4117-15-1

Basic information

• Product Name: 1,10-Undecadiyne
• Synonyms: 1,10-Undecadiyne
• CAS NO: 4117-15-1
• Molecular Formula: C₁₁H₁₆
• Molecular Weight: 148.24
• Mol File: 4117-15-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: -17°C
• Boiling Point: 218.87°C (estimate)
• Flash Point: 72°C
• Appearance: /
• Density: 0.8182
• Vapor Pressure: 0.362mmHg at 25°C
• Refractive Index: 1.4530
• CAS DataBase Reference: 1,10-Undecadiyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-Undecadiyne(4117-15-1)
• EPA Substance Registry System: 1,10-Undecadiyne(4117-15-1)

Safety Data

• Hazardous Substances Data: 4117-15-1(Hazardous Substances Data)

Usage

Description

1,10-Undecadiyne is a chemical compound with the molecular formula C11H18, belonging to the class of organic compounds known as alkynes, characterized by the presence of a carbon-carbon triple bond. This colorless liquid at room temperature is widely utilized in organic synthesis, materials science, and holds potential applications in the medical and pharmaceutical fields, making it a versatile and significant compound across various industries.

Uses

Used in Organic Synthesis:
1,10-Undecadiyne is used as a key intermediate for the synthesis of various organic compounds, leveraging its unique triple bond to facilitate a range of chemical reactions and the formation of diverse molecular structures.
Used in Materials Science:
In the field of materials science, 1,10-Undecadiyne is utilized as a component in the development of novel materials, taking advantage of its structural properties to enhance material characteristics such as strength, flexibility, or conductivity.
Used in Polymer Production:
1,10-Undecadiyne is used as a monomer in the production of polymers, contributing to the formation of polymer chains with specific properties tailored for various applications, including plastics, elastomers, and fibers.
Used in Chemical Product Synthesis:
1,10-Undecadiyne serves as a monomer in the synthesis of a variety of chemical products, allowing for the creation of new molecules with potential applications in different industries.
Used in Medicine and Pharmaceuticals:
1,10-Undecadiyne has potential applications in the medical and pharmaceutical fields, where its unique properties may be harnessed for the development of new drugs or therapeutic agents.

InChI:InChI=1/C11H16/c1-3-5-7-9-11-10-8-6-4-2/h1-2H,5-11H2

Upstream product

• 4549-31-9 1,7-dibromoheptane 
• 70277-75-7 lithium acetylide 
• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 91329-94-1 2,10-dibromo-undeca-1,10-diene 
• 111-24-0 1,5-dibromo-pentane 
• 106-96-7 propargyl bromide 
• 1066-26-8 sodium acetylide 

Downstream Products

• 1235543-31-3 pentadeca-5,14-diyn-1-ol 

Relevant articles and documents

Triply Threaded [4]Rotaxanes

[4]Rotaxanes featuring three axles threaded through a single ring have been prepared through active metal template synthesis. Nickel-catalyzed sp3-sp3 homocouplings of alkyl bromide "half-threads" through 37- and 38-membered 2,2′:6′,2″-terpyridyl macrocycles generate triply threaded [4]rotaxanes in up to 11% yield. An analogous 39-membered macrocycle produced no rotaxane products under similar conditions. The constitutions of the [4]rotaxanes were determined by NMR spectroscopy and mass spectrometry. Doubly threaded [3]rotaxanes were also obtained from the reactions but no [2]rotaxanes were isolated, suggesting that upon demetalation the axle of a singly threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.

17(R),18(S)-Epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: Structure-activity relationships and stable analogues

17(R),18(S)-Epoxyeicosatetraenoic acid [17(R),18(S)-EETeTr], a cytochrome P450 epoxygenase metabolite of eicosapentaenoic acid (EPA), exerts negative chronotropic effects and protects neonatal rat cardiomyocytes against Ca 2+-overload with EC50 ≈ 1-2 nM. Structure-activity studies revealed that a cis-Δ11,12- or Δ14,15- olefin and a 17(R),18(S)-epoxide are minimal structural elements for antiarrhythmic activity whereas antagonist activity was often associated with the combination of a Δ14,15-olefin and a 17(S),18(R)-epoxide. Compared with natural material, the agonist and antagonist analogues are chemically and metabolically more robust and several show promise as templates for future development of clinical candidates.

Cyclic Diynes by Alkyne Metathesis

The preparation of α,ω-diynes with methyl groups at the termini (11a-i) is described. The methylene groups between the alkyne units vary between n = 12 (a) and n = 4 (i). Ring closing metathesis with Mo(CO) 6/CF3C6H4OH yielded the monocyclic alkyne 12a with 11a as starting material, whereas 11b-g yielded the cyclic diynes 13b-g. Detailed structural parameters were obtained for 13b and 13c by X-ray crystallography.