1-Cyclopropyl-1,3-butanedione

Base Information

• Chemical Name: 1-Cyclopropyl-1,3-butanedione
• CAS No.: 21573-10-4
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2914299000
• European Community (EC) Number: 696-044-9
• DSSTox Substance ID: DTXSID40452004
• Nikkaji Number: J2.429.021B
• Wikidata: Q72460757
• Mol file: 21573-10-4.mol

Synonyms:1-Cyclopropyl-1,3-butanedione;1-cyclopropylbutane-1,3-dione;21573-10-4;1,3-Butanedione, 1-cyclopropyl-;1-cyclopropyl-butane-1,3-dione;1-Cyclopropyl-1,3-Butandione;SCHEMBL221424;1-cyclopropylbutan-1,3-dione;4-cyclopropylbutan-2,4-dione;4-cyclopropyl-2,4-butanedione;DTXSID40452004;KLCGMDWRXACELA-UHFFFAOYSA-N;BCP23092;MFCD00511094;AKOS009265119;CS-W006361;AS-11349;1-Cyclopropyl-1,3-butanedione, AldrichCPR;AM20090193;BB 0262839;FT-0659532;EN300-70179;O10401;A815490;Q-103240

Chemical Property of 1-Cyclopropyl-1,3-butanedione

Chemical Property:

• Vapor Pressure: 0.359mmHg at 25°C
• Refractive Index: 1.476
• Boiling Point: 198.5 °C at 760 mmHg
• PKA: 9.63±0.20(Predicted)
• Flash Point: 70.1 °C
• PSA: 34.14000
• Density: 1.1 g/cm³
• LogP: 0.94460
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

1-Cyclopropyl-1,3-butanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)C1CC1
• General Description: 1-Cyclopropyl-1,3-butanedione is a key intermediate in the synthesis of cyclopropylpolyketides, serving as a starting material for cyclopropanation reactions. It participates in chain elongation and subsequent transformations to form cyclopropane derivatives, such as cyclopropyltriketides, with its structure and reactivity validated through experimental and theoretical analyses. 1-Cyclopropyl-1,3-butanedione's role highlights its utility in constructing complex polyketide frameworks.

Technology Process of 1-Cyclopropyl-1,3-butanedione

There total 8 articles about 1-Cyclopropyl-1,3-butanedione 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: 90.4%

Cyclopropyl methyl ketone (765-43-5) + ethyl acetate (141-78-6) → 1-cyclopropyl-butane-1,3-dione (21573-10-4)

Guidance literature:

With sodium methylate; In tert-butyl methyl ether; Inert atmosphere;

DOI:10.1002/jlcr.1657

Reference yield:

magnesium acetoacetate + cyclopropanecarboxylic acid (1759-53-1) → 1-cyclopropyl-butane-1,3-dione (21573-10-4)

Guidance literature:

cyclopropanecarboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;

magnesium acetoacetate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 92h;

With hydrogenchloride; water; In N,N-dimethyl-formamide;

Reference yield:

magnesium acetoacetate → 1-cyclopropyl-butane-1,3-dione (21573-10-4)

Guidance literature:

cyclopropanecarboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;

magnesium acetoacetate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 92h;

With hydrogenchloride; water; In N,N-dimethyl-formamide;

upstream raw materials:

Cyclopropyl methyl ketone

acetic anhydride

ethyl acetate

cyclopropanecarboxylic acid

Downstream raw materials:

3-(acetylpropylcarbonylmethyl)-1,2,3-triphenylcyclopropene

2-chloro-1-cyclopropylbutane-1,3-dione

4-cyclopropyl-6-methyl-N-phenylpyrimidin-2-amine

2-Amino-4-cyclopropyl-6-methyl-pyrimidine

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.

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