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:

Dehydracetic acid

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

3-oxo-N-(pyrid-2-yl)butyramide

N-(4-methyl-2-pyridinyl)-3-oxobutanamide

Refernces

Synthesis of 1-substituted-6-methyluracils.

10.1248/cpb.51.1025

The study focuses on the design and synthesis of uracil-based heterocyclic compounds, which are significant in organic and medicinal chemistry due to their therapeutic potential and presence in natural products with strategic biological functions. The researchers synthesized various 6-methyluracil derivatives with different substituents at the 1-position, aiming to create new biologically active compounds. Key chemicals used include substituted ureas, diketene, and piperazine derivatives, which serve as starting materials and building blocks for the synthesis of the target uracil derivatives. The purpose of these chemicals is to create a range of compounds with potential pharmacological actions, such as antineoplastic, antihypertensive, anti-inflammatory, antiviral, and reverse transcriptase inhibitory effects. The study also details the synthetic strategies and confirms the structures of the synthesized compounds through analytical and spectroscopic data.

Memory of chirality effects in aldol cyclisations of 1-(3-oxobutyryl) derivatives of L-4-oxaproline and L-proline isopropyl esters

10.1016/S0040-4039(02)00632-9

The research investigates the stereoretentive C-C bond formations in aldol cyclisations of 1-(3-oxobutyryl) derivatives of L-4-oxaproline and L-proline isopropyl esters. The purpose of the study was to explore the possibility of simplifying the self-generation of stereocenters in the synthesis of β-C-substituted β-amino acids, a class of compounds with wide-ranging biological properties, by leveraging the chirality memory effects observed in enolate intermediates. The researchers concluded that the aldol cyclisations conducted on oxaproline and proline scaffolds demonstrated significant retention of configuration, extending the scope of stereoinductions attributable to axially chiral enolate intermediates. Key chemicals used in the process included L-serine, isopropyl esters, L-oxaproline, L-proline, diketene, triethylamine, and potassium cyanide, among others. The study's findings are significant as they provide insights into the role of axially chiral enolate intermediates in stereoselective synthesis and contribute to the development of more efficient methods for producing enantioenriched β-C-substituted β-amino acids embedded in heterocyclic frameworks.