4920-84-7

Basic information

• Product Name: 2,4-Dimethoxy-1-nitrobenzene
• Synonyms: 4-NITRO-1,3-DIMETHOXYBENZENE;1,3-DIMETHOXY-4-NITROBENZENE;2,4-DIMETHOXY-1-NITROBENZENE;2,4-DIMETHOXYNITROBENZENE;4-Nitroresorcinol dimethyl ether;2,4-DIMETHOXY-1-NITROBENZENE 98%;2,4-Dimethoxy-1-nitrobenzene,98%;2,4-diMethoxylnitrobenzene
• CAS NO: 4920-84-7
• Molecular Formula: C₈H₉NO₄
• Molecular Weight: 183.16
• EINECS: 225-551-6
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4920-84-7.mol
• Article Data: 22

Chemical Properties

• Melting Point: 72-76 °C(lit.)
• Boiling Point: 256.82°C (rough estimate)
• Flash Point: 156.7 °C
• Appearance: yellow crystals
• Density: 1.1876
• Vapor Pressure: 0.000695mmHg at 25°C
• Refractive Index: 1.5310 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Toluene
• CAS DataBase Reference: 2,4-Dimethoxy-1-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethoxy-1-nitrobenzene(4920-84-7)
• EPA Substance Registry System: 2,4-Dimethoxy-1-nitrobenzene(4920-84-7)

Safety Data

• Safety Statements: 24/25-22
• WGK Germany: 3
• Hazardous Substances Data: 4920-84-7(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystals

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4501, 1988 DOI: 10.1016/S0040-4039(00)80531-6

InChI:InChI=1/C8H9NO4/c1-12-6-3-4-7(9(10)11)8(5-6)13-2/h3-5H,1-2H3

Upstream product

• 611-06-3 2,4-dichloronitrobenzene 
• 124-41-4 sodium methylate 
• 6627-53-8 1-chloro-3-methoxy-4-nitrobenzene 
• 3962-77-4 2,5-dinitro-anisole 
• 446-35-5 2,4-Difluoronitrobenzene 
• 610-38-8 4-bromo-1,2-dinitrobenzene 
• 4280-28-8 3,4-dinitroanisole 
• 103966-66-1 4-bromo-2-methoxy-1-nitro-benzene 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 77-78-1 dimethyl sulfate 
• 151-10-0 1,3-Dimethoxybenzene 
• 186581-53-3 diazomethane 
• 85238-99-9 α,α-bis(2,4-dimethoxyphenyl)-β,β-dimethylethane 
• 64-19-7 acetic acid 

Downstream Products

• 1210-96-4 1,3-dimethoxy-4,6-dinitrobenzene 
• 778599-56-7 1-bromo-2,4-dimethoxy-5-nitrobenzene 
• 138849-49-7 N-acetyl-6-chloro-2,4-dimethoxyaniline 
• 2735-04-8 2,4-Dimethoxyaniline 
• 164290-83-9 N-(2,4-dimethoxyphenyl)benzamide 
• 195136-62-0 1-Fluoro-2,4-dimethoxy-5-nitro-benzene 
• 704-14-3 3-methoxy-6-nitro-phenol 
• 169883-36-7 5-bromo 2,4-dimethoxy aniline 
• 1276581-99-7 1-azido-5-bromo-2,4-dimethoxybenzene 
• 1276582-20-7 4,4'-(2,5-dimethoxy-1,4-phenylene)bis(1-(5-bromo-2,4-dimethoxyphenyl)-1H-1,2,3-triazole) 
• 1380392-43-7 (E)-N-(but-3-en-2-ylidene)-2,4-dimethoxyaniline oxide 
• 151929-97-4 2-ethoxy-4-methoxy-1-nitrobenzene 

Relevant articles and documents

Aromatic nitration with bismuth nitrate in ionic liquids and in molecular solvents: A comparative study of Bi(NO3)3·5H 2O/[bmim][PF6] and Bi(NO3)3· 5H2O/1,2-DCE systems

A suspension of bismuth nitrate pentahydrate (BN) in [bmim][PF6] or [bmim][BF4] imidazolium ionic liquid (IL) is an effective reagent for ring nitration of activated aromatics under mild conditions without the need for external promoters. Nitration can also be effected in 1,2-DCE, MeCN, or MeNO2 without additives. Nitration of activated arenes (anisole, toluene, ethylbenzene, cumene, p-xylene, mesitylene, durene, and 1,3-dimethoxybenzene) is considerably faster (time to completion) in BN/[bmim][PF6] relative to BN/1,2-DCE and there are also differences in isomer distributions (for anisole, toluene, and ethylbenzene). With introduction of strongly deactivating substituents (-CHO; -MeCO; -NO 2) the BN/IL system is no longer active but reactions still proceed with BN/1,2-DCE in reasonable yields. The ready availability and low cost of BN, simple operation, and absence of promoters, coupled to recycling and reuse of the IL, provide an attractive alternative to classical nitration methods for activated arenes. Switching from Bi(NO3)3·5H 2O/[bmim][PF6] to Bi(NO3)3· 5H2O/1,2-DCE increases the scope of the substrates that can be nitrated.

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

Regioselective SNAr reactions of substituted difluorobenzene derivatives: practical synthesis of fluoroaryl ethers and substituted resorcinols

In this Letter, we describe a practical and highly selective method for the preparation of fluoroaryl ethers and differentially substituted resorcinol derivatives. This synthetic strategy relies on a selective SNAr of substituted difluorobenzen