6940-53-0

Basic information

• Product Name: 1-Chloro-2,5-dimethoxy-4-nitrobenzene
• Synonyms: 1-chloro-2,5-dimethoxy-4-nitro-benzen;1-CHLORO-2,5-DIMETHOXY-4-NITROBENZENE;2,5-DIMETHOXY-4-CHLORONITROBENZENE;4-CHLORO-2,5-DIMETHOXYNITROBENZENE;6-CHLORO-1,4-DIMETHOXY-3-NITROBENZENE;NITROCHLOROHYDROQUINONEDIMETHYL ETHER;4-Chloro-2,5-dimethyoxy nitrobenzene;2-Chloro-5-nitro-1,4-dimethoxybenzene
• CAS NO: 6940-53-0
• Molecular Formula: C₈H₈ClNO₄
• Molecular Weight: 217.61
• EINECS: 230-086-7
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 6940-53-0.mol

Chemical Properties

• Melting Point: 141°C
• Boiling Point: 345.8 °C at 760 mmHg
• Flash Point: 162.9 °C
• Appearance: /
• Density: 1.349 g/cm³
• Vapor Pressure: 0.00012mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-Chloro-2,5-dimethoxy-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-2,5-dimethoxy-4-nitrobenzene(6940-53-0)
• EPA Substance Registry System: 1-Chloro-2,5-dimethoxy-4-nitrobenzene(6940-53-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 6940-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Chloro-2,5-dimethoxy-4-nitrobenzene is used as a synthetic intermediate for the production of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Chloro-2,5-dimethoxy-4-nitrobenzene is utilized as a starting material for the synthesis of different agrochemicals. Its properties make it suitable for the creation of compounds that can be used in agricultural applications to protect crops and enhance yields.
Used in Organic Synthesis:
1-Chloro-2,5-dimethoxy-4-nitrobenzene is also used as a starting material in organic synthesis for the preparation of other organic compounds. Its versatile structure makes it a valuable building block in the synthesis of a wide range of chemical entities for various applications.

InChI:InChI=1/C8H8ClNO4/c1-13-7-4-6(10(11)12)8(14-2)3-5(7)9/h3-4H,1-2H3

Upstream product

• 2100-42-7 2-chloro-1,4-dimethoxybenzene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 615-67-8 chloro-p-hydroquinone 
• 6313-37-7 2,5-dimethoxy-4-nitroaniline 

Downstream Products

• 14227-14-6 1,2,4-trimethoxy-5-nitrobenzene 
• 1268259-03-5 4-chloro-2,5-dimethoxy-N,N-dimethylaniline 
• 1116229-15-2 1-[2,5-bis(methyloxy)-4-nitrophenyl]-4-(1-methylethyl)piperazine 
• 1089280-79-4 1-{1-[2,5-bis(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine 
• 90064-46-3 1-chloro-4-iodo-2,5-dimethoxybenzene 
• 252044-86-3 1-Chloro-4-((E)-3,7-dimethyl-octa-2,6-dienyl)-2,5-dimethoxy-3-(3-methyl-but-2-enyl)-benzene 
• 252044-88-5 5-Chloro-2-((E)-3,7-dimethyl-octa-2,6-dienyl)-3-(3-methyl-but-2-enyl)-[1,4]benzoquinone 
• 252044-85-2 3-Bromo-1-chloro-4-((E)-3,7-dimethyl-octa-2,6-dienyl)-2,5-dimethoxy-benzene 
• 252044-84-1 3-bromo-1-chloro-4-iodo-2,5-dimethoxybenzene 
• 252044-81-8 2-bromo-4-chloro-3,6-dimethoxyaniline 
• 6938-75-6 N-(4-chloro-2,5-dimethoxyphenyl)acetamide 
• 252044-83-0 1-bromo-3-chloro-2,5-dimethoxy-benzene 
• 2072-09-5 2-acetamido-5-chloro-1,4-benzoquinone 
• 85896-13-5 1,4-dimethoxy-2-nitro-5-p-tolylsulfanyl-benzene 

Relevant articles and documents

Electrochemical Nitration with Nitrite

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve as versatile building blocks. This study represents the electrochemical aromatic nitration with NBu4NO2, which serves a dual role as supporting electrolyte and as a safe, readily available, and easy-to-handle nitro source. Stoichiometric amounts of 1,1,1-3,3,3-hexafluoroisopropan-2-ol (HFIP) in MeCN significantly increase the yield by solvent control. The reaction mechanism is based on electrochemical oxidation of nitrite to NO2, which initiates the nitration reaction in a divided electrolysis cell with inexpensive graphite electrodes. Overall, the reaction is demonstrated for 20 examples with yields of up to 88 %. Scalability is demonstrated by a 13-fold scale-up.

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.

Synthetic studies on lactonamycins: Synthesis of the model BCDEF aglycon

The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.

A concise total synthesis of (±)-A80915G, a member of the napyradiomycin family of antibiotics

(±)-A80915G, a member of the napyradiomycin family of antibiotics, has been synthesized from 1-amino-2,5-dimethoxy-4-nitrobenzene via the sequential palladium-catalyzed cross-coupling reactions (the Stille reaction) of aryl halides with allyltins and the Diels-Alder reaction of the chloroquinone with the Danishefsky-Brassard diene.

Synthesis of quinones from hydroquinone dimethyl ethers. Oxidative demethylation with cobalt(III) fluoride

The oxidative demethylation of 1,4-dimethoxynaphthalene and 1,4- dimethoxybenzene derivatives with cobalt(III) fluoride proceeded in good to excellent yield to afford the corresponding naphthoquinone and benzoquinone derivatives.

NITRIC ACID ON SILICA GEL: A USEFUL NITRATING REAGENT FOR ACTIVATED AROMATIC COMPOUNDS

Phenols and arylmethyl ethers are rapidly mononitrated by nitric acid adsorbed in silica gel at room temperature in high yields.