1-Undecyne

Base Information

• Chemical Name: 1-Undecyne
• CAS No.: 2243-98-3
• Molecular Formula: C11H20
• Molecular Weight: 152.28
• Hs Code.: 2901299090
• European Community (EC) Number: 218-825-1
• NSC Number: 87633
• UNII: Y07U3Q24US
• DSSTox Substance ID: DTXSID8062288
• Nikkaji Number: J125.121J
• Wikidata: Q27159718
• Mol file: 2243-98-3.mol

Synonyms:1-Undecyne;2243-98-3;undec-1-yne;undecyne;102681-76-5;UNII-Y07U3Q24US;Y07U3Q24US;EINECS 218-825-1;NSC 87633;NSC-87633;1-C11H20;Rutylidene;NSC87633;1-Undecyne, AldrichCPR;NCIOpen2_001194;DTXSID8062288;CHEBI:87545;CAA24398;C11H20;MFCD00015063;AKOS006230421;AS-56253;CS-0206842;FT-0608328;U0033;D92754;EN300-124916;Q27159718

Chemical Property of 1-Undecyne

Chemical Property:

• Vapor Pressure: 0.605mmHg at 25°C
• Melting Point: -25°C
• Refractive Index: 1.4300
• Boiling Point: 73°C 10mm
• Flash Point: 65.2°C
• PSA: 0.00000
• Density: 0.785g/cm³
• LogP: 3.76030
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Methanol (Sparingly)
• Water Solubility.: Miscible with acetone, ether, ethanol and benzene. Slightly miscible with water.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 152.156500638
• Heavy Atom Count: 11
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Undecyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-53-36
• Safety Statements: 24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC#C
• Uses: 1-Undecyne is a reagent used in organic chemical synthesis. Used in the synthesis of antimalarial and antitrypanosomal agents.

Technology Process of 1-Undecyne

There total 50 articles about 1-Undecyne 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: 89.0%

(Z)-1-bromoundec-1-ene (66142-59-4) → 1-undecyne (2243-98-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In N,N-dimethyl-formamide; at 60 ℃; for 2h;

DOI:10.1021/jo802101a

Reference yield: 88.0%

Methyl decanoate (110-42-9) + dimethyl 1-(1-diazo-2-oxopropyl)phosphonate (90965-06-3) → 1-undecyne (2243-98-3)

Guidance literature:

Methyl decanoate; With diisobutylaluminium hydride; In n-heptane; dichloromethane; at -78 ℃;

dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; With potassium carbonate; In methanol; n-heptane; dichloromethane; at 20 ℃; Further stages.;

DOI:10.1016/j.tetlet.2004.05.139

Reference yield: 82.0%

1-(benzotriazol-1-yl)-2-undecanone p-tosylhydrazone (189343-58-6) → 1-undecyne (2243-98-3)

Guidance literature:

With n-butyllithium; In diethyl ether; 1) -78 deg C, 0.5 h; 2) rt, 48 h;

DOI:10.1021/jo962291t

upstream raw materials:

2,2-dichloro-undecane

1-Bromononane

sodium acetylide

1-iodononane

Downstream raw materials:

(E)-2-iodo-1-tosyl-1-undecene

methyl nonyl ketone

C₂₆H₃₈N₆O

4-(1,3-tridecadiynyl)benzoic acid

Refernces

• 1、 Kerl, Thomas,Berger, Florian,Schmalz, Hans-Günther. "Total Synthesis of the Antiviral Natural Product Houttuynoid B". supporting information. p. 2935 - 2938. Retrieved 2016/03/25.
• 2、 Listunov, Dymytrii,Billot, Chelmia,Joly, Etienne,Fabing, Isabelle,Volovenko, Yulian,Génisson, Yves,Maraval, Valérie,Chauvin, Remi. "Extended structural modulation of bio-inspired chiral lipidic alkynylcarbinols as antitumor pharmacophores". . p. 7920 - 7930. Retrieved 2015/09/15.