tert-Butyl(phenylacetylenyl)ketone

Base Information

• Chemical Name: tert-Butyl(phenylacetylenyl)ketone
• CAS No.: 32398-67-7
• Molecular Formula: C13H14O
• Molecular Weight: 186.254
• NSC Number: 138597
• DSSTox Substance ID: DTXSID70186108
• Nikkaji Number: J434.289E
• Wikidata: Q83057312
• Mol file: 32398-67-7.mol

Synonyms:tert-Butyl(phenylacetylenyl)ketone;4,4-dimethyl-1-phenylpent-1-yn-3-one;32398-67-7;NSC138597;SCHEMBL1317265;DTXSID70186108;QXGIWMOPVOXYCX-UHFFFAOYSA-N;NSC 138597;NSC-138597;UNM-0000306040;UNM000011085601

Chemical Property of tert-Butyl(phenylacetylenyl)ketone

Chemical Property:

• Vapor Pressure: 0.0023mmHg at 25°C
• Boiling Point: 288.7°Cat760mmHg
• Flash Point: 107.5°C
• Density: 1g/cm³
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 186.104465066
• Heavy Atom Count: 14
• Complexity: 263

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of tert-Butyl(phenylacetylenyl)ketone

There total 25 articles about tert-Butyl(phenylacetylenyl)ketone 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: 99.0%

pivaloyl chloride (3282-30-2) + phenylacetylene (536-74-3) → 4,4-dimethyl-1-phenyl-1-pentyn-3-one (32398-67-7)

Guidance literature:

With bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide; triethylamine; In decane; toluene; at 110 ℃; for 4h;

DOI:10.1021/jo035761+

Reference yield: 98.0%

pivaloyl chloride (3282-30-2) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 4,4-dimethyl-1-phenyl-1-pentyn-3-one (32398-67-7)

Guidance literature:

With copper(l) chloride; In various solvent(s); at 80 ℃; for 5h;

DOI:10.1016/S0040-4039(97)00794-6

Reference yield: 93.0%

1-iodo-2-phenylethyne (932-88-7) + pivalaldehyde (630-19-3) → 4,4-dimethyl-1-phenyl-1-pentyn-3-one (32398-67-7)

Guidance literature:

With indium; In 1,2-dichloro-ethane; at 80 ℃; for 5h;

DOI:10.1016/S0040-4039(02)02635-7

upstream raw materials:

pivaloyl chloride

phenylacetylene

5-chloro-2,2,5,6,6-pentamethyl-heptan-3-one

lithium phenylacetylide

Downstream raw materials:

(Z)-4,4-dimethyl-1-phenylpent-1-en-3-one

(E)-benzylidenepinacolone

4,4-dimethyl-1-phenylpentan-3-one

Refernces

• 1、 Zhang, Lingchun,Chu, Yanle,Ma, Peizhi,Zhao, Shujuan,Li, Qiaoyan,Chen, Boya,Hong, Xuejiao,Sun, Jun. "Visible-light-mediated photocatalytic cross-coupling of acetenyl ketones with benzyl trifluoroborate". supporting information. p. 1073 - 1077. Retrieved 2020/02/22.
• 2、 Tsuzuki, Saori,Sakamoto, Ryu,Maruoka, Keiji. "Practical synthesis of α,β-Alkynyl ketones by oxidative alkynylation of aldehydes with hypervalent alkynyliodine reagents". supporting information. p. 633 - 636. Retrieved 2020/10/08.