Diketene

Base Information

• Chemical Name: Diketene
• CAS No.: 674-82-8
• Deprecated CAS: 2130-41-8,6842-10-0,6144-29-2
• Molecular Formula: C4H4O2
• Molecular Weight: 84.0746
• European Community (EC) Number: 211-617-1
• ICSC Number: 1280
• NSC Number: 93783
• UN Number: 2521
• UNII: 0DZ97C3Z7D
• DSSTox Substance ID: DTXSID9027289
• Nikkaji Number: J1.226B
• Wikipedia: Diketene
• Wikidata: Q418541
• Mol file: 674-82-8.mol

Synonyms:diketene

Chemical Property of Diketene

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 7.9 mm Hg ( 20 °C)
• Melting Point: -7.5 °C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 127.4 °C at 760 mmHg
• Flash Point: 97.9 °C
• PSA: 26.30000
• Density: 1.10 g/cm³
• LogP: 0.44700
• Storage Temp.: 2-8°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 84.021129366
• Heavy Atom Count: 6
• Complexity: 104
• Transport DOT Label: Poison Inhalation Hazard Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

Diketene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-20-40-36/37/38
• Safety Statements: 3-36/37-33-24/25-23-16-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: C=C1CC(=O)O1
• 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.
• Effects of Short Term Exposure: The substance may be irritating to the respiratory tract, eyes and skin.
• Uses: Diketene is used as a reactant in the manufacture of paper and control of its sizing. In addition its used in the preparation of potent and selective inhibitor of histone methyltransferase EZH2 in the treatment of B-Cell lymphomas.

Technology Process of Diketene

There total 34 articles about Diketene 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: 83.0%

bis(triphenylphosphine)-3,3-dimethylnickelacyclobutane → 4-methyleneoxetan-2-one (674-82-8,2130-41-8) + bis(triphenylphosphine)nickel(0) dicarbonyl (13007-90-4) + isobutene (115-11-7,15220-85-6)

Guidance literature:

With carbon monoxide; In toluene; High Pressure; 5 atm CO, 50°C, 1 h; pptn. of complex;

DOI:10.1016/0022-328X(80)83011-7

Reference yield: 75.0%

Ketene (463-51-4) → 4-methyleneoxetan-2-one (674-82-8,2130-41-8)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In hexane; at -15 - -10 ℃; for 3.5h;

DOI:10.1007/BF00798288

Reference yield:

N-(3'-methoxyphenyl)-3-oxobutanamide (25233-47-0) → 4-methyleneoxetan-2-one (674-82-8,2130-41-8) + m-Anisidine (536-90-3,918666-97-4)

Guidance literature:

In cyclohexane; at 25 ℃; Equilibrium constant;

upstream raw materials:

Ketene

acetic anhydride

ethylmagnesium bromide

N-acetylphthalimide

Downstream raw materials:

N-(2-mercapto-ethyl)-acetoacetamide

1-(morpholin-4-yl)butane-1,3-dione

Dehydracetic acid

1-<2,4-Dimethyl-pyrryl-(5)>-butandion-(1,3)

Refernces

• 1、 Nguyen, Henry,Ma, Gil,Gladysheva, Tatiana,Fremgen, Trisha,Romo, Daniel. "Bioinspired total synthesis and human proteasome inhibitory activity of (-)-salinosporamide A, (-)-homosalinosporamide A, and derivatives obtained via organonucleophile promoted bis-cyclizations". scheme or table. p. 2 - 12. Retrieved 2011/03/23.
• 2、 Adam, Waldemar,Kliem, Ulrike,Lucchini, Vittorio. "Preparative UV-VIS Laser Photochemistry: Photocycloadditions of Methylenelactones with Benzophenone and p-Benzoquinone. Oxygen Trapping of Paterno-Buechi Triplet 1,4-Diradicals as Model Reactions for Quinghaosu-Type 1,2,4-Trioxanes". . p. 869 - 876. Retrieved 2007/10/02.