2,2,7,7-Tetramethylocta-3,5-diyne

Base Information

• Chemical Name: 2,2,7,7-Tetramethylocta-3,5-diyne
• CAS No.: 6130-98-9
• Molecular Formula: C12H18
• Molecular Weight: 162.275
• Hs Code.: 2901299090
• European Community (EC) Number: 625-622-5
• NSC Number: 147145
• DSSTox Substance ID: DTXSID30210211
• Nikkaji Number: J793.944B
• Wikidata: Q83084810
• Mol file: 6130-98-9.mol

Synonyms:2,2,7,7-Tetramethylocta-3,5-diyne;6130-98-9;2,2,7,7-Tetramethyl-3,5-octadiyne;2 2 7 7-TETRAMETHYL-3 5-OCTADIYNE 99;NSC147145;Bis(tert-butyl)diacetylene;(tert-C4H9C.equiv.C)2;3, 2,2,7,7-tetramethyl-;DTXSID30210211;2,7,7-Tetramethyl-3,5-octadiyne;AKOS015912877;NSC 147145;NSC-147145;2,2,7,7-Tetramethyl-3,5-octadiyne, 99%;F88081;InChI=1/C12H18/c1-11(2,3)9-7-8-10-12(4,5)6/h1-6H

Chemical Property of 2,2,7,7-Tetramethylocta-3,5-diyne

Chemical Property:

• Vapor Pressure: 0.111mmHg at 25°C
• Melting Point: 130-132 °C(lit.)
• Boiling Point: 228.3°C at 760 mmHg
• Flash Point: 83.4°C
• PSA: 0.00000
• Density: 0.839g/cm³
• LogP: 3.08540
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 162.140850574
• Heavy Atom Count: 12
• Complexity: 234

Purity/Quality:

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

2,2,7,7-TETRAMETHYL-3,5-OCTADIYNE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)C#CC#CC(C)(C)C

Technology Process of 2,2,7,7-Tetramethylocta-3,5-diyne

There total 10 articles about 2,2,7,7-Tetramethylocta-3,5-diyne 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: 88.0%

1,1,1,2,2,3,3-heptafluoro-3-iodo-propane (754-34-7) + (3,3-dimethyl-1-butynyl)trimethylstannane (34664-54-5) → 2,2,7,7-tetramethyl-octa-3,5-diyne (6130-98-9) + trimethyltin(IV)chloride (1066-45-1) + 5,5,6,6,7,7,7-heptafluoro-2,2-dimethyl-3-heptyne (126260-37-5) + trimethylstannyl iodide (811-73-4)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dichloro-ethane; 100°C, 3 h, sealed glass ampul purged with argon; 0.5 M Me3SnCCBu-t, 1 M C3F7I, catalyst concn. 1 mol % of the amount of Me3SnCCBu-t;

Reference yield: 85.0%

4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone (65457-77-4) + (3,3-dimethylbut-1-ynyl)dimethylaluminium (66530-03-8) → 2,2,7,7-tetramethyl-octa-3,5-diyne (6130-98-9) + trans-3-(3,3-dimethyl-1-butynyl)-4-(cumyloxy)-cyclopentanone (66530-00-5)

Guidance literature:

bis(acetylacetonate)nickel(II); diisobutylaluminium hydride; In diethyl ether; toluene; at -5 ℃; for 1.5h;

DOI:10.1021/jo01303a024

Reference yield: 79.0%

1-Bromo-2-phenylacetylene (932-87-6) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2,2,7,7-tetramethyl-octa-3,5-diyne (6130-98-9) + 1,4-diphenyl-1,3-butadiyne (886-66-8) + 2-methyl-6-phenylhexa-3,5-diyn-2-ol (16900-79-1)

Guidance literature:

With copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.catcom.2011.10.027

upstream raw materials:

3,3-Dimethylbut-1-yne

[di(4-nitrobenzoyloxy)iodo]benzene

(3,3-dimethyl-1-butynyl)trimethylsilane

4-<(1,1'-dimethylbenzyl)oxy>-2-cyclopentenone

Downstream raw materials:

tetrakis(2,4,6-triisopropylphenyl)disilene

3,6-bis(diphenylphosphanyl)-2,2,7,7-tetramethylocta-3,4-diene

(Z,Z)-3,6-bis(diphenylphosphanyl)-2,2,7,7-tetramethylocta-3,5-diene

C₂₆H₃₀Cl₂O₂

Refernces

• 1、 Li, Hongling,Wang, Lailai,Yang, Min,Qi, Yanxing. "Palladium supported on amine-functionalized mesoporous silica: Highly efficient phosphine-free catalyst for alkyne-alkyne cross-coupling reaction". experimental part. p. 179 - 183. Retrieved 2012/02/16.
• 2、 Kitamura, Tsugio,Tanaka, Toshimasa,Taniguchi, Hiroshi,Stang, Peter J.. "Selective Coupling Reactions of Alkynyl(phenyl)iodonium Tosylates with Alkynylcopper Reagents". . p. 2892 - 2893. Retrieved 2007/10/02.