5670-65-5

Basic information

• Product Name: (Z)-1-Nitro-2-phenyl-1-propene
• Synonyms: (Z)-1-Nitro-2-phenyl-1-propene;(Z)-α-Methyl-β-nitrostyrene;[(Z)-1-Methyl-2-nitroethenyl]benzene
• CAS NO: 5670-65-5
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• Mol File: 5670-65-5.mol
• Article Data: 51

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-1-Nitro-2-phenyl-1-propene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-Nitro-2-phenyl-1-propene(5670-65-5)
• EPA Substance Registry System: (Z)-1-Nitro-2-phenyl-1-propene(5670-65-5)

Safety Data

• Hazardous Substances Data: 5670-65-5(Hazardous Substances Data)

Usage

General Description

(Z)-1-Nitro-2-phenyl-1-propene, also known as beta-nitrostyrene, is a chemical compound with the molecular formula C9H9NO2. It is a yellow, crystalline solid with a sweet, fruity odor, and is insoluble in water but soluble in organic solvents. (Z)-1-Nitro-2-phenyl-1-propene is widely used in organic synthesis and as a precursor for various pharmaceuticals and fine chemicals. It is known for its potential as a precursor in the synthesis of amphetamines and other psychoactive substances, and as a reactant in the production of various polymers. However, due to its potential use in illegal drug synthesis, it is also a controlled substance in some countries and is tightly regulated.

Upstream product

• 75-52-5 nitromethane 
• 98-86-2 acetophenone 
• 98-83-9 isopropenylbenzene 
• 66291-23-4 2-acetoxy-1-nitro-2-phenylpropane 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 637-50-3 1-phenylpropene 
• 704-79-0 3-phenylbut-2-enoic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 5670-65-5 (E)-1-nitro-2-phenyl-1-propene 

Downstream Products

• 109757-73-5 1-nitro-2-phenylpropane 
• 70303-28-5 (E)-pent-2-en-2-ylbenzene 
• 59647-78-8 2-phenylpropanal oxime 
• 7796-75-0 (+)-(R)-1-nitro-2-phenylpropane 
• 746647-15-4 (S)-1-nitro-2-phenylpropane 
• 1018699-20-1 4-(5-(1-phenylvinyl)-2H-1,2,3-triazol-4-yl)pyridine 
• 1018699-16-5 3-(5-(1-phenylvinyl)-2H-1,2,3-triazol-4-yl)pyridine 
• 1018699-25-6 4-(naphthalen-1-yl)-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018699-12-1 N 4-(2,6-dichlorophenyl)-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018698-92-4 4-(3-nitrophenyl)-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018698-84-4 4-phenyl-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018699-08-5 4-(4-methoxyphenyl)-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018699-30-3 4-(naphthalen-2-yl)-5-(1-phenylvinyl)-2H-1,2,3-triazole 
• 1018699-00-7 4-(5-(1-phenylvinyl)-2H-1,2,3-triazol-4-yl)benzonitrile 

Relevant articles and documents

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

Metal-free Synthesis of β-Nitrostyrenes via DDQ-Catalyzed Nitration

-

Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

Unprecedented in literature, the conversion of aryl alkenes into β-nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium-based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β-nitrostyrenes, while tetraalkylammonium-based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.