Cyclopropene

Base Information

• Chemical Name: Cyclopropene
• CAS No.: 2781-85-3
• Molecular Formula: C3H4
• Molecular Weight: 40.0648
• UNII: 7B8994OHJ0
• DSSTox Substance ID: DTXSID20893759,DTXSID801027116
• Nikkaji Number: J2.384.276I,J80.561K
• Wikipedia: Cyclopropene,Cyclopropenylidene
• Wikidata: Q414101,Q3008567,Q83053856
• Metabolomics Workbench ID: 57653
• Mol file: 2781-85-3.mol

Synonyms:cyclopropene

Chemical Property of Cyclopropene

Chemical Property:

• Melting Point: -5 °C
• Refractive Index: 1.4890 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 0.86g/cm³
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 40.0313001276
• Heavy Atom Count: 3
• Complexity: 23

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=C1
• General Description: Cyclopropene is a highly reactive three-membered ring hydrocarbon with significant utility in bioorthogonal chemistry, enabling selective biomolecule labeling without disrupting native biological processes. Its isomeric forms, such as 1,3-disubstituted and 3,3-disubstituted cyclopropenes, exhibit unique reactivities—participating in inverse electron-demand Diels-Alder reactions with tetrazines and 1,3-dipolar cycloadditions with nitrile imines, respectively—allowing for orthogonal, simultaneous tagging of multiple biomolecules in complex systems. Additionally, cyclopropene derivatives like 3,3-dichlorocyclopropene serve as effective activators in nucleophilic acyl substitution reactions, facilitating mild and rapid carboxylic acid derivatization. These properties make cyclopropene a versatile tool in synthetic and biological applications.

Technology Process of Cyclopropene

There total 20 articles about Cyclopropene 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: 40.0%

3-chloroprop-1-ene (107-05-1) → cyclopropene (2781-85-3)

Guidance literature:

With sodium hexamethyldisilazane; In toluene; at 110 ℃; for 0.833333h;

DOI:10.1021/jo960728r

Reference yield: 14.7%

2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.01,5.04,6>undeca-8,10-diene (82323-32-8) → cyclopropene (2781-85-3) + 3-methyl-1,2-diphenyl-3-(2-phenylallyl)cyclopropene (82323-13-5)

Guidance literature:

In benzene; for 5.08h; Yield given; Irradiation;

DOI:10.1021/jo00139a002

Reference yield:

cyclopropyl bromide (4333-56-6,130561-87-4) → cyclopropene (2781-85-3)

Guidance literature:

With potassium tert-butylate; at 110 ℃; under 0.02 Torr; Yield given;

DOI:10.1016/S0040-4039(01)85542-8

upstream raw materials:

furan

1,2-dibromo-cyclopropane

cyclopropyl bromide

2-methylene-4-methyl-5,6-diphenyltetracyclo<5.4.0.0^1,5.0^4,6>undeca-8,10-diene

Downstream raw materials:

C₁₀H₁₄

1-Butyl-2-ethyl-cyclopropene

1-butylcyclopropene

1-Ethylcyclopropene

Refernces

Nucleophilic acyl substitution via aromatic cation activation of carboxylic acids: Rapid generation of acid chlorides under mild conditions

10.1021/ja101292a

The study explores a novel method for nucleophilic acyl substitution via aromatic cation activation of carboxylic acids to rapidly generate acid chlorides under mild conditions. The researchers hypothesized that treating a carboxylic acid with a cyclopropene bearing geminal leaving groups would produce a cyclopropenium carboxylate intermediate, which could then undergo nucleophilic acyl substitution to yield a carboxylic acid derivative and cyclopropenone. They found that using 3,3-dichlorocyclopropenes effectively activated carboxylic acids, with the structure of the cyclopropene significantly influencing the reaction rate. For instance, replacing phenyl groups with isopropyl substituents in the cyclopropene accelerated the reaction. The addition of an amine base, such as Hünig's base, further enhanced the reaction rate. This method enabled the conversion of carboxylic acids to acid chlorides and subsequently to amides, even with acid-sensitive substrates. The study also demonstrated the potential for cyclopropenium-mediated peptide couplings, highlighting the versatility and mildness of this activation strategy for acylation technologies.

Isomeric cyclopropenes exhibit unique bioorthogonal reactivities

10.1021/ja407737d

The study focuses on the identification and application of isomeric cyclopropenes in bioorthogonal chemistry, which allows for the selective labeling and tracking of biomolecules within complex biological systems without interfering with native biochemical processes. The researchers utilized two types of cyclopropenes: 1,3-disubstituted cyclopropenes, which react with tetrazines through an inverse electron-demand Diels?Alder (IED-DA) reaction, and 3,3-disubstituted cyclopropenes, which undergo 1,3-dipolar cycloaddition with nitrile imines. These reactions were selected for their orthogonality, meaning they can occur simultaneously without interfering with each other, which is crucial for studying multiple biomolecules at once. The purpose of using these specific chemicals was to develop a method for concurrent tagging of biomolecules in complex environments, such as cells and organisms, to monitor multicomponent processes. The study also involved computational analyses using density functional theory (DFT) to predict the reactivity of these cyclopropenes and experimental synthesis and testing of the cyclopropenes with model tetrazines and nitrile imines to validate the theoretical predictions.