2562-38-1

Basic information

• Product Name: NITROCYCLOPENTANE
• Synonyms: NITROCYCLOPENTANE;nitro-cyclopentan;NITROCYCLOPENTANE, 97+%;1-Nitrocyclopentane;(1S,2S)-Methyl 2-aMinocyclopropanecarboxylate
• CAS NO: 2562-38-1
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• EINECS: 219-884-6
• Product Categories: Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 2562-38-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 143-144 °C
• Boiling Point: 180 °C(lit.)
• Flash Point: 153 °F
• Appearance: /
• Density: 1.086 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.866mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• PKA: 8.46±0.20(Predicted)
• BRN: 907079
• CAS DataBase Reference: NITROCYCLOPENTANE(CAS DataBase Reference)
• NIST Chemistry Reference: NITROCYCLOPENTANE(2562-38-1)
• EPA Substance Registry System: NITROCYCLOPENTANE(2562-38-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• WGK Germany: 3
• RTECS: GY4657500
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2562-38-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear pale yellow liquid

Preparation

Bromocyclopentane (22.0 g, 0.15 mol) was added to a soln of NaNO2 (18 g, 0.26 mol) in dry DMSO (100 mL) at 15 ℃ and the mixture was stirred at this temperature for 3 h. The mixture was poured into ice water (250 mL) and extracted with petroleum ether (bp 35-37 ℃; 4 × 50 mL). The combined organic extracts were washed with H2O (4× 50 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was distilled to give Nitrocyclopentane; yield: 9.9 g (58%); bp 62 ℃/8 Torr; nD/20 1.4538. Synthesis of Nitrocyclopentane

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1117, 1980 DOI: 10.1016/S0040-4039(01)83928-9

General Description

Nitrocyclopentane, a secondary nitroalkane, was examined for its ability to induce DNA repair in rat hepatocytes. The nitronate of nitrocyclopentane was mutagenic in Salmonella strains TA100 and TA102.

InChI:InChI=1/C5H9NO2/c7-6(8)5-3-1-2-4-5/h5H,1-4H2

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 1192-28-5 Cyclopentanone oxime 
• 287-92-3 Cyclopentane 
• 7697-37-2 nitric acid 
• 60-29-7 diethyl ether 
• 1556-18-9 cyclopentyl iodide 
• 111-24-0 1,5-dibromo-pentane 
• 3400-45-1 cyclopentanecarboxylic acid 
• 96-41-3 Cyclopentanol 
• 82655-19-4 1-bromo-5-nitropentane 
• 29788-21-4 1-bromo-1-nitrocyclopentane 
• 1003-03-8 Cyclopentamine 
• 694-63-3 1-chloro-1-nitrosocyclopentane 
• 33670-50-7 cyclopentyl azide 

Downstream Products

• 675-20-7 piperidin-2-one 
• 110-94-1 1,5-pentanedioic acid 
• 1192-28-5 Cyclopentanone oxime 
• 31376-96-2 cyclopentanone O-ethyl oxime 
• 803706-21-0 (+)-3-(1-nitrocyclopentyl) cyclohexanone 
• 504410-61-1 (+/-)-1-(1-nitrocyclopentyl)-3-phenyl-1-propanol 
• 97764-00-6 ((2-cyclopentylethyl)sulfonyl)benzene 
• 484001-75-4 4-(1'-nitrocyclopentyl)-4-phenylbutan-2-one 
• 1227746-91-9 (S)-3-(1-nitrocyclopentyl)-1,3-diphenylpropan-1-one 
• 1350629-94-5 4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)benzaldehyde 
• 1350629-96-7 C₁₇H₂₀N₄O₄ 
• 1350629-95-6 C₁₇H₁₉N₃O₂ 
• 1374015-56-1 1-nitro-2-((1-nitrocyclopentyl)methyl)benzene 
• 1279722-89-2 2-(cyclopentylidenemethyl)benzenamine 

Relevant articles and documents

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Site-specific catalytic activities to facilitate solvent-free aerobic oxidation of cyclohexylamine to cyclohexanone oxime over highly efficient Nb-modified SBA-15 catalysts

The development of highly active and selective heterogeneous catalysts for efficient oxidation of cyclohexylamine to cyclohexanone oxime is a challenge associated with the highly sensitive nitrogen center of cyclohexylamine. In this work, dispersed Nb oxide supported on SBA-15 catalysts are disclosed to efficiently catalyze the selective oxidation of cyclohexylamine with high conversion (>75%) and selectivity (>84%) to cyclohexanone oxime by O2without any addition of solvent (TOF = 469.8 h?1, based on the molar amount of Nb sites). The role of the active-site structure identity in dictating the site-specific catalytic activities is probed with the help of different reaction and control conditions and multiple spectroscopy methods. Complementary to the experimental results, further poisoning tests (with KSCN or dehydroxylation reagents) and DFT computational studies clearly unveil that the surface exposed active centers toward activation of the reactants are quite different: the surface -OH groups can catch the NH2group from cyclohexylamine by forming a hydrogen bond and lead to a more facile cyclohexylamine oxidation to desired products, while the monomeric or oligomeric Nb sites with a highly distorted structure play a key role in the dissociation of O2molecules beneficial for insertion of active oxygen species into cyclohexylamine. These catalysts exhibit not only satisfactory recyclability for cyclohexylamine oxidation but also efficiently catalyze the aerobic oxidation of a wide range of amines under solvent-free conditions.

Green synthesis method for preparing nitroalkanes by oxime oxidation

The invention belongs to the field of organic chemical industries, and provides a green synthesis method for preparing nitroalkanes by oxime oxidation. At the temperature of 55 to 120 DEG C and under the pressure of 0 to 1.0 MPa, oxime, a solvent and hydrogen peroxide are reacted for 20 to 200min in the presence of certain amounts of nanoporous skeleton metal hybrid catalysts and cocatalysts, a reaction liquid is subjected to membrane separation, the catalysts can be repeatedly used for more than 7 times, and distilled to obtain nitroalkane products, the purity of the products is not less than 99%, and the yield of the products is not less than 95%. Furthermore, the green synthesis method for preparing nitroalkanes by the oxime oxidation disclosed by the invention is a green synthesis method of nitroalkanes, and suitable for large-scale industrialized production.