646-14-0

Usage

Uses

1. Used in Chemical Synthesis:
1-Nitrohexane is used as a reagent for the preparation of amines through the reduction of nitro compounds with pinacolborane under the catalysis of cyclic (alkyl) (amino) carbene chromium complex. This application is particularly relevant in the chemical industry for the synthesis of various amine-based compounds.
2. Used in the Pharmaceutical Industry:
In the pharmaceutical industry, 1-Nitrohexane can be utilized as an intermediate in the synthesis of various pharmaceutical compounds, taking advantage of its reactivity in chemical reactions.
3. Used in the Production of Fine Chemicals:
1-Nitrohexane is also used as a starting material or intermediate in the production of fine chemicals, which are essential in various applications such as fragrances, dyes, and agrochemicals.
4. Used in the Automotive Industry:
1-Nitrohexane can be used as a component in the formulation of certain types of fuels or additives for the automotive industry, due to its compatibility with other fuel components and its potential to enhance fuel properties.
5. Used in the Research and Development Sector:
In the research and development sector, 1-Nitrohexane serves as a valuable compound for conducting experiments and exploring new chemical reactions, which can lead to the discovery of novel materials and applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 659, 1979 DOI: 10.1021/jo01318a050Synthesis, p. 835, 1978 DOI: 10.1055/s-1978-24907

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitroalkanes, such as 1-NITROHEXANE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. Flammable/combustible material. May be ignited by heat, sparks or flames.

Fire Hazard

Flash point data for 1-NITROHEXANE are not available. 1-NITROHEXANE is combustible.

InChI:InChI=1/C6H13NO2/c1-2-3-4-5-6-7(8)9/h2-6H2,1H3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 3638-64-0 1-nitroethylene 
• 60-29-7 diethyl ether 
• 111-25-1 1-bromo-hexane 
• 638-45-9 1-Iodohexane 
• 110-62-3 pentanal 
• 75-52-5 nitromethane 
• 111-26-2 hexan-1-amine 
• 2207-98-9 sodium n-hexylsulfate 
• 6033-61-0 hexanal oxime 
• 110-54-3 hexane 
• 1402832-93-2 1-(p-chlorophenylthio)-1-nitrohexane 
• 106-54-7 p-Chlorothiophenol 
• 6926-45-0 1-azidohexane 

Downstream Products

• 111-26-2 hexan-1-amine 
• 628-02-4 Caproamide 
• 37567-56-9 4-(2-Nitro-heptyl)-phenol 
• 37567-57-0 C₂₀H₂₅NO₄ 
• 63819-75-0 1-Benzyl-1-nitro-hexan 
• 53917-03-6 1-(4-Methoxyphenyl)-2-heptanone 
• 138668-20-9 (E)-2-nitro-1-cyclohexyl-1-heptene 
• 58588-50-4 [2,3-Dichloro-4-((E)-2-nitro-hept-1-enyl)-phenoxy]-acetic acid 
• 138693-75-1 1-cyclohexyl-2-nitroheptan-1-ol 
• 142-62-1 hexanoic acid 
• 244195-88-8 3-Hex-(E)-ylidene-hexane-2,5-dione 
• 106-70-7 methyl hexanoate 
• 66-25-1 hexanal 

Relevant academic research and scientific papers

Metal Chelate Molluscicides: The Redistribution of Iron Diazaalkanolates from the Gut Lumen of the Slug, Deroceras reticulatum (Mueller) (Pulmonata: Limacidae)

Two related iron chelates, one toxic to slugs by ingestion, the other not, were introduced into the foregut of D. reticulatum. The subsequent movement and redistribution of the metal within the slug tissues was studied by labelling the chelates with the radioactive isotope 55Fe. In slugs which survived treatment approximately half of the 55Fe was voided in faeces. The iron retained became unevenly distributed, the highest concentration occurring in the digestive gland, irrespective of the chelate used. At high doses, slugs treated with tris(1-oxo-1,2-diazabutan-2-oxido)Fe(III) were fatally poisoned while those treated with the homologue, tris(1-oxo-1,2-diazaoctan-2-oxido)Fe(III) were not. Slugs killed by the toxic chelate consistently contained proportionally less iron in the digestive gland and proportionally more in the body wall and reproductive system. Dosing slugs already killed by carbon dioxide asphyxiation gave a similar pattern, suggesting that the greater mobility of the iron from the toxic chelate was not a function of the slugs' metabolism.

Continuous Platform to Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor

The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction is reported. A uniquely designed pipes-in-series plug-flow tube reactor addresses a range of process challenges, including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.

Green synthesis of low-carbon chain nitroalkanes via a novel tandem reaction of ketones catalyzed by TS-1

A green and efficient one-pot method has been developed for the synthesis of low-carbon chain nitroalkanes via a novel TS-1 catalyzed tandem oxidation of ketones with H2O2 and NH3. The tandem reaction including ammoxidation, oximation and oxidation of oximes, afforded up to 88% yield and 98% chemo-selectivity requiring only 90 min, at 70 °C and atmospheric pressure. Moreover, this method was even amenable to 100-fold scale-up without loss of chemical efficiency with 87% yield, represents a significant advance towards industrial production of nitroalkanes. Furthermore, the plausible mechanism of TS-1 catalyzed tandem oxidation of ketones to prepare nitroalkanes was proposed.

A simple and efficient approach for highly selective preparation of nitrocyclohexane from cyclohexane with tert-butyl nitrite catalyzed by N-hydroxyphthalimide

A simple and effective approach for highly selective preparation of nitrocyclohexane from cyclohexane using tert-butyl nitrite as a nitrating agent under atmospheric pressure has been successfully developed in this work. The results indicate that the N-hydroxyphthalimide catalyst gave the best results with 27.3 % of cyclohexane conversion and 88.0 % of selectivity to nitrocyclohexane under optimal reaction conditions. The present reaction provides a novel strategy for the synthesis of nitroalkanes from the nitration of low-carbon alkanes because of the mild reaction condition, simple experimental procedure and high selectivity towards the desired product. This method may be very significant to establish such a synthesis method for aliphatic nitro-compounds from the low-carbon alkanes in organic fields.

Easily-controlled chemoselective hydrogenation by using palladium on boron nitride

The hydrogenation catalyzed heterogeneously by palladium on boron nitride (Pd/BN) in methanol realized the chemoselective hydrogenation of only azides, alkenes, and alkynes in the presence of other reducible functionalities such as benzyl ethers, aryl halides, aryl ketones, and nitro groups. Furthermore, the totally chemoselective semihydrogenation of alkynes could also be achieved without the reduction of other coexisting reducible functionalities, which include azides and alkenes, by using Pd/BN in pyridine as a solvent. Be unique, be selective: The chemoselective hydrogenation of azides, alkenes, and alkynes was achieved without the reduction of other reducible functionalities by the use of a heterogeneous palladium on boron nitride (Pd/BN) catalyst. Furthermore, Pd/BN was applicable to the unique and chemoselective semihydrogenation of alkynes without the reduction of azido functionalities in the presence of pyridine or diethylenetriamine.

Rhodium-catalyzed arylthiolation reaction of nitroalkanes, diethyl malonate, and 1,2-diphenylethanone with diaryl disulfides: Control of disfavored equilibrium reaction

In the presence of catalytic amounts of RhH(PPh3)4 and 1,2-bis(diphenylphosphino)ethane (dppe), 1-nitroalkanes reacted with a diaryl disulfide giving 1-arylthio-1-nitroalkanes in air. The equilibrium to form thermodynamically disfavored products was shifted by the rhodium-catalyzed oxidation of thiols to disulfides and water. The thiolation reaction of cyclic nitroalkanes proceeded in high yields provided that suitable diaryl disulfides were employed depending on the substrate: di(p-chlorophenyl) disulfide was used for the thiolation reaction of 1-nitroalkanes, 1-nitrocyclopentane and 1-nitrocycloheptane with acidic α-protons (pKa 16 and 17); di(p-methoxyphenyl) disulfide for 1-nitrocyclobutane and 1-nitrocyclohexane with less acidic α-protons (pKa ca. 18). Related reactivities were observed in the thiolation reactions of malonate and 1,2-diphenylethanone.

Sequential continuous flow processes for the oxidation of amines and azides by using HOF·MeCN

The generation and use of the highly potent oxidising agent HOF·MeCN in a controlled single continuous flow process is described. Oxidations of amines and azides to corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Oxidation in flow: The oxidation of amines and azides to the corresponding nitrated systems by using fluorine gas, water and acetonitrile by sequential gas-liquid/liquid-liquid continuous flow procedures are reported. Copyright

Chemoselective hydrogenation using molecular sieves-supported Pd catalysts: Pd/MS3A and Pd/MS5A

Palladium catalysts embedded on molecular sieves (MS3A and MS5A) were prepared by the adsorption of Pd(OAc)2 onto molecular sieves with its in situ reduction to Pd0 by MeOH as a reducing agent and solvent. 0.5% Pd/MS3A and 0.5% Pd/MS5A catalyzed the hydrogenation of alkynes, alkenes, and azides with a variety of coexisting reducible functionalities, such as nitro group, intact. It is noteworthy that terminal alkenes of styrene derivatives possessing electron-donating functionalities on the benzene nucleus were never hydrogenated under 0.5% Pd/MS5A-catalyzed conditions, while internal alkenes of 1-propenylbenzene derivatives were readily reduced to the corresponding alkanes.

PROCESS FOR MAKING AND USING HOF.RCN

The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.

Development of molecular sieves-supported palladium catalyst and chemoselective hydrogenation of unsaturated bonds in the presence of nitro groups

The chemoselective hydrogenation of unsaturated bonds and azide functionalities is achieved in the presence of nitro groups by a heterogeneous palladium catalyst supported on molecular sieves (MS3A). The present method shows a widerange of applicability with regard to substrates and the catalyst can be easily prepared and reused at least three times without any loss of activity.