13021-02-8

Basic information

• Product Name: nitrocyclopropane
• Synonyms: cyclopropane, nitro-; Nitrocyclopropane
• CAS NO: 13021-02-8
• Molecular Formula: C₃H₅NO₂
• Molecular Weight: 87.0773
• Mol File: 13021-02-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 137.814°C at 760 mmHg
• Flash Point: 52.931°C
• Density: 1.207g/cm³
• Vapor Pressure: 6.925mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: nitrocyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: nitrocyclopropane(13021-02-8)
• EPA Substance Registry System: nitrocyclopropane(13021-02-8)

Safety Data

• Hazardous Substances Data: 13021-02-8(Hazardous Substances Data)

Upstream product

• 75-19-4 cyclopropane 
• 57308-87-9 1-iodo-3-nitropropane 
• 7697-37-2 nitric acid 
• 10544-72-6 dinitrogen tetraoxide 
• 765-30-0 Cyclopropylamine 
• 16694-53-4 1-bromo-3-nitropropane 
• 16694-52-3 3-chloro-1-nitropropane 

Downstream Products

• 765-30-0 Cyclopropylamine 
• 232598-24-2 (1α, 5α, 6α)-6-Acetamido-3-benzyl-3-azabicyclo[3.1.0]hexane 

Relevant articles and documents

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Synthesis method of nitrocyclopropane

The invention discloses a synthesis method of nitrocyclopropane. The synthesis method comprises the following steps: taking 1-halogenated-3-nitropropane as a raw material and taking benzyl triethyl ammonium chloride as a phase transfer catalyst under the action of sodium hydroxide to prepare the nitrocyclopropane. The method disclosed by the invention has the advantages of simplicity in operation,rapid reaction and high yield; the difficulty of rapidly and efficiently synthesizing the nitrocyclopropane is overcome; the synthesis method disclosed by the invention can be used for synthesizing an organic molecule containing a nitrocyclopropane structural unit.

Structure, Synthesis, and Properties of Some Persubstituted 1,2-Dinitroethanes. In Quest of Nitrocyclopropyl-Anion Derivatives

Attempts to deprotonate nitrocyclopropane led to solutions which showed strong ESR. signals (Fig. 1) and from which 1-nitro-1'-nitroso-bicyclopropyl (3) and 1,1'-dinitro-bicyclopropyl (2) were isolated.The activation energy for rotation about the central C,C-bond of 2 is estimated to be about 12 kcal/mol (1H-NMR. spectra in Fig. 2).In contrast, the open-chain analoque 2,3-dimethyl-2,3-dinitrobutane (1) shows a metyl singlet down to -70 deg C.Low-temperature X-ray analyses of 1, 2, 3, and also of 1,1'-dinitro-bicyclobutyl (4) show that all four molecules have gauche-conformations but reveal striking structural differences between the open-chain and the cyclic derivatives (Fig. 4-6): the central C,C-bond is long in 1 (1.575 Angstroem), short in 2 (1.479 Angstroem); the C,N-bonds are long in 1 (1.549 Angstroem), short in 2 (1.488 Angstroem); the orientation of the nitro groups is bisected in 2 and perpendicular in 1.The crystal structure of the nitro-nitroso compound 3 is isimorphous with that of the dinitro compound 2 and thus disordered (Fig. 15-16).The effect of the nitro group as ?-electron acceptor on the molecular conformations and bond lengths is discussed.From analysis of the anisotropic vibrational parameters of 2 the root-mean-square librational amplitude of the nitro groups about their C,N-bonds is estimated to be about 5.8 deg at 95 K, corresponding to a rotational barrier of about 9 kcal/mol, i. e. the same order of magnitude as the NMR. estimate of about 12 kcal/mol for C,C-rotation.