Nitrocyclohexane

Base Information

• Chemical Name: Nitrocyclohexane
• CAS No.: 1122-60-7
• Molecular Formula: C6H11 N O2
• Molecular Weight: 129.159
• Hs Code.: 29049090
• European Community (EC) Number: 214-354-0
• NSC Number: 66277
• UN Number: 3382,2810
• UNII: LL1X024M73
• DSSTox Substance ID: DTXSID6061529
• Nikkaji Number: J72.712A
• Wikipedia: Nitrocyclohexane
• Wikidata: Q7041461
• ChEMBL ID: CHEMBL4590012
• Mol file: 1122-60-7.mol

Synonyms:NITROCYCLOHEXANE;1122-60-7;Cyclohexane, nitro-;nitro-cyclohexane;CCRIS 7162;HSDB 6414;EINECS 214-354-0;NSC 66277;BRN 0907243;UNII-LL1X024M73;AI3-14828;LL1X024M73;NSC-66277;4-05-00-00081 (Beilstein Handbook Reference);1-nitrocyclohexan;1-nitrocyclohexane;Cyclohexane,nitro-;Hexahydronitrobenzene;Nitrocyclohexane, 97%;SCHEMBL62178;CHEMBL4590012;DTXSID6061529;SCHEMBL17347348;CHEBI:74164;NSC66277;MFCD00003843;AKOS005206998;AKOS040744587;AS-48042;LS-56954;FT-0601866;N0187;EN300-396084;F17587;A802528;J-002737;Q7041461

Chemical Property of Nitrocyclohexane

Chemical Property:

• Vapor Pressure: 768 mm Hg ( 205 °C)
• Melting Point: −34 °C(lit.)
• Refractive Index: n20/D 1.462(lit.)
• Boiling Point: 205.5-206 °C768 mm Hg(lit.)
• PKA: 8.44±0.20(Predicted)
• Flash Point: 81.2°C
• PSA: 45.82000
• Density: 1.05g/cm³
• LogP: 2.11900
• Solubility.: soluble in Alcohol
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 102
• Transport DOT Label: Poison Inhalation Hazard

Purity/Quality:

97% ^*data from raw suppliers

Nitrocyclohexane >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aliphatic
• Canonical SMILES: C1CCC(CC1)[N+](=O)[O-]
• General Description: Nitrocyclohexane is a nitroalkane derivative that can be synthesized through various methods, including the reduction of 1,1-dinitrocyclohexane, where it forms as a product alongside other compounds like 1,1′-dinitrobicyclohexyl. It is also produced selectively in the vapor-phase catalytic nitration-oxidation of cyclohexane with NO₂, yielding nitrocyclohexane and adipic acid. NITROCYCLOHEXANE exhibits reactivity in electron transfer reactions, where its radical intermediates participate in chain reactions. Additionally, nitrocyclohexane can be derived from the reduction of gem-bromonitro compounds or through the oxidation of azides using HOF·CH₃CN. These synthetic routes highlight its versatility as an intermediate in organic transformations.

Technology Process of Nitrocyclohexane

There total 72 articles about Nitrocyclohexane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

cyclohexane (110-82-7,25012-93-5) → nitrosocyclohexane (2696-95-9) + 1-nitrocyclohexane (1122-60-7)

Guidance literature:

With tert.-butylnitrite; N-hydroxyphthalimide; In tetradeuterioacetic acid; at 80 ℃; for 2h; Further Variations:; Solvents; Temperatures; Reagents; reaction times; Product distribution;

DOI:10.1002/anie.200352741

Reference yield: 43.0%

cyclohexylamine (108-91-8,157973-60-9) + acetone (67-64-1) → 2-Cyclohexyl-3,3-dimethyloxaziridine (2763-76-0) + cyclohexanone-oxime (100-64-1) + N,N'-dicyclohexyldiazene N,N'-dioxide (3378-45-8,17606-86-9,26049-06-9) + 1-nitrocyclohexane (1122-60-7)

Guidance literature:

With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate; sodium hydrogencarbonate; In dichloromethane; water;

DOI:10.1021/jo00051a017

Reference yield: 7.0%

(1-Nitro-cyclohexyl)-[4]pyridyl-methanol (77280-42-3) → [1,1']bicyclohexyl-1,1'-diene (1128-65-0) + 1,2-di(pyridin-4-yl)ethane-1,2-diol (5486-06-6) + 1-nitrocyclohexane (1122-60-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; electrochemical reduction: mercury electrode;

upstream raw materials:

cyclohexanone-oxime

cyclohexane

Cyclohexyl iodide

1-bromo-1-nitrocyclohexane

Downstream raw materials:

(1-Nitro-cyclohexyl)-[2]pyridyl-methanol

(1-Nitro-cyclohexyl)-[4]pyridyl-methanol

(6-Methyl-[2]pyridyl)-(1-nitro-cyclohexyl)-methanol

5,5-dimethyl-2-(1-nitro-cyclohexylmethyl)-cyclohexane-1,3-dione

Refernces

New approach to oximes through reduction of nitro compounds enabled by visible light photoredox catalysis

10.1021/ol4009443

The study explores a new method for synthesizing oximes through the reduction of nitro compounds using visible light photoredox catalysis. Key chemicals involved include the Ru(bpy)?Cl? photocatalyst, which absorbs visible light and initiates the reduction process; Hünig’s base (iPr?NEt), which acts as an amine reductive quencher to facilitate the reaction; and Mg(ClO?)?, a Lewis acidic additive that enhances the reaction efficiency. The solvent MeCN (acetonitrile) is crucial for achieving high yields. The study demonstrates that this mild and environmentally benign protocol can efficiently convert a variety of aliphatic and aromatic nitro compounds into their corresponding oximes, with yields ranging from 35% to 86%. The oximes produced can undergo further transformations, such as [3+2] dipolar cycloaddition, oxidation, and cleavage reactions, showcasing the synthetic utility of this method. Additionally, the protocol enables the conversion of nitrocyclohexane to caprolactam, an important industrial feedstock, highlighting its potential for practical applications.

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