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:

98%,99%, ^*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-]

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:

cyclohexanone N-cyclohexylimine

Cyclohexyl trimethylsilyl nitronate

1-methyl-5-nitro-2-[3-(1-nitrocyclohexyl)-2-(1-nitrocyclohexylmethyl)propenyl]-1H-imidazole

bis-(1-nitro-cyclohexylmethyl)-amine

Refernces

• 1、 Gupta, Anuradha,Haque, Azizul,Vankar, Yashwant D.. "Zeolite (H-ZSM 5)-catalysed reduction of conjugated nitroalkenes with sodium cyanoborohydride". . p. 1653 - 1654. Retrieved 1996.
• 2、 Rühl, Janet C.,Evans, Dennis H.,Hapiot, Philippe,Neta, Pedatsur. "Fast cleavage reactions following electron transfer. Reduction of 1,1-dinitrocyclohexane". . p. 5188 - 5194. Retrieved 1991.
• 3、 Kornblum,Graham. "". . p. 4041. Retrieved 1951.
• 4、 Kai, Yasushi,Knochel,Paul,Kwiatkowski, Stefan,Dunitz, Jack D.,Oth, Jean F. M.,et al.. "Structure, Synthesis, and Properties of Some Persubstituted 1,2-Dinitroethanes. In Quest of Nitrocyclopropyl-Anion Derivatives". . p. 137 - 161. Retrieved 1982.
• 5、 Emmons,Pagano. "-". . p. 4557. Retrieved 1955.
• 6、 Waller,Toogood,Karuppiah,Rattray,Mansell,Leys,Gardiner,Fryszkowska,Ahmed,Bandichhor,Reddy,Scrutton. "Structural insights into the ene-reductase synthesis of profens". . p. 4440 - 4448. Retrieved 2017.
• 7、 -. "Method for co-producing adipic acid and cyclohexanone-oxime from cyclohexane". Paragraph 0111-0113. . Retrieved 2021/06/13.
• 8、 Skrotzki, Eric A.,Vandavasi, Jaya Kishore,Newman, Stephen G.. "Ozone-Mediated Amine Oxidation and Beyond: A Solvent-Free, Flow-Chemistry Approach". supporting information. p. 14169 - 14176. Retrieved 2021/06/30.