1-(Buta-1,3-diyn-1-yl)-2-methylbenzene

Base Information

• Chemical Name: 1-(Buta-1,3-diyn-1-yl)-2-methylbenzene
• CAS No.: 131292-30-3
• Molecular Formula: C₁₁H₈
• Molecular Weight: 140.185
• DSSTox Substance ID: DTXSID60562831
• Nikkaji Number: J603.655D
• Wikidata: Q82447116
• Mol file: 131292-30-3.mol

Synonyms:131292-30-3;1-buta-1,3-diynyl-2-methylbenzene;Benzene, 1-(1,3-butadiynyl)-2-methyl- (9CI);butadiynyltoluene;1-(Buta-1,3-diyn-1-yl)-2-methylbenzene;DTXSID60562831

Chemical Property of 1-(Buta-1,3-diyn-1-yl)-2-methylbenzene

Chemical Property:

• PSA: 0.00000
• LogP: 1.97970
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 140.062600255
• Heavy Atom Count: 11
• Complexity: 227

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1C#CC#C

Technology Process of 1-(Buta-1,3-diyn-1-yl)-2-methylbenzene

There total 7 articles about 1-(Buta-1,3-diyn-1-yl)-2-methylbenzene 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:

ethyl 5-(2-methylphenyl)-3-oxo-2-triphenylphosphoranylidenepent-4-ynoate (131292-09-6) → 1-(buta-1,3-diyn-1-yl)-2-methylbenzene (131292-30-3) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

at 750 ℃; for 1h; under 0.001 - 0.1 Torr;

DOI:10.1039/P19940002461

Reference yield:

2-methyl-6-(2-methylphenyl)hexa-3,5-diyn-2-ol → 1-(buta-1,3-diyn-1-yl)-2-methylbenzene (131292-30-3)

Guidance literature:

With sodium hydroxide; In toluene; at 115 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/jacs.7b03005

Reference yield:

1-ethynyl-2-methylbenzene (766-47-2) → 1-(buta-1,3-diyn-1-yl)-2-methylbenzene (131292-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-Bromosuccinimide; silver nitrate / acetone / 5 h / 23 °C / Inert atmosphere; Darkness

2.1: copper(l) chloride; N-butylamine; hydroxylamine hydrochloride / water / 0.17 h

2.2: 3 h / 23 °C

3.1: sodium hydroxide / toluene / 0.25 h / 115 °C / Inert atmosphere

With N-Bromosuccinimide; hydroxylamine hydrochloride; silver nitrate; N-butylamine; copper(l) chloride; sodium hydroxide; In water; acetone; toluene;

DOI:10.1021/jacs.7b03005

upstream raw materials:

ethyl 5-(2-methylphenyl)-3-oxo-2-triphenylphosphoranylidenepent-4-ynoate

3-(2-methylphenyl)prop-2-ynoic acid

o-Tolyl-propynoyl chloride

ethyl 3-(2-methylphenyl)prop-2-ynoate

Refernces

• 1、 De Orbe, M. Elena,Amenós, Laura,Kirillova, Mariia S.,Wang, Yahui,López-Carrillo, Verónica,Maseras, Feliu,Echavarren, Antonio M.. "Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture". . p. 10302 - 10311. Retrieved 2017/08/09.