10342-59-3

Basic information

• Product Name: 1-NITRO-4-N-PROPYLBENZENE
• Synonyms: 1-NITRO-4-N-PROPYLBENZENE;1-Nitro-4-propylbenzene;4-Nitro-n-propylbenzene;Benzene, 1-nitro-4-propyl-;p-Propylnitrobenzene;4-n-Propylnitrobenzene;Einecs 233-743-6
• CAS NO: 10342-59-3
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 233-743-6
• Mol File: 10342-59-3.mol

Chemical Properties

• Melting Point: -14°C
• Boiling Point: 96-100°C 2mm
• Flash Point: 96-100°C/2mm
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: 1.5370
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 2043939
• CAS DataBase Reference: 1-NITRO-4-N-PROPYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NITRO-4-N-PROPYLBENZENE(10342-59-3)
• EPA Substance Registry System: 1-NITRO-4-N-PROPYLBENZENE(10342-59-3)

Safety Data

• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 10342-59-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 25, p. 630, 1982 DOI: 10.1021/jm00348a005

InChI:InChI=1/C9H11NO2/c1-2-3-8-4-6-9(7-5-8)10(11)12/h4-7H,2-3H2,1H3

Upstream product

• 103-65-1 phenylpropane 
• 598-58-3 methyl nitrate 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 17745-45-8 propylboronic acid 
• 17763-80-3 para-nitrophenyl triflate 
• 586-78-7 para-nitrophenyl bromide 
• 6921-44-4 4-nitrophenylcyclopropane 
• 134150-01-9 4-propylphenylboric acid 

Downstream Products

• 4693-31-6 2-Propylhydroquinone 
• 2696-84-6 4-propylaniline 
• 15145-27-4 meso-3,4-bis-(4-amino-phenyl)-hexane 
• 6247-02-5 racem-3.4-bis-(4-amino-phenyl)-hexane 
• 67083-39-0 1-propyl-4-nitrosobenzene 
• 75738-01-1 (4-Propyl-phenyl)-p-tolyl-diazene 
• 75738-09-9 (4-Ethyl-phenyl)-(4-propyl-phenyl)-diazene 
• 106132-90-5 (4-Butyl-phenyl)-(4-propyl-phenyl)-diazene 
• 137532-44-6 4-n-pentyl-4'-n-propylazobenzene 
• 95857-04-8 N-(4-Ethyl-phenyl)-N'-(4-propyl-phenyl)-diazene N'-oxide 
• 95856-99-8 N-(4-Ethyl-phenyl)-N'-(4-propyl-phenyl)-diazene N-oxide 
• 106132-88-1 (4-Hexyl-phenyl)-(4-propyl-phenyl)-diazene 
• 106132-87-0 4-n-propyl-4'-n-heptylazobenzene 
• 95857-09-3 N-(4-Butyl-phenyl)-N'-(4-propyl-phenyl)-diazene N-oxide 

Relevant articles and documents

Metal Nanoparticles Catalyzed Selective Carbon-Carbon Bond Activation in the Liquid Phase

Understanding the C-C bond activation mechanism is essential for developing the selective production of hydrocarbons in the petroleum industry and for selective polymer decomposition. In this work, ring-opening reactions of cyclopropane derivatives under hydrogen catalyzed by metal nanoparticles (NPs) in the liquid phase were studied. 40-atom rhodium (Rh) NPs, encapsulated by dendrimer molecules and supported in mesoporous silica, catalyzed the ring opening of cyclopropylbenzene at room temperature under hydrogen in benzene, and the turnover frequency (TOF) was higher than other metals or the Rh homogeneous catalyst counterparts. Comparison of reactants with various substitution groups showed that electron donation on the three-membered ring boosted the TOF of ring opening. The linear products formed with 100% selectivity for ring opening of all reactants catalyzed by the Rh NP. Surface Rh(0) acted as the active site in the NP. The capping agent played an important role in the ring-opening reaction kinetics. Larger particle size tended to show higher TOF and smaller reaction activation energy for Rh NPs encapsulated in either dendrimer or poly(vinylpyrrolidone). The generation/size of dendrimer and surface group also affected the reaction rate and activation energy.

Ipso-nitration of arylboronic acids with copper nitrate and trifluoroace-tic acid

An efficient and novel nitrating reagent has been developed for ipso-nitration of arylboronic acids. By using inexpensive and commercially available Cu(NO3)2/CF3COOH as nitrating reagent, various nitroarenes are produced in moderate to excellent yields (51-96%). Advantages of this procedure are the operational simplicity and no need of extra catalyst.

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.

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.

Highly regioselective dinitration of toluene over reusable zeolite Hβ

A nitration system comprising nitric acid, propanoic anhydride, and zeolite Hβ has been developed for dinitration of toluene to give 2,4-dinitrotoluene in 98% yield, with a 2,4-:2,6-dinitrotoluene ratio of over 120. This represents the most selective quantitative method for 2,4-dinitration of toluene; the catalyst is reusable, solvent is not needed, and an aqueous work-up is not required.

Design and synthesis of boronic acid inhibitors of endothelial lipase

Endothelial lipase (EL) and lipoprotein lipase (LPL) are homologous lipases that act on plasma lipoproteins. EL is predominantly a phospholipase and appears to be a key regulator of plasma HDL-C. LPL is mainly a triglyceride lipase regulating (V)LDL levels. The existing biological data indicate that inhibitors selective for EL over LPL should have anti-atherogenic activity, mainly through increasing plasma HDL-C levels. We report here the synthesis of alkyl, aryl, or acyl-substituted phenylboronic acids that inhibit EL. Many of the inhibitors evaluated proved to be nearly equally potent against both EL and LPL, but several exhibited moderate to good selectivity for EL.

Clay supported ammonium nitrate "clayan": A new reagent for selective nitration of arenes

The nitration of activated, deactivated and highly functionalized arenes is described using clay-supported ammonium nitrate in the presence of perchloric acid.

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.

PARA-SELECTIVE MONONITRATION OF ALKYLBENZENES UNDER MILD CONDITIONS BY USE OF BENZOYL NITRATE IN THE PRESENCE OF A ZEOLITE CATALYST

Toluene and other alkylbenzenes are mononitrated in essentially quantitative yield at ambient temperature by benzoyl nitrate in the presence of aluminium/proton exchanged large port mordenite; the reaction is highly para-selective.

REGIOSELECTIVE NITRATION OF AROMATIC HYDROCARBONS BY METALLIC NITRATES ON THE K10 MONTMORILLONITE UNDER MENKE CONDITIONS

Aromatic hydrocarbons are nitrated with good regioselectivities by clay-supported cupric nitrate in the presence of acetic anhydride.The procedure commends itself by its simplicity and gives useful yields (75-98percent).In each case, the predominant product can be predicted by consideration of the Hueckel HOMO for the aromatic ring.