20521-44-2

Basic information

• Product Name: 1,11-DODECADIYNE
• Synonyms: TIMTEC-BB SBB008726;1,11-DODECADIYNE;1,11-Dodecanediyne;Ai3-36571
• CAS NO: 20521-44-2
• Molecular Formula: C₁₂H₁₈
• Molecular Weight: 162.27
• Mol File: 20521-44-2.mol

Chemical Properties

• Boiling Point: 99°C 15mm
• Flash Point: 86.5°C
• Appearance: /
• Density: 0.835g/cm³
• Vapor Pressure: 0.128mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: 1,11-DODECADIYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,11-DODECADIYNE(20521-44-2)
• EPA Substance Registry System: 1,11-DODECADIYNE(20521-44-2)

Safety Data

• Hazardous Substances Data: 20521-44-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,11-Dodecadiyne is used as a key intermediate in the synthesis of various organic compounds due to its high reactivity and the presence of a terminal triple bond. It facilitates the formation of new chemical entities through reactions such as hydroamination, hydrosilylation, and cross-coupling, which are essential in the development of novel materials and pharmaceuticals.
Used in Polymer Production:
1,11-Dodecadiyne is used as a monomer in the production of polymers for various applications. Its ability to undergo polymerization reactions allows for the creation of polymers with unique properties, such as high strength, flexibility, and thermal stability. These polymers find use in industries like plastics, coatings, and adhesives.
Used in Pharmaceutical Industry:
1,11-Dodecadiyne is used as a building block in the synthesis of pharmaceutical compounds. Its reactivity enables the formation of complex molecular structures with potential therapeutic properties. Researchers leverage its chemical properties to develop new drugs and improve existing ones, contributing to advancements in medicine.
Used in Agricultural Chemicals:
1,11-Dodecadiyne is used as a precursor in the synthesis of agricultural chemicals, such as pesticides and herbicides. Its reactivity allows for the creation of effective compounds that can protect crops from pests and weeds, ensuring higher yields and food security.
Used in Material Science:
1,11-Dodecadiyne is used as a component in the development of advanced materials with specific properties. Its ability to form stable and functional materials through polymerization and other chemical reactions makes it valuable in the creation of materials for applications in electronics, energy storage, and nanotechnology.

InChI:InChI=1/C12H18/c1-3-5-7-9-11-12-10-8-6-4-2/h1-2H,5-12H2

Upstream product

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• 24772-63-2 1,8-diiodooctane 
• 629-41-4 1,8-Octanediol 
• 1066-54-2 trimethylsilylacetylene 
• 160515-66-2 1,12-bis(trimethylsilyl)dodeca-1,11-diyne 

Downstream Products

• 859994-31-3 1,18-bis-(4-methoxy-phenoxy)-octadeca-4,14-diyne 
• 94441-75-5 19-bromo-nonadeca-1,11-diyne 
• 6568-68-9 cyclononadeca-1,10-diyne 
• 71673-32-0 hexadeca-1,11-diyne 
• 298693-77-3 1,12-di(4-bromophenyl)dodeca-1,11-diyne 
• 50678-59-6 1,12-di(4-bromophenyl)dodecane 
• 31772-06-2 1,18-dibromooctadecane 
• 408328-04-1 1,18-bis-(4-methoxy-phenoxy)-octadecane 

Relevant articles and documents

Alkynol natural products target ALDH2 in cancer cells by irreversible binding to the active site

Falcarinol and stipudiol are natural products with potent anti-cancer activity found in several vegetables. Here, we use a chemical proteomic strategy to identify ALDH2 as a molecular target of falcarinol in cancer cells and confirm enzyme inhibition via covalent alkylation of the active site. Furthermore, the synthesis of stipudiol led to the observation that ALDH2 exhibits preference for alkynol-based binders. Inhibition of ALDH2 impairs detoxification of reactive aldehydes and limits oxidative stress response, two crucial pathways for cellular viability.

Intramolecular cyclohexadienone annulations of fischer carbene complexes: Model studies for the synthesis of phomactins

The intramolecular cyclohexadienone annulation of chromium carbene complexes is examined as a method to provide general access to the Phomactin family of natural products. The importance of the stereochemistry of the carbene complex and the number of carbons in the tether connecting the carbene complex and the alkyne are probed. Additionally, the degree of the 1,4-asymmetric induction is examined.

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.

EXO- AND ENDOHORMONES. XIV. STEREOSPECIFIC SYNTHESIS OF 3Z, 13Z- AND 3E, 13E-3,13-OCTADECADIEN-1-YL ACETATE

The two geometric isomers, 3Z, 13Z-, (I) and 3E, 13E-, (II), of 3,13-octadecadien-1-yl acetate, coponents of the phermonal lure of many lepidopteran insect species, were prepared in high isomeric purity by using 1,11-dodecadiine.