27861-39-8

Basic information

• Product Name: (nitromethylidene)cyclohexane
• Synonyms: Cyclohexane, (nitromethylene)-
• CAS NO: 27861-39-8
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.1677
• Mol File: 27861-39-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 242.6°C at 760 mmHg
• Flash Point: 107.8°C
• Density: 1.177g/cm³
• Vapor Pressure: 0.0523mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: (nitromethylidene)cyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (nitromethylidene)cyclohexane(27861-39-8)
• EPA Substance Registry System: (nitromethylidene)cyclohexane(27861-39-8)

Safety Data

• Hazardous Substances Data: 27861-39-8(Hazardous Substances Data)

Usage

General Description

"(Nitromethylidene)cyclohexane" is a chemical compound with the molecular formula C7H11NO2. It is a nitroalkene derivative of cyclohexane, featuring a nitro group and a double bond attached to a six-carbon ring. (nitromethylidene)cyclohexane is typically used as a reactant in organic synthesis, especially in the preparation of various derivatives and functionalized cyclohexane compounds. It may also have potential applications in the pharmaceutical and agrochemical industries due to its versatile reactivity and ability to form valuable intermediates for the synthesis of bioactive molecules. However, it is important to note that as with any chemical compound, proper handling and safety precautions should be observed when working with (nitromethylidene)cyclohexane.

Upstream product

• 110-89-4 piperidine 
• 3164-74-7 1-(nitromethyl)cyclohexyl acetate 
• 71-43-2 benzene 
• 3164-73-6 1-nitromethylcyclohexanol 
• 108-94-1 cyclohexanone 
• 94421-33-7 1-nitromethyl-1-phenylthiocyclohexane 
• 128869-47-6 1-(allylthio)-1-nitromethylcyclohexane 
• 335458-24-7 1-benzylthio-1-nitromethylcyclohexane 
• 75-52-5 nitromethane 
• 127-09-3 sodium acetate 

Downstream Products

• 99063-44-2 2-cyclohex-1-enyl-2-nitro-propane-1,3-diol 
• 890-75-5 (E)-2-(4-chloro-phenyl)-1-cyclohex-1-enyl-1-nitro-ethene 
• 890-75-5 2-<4-Chlor-phenyl>-1-nitro-1--aethylen 
• 177270-77-8 4-(cyclohex-1-en-1-yl)-5-phenyl-2H-1,2,3-triazole 

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.

Selective conversion of nitroalcohols to nitroolefins over sulfonic acid functionalized mesoporous SBA-15 material

Highly ordered 2D-hexagonal mesoporous SBA-15 has been synthesized by using triblock copolymer as template and its surface has been functionalized by 3-propylsulfonic acid group via post-synthetic grafting with 3-mercaptopropyltrimethoxy silane. A variety of α,β-substituted nitroalcohols are converted to their corresponding nitroolefins under mild reaction conditions using this 3-propylsulfonic acid-functionalized SBA-15 material. Nitroalcohols with open-chain, cyclic, and heterocyclic substituents at the α-position are smoothly converted into their corresponding nitroolefins in high yields over this solid acid catalyst. Propylsulfonic acid functionalized SBA-15 materials are found to be more efficient catalysts than microporous zeolites under similar reaction conditions.

An improved and easy method for the preparation of 2,2-disubstituted 1-nitroalkenes

Reactions of ketones 1, nitromethane 2, and catalytic amount of piperidine 3 in the presence of mercaptan 6 generate β-nitroalkyl sulfides 7-9. At 0 °C and by the use of dichloromethane as solvent, β-nitroalkyl sulfides 7-9 can be oxidized by m-chloroperoxybenzoic acid (m-CPBA) 10 to generate β-nitroalkyl sulfoxides 11-13 and undergo elimination in carbon tetrachloride solution to produce medium to high yield of 2,2-disubstituted 1-nitroalkenes 5. The irreversibility of the synthetic mechanism not only can overcome the reversibility of the Henry reaction in the synthesis of 2,2-disubstituted 1-nitroalkenes 5 but also can generate the major products "exo-nitro olefins" 5c-e when cyclic ketones 1c-e were used. Under similar conditions, medium to high yield of 5-substituted-2-nitromethyl-2-phenylthioadamantane 17 also can be prepared from the reaction of 5-substituted-2-adamantanones 15, nitromethane 2, piperidine 3, thiophenol 6a. The intermediate 17 can be oxidized by m-CPBA 10 in dichloromethane solution and then undergo elimination at room temperature or can be dissolved in solvent, coated on silica gel, and then heated at 90-100 °C to generate 5-substituted-2-nitromethyleneadamantane 16.