Cycloheptanone

Base Information

• Chemical Name: Cycloheptanone
• CAS No.: 502-42-1
• Molecular Formula: C7H12O
• Molecular Weight: 112.172
• Hs Code.: 29142990
• European Community (EC) Number: 207-937-6
• NSC Number: 9471
• UNII: QH80295937
• DSSTox Substance ID: DTXSID8060113
• Nikkaji Number: J6.199I
• Wikipedia: Cycloheptanone
• Wikidata: Q413525
• ChEMBL ID: CHEMBL18607
• Mol file: 502-42-1.mol

Synonyms:Ketocycloheptane;Ketoheptamethylene;NSC 9471;Suberon;Suberone;

Chemical Property of Cycloheptanone

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 0.915mmHg at 25°C
• Melting Point: -21 °C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 180 °C at 760 mmHg
• Flash Point: 55.6 °C
• PSA: 17.07000
• Density: 0.929 g/cm³
• LogP: 1.90970
• Storage Temp.: Flammables area
• Water Solubility.: INSOLUBLE
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.088815002
• Heavy Atom Count: 8
• Complexity: 76.4

Purity/Quality:

99% ^*data from raw suppliers

Cycloheptanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 10-36/37/38-41-22
• Safety Statements: 23-24/25-36-26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: C1CCCC(=O)CC1
• Uses: Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals. A spasmolytic agent and vasodilator is produced from this chemical. They are also used in certain stereospecific enzymatic reactions.

Technology Process of Cycloheptanone

There total 228 articles about Cycloheptanone 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: 90.0%

1,4-dioxaspiro[4.6]undecane (184-26-9) → cycloheptanone (502-42-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In methanol; water; at 20 ℃; for 0.166667h;

Reference yield: 65.0%

cycloheptane (291-64-5) → cycloheptanol (502-41-0) + cycloheptanone (502-42-1)

Guidance literature:

With [PPh₄]₂[Mn^V(N)(CN)₄]; tetrabutylammonium periodite; acetic acid; In 2,2,2-trifluoroethanol; at 23 ℃; Inert atmosphere;

DOI:10.1002/asia.201601027

Reference yield: 45.0%

cycloheptane (291-64-5) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + Cycloheptyl Nitrate (54894-22-3) + acetylene (74-86-2,25067-58-7) + cycloheptanone (502-42-1)

Guidance literature:

With water; nitrogen(II) oxide; for 5.15h; Product distribution; Irradiation; further reaction times, initial conc.,;

DOI:10.1021/j150618a028

upstream raw materials:

diazomethane

methanol

diethyl ether

cyclohexanone

Downstream raw materials:

2,7-bis-[1]naphthylmethylene-cycloheptanone

2-veratrylidene-cycloheptanone

2,7-diveratrylidene-cycloheptanone

1,4-dioxaspiro[4.6]undecane

Refernces

THE STEREOSELECTIVITY OF KETAL CLAISEN REARRANGEMENTS WITH KETALS OF SIMPLE CYCLIC KETONES

10.1016/S0040-4039(00)87795-3

The study investigates the stereoselectivity of ketal Claisen rearrangements involving ketals of simple cyclic ketones such as cyclopentanone, cyclohexanone, and cycloheptanone. The reactions of these ketals with allylic alcohols produce mixtures of diastereomeric products, with the m isomer generally favored. The selectivity is influenced by enolization processes, particularly in the 5- and 6-membered ring systems. The study finds that the initial selectivity is quite good, especially when the allylic alcohol contains a methyl substituent, which induces significant diastereoselectivity. The identity of the major Claisen product is confirmed through independent methods like Wittig olefination and Cope rearrangement. The overall yields are good, and useful reaction products can be obtained, although the separation of isomers varies in difficulty depending on the cyclic ketone used. The researchers are working to expand the scope of the reaction to achieve higher diastereoselectivity.