7137-55-5

Basic information

• Product Name: 1-butyl-2-nitrobenzene
• Synonyms: 1-butyl-2-nitrobenzene;1-Nitro-2-butylbenzene;Einecs 230-435-3
• CAS NO: 7137-55-5
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.21572
• EINECS: 230-435-3
• Mol File: 7137-55-5.mol

Chemical Properties

• Boiling Point: 127 °C / 10mmHg
• Flash Point: 101.8°C
• Appearance: /
• Density: 1.06
• Vapor Pressure: 0.0246mmHg at 25°C
• Refractive Index: 1.5200-1.5240
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-butyl-2-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-butyl-2-nitrobenzene(7137-55-5)
• EPA Substance Registry System: 1-butyl-2-nitrobenzene(7137-55-5)

Safety Data

• Hazardous Substances Data: 7137-55-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13NO2/c1-2-3-6-9-7-4-5-8-10(9)11(12)13/h4-5,7-8H,2-3,6H2,1H3

Upstream product

• 61644-32-4 4-butyl-3-nitroaniline 
• 109-65-9 1-bromo-butane 
• 577-19-5 2-nitrophenyl bromide 
• 693-04-9 butyl magnesium bromide 
• 98-95-3 nitrobenzene 
• 4426-47-5 butylboronic acid 
• 122-56-5 tributyl borane 
• 62-53-3 aniline 
• 1126-78-9 N-(n-butyl)aniline 
• 104-13-2 4-Butylaniline 
• 693-03-8 n-butyl magnesium bromide 
• 104-51-8 1-butylbenzene 

Downstream Products

• 61644-32-4 4-butyl-3-nitroaniline 
• 2696-85-7 2-butyl-benzenamine 

Relevant articles and documents

Direct Catalytic Decarboxylative Amination of Aryl Acetic Acids

The decarboxylative coupling of a carboxylic acid with an amine nucleophile provides an alternative to the substitution of traditional organohalide coupling partners. Benzoic and alkynyl acids may be directly aminated by oxidative catalysis. In contrast, methods for intermolecular alkyl carboxylic acid to amine conversion, including amidate rearrangements and photoredox-promoted approaches, require stoichiometric activation of the acid unit to generate isocyanate or radical intermediates. Reported here is a process for the direct chemoselective decarboxylative amination of electron-poor arylacetates by oxidative Cu catalysis. The reaction proceeds at (or near) room temperature, uses native carboxylic acid starting materials, and is compatible with protic, electrophilic, and other potentially complicating functionality. Mechanistic studies support a pathway in which ionic decarboxylation of the acid generates a benzylic nucleophile which is aminated in a Chan–Evans–Lam-type process.

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.

Palladium-catalyzed cross-coupling alkylation of arenediazonium o-benzenedisulfonimides

Arenediazonium o-benzenedisulfonimides were reacted with tetramethyltin, tetrabutyltin or trialkylboranes. The reactions, carried out in the presence of palladium(II) derivatives as precatalysts, gave the methylation and alkylation products with good over

Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids

Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.

Electrochemical synthesis of alkyl nitroaromatic compounds

Alkyl nitroaromatic compounds were readily prepared via nucleophilic aromatic substitution for hydrogen or a heteroatom by electrochemical oxidation of the a-complex. Butyllithium and butylmagnesium chloride were used as nucleophiles, and several nitrocompounds were tested to explore the possibilities of the NASH and NASX reactions promoted electrochemically.

7-Alkyl indole synthesis via a convenient formation/alkylation of lithionitrobenzenes and an improved Bartoli reaction

A more convenient and efficient method for metalation/alkylation of nitrobenzenes to give 2-substituted nitrobenzenes was developed. Their conversion to 7-alkylindoles using the Bartoli reaction with vinyl magnesium bromide was performed with an improved protocol.

Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen

Alkylation of nitroarenes with Grignard reagents via oxidative nucleophilic substitution of hydrogen (ONSH) can be efficiently executed with potasium permanganate in liquid ammonia as an oxidative system for the σH adducts. The addition of RMgX to ArNO2 of stoichiometry 1:1 is accompanied with a redox process apparently of stoichiometry 2:1. Because of that, real stoichiometry of the reaction between nitroarenes and Grignard reagents is ca. 1:1.5.

Nitration of alkylbenzenes in acid medium: Regioselectivity of the reaction and acidity of the medium

Isomer distribution in the nitration of toluene and its homologs with nitric acid in acid media (trifluoroacetic acid and solutions of sulfuric acid in acetic acid) is determined by the acidity of the medium, the degree of para substitution changing in parallel with the acidity. The ortholpara regioselectivity is governed by the polarity of the transition state. The sensitivity of the ortholpara ratio to variation of the acidity of the medium and reaction temperature is directly related to steric effects of the alkyl groups.

Nitration of Alkylbenzenes in Trifluoroacetic Acid

The substrate selectivity of alkylbenzene nitration with nitric acid in trifluoroacetic acid is controlled either by electronic or by steric effects of the substituents, depending the medium composition and temperature. The positional selectivity of this reaction is sterically controlled, even under electronic control of substrate selectivity.

Ozone-mediated nitration of phenylalkyl ethers, phenylacetic esters, and related compounds with nitrogen dioxide. the highest ortho substitution observed in the electrophilic nitration of arenes

By the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with hiigh ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis. The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.