Diethyl(phenylethynyl)alumane

Base Information

• Chemical Name: Diethyl(phenylethynyl)alumane
• CAS No.: 5075-59-2
• Molecular Formula: C12H15Al
• Molecular Weight: 186.233
• DSSTox Substance ID: DTXSID70586886
• Mol file: 5075-59-2.mol

Synonyms:Diethyl(phenylethynyl)alumane;5075-59-2;DTXSID70586886

Chemical Property of Diethyl(phenylethynyl)alumane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 186.0989139
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[Al](CC)C#CC1=CC=CC=C1

Technology Process of Diethyl(phenylethynyl)alumane

There total 6 articles about Diethyl(phenylethynyl)alumane 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: 95.0%

triethylaluminum (97-93-8) + phenylacetylene (536-74-3) → diethyl(phenylethynyl)aluminum (5075-59-2)

Guidance literature:

With C₃₁H₅₅Al₃BN₂O₂Y; In benzene-d6; at 60 ℃; for 2h; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.202000325

Reference yield:

1-phenyl-2-bis(dimethylamino)borylethyne (14610-26-5) + triethylaluminum (97-93-8) → triethyl borane (97-94-9) + (dimethylamino)diethylborane (7397-47-9) + Et2AlN(Me)2 (13154-82-0) + diethyl(phenylethynyl)aluminum (5075-59-2)

Guidance literature:

In hexane; N2-atmosphere; addn. of 2 equiv. AlEt3 to borane (-78°C), stirring (room temp., 20 h); not isolated, reaction followed by (11)B- and (27)Al-NMR spectroscopy;

DOI:10.1016/0022-328X(94)05147-4

Reference yield:

diethylaluminium chloride (96-10-6) + phenylacetylene (536-74-3) → diethyl(phenylethynyl)aluminum (5075-59-2)

Guidance literature:

With n-butyllithium; In hexane; under Ar, BuLi in hexane added to PhC2H (slightly more than 1 equiv.) at 0°C, after 10 min Et2AlCl hexane soln. added, stirred for 15 min at 0°C; concd. in vac. below room temp.;

DOI:10.1246/bcsj.54.2151

upstream raw materials:

diethylaluminium chloride

phenylacetylene

1-phenyl-2-bis(dimethylamino)borylethyne

triethylaluminum

Downstream raw materials:

β-1,5-anhydro-1-C-(2-phenylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol

α-1,5-anhydro-1-C-(2-phenylethynyl)-2,3,4,6-tetra-O-benzyl-D-glucitol

1,3,4-triphenyl-1-pentyn-3-ol

threo-1-cyclohexyl-2-methyl-4-phenyl-3-butyn-1-ol

Refernces

• 1、 Kanbur, Uddhav,Ellern, Arkady,Sadow, Aaron D.. "Alkynylaluminum Synthesis Catalyzed by a Zwitterionic Neodymium(III) Heterobimetallic Compound". . p. 4409 - 4414. Retrieved 2019/01/03.
• 2、 Feulner, Herta,Metzler, Nils,Noeth, Heinrich. "Beitraege zur Chemie des bors, 226: Funktionalisierung von Alkinylboranen-Umsetzung mit Nucleophilen". . p. 51 - 62. Retrieved 2007/10/02.