene(2100-42-7)
• EPA Substance Registry System: 2-Chloro-1,4-dimethoxybenzene(2100-42-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2100-42-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Chloro-1,4-dimethoxybenzene is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block in the synthesis of a wide range of drugs, including those with analgesic, anti-inflammatory, and antipyretic properties.
Used in Chemical Synthesis:
2-Chloro-1,4-dimethoxybenzene is used as a reactant in Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids. This reaction is a widely employed method in organic chemistry for the formation of carbon-carbon bonds, leading to the synthesis of various organic compounds with potential applications in different industries.
Used in Flavor and Fragrance Industry:
Due to its distinct aromatic properties, 2-Chloro-1,4-dimethoxybenzene is used as a component in the flavor and fragrance industry. It contributes to the development of various scents and flavors in products such as perfumes, cosmetics, and food additives.
Used in Dye and Pigment Industry:
The compound's unique color characteristics make it a valuable component in the dye and pigment industry. It is used in the production of dyes and pigments for various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C8H9ClO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 615-67-8 chloro-p-hydroquinone 
• 150-78-7 1,4-dimethoxybezene 
• 102-56-7 2,5-dimethoxyaniline 
• 92546-98-0 N-chloro-N-methyl-4-phenylbutylamine 
• 102102-20-5 N-chloro-n-pentylmethylamine 
• 74-88-4 methyl iodide 
• 15791-03-4 1,1,4,4-tetramethoxycyclohexa-2,5-diene 
• 10026-13-8 phosphorus pentachloride 
• 7782-50-5 chlorine 
• 21112-37-8 1,4-dimethoxy-2-tert-butylbenzene 
• 74-87-3 methylene chloride 

Downstream Products

• 90064-46-3 1-chloro-4-iodo-2,5-dimethoxybenzene 
• 6940-53-0 4-chloro-2,5-dimethoxy nitrobenzene 
• 54787-17-6 1,4-Dimethoxy-9-benzyl-triptycen 
• 140118-90-7 N-benzyl-1,2,3,4-tetrafluoro-5,8-dimethoxy-9,10-dihydroanthracene-9,10-immine 
• 90064-48-5 4-chloro-2,5-dimethoxybenzaldehyde 
• 92500-43-1 <2,5-Dimethoxy-phenyl>-diaethylacetonitril 
• 356031-77-1 9-((2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-((2R,4R,5S,6R)-4,5-dimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-3,6-dimethoxy-11-oxa-tricyclo[6.2.1.0^2,7]undeca-2⁽⁷⁾,3,5,9-tetraene 
• 951235-92-0 C₁₄H₁₃ClO₃S 
• 951235-95-3 C₁₄H₁₃ClO₃S 
• 481-73-2 citreorosein 
• 569-05-1 1,8-dihydroxy-3-hydroxymethyl-6-methoxy-anthraquinone 
• 25186-77-0 4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid 
• 124010-10-2 3-Carbethoxy-4-(4-chloro-2,5-dimethoxyphenyl)-3-butenoic acid 
• 124010-11-3 Ethyl 4-(acetyloxy)-6-chloro-5,8-dimethoxy-2-naphthalenecarboxylate 

Relevant articles and documents

Homogeneous catalysis and selectivity in electrochemistry

The relationship between homogeneous catalysis and electrochemistry is examined in light of two examples based on our work concerning (a) catalyst activation, regarding selective electrochemical C-H oxidation with RuIII/RuIV mediation, and (b) catalyst suppression, regarding controlling selectivity in electrochemical aromatic chlorination. The first example (a) deals with the role of catalysis at the working electrode. The electrochemical (EC) oxidation of specific hydrocarbons such as tetralin and indane is performed using tris(acetonitrile)ruthenium trichloride (Ru(CH3CN)3Cl3) as a mediator. The role of this mediator in the oxidation of tetralin has been reported. This homogeneous C-H activation by electron transfer (ET) is accompanied by the redox transitions of the mediator in the course of the catalytic oxidation, and these are the main points of interest here. Additional studies with a rotating ring disk electrode (RRDE) provided a follow-up of creation and recovery of RuIII/RuII and RuIII/RuIV species in the process. Using electrochemistry linked with electrospray ionization mass spectrometry (EC/ESI-MS) gave additional information on the structure of the reduced and oxidized forms of Ru(CH3CN)3Cl3 and the effect of water in the solvent on their lifetimes. The second example (b) of electrochlorination has been reported elsewhere and is brought up as complementary remarks. Aromatic electrophilic chlorination of 1,4-dimethoxy-2-tertbutylbenzene is autocatalyzed and unselective. The EC procedure provides a simple means to inhibit the catalytic runaway reaction. This example shows how the counter electrode affects catalysis and selectivity. (Figure Presented)

Simple and efficient chlorination and bromination of aromatic compounds with aqueous TBHP (or H2O2) and a hydrohalic acid

A combination of aqueous tert-butylhydroperoxide (70%) or hydrogen peroxide (34%) and a hydrohalic acid was found effective in chlorination and bromination of aromatic compounds.

Efficient halogenation synthesis method of aryl halide

The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.

Method for synthesizing 4-chloro-2, 5-dimethoxynitrobenzene by using microreactor

The invention relates to a method for synthesizing 4-chloro-2, 3, 5-tetramethylpiperidine by using a microreactor. According to the method, intermediate 2, 5-dimethoxychlorobenzene of 4-chloro-2, 5-dimethoxynitrobenzene and nitric acid are used as raw materials, 4-chloro-2, 5-dimethoxynitrobenzene is synthesized through the microreactor, in the reaction process, the mass fraction of nitric acid is50%-95%, and the mass fraction of a 2, 5-dimethoxychlorobenzene solution is 15%-50%; the feeding molar ratio of nitric acid to 2, 5-dimethoxychlorobenzene is (1.0-1.5): 1, the reaction temperature is50-85 DEG C, the feeding temperature is not higher than 50 DEG C, and the reaction retention time is 30-120 seconds. According to the method, on one hand, the process conditions such as the materialratio and the reaction temperature are accurately controlled, the dosage of nitric acid is reduced, the method is environmentally friendly, the conversion rate of 2, 5-dimethoxychlorobenzene reaches 99.98%, and the yield of 4-chloro-2, 5-dimethoxynitrobenzene reaches 99.5% or above; on the other hand, the key problems of corrosivity of nitric acid, difficulty in controlling the reaction temperature, poor mass and heat transfer effect, poor safety and the like in the conventional synthesis process are solved, and the reaction risk is low; strong operability.

Preparation method of 2,5-dimethoxychlorobenzene

The invention relates to a preparation method of 2,5-dimethoxychlorobenzene, which comprises the following steps: 1) one-pot oxidatiion and chlorination: dissolving phenol in a solvent, putting a formed solution into a high-pressure reaction kettle, adding a copper salt catalyst, conducting stirring to conduct reaction at a temperature range of room temperature to 50 DEG C under the oxygen pressure of 0.5-3 MPa, introducing 0.1-2 MPa dry HCl gas into the solution after the reaction is completed, and conducting stirring to conduct reaction at room temperature, and after the reaction is completed, conducting decompressing and rectifying to obtain a 2-chlorohydroquinone intermediate; and 2) methylation: adding 2-chlorohydroquinone into a high-pressure reaction kettle, conducting dissolving, introducing 0.1-2MPa of chloromethane gas under an alkaline condition, maintaining the pressure, conducting reacting at 50-120 DEG C until the raw materials are completely consumed, conducting filtering and desolventizing, and carrying out reduced pressure distillation to obtain the product 2,5-dimethoxychlorobenzene. Compared with a traditional preparation method, the method has the advantages ofless emission of three wastes, low cost, environmental friendliness and the like.

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.

Preparation, structure, and oxidative reactivity of (dichloroiodo)pyridines: Recyclable hypervalent iodine reagents

New pyridine-based hypervalent iodine reagents, (dichloroiodo)pyridines, were prepared by chlorination of 2-, 3-, or 4-iodopyridines with NaOCl-HCl at room temperature. Structures of 2-(dichloroiodo)pyridine and 2-(dichloroiodo)-3-propoxypyridine were established by X-ray crystallography. The new (dichloroiodo)pyridines can be used as efficient reagents for oxidation of alcohols to carbonyl compounds and also as chlorinating reagents. The reduced form of the reagents such as 2-iodo-3-propoxypyridine, can be recovered from the reaction mixture in good yields by an acid-base liquid-liquid biphasic protocol.

Aromatic Monochlorination Photosensitized by DDQ with Hydrogen Chloride under Visible-Light Irradiation

Photochlorination of aromatic substrates by hydrogen chloride with 2,3-dichloro-5,6-cyano-p-benzoquinone (DDQ) occurs efficiently to produce the corresponding monochlorinated products selectively under visible-light irradiation. The yields for the chlorination of phenol were 70 % and 18 % for p- and o-chlorophenol, respectively, without formation of further chlorinated products. The photoinduced chlorination is initiated by electron transfer from Cl- to the triplet excited state of DDQ. The radical intermediates involved in the photochemical reaction have been detected by time-resolved transient absorption measurements.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.