629-89-0

Basic information

• Product Name: 1-OCTADECYNE
• Synonyms: CETYLACETYLENE;1-OCTADECYNE;TIMTEC-BB SBB009112;N-HEXADECYLACETYLENE;octadec-1-yne;octadecyne;1-OCTADECYNE 90%;1-OCTADECYNE TECH 85%
• CAS NO: 629-89-0
• Molecular Formula: C₁₈H₃₄
• Molecular Weight: 250.46
• EINECS: 211-114-7
• Product Categories: Acetylenes;Acetylenic Hydrocarbons
• Mol File: 629-89-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 22,5°C
• Boiling Point: 180°C 15mm
• Flash Point: 25 °C
• Appearance: /
• Density: 0,803 g/cm3
• Vapor Pressure: 0.000908mmHg at 25°C
• Refractive Index: 1.4774
• CAS DataBase Reference: 1-OCTADECYNE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-OCTADECYNE(629-89-0)
• EPA Substance Registry System: 1-OCTADECYNE(629-89-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 629-89-0(Hazardous Substances Data)

Usage

General Description

1-Octadecyne, also known by its IUPAC name as "Octadec-1-yne," is an organic compound classified as a long-chain alkyne. Structurally, it consists of a hydrocarbon chain that is 18 carbon atoms long, with a triple bond located at one end. It is typically used in industrial applications, more specifically in the synthesis of other complex molecules. Like other alkynes, it can undergo a broad range of chemical reactions, most notably addition reactions. Despite its utility, it should be handled carefully as it is a combustible substance and it may cause skin, eye, and respiratory irritation.

InChI:InChI=1/C18H34/c1-3-5-7-9-11-13-15-17-18-16-14-12-10-8-6-4-2/h1H,4-18H2,2H3

Upstream product

• 26038-78-8 1,2-dibromooctadecane 
• 112-82-3 hexadecanyl bromide 
• 74-86-2 acetylene 
• 61847-97-0 octadec-2-yne 
• 70277-75-7 lithium acetylide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1066-26-8 sodium acetylide 
• 544-77-4 1-iodohexadecane 

Downstream Products

• 112-88-9 octadec-1-ene 
• 1229010-14-3 5,6-di(octadec-1-ynyl)-2-((R)-1-phenylethyl)isoindoline-1,3-dione 
• 1401439-85-7 C₃₂H₅₅N₄O⁽¹⁺⁾*Br^(1-) 
• 1401439-91-5 C₃₂H₅₆N₅O⁽¹⁺⁾*Br^(1-) 
• 1401439-97-1 C₃₁H₅₁N₄O₂⁽¹⁺⁾*Br^(1-) 
• 1401440-03-6 C₃₂H₅₄N₅O⁽¹⁺⁾*Br^(1-) 
• 61847-97-0 octadec-2-yne 
• 593-45-3 octadecane 
• 1048973-90-5 4-(1,3-icosadiynyl)benzoic acid 
• 68183-16-4 hexatriaconta-17,19-diyne 
• 3031-68-3 Hexa-2,4-diyne-1,6-diol 
• 70283-74-8 deca-4,6-diyne-1,10-diol 
• 506-51-4 tetracosyl alcohol 
• 593-50-0 melissyl alcohol 

Relevant articles and documents

Total Synthesis of Natural Lembehyne C and Investigation of Its Cytotoxic Properties

The first Z-stereoselective method for the synthesis of the natural marine alkynol lembehyne C, containing a 1Z,5Z,9Z-triene moiety, in 41% yield was developed using the new Ti-catalyzed cross-coupling of oxygenated and aliphatic 1,2-dienes as the key step. It was found for the first time that lembehyne C exhibits moderate cytotoxicity against Jurkat, K562, U937, and HL60 cancer cells and also efficiently induces apoptosis in Jurkat cells, with the cell death mechanism being activated by the mitochondrial pathway. The lembehyne C inhibition of the cell cycle follows the mitotic catastrophe mechanism.

Development of a benzophenone and alkyne functionalised trehalose probe to study trehalose dimycolate binding proteins

Trehalose dimycolates (TDMs) are the most abundant glycolipids found in the cell wall of Mycobacterium tuberculosis (M. tb). TDMs play an important role in the pathogenesis of M. tb yet the only known receptor for TDM is the macrophage inducible C-type lectin (mincle). To understand more about the interaction of TDMs with immune cells, affinity based proteome profiling (AfBPP) can be used to determine receptors that bind TDMs. To this end, we present the synthesis of the first AfBPP-TDM probe and report on its ability to activate macrophages. By doing so, we establish that the AfBPP-TDM probe appears to be a suitable substrate for future proteomic profiling experiments.

PMHS-mediated couplings of alkynes or benzothiazoles with various electrophiles: Application to the synthesis of (-)-akolactone A

Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature and under amine-free conditions. To demonstrate the applicability of the method, a total synthesis of the cyctotoxic butanolide (-)-akolactone A was carried out.