1-Hexyn-3-one, 1-phenyl-

Base Information

• Chemical Name: 1-Hexyn-3-one, 1-phenyl-
• CAS No.: 14252-32-5
• Molecular Formula: C12H12 O
• Molecular Weight: 172.227
• DSSTox Substance ID: DTXSID00162071
• Nikkaji Number: J1.296.111A
• Wikidata: Q83030597
• Mol file: 14252-32-5.mol

Synonyms:1-phenylhex-1-yn-3-one;14252-32-5;1-Hexyn-3-one, 1-phenyl-;1-Phenyl-1-hexyn-3-one;1-phenyl-hex-1-yn-3-one;BRN 2208758;3-07-00-01656 (Beilstein Handbook Reference);BUTYRYLPHENYLACETYLENE;SCHEMBL14969612;DTXSID00162071;LS-75771

Chemical Property of 1-Hexyn-3-one, 1-phenyl-

Chemical Property:

• Vapor Pressure: 0.00282mmHg at 25°C
• Boiling Point: 285.3°Cat760mmHg
• Flash Point: 106.2°C
• Density: 1.01g/cm³
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 172.088815002
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(=O)C#CC1=CC=CC=C1

Technology Process of 1-Hexyn-3-one, 1-phenyl-

There total 23 articles about 1-Hexyn-3-one, 1-phenyl- 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: 97.0%

1-phenyl-1-hexyn-3-ol (1817-51-2) → 1-phenyl-hex-1-yn-3-one (14252-32-5)

Guidance literature:

With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite; In dichloromethane; acetic acid; at 20 ℃; for 6h;

DOI:10.1021/jo202301s

Reference yield: 89.0%

tert.-butylhydroperoxide (75-91-2) + (hex-1-yn-1-yl)benzene (1129-65-3) → 3-tert-butylperoxy-1-phenyl-1-hexyne + 1-phenyl-hex-1-yn-3-one (14252-32-5)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium carbonate; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt; CuCl₂*2H₂O; In water; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2006.03.140

Reference yield: 85.0%

(hex-1-yn-1-yl)benzene (1129-65-3) → 1-phenyl-hex-1-yn-3-one (14252-32-5)

Guidance literature:

With tert.-butylhydroperoxide; C₄₈H₇₂O₁₂Rh₂; In ethyl acetate; at 40 ℃; for 24h; under 760.051 Torr; Sealed tube;

DOI:10.1016/j.jorganchem.2021.122078

upstream raw materials:

butanoic acid anhydride

(phenylethynyl)sodium

isopentyl butanoate

butyryl bromide

Downstream raw materials:

3-[bis(2-phenylethyl)phosphoryl]-1-phenylhex-1-yn-3-ol

C₁₃H₁₄

1-phenyl-1,3-hexanedione

3-Propyl-5-phenylisoxazole

Refernces

• 1、 Zhao, Yi,Ng, Angela Wan Ting,Yeung, Ying-Yeung. "Mild propargylic oxidation using a diacetoxyiodobenzene/tert-butyl hydroperoxide protocol". . p. 4370 - 4372. Retrieved 2014.
• 2、 Ning, Yangbo,Tan, Jiantao,Wang, Yuanhua,Wang, Zhifan. "Fine-tuning dirhodium compounds with bridging ligands: Synthesis, structure, catalytic efficiency". supporting information. . Retrieved 2021/09/28.
• 3、 Reddy, T. Prabhakar,Gujral, Jagjeet,Roy, Pritam,Ramachary, Dhevalapally B.. "Catalytic Ynone-Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines". supporting information. p. 9653 - 9657. Retrieved 2021/01/09.