Cyclohexanone oxime

Base Information

• Chemical Name: Cyclohexanone oxime
• CAS No.: 100-64-1
• Deprecated CAS: 136056-95-6,136057-01-7,1071540-61-8,1071540-61-8,136057-01-7
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 2928.00
• European Community (EC) Number: 202-874-0
• NSC Number: 6300
• UN Number: 2811
• UNII: 2U60L00CGF
• DSSTox Substance ID: DTXSID4021842
• Nikkaji Number: J45.666G
• Wikipedia: Cyclohexanone_oxime
• Wikidata: Q1147519
• ChEMBL ID: CHEMBL137035
• Mol file: 100-64-1.mol

Synonyms:cyclohexanone oxime

Chemical Property of Cyclohexanone oxime

Chemical Property:

• Appearance/Colour: tan crystals
• Vapor Pressure: 0.0879mmHg at 25°C
• Melting Point: 86-89 °C(lit.)
• Refractive Index: 1.529
• Boiling Point: 208 °C at 760 mmHg
• PKA: 12.42±0.20(Predicted)
• Flash Point: 112.4 °C
• PSA: 32.59000
• Density: 1.1 g/cm³
• LogP: 1.78070
• Storage Temp.: Store below +30°C.
• Solubility.: 17.7g/l
• Water Solubility.: <0.1 g/100 mL at 20℃
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 90.7
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexanone Oxime >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Oximes
• Canonical SMILES: C1CCC(=NO)CC1
• General Description: Cyclohexanone oxime is a versatile intermediate used in organic synthesis, particularly in the formation of heterocyclic compounds such as 4,5,6,7-tetrahydroindoles and their derivatives. It reacts with dihaloethanes in superbase systems (e.g., MOH-DMSO) to yield these products, offering a safer alternative to acetylene-based methods. The reaction conditions, including reactant ratios and duration, can be optimized to achieve moderate yields (30-60%), demonstrating its utility in synthetic chemistry.

Technology Process of Cyclohexanone oxime

There total 165 articles about Cyclohexanone oxime 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: 100.0%

N-cyclohexyl-hydroxylamine (2211-64-5) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethylsulfoxide-d6; at 45 ℃; for 0.5h;

DOI:10.1055/s-0036-1588457

Reference yield: 91.0%

cyclohexylamine (108-91-8,157973-60-9) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With diperoxydodecanedioic acid; In N,N-dimethyl-formamide; at 20 - 55 ℃; for 0.333333h;

DOI:10.1039/c5nj00801h

Reference yield: 90.0%

trimethylsilyl cyclohexyl ether (13871-89-1) → cyclohexanone-oxime (100-64-1)

Guidance literature:

With trichloroisocyanuric acid; hydroxylamine hydrochloride; In neat (no solvent); at 100 ℃; for 4.25h; Green chemistry;

DOI:10.1080/10426507.2014.990015

upstream raw materials:

cyclohexyl-1-phenyl-1-hydroperoxide

cyclohexane

1-chloro-1-nitrosocyclohexane

1-chloro-1-nitrocyclohexane

Downstream raw materials:

caprolactam

cyclohexanone O-ethyl oxime

cyclohexanone-[O-(1,1,2,2-tetrafluoro-ethyl)-oxime ]

cyclohexanone-[O-(3,3-dichloro-2-methyl-allyl)-oxime ]

Refernces

PYRROLES FROM KETOXIMES AND ACETYLENE. 22. DIHALOETHANES IN PLACE OF ACETYLENE IN REACTIONS WITH CYCLOHEXANONE OXIME

10.1007/BF00513432

The research focuses on the synthesis of 4,5,6,7-tetrahydroindoles and their 1-vinyl derivatives from cyclohexanone oxime and 1,2-dihaloethanes in a superbase system composed of MOH-dimethyl sulfoxide (DMSO), where M represents alkali metals potassium (K), sodium (Na), and lithium (Li). The purpose of this study was to develop an alternative method to the traditional synthesis involving acetylene, which can be hazardous and challenging to handle, making it more suitable for laboratories without access to free acetylene. The conclusions drawn from the research indicate that by adjusting the reaction conditions, such as the molar ratios of the reactants and the reaction time, it is possible to achieve overall yields of 30-60% for the desired products.