138668-14-1

Basic information

• Product Name: [(3E)-4-nitropent-3-en-1-yl]benzene
• Synonyms: Benzene, ((3E)-4-nitro-3-pentenyl)-; Benzene, (4-nitro-3-pentenyl)-, (E)-
• CAS NO: 138668-14-1
• Molecular Formula: C₁₁H₁₃NO₂
• Molecular Weight: 191.2264
• Mol File: 138668-14-1.mol

Chemical Properties

• Boiling Point: 326.2°C at 760 mmHg
• Flash Point: 149.7°C
• Density: 1.074g/cm³
• Vapor Pressure: 0.000415mmHg at 25°C
• Refractive Index: 1.537
• CAS DataBase Reference: [(3E)-4-nitropent-3-en-1-yl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(3E)-4-nitropent-3-en-1-yl]benzene(138668-14-1)
• EPA Substance Registry System: [(3E)-4-nitropent-3-en-1-yl]benzene(138668-14-1)

Safety Data

• Hazardous Substances Data: 138668-14-1(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 79-24-3 Nitroethane 
• 89449-82-1 4-nitro-1-phenyl-3-pentanol 

Downstream Products

• 112402-46-7 (E)-2-Methyl-2-nitro-5-phenyl-pent-3-en-1-ol 
• 2235-83-8 5-phenyl-2-pentanone 
• 730240-92-3 (S)-3-amino-1-phenylpentane 
• 377080-81-4 (4R,1'S)-3-(1'-ethyl-3'-phenylpropyl)-4-phenyloxazolidin-2-one 
• 1618669-02-5 (4-nitropentyl)benzene 

Relevant articles and documents

An improved synthesis of conjugated nitroolefins

β-Nitro alcohols 1 react with triphenylphosphine/carbon tetrachloride/triethylamine under reflux to give the corresponding nitroolefins 2 in good yields (80-95%). Other groups such as tertiary hydroxyl, ether, halide etc. remain unaffected, and the nitroolefins so produced are exclusively the (E)-isomers.

Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes

A new method for the synthesis of conjugated silyl nitronates from nitroalkenes is described. The procedure has wide substrate scope and is compatible with in situ generation of the substrates from 2-nitroalcohols or 2-chloro-nitroalkanes. A cascade transformation to give 3,4,5,6-tetrahydropyridine N-oxide derivatives was disclosed.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

Selective nitroaldol condensations over heterogeneous catalysts in the presence of supercritical carbon dioxide

(Chemical Equation Presented) At 40-60°C, in the presence of heterogeneous catalysts based on Al2O3, supercritical carbon dioxide not only acts as a good solvent for the reaction of aromatic and aliphatic aldehydes with 1-nitroalkanes but, most importantly, it also allows the selectivity to be tuned between the competitive formation of β-nitroalcohols and nitroalkenes (from the Henry reaction and the nitroaldol condensation, respectively). In particular, when the pressure (and the density) of the supercritical phase is enhanced from 80 to 140 bar, the nitroalkene's selectivity increases, on average, from ～60 to >90%. Experiments show that, in the same pressure range, a steep increase of the concentration profiles of reactant aldehydes takes place. By contrast, under solvent-free conditions, the reaction usually proceeds with a higher conversion, but nitroalkanols are the major products.

Enantioselective synthesis of α,α-disubstituted amines from nitroalkenes

Disubstituted nitroalkenes were converted into enantiomerically enriched amines (isolated as their hydrochloride salts) with enantiometric excesses of 88 to >95% in there steps: (a) highly stereoselective conjugate addition of the potassium salt of 4-phenyloxazolidin-2-one; (b) radical-mediated removal of the nitro group; (c) cleavage of the oxazolidinone.