Phorone

Base Information

• Chemical Name: Phorone
• CAS No.: 504-20-1
• Molecular Formula: C9H14 O
• Molecular Weight: 138.21
• Hs Code.: 2914190090
• European Community (EC) Number: 207-986-3
• ICSC Number: 1157
• NSC Number: 403517,38718
• UN Number: 1993
• UNII: 8F20OEI0MV
• DSSTox Substance ID: DTXSID1021584
• Nikkaji Number: J4.072J
• Wikipedia: Phorone
• Wikidata: Q612199
• Metabolomics Workbench ID: 55144
• ChEMBL ID: CHEMBL2766015
• Mol file: 504-20-1.mol

Synonyms:diisopropylideneacetone;phorone

Chemical Property of Phorone

Chemical Property:

• Vapor Pressure: 0.38 mm Hg ( 20 °C)
• Melting Point: 23-26 °C(lit.)
• Refractive Index: n20/D 1.497(lit.)
• Boiling Point: 198-199 °C(lit.)
• Flash Point: 79 ºC
• PSA: 17.07000
• Density: 0.885
• LogP: 2.48790
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 138.104465066
• Heavy Atom Count: 10
• Complexity: 157
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

DiisopropylideneAcetone ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC(=CC(=O)C=C(C)C)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Uses: Diisopropylidene Acetone is a reagent used in the preparation of biaryls by Suzuki-Miyaura cross coupling reaction.

Technology Process of Phorone

There total 112 articles about Phorone 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%

Phenyl vinyl ketone (768-03-6,26742-84-7) → phorone (504-20-1) + isophorol (470-99-5)

Guidance literature:

With aluminium tris(2,6-diphenylphenoxide); n-butyllithium; diisobutylaluminium hydride; In toluene; at -78 - 25 ℃; for 0.25h; Yields of byproduct given;

DOI:10.1021/jo960161e

Reference yield: 90.0%

1-nitroso-2,2,6,6-tetramethyl-4-piperidone (640-01-7) → phorone (504-20-1)

Guidance literature:

With sodium isopropylate; In isopropyl alcohol; at 20 - 60 ℃; for 6h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 90.0%

N-benzyl-2,2,6,6-tetramethyl-piperidin-4-one (52981-86-9) → phorone (504-20-1)

Guidance literature:

With C₂₀H₂₉ClO₂P₂Pt; In water; toluene; at 105 ℃; for 5h; Reagent/catalyst;

DOI:10.1039/c9ra08709e

upstream raw materials:

6-hydroxy-2,6-dimethyl-hept-2-en-4-one

3,5-dibromo-2,6-dimethylhepta-2,5-dien-4-one

2,6-dihydroxy-2,6-dimethyl-heptan-4-one

oxalic acid

Downstream raw materials:

diisobutyl ketone

1,1,2,2-tetraphenylethylene

1,1,4,4-tetraphenyl-butane

dimedone

Refernces

• 1、 Nakada,Y. et al.. "-". . p. 1072 - 1074. Retrieved 1976.
• 2、 Fresia, Marvin,Lindel, Thomas. "Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G". supporting information. . Retrieved 2022/02/05.
• 3、 Orel, Vladimir B.,Vitkovskaya, Nadezhda M.,Bobkov, Alexander S.,Semenova, Nadezhda V.,Schmidt, Elena Yu.,Trofimov, Boris A.. "Aldol Condensation Versus Superbase-Catalyzed Addition of Ketones to Acetylenes: A Quantum-Chemical and Experimental Study". . p. 7439 - 7449. Retrieved 2021/06/21.