Cyclopropanecarbonyl chloride

Base Information

• Chemical Name: Cyclopropanecarbonyl chloride
• CAS No.: 4023-34-1
• Molecular Formula: C4H5ClO
• Molecular Weight: 104.536
• Hs Code.: 29162000
• European Community (EC) Number: 223-684-4
• DSSTox Substance ID: DTXSID2063266
• Nikkaji Number: J23.515F
• Wikidata: Q72460593
• Mol file: 4023-34-1.mol

Synonyms:Cyclopropanecarbonyl chloride;4023-34-1;Cyclopropanecarboxylic acid chloride;Cyclopropane carbonyl chloride;MFCD00001277;Cyclopropyl carboxylic chloride;Cyclopropylbenzoyl chloride;cyclopropylcarbonyl chloride;cyclopropane-d5-carbonyl chloride;cyclopropane carboxylic acid chloride;EINECS 223-684-4;EC 223-684-4;1219794-96-3;Cyclopropylcarboxyl chloride;cyclopropyl carbonyl chloride;Cyclopropanoyl chloride;cyclopropylformyl chloride;cyclopropylcarbonylchloride;cycloproylcarbonyl chloride;cyclopropanecarbonylchloride;cyclopropancarbonyl chloride;cyclopropanoic acid chloride;cyclopropane-carbonylchloride;SCHEMBL4279;cyclo-propylcarbonyl chloride;Cyclopropane carbonylchloride;cyclopropyl-carbonyl chloride;Cyclopropane carbony chloride;cyclopropane-carbonyl chloride;cyclopropanecarboxylic chloride;cyclopropyl- carbonyl chloride;cyclopropanyl carbonyl chloride;1-cyclopropanecarbonyl chloride;3-cyclopropanecarbonyl chloride;DTXSID2063266;AMY3975;cyclopropylcarboxylic acid chloride;Cyclopropanecarbonyl chloride, 98%;cyclopropyl carboxylic acid chloride;cyclopropane-carboxylic acid chloride;BBL011354;STL146445;AKOS005720834;VS-02928;C1059;FT-0624280;EN300-29630;D78023;J-520188;Q-200909;F2190-0019

Chemical Property of Cyclopropanecarbonyl chloride

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 16.3mmHg at 25°C
• Melting Point: 77.5-78.5 °C(Solv: hexane (110-54-3))
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 119 °C at 760 mmHg
• Flash Point: 23.3 °C
• PSA: 17.07000
• Density: 1.317 g/cm³
• LogP: 1.16180
• Storage Temp.: 0-6°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: decomposes
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 104.0028925
• Heavy Atom Count: 6
• Complexity: 75.6

Purity/Quality:

99.9% ^*data from raw suppliers

Cyclopropanecarbonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F
• Hazard Codes: C,F
• Statements: 10-34-29-25-36-38
• Safety Statements: 26-36/37/39-45-8-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C(=O)Cl
• Uses: Cyclopropanecarbonyl chloride can be used as an alkylating reagent in the preparation of some chemical building blocks such as formylcyclopropane, cyclopropanecarboxylic acid hydrazide, bis(cyclopropylcarbonyl) peroxide, 1-cyclopropanecarboxamide, 2-cyclopropylcarbonylcyclohexane-1,3-diones and cyclopropyl analog of triazolopiperazine-amides.

Technology Process of Cyclopropanecarbonyl chloride

There total 7 articles about Cyclopropanecarbonyl chloride 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%

cyclopropanecarboxylic acid (1759-53-1) → cyclopropanecarboxylic acid chloride (4023-34-1)

Guidance literature:

With thionyl chloride; In toluene; Heating;

DOI:10.1016/j.ejmech.2005.02.011

Reference yield:

cyclopropanecarboxylic acid Na-salt (155-22-6) → cyclopropanecarboxylic acid chloride (4023-34-1)

Guidance literature:

With oxalyl dichloride;

DOI:10.1016/S0040-4039(01)80570-0

Reference yield:

cyclopropanecarboxylic acid (1759-53-1) → 5-cyclopropanepentanoyl chloride (663618-19-7) + cyclopropanecarboxylic acid chloride (4023-34-1)

Guidance literature:

upstream raw materials:

cyclopropanecarboxylic acid

cyclopropanecarboxylic acid Na-salt

oxalyl dichloride

Downstream raw materials:

cyclopropylacetic acid

methyl cyclopropylcarboxylate

cyclopropanecarboxylic acid propyl ester

ethyl cyclopropylcarboxylate

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.