(1.1.1)Propellane

Base Information

• Chemical Name: (1.1.1)Propellane
• CAS No.: 35634-10-7
• Molecular Formula: C5H6
• Molecular Weight: 66.1026
• UNII: B99AQN9D35
• DSSTox Substance ID: DTXSID20189149
• Nikkaji Number: J264.146A
• Wikipedia: 1.1.1-Propellane
• Wikidata: Q4545828
• Mol file: 35634-10-7.mol

Synonyms:(1.1.1)Propellane;Tricyclo[1.1.1.01,3]pentane;35634-10-7;[1.1.1]Propellane;1.1.1-propellane;B99AQN9D35;tricyclo[1.1.1.0(1,3)]pentane;[1.1.1] propellane;UNII-B99AQN9D35;DTXSID20189149;F71090;Q4545828

Chemical Property of (1.1.1)Propellane

Chemical Property:

• Vapor Pressure: 143mmHg at 25°C
• Boiling Point: 69.9°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 1.2g/cm³
• LogP: 1.17030
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 66.0469501914
• Heavy Atom Count: 5
• Complexity: 73.2

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C23C1(C2)C3
• General Description: Tricyclo[1.1.1.0^1,3]pentane, also known as [1.1.1]propellane, is a highly strained hydrocarbon characterized by its unique structure featuring three fused cyclopropane rings sharing a central carbon-carbon bond. Tricyclo[1.1.1.01,3]pentane exhibits significant steric strain due to the forced proximity of its bridgehead carbons, leading to unusual reactivity and bonding properties. It serves as a valuable scaffold in organic synthesis and materials science, particularly for constructing rigid, three-dimensional frameworks. The molecule's strained geometry and high energy content make it a subject of interest in theoretical and experimental studies of small-ring systems.

Technology Process of (1.1.1)Propellane

There total 2 articles about (1.1.1)Propellane 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: 26.0%

phenyllithium (591-51-5) + 1-(1-pyridinio)-3-iodobicyclo<1.1.1>pentane iodide (144443-32-3) → pyridine (110-86-1) + iodobenzene (591-50-4) + [1.1.1]propellane (35634-10-7)

Guidance literature:

In tetrahydrofuran;

DOI:10.1021/jo00049a030

Reference yield:

1,1-bis(chloromethyl)-2,2-dibromocyclopropane (98577-44-7) → methoxyethene (107-25-5,9003-09-2) + methylidenecyclobutane (1120-56-5) + bicyclo[1.1.1]pentane (311-75-1) + [1.1.1]propellane (35634-10-7)

Guidance literature:

With sodium; lithium; In decane; at 73 ℃; for 1.5h; under 14 Torr; Yield given. Further byproducts given;

Reference yield: 100.0%

[1.1.1]propellane (35634-10-7) + thiophenol (108-98-5) → Bicyclo<1.1.1>pent-1-ylphenylthioether (98585-81-0)

Guidance literature:

In diethyl ether; at 20 ℃; for 0.25h;

DOI:10.3762/bjoc.15.114

upstream raw materials:

1,1-bis(chloromethyl)-2,2-dibromocyclopropane

phenyllithium

1-(1-pyridinio)-3-iodobicyclo<1.1.1>pentane iodide

Downstream raw materials:

methyl 3''-phenyl<3>staffane-3-carboxylate

methyl 3'''-phenyl<4>staffane-3-carboxylate

1,3-bisiodobicyclo[1.1.1]pentane

1-(1-pyridinio)-3-iodobicyclo<1.1.1>pentane iodide

Refernces

Trapping the 3-Halobicyclo[1.1.1]pent-1-yl Cation. Mechanistic Implications and Synthesis of Mixed 1,3-Dihalobicyclo[1.1.1]pentanes

10.1021/jo9722764

The research investigates the trapping of 3-halobicyclo[1.1.1]pent-1-yl cations and the synthesis of mixed 1,3-dihalobicyclo[1.1.1]pentanes. The study explores the solvolysis behavior of bridgehead-substituted bicycloalkanes and the role of strain energy in their reaction rates. The researchers successfully trapped 3-iodo- and 3-bromobicyclo[1.1.1]pent-1-yl cations using external nucleophiles, such as lithium bromide and lithium chloride, in the presence of halogens like iodine and bromine. This trapping method allowed for the synthesis of several mixed dihalides, which are otherwise difficult to produce. Key chemicals involved in the research include [1.1.1]propellane, lithium bromide, lithium chloride, iodine, bromine, and various solvents like tetrahydrofuran (THF) and ether/pentane mixtures. The results highlight the stability of these cations and provide a novel approach to synthesizing mixed dihalides.

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