612-22-6

Basic information

• Product Name: 2-Ethylnitrobenzene
• Synonyms: 2-ethvlnitrobenzene;2-Ethyl-1-nitrobenzene;2-Ethylnitrlobenzene;benzene,1-ethyl-2-nitro-;2-ETHYLNITROBENZENE;2-NITROETHYLBENZENE;1-ETHYL-2-NITROBENZENE;O-NITROETHYLBENZENE
• CAS NO: 612-22-6
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 210-299-1
• Product Categories: Intermediates of Dyes and Pigments;Benzene derivates
• Mol File: 612-22-6.mol

Chemical Properties

• Melting Point: -13--10 °C(lit.)
• Boiling Point: 172-174 °C18 mm Hg(lit.)
• Flash Point: 228 °F
• Appearance: Colorless or light yellow to green oily liquid
• Density: 1.127 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.537(lit.)
• BRN: 1865655
• CAS DataBase Reference: 2-Ethylnitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylnitrobenzene(612-22-6)
• EPA Substance Registry System: 2-Ethylnitrobenzene(612-22-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• RIDADR: 2810
• WGK Germany: 3
• Hazardous Substances Data: 612-22-6(Hazardous Substances Data)

Usage

Uses

Used in Analytical Chemistry:
2-Ethylnitrobenzene is used as a solvent for the supported liquid membrane (SLM) in electromembrane extractions (EMEs). It serves as a medium to facilitate the selective transport of target analytes from the sample matrix to the acceptor solution, enhancing the efficiency and selectivity of the extraction process.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 765, 1981 DOI: 10.1021/jo00317a023Tetrahedron, 48, p. 5317, 1992 DOI: 10.1016/S0040-4020(01)89028-1

InChI:InChI=1/C8H9NO2/c1-2-7-5-3-4-6-8(7)9(10)11/h3-6H,2H2,1H3

Upstream product

• 625-58-1 ethyl nitrate 
• 100-41-4 ethylbenzene 
• 591-09-3 nitro acetate 
• 578-54-1 ortho-ethylaniline 
• 64-17-5 ethanol 
• 98-95-3 nitrobenzene 
• 16433-96-8 2-ethynyl-1-nitrobenzene 
• 90002-36-1 2-ethylphenyl boronic acid 
• 97-94-9 triethyl borane 
• 7697-37-2 nitric acid 
• 598-58-3 methyl nitrate 

Downstream Products

• 10342-62-8 1-(2-nitro-phenyl)-ethanone oxime 
• 61653-34-7 1,2-bis(2-ethylphenyl)diazene 
• 90006-42-1 2-ethyl-3-chloro-aniline 
• 748789-25-5 3-Ethyl-phenylcyanomethylen-chinon 
• 50522-37-7 2-ethylaniline hydrochloride 
• 4264-36-2 diethyl (2-ethylphenyl)phosphoramidate 
• 4264-37-3 N-(o-Aethyl-phenyl)-phosphorsaeureimid-triaethylester 
• 120-72-9 indole 
• 577-59-3 2-acetylnitrobenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 74-90-8 hydrogen cyanide 
• 578-54-1 ortho-ethylaniline 
• 7664-41-7 ammonia 
• 501-60-0 1,2-di(p-tolyl)diazene 

Relevant articles and documents

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

Method for continuously synthesizing 4-ethylnitrobenzene and 2-ethylnitrobenzene

The invention belongs to the technical field of chemical engineering, and particularly relates to a method for continuously synthesizing 4-ethylnitrobenzene and 2-ethylnitrobenzene by adopting a micro-channel reactor. The method sequentially comprises the

Regioselective mononitration of aromatic compounds with N2O5 by acidic ionic liquids via continuous flow microreactor

We employed N2O5 as highly active nitrating reagents and a host of acidic ionic liquid as catalysts in these reactions which were conducted in a continuous flow microreactor. When we utilized PEG400-DAIL as catalysts, the conversion of toluene was increased to 95.5 % and the yield of mononitration product (o/p ratio reached 1.10) significantly improved to 99 %, meanwhile the reaction time was drastically shortened to 1/120 of the conventional reactor. Nitration in ionic liquids was surveyed using a host of aromatic substrates with similar reactivity. The ionic liquid recycling procedures had also been devised.

Conformations, equilibrium thermodynamics and rotational barriers of secondary thiobenzanilides

The article deals with conformational behaviour of 2-methoxy-2′-hydroxythiobenzanilides. The CS-NH group of these compounds preferentially adopts the Z-conformation. Entropy favours the Z-conformer over the E-conformer, whereas enthalpy slightly favours the E-conformer over the Z-conformer. The rotational barrier about the CS-NH bond was determined to be (81.5±0.4) kJ/mol. No significant rotational barrier was found on the Ar-CS and Ar-NH bonds. All experimental outcomes are compared with the results of quantum-chemical calculations.

NITRATION OF AROMATIC COMPOUNDS

The present invention provides a process for nitrating aromatic compounds without the need for a solid catalyst and/or any organic solvents and/or any other additives. A typical process includes combining or admixing a nitric acid and an anhydride compound under conditions sufficient to produce a reactive intermediate. The aromatic compound to be nitrated is then added to this reactive intermediate to produce a nitroaromatic compound. The nitroaromatic compound can be substituted with one or more, typically, one to three, and often one or two nitrate (-NO2) groups.

Poly(4-vinylpyridine)-nitrating mixture complex (PVP-NM): Solid nitrating mixture equivalent for safe and efficient aromatic nitration

Friedel-Crafts type aromatic nitration has served as an indispensable reaction within both industrial and academic applications. However, growing concern over the use of copious amounts of strong acids has prompted the search for more environmentally friendly alternatives. Polymer-bound Bronsted acids, on the other hand, have been shown useful as convenient alternatives to liquid acids. Nitric acid and sulfuric acids have, therefore, been combined, both individually and as a mixture, with poly(4-vinylpyridine). The new solid acid systems have been used to nitrate both activated and deactivated arenes under mild conditions and proved to be effective nitrating agent.

Eco-friendly nitration of benzenes over zeolite-β-SBA-15 composite catalyst

Direct synthesis of microporous-mesoporous zeolite-β-SBA-15 (ZBS-15) composite catalyst from the synthetic precursors of SBA-15and zeolite-β seeds under acidic hydrothermal conditions through the simultaneous self-assembly of mesoporous silica SBA-15 and zeolite-β has been accomplished and characterized the ZBS-15 catalyst by XRD, N2 sorption, FT-IR, TPD of ammonia and SEM techniques. The activity of the ZBS-15 composite catalyst for the nitration of benzenes under solvent-free conditions has been investigated, which revealed that there is a significant synergistic influence of both zeolite-β and SBA-15 materials on the activity of the ZBS-15 catalyst.

Bismuth triflate catalyzed mononitration of aromatic compounds with N 2O5

This page isvestigated that bismuth triflate catalysed the nitration of a range of simple aromatic compounds in good to excellent yields at 0-30 °C within 2 h using N2O5 and the catalyst can be recycled without apparent loss of activity. Mechanistic insights demonstrate that triflic acid is generated and that, at least, when two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the bismuth triflate.

Regioselective dinitration of simple aromatics over zeolite Hβ/nitric acid/acid anhydride systems

Various nitration systems comprising nitric acid, acid anhydride and zeolite H￡] in the absence of solvent are described. Direct double nitration of toluene with a nitric acid, propanoic anhydride and zeolite Hβ system has been developed to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of 123:1. This system also nitrates activated mono-substituted benzenes (anisole and phenetole) and moderately activated mono-substituted benzenes (ethylbenzene and propylbenzene) to give mainly 2,4-dinitro derivatives. The zeolite can be recovered, regenerated and reused to give almost the same yield as that given when fresh zeolite is used. ARKAT-USA, Inc.

Regioselective nitration of aromatics with nanomagnetic solid superacid SO42-/ZrO2-MxOy-Fe 3O4 and its theoretical studies

A series of micro- and nanosulfated zirconia loaded on Fe3O 4 or other metal oxides (SO42-/ZrO 2-MxOy-Fe3O4 (M=Ti 4+, V5+, and Zn2+)) was prepared, characterized, and used in nitration. The nitration conditions with these solid superacids were then optimized to achieve the best regioselectivity and improve the performances of the catalysts as well. In the experimental results, SZTF (SO42-/ZrO2-TiO2-Fe 3O4) showed excellent catalytic activity and it increased the surface area of SO42-/ZrO2 by up to 15 %. The increase not only facilitated the generation of NO2+, but also provided more opportunities for metal ions to interact with aromatic compounds. With chlorobenzene as substrate, theoretical research on its geometric parameters, electron clouds, and electron spin density was used to investigate the interaction between transition metals and chlorobenzene.