Cyclopropyl methyl ketone

Base Information

• Chemical Name: Cyclopropyl methyl ketone
• CAS No.: 765-43-5
• Molecular Formula: C5H8O
• Molecular Weight: 84.1179
• Hs Code.: 29142900
• European Community (EC) Number: 212-146-4
• NSC Number: 1940
• UNII: N27YY1XCFH
• DSSTox Substance ID: DTXSID9074854
• Nikkaji Number: J23.522I
• Wikidata: Q1975324
• Mol file: 765-43-5.mol

Synonyms:Cyclopropyl methyl ketone;765-43-5;1-Cyclopropylethanone;Acetylcyclopropane;Ethanone, 1-cyclopropyl-;Methyl cyclopropyl ketone;1-cyclopropyl-ethanone;Ketone, cyclopropyl methyl;1-Cyclopropylethan-1-One;cyclopropylmethylketone;NSC 1940;EINECS 212-146-4;UNII-N27YY1XCFH;N27YY1XCFH;cyclopropyl methyl ketone-d8;AI3-08707;NSC-1940;EC 212-146-4;1219799-33-3;Cyclopropylethanone;acetyl cyclopropane;cyclopropyl methylketone;methylcyclopropyl ketone;1-cyclopropyl-1-ethanone;CYCLOPROPYLMETHYL KETONE;Cyclopropyl methyl ketone, 99%;DTXSID9074854;NSC1940;BCP34273;MFCD00001297;STK050796;AKOS000119335;AM83286;LS-67304;A4506;FT-0621828;FT-0624287;EN300-19825;A838742;Q1975324;W-104358;F3204-0177

Chemical Property of Cyclopropyl methyl ketone

Chemical Property:

• Appearance/Colour: clear colorless to very slightly yellow liquid
• Melting Point: <-70 °C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 114.2 °C at 760 mmHg
• Flash Point: 21.1 °C
• PSA: 17.07000
• Density: 0.995 g/cm³
• LogP: 0.98540
• Storage Temp.: Flammables area
• Solubility.: 185g/l
• Water Solubility.: Fully miscible in water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 84.057514874
• Heavy Atom Count: 6
• Complexity: 72

Purity/Quality:

99%, ^*data from raw suppliers

Cyclopropyl methyl ketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-29-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC(=O)C1CC1
• Uses: Cyclopropyl methyl ketone was used in the preparation of homoallylic alcohols. Acetylcyclopropane is used as an intermediate for the manufacturing pharmaceuticals, agrochemicals and other organic compounds.

Technology Process of Cyclopropyl methyl ketone

There total 71 articles about Cyclopropyl methyl ketone 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: 99.0%

1-cyclopropylethanol (765-42-4) → Cyclopropyl methyl ketone (765-43-5)

Guidance literature:

With acetic acid; 1,1'-(phenyl-λ³-iodane)bis(pyridinium) trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 60 ℃; chemoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/acs.orglett.9b02018

Reference yield: 97.12%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1) → Cyclopropyl methyl ketone (765-43-5)

Guidance literature:

With sodium iodide; at 192 ℃; under 4500.45 Torr; Reagent/catalyst; Temperature; Pressure;

Reference yield: 88.04%

5-chloro-2-pentanone (5891-21-4) → Cyclopropyl methyl ketone (765-43-5)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; at 90 - 100 ℃; for 1.5h; Reagent/catalyst; Temperature;

upstream raw materials:

2-Methyl-4,5-dihydrofuran

5-chloro-2-pentanone

bromo-5-pentanone-2

isopropenylcyclopropane

Downstream raw materials:

1-cyclopropyl-5t-phenyl-penta-2t,4-dien-1-one

2-cyclopropyl-4-phenylbut-3-yn-2-ol

Methylethylallylcarbinol

4-iodo-4-methyl-hex-1-ene

Refernces

Synthesis and characterization of cyclopropylpolyketides: A combined experimental and theoretical study

10.1002/ejoc.200701140

The study presents the first synthesis and characterization of open-chain cyclopropylpolyketides through a combination of experimental and computational methods. Researchers synthesized cyclopropylpolyketides by a sequence of chain elongation via acylation and subsequent cyclopropanation. Key chemicals involved include 1(cyclopropyl)butane-1,3-dione and benzoylacetone, which were used as starting materials for cyclopropanation with 1,2-dibromoethane to form cyclopropanes 2a and 2b. These cyclopropanes were then reacted with cyclopropanecarboxylic chloride and benzoyl chloride to produce compounds 3a–c, which were further cyclopropanated to yield the desired cyclopropyltriketides 4a–c. The structure of 4c was confirmed by X-ray crystal structure analysis. Additionally, dimethyl cyclopropane-1,1-dicarboxylate (5) was reacted with 1-cyclopropylethan-1-one to form 7, which was transformed into triketide 8. The study also involved density functional theory computations to analyze the structural and energetic properties of the cyclopropylpolyketides, providing insights into their conformations and stabilities.