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Diketene information


Diketene
Names
Preferred IUPAC name
4-Methylideneoxetan-2-one
Other names
γ-Methylenepropiolactone
Identifiers
CAS Number
  • 674-82-8 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 12140 checkY
ECHA InfoCard 100.010.562 Edit this at Wikidata
EC Number
  • 211-617-1
PubChem CID
  • 12661
RTECS number
  • RQ8225000
UNII
  • 0DZ97C3Z7D
UN number 2521
CompTox Dashboard (EPA)
  • DTXSID9027289 Edit this at Wikidata
InChI
  • InChI=1S/C4H4O2/c1-3-2-4(5)6-3/h1-2H2 checkY
    Key: WASQWSOJHCZDFK-UHFFFAOYSA-N checkY
  • InChI=1/C4H4O2/c1-3-2-4(5)6-3/h1-2H2
    Key: WASQWSOJHCZDFK-UHFFFAOYAM
SMILES
  • O=C1OC(=C)C1
Properties
Chemical formula
C4H4O2
Molar mass 84.074 g·mol−1
Density 1.09 g cm−3
Melting point −7 °C (19 °F; 266 K)
Boiling point 127 °C (261 °F; 400 K)
Viscosity 0.88 mPa.s
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Signal word
Danger
Hazard statements
H226, H301, H302, H315, H318, H330, H331, H332, H335
Precautionary statements
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P284, P301+P310, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P330, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 33 °C (91 °F; 306 K)
Autoignition
temperature
275
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene, H2C=C=O. Diketene is a member of the oxetane family. It is used as a reagent in organic chemistry.[1] It is a colorless liquid.

  1. ^ Beilstein E III/IV 17: 4297.

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Diketene

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Diketene is an organic compound with the molecular formula C4H4O2, and which is sometimes written as (CH2CO)2. It is formed by dimerization of ketene,...

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Claisen condensation

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work on the reaction in 1887. The reaction has often been displaced by diketene-based chemistry, which affords acetoacetic esters. At least one of the...

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Ethyl acetoacetate

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large scale, ethyl acetoacetate is industrially produced by treatment of diketene with ethanol. The small scale preparation of ethyl acetoacetate is a classic...

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Acetoacetic acid

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may be prepared by the hydrolysis of diketene. Its esters are produced analogously via reactions between diketene and alcohols, and acetoacetic acid can...

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C4H4O2

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molecular formula C4H4O2 may refer to: Cycloprop-2-ene carboxylic acid Diketene Dioxins 1,2-Dioxin 1,4-Dioxin 2-Furanone Methyl propiolate Tetrolic acid...

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Ester

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[(C6H4)(CO2)2(C2H4)]n + 2n CH3OH A subset of transesterification is the alcoholysis of diketene. This reaction affords 2-ketoesters. (CH2CO)2 + ROH → CH3C(O)CH2CO2R Alkenes...

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Pigment yellow 83

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from three components. Treatment of 2,5-dimethoxy-4-chloroaniline with diketene gives an acetoacetylated aniline. This compound is then coupled to the...

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Lonza Group

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Lonza converted most of its ketene to diketene, which was then converted to a range of chemical precursors. Diketene capacity rose to 18'000t per year in...

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Ketene

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propen-2-yl acetate: At room temperature, ketene quickly dimerizes to diketene, but the ketene can be recovered by heating: Ketenes can react with alkenes...

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Alkyl ketene dimer

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oxetan-2-one, which is also the central structural element of propiolactone and diketene. Attached to the oxetane ring of technically relevant alkyl ketene dimers...

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Malonic anhydride

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oxetane. Malonic anhydride was first synthesized in 1988 by ozonolysis of diketene. Some derivatives, such as 3,3-dimethyl-oxetane-2,4-dione, are known. Cotton...

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Dehydroacetic acid

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organic solvents. It is prepared by the base-catalysed dimerization of diketene. Commonly used organic bases include imidazole, DABCO, and pyridine. Industrially...

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Benzimidazolinone

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dyes and pigments. For example 4-amino-2-benzimidazolinone condenses with diketene to give the acetoacetanilide, which undergoes diazo coupling with various...

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Chloroacetone

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Chloroacetone may be synthesized from the reaction between chlorine and diketene, or by the chlorination of acetone. Chloroacetone is used to make dye couplers...

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Acetoacetanilide

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crystallography. Acetoacetanilide is prepared by acetoacetylation of aniline using diketene. Many analogues have been prepared. To make the dyes, acetoacetanilides...

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Polyorthoester

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transesterification of orthoesters with diols or by polyaddition between a diol and a diketene acetal, such as 3,9-diethylidene-2,4,8,10-tetraoxaspiro[5.5]undecane. Polyorthoesters...

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Pigment Yellow 81

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synthesized from three components. Treatment of 2,4-dimethylaniline with diketene gives an acetoacetylated aniline. This compound is then coupled to the...

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Ethenone

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prepared for each use and processed immediately, otherwise a dimerization to diketene occurs or it reacts to polymers that are difficult to handle. The polymer...

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Isophytol

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by palladium catalysis results in 3-methyl-1-buten-3-ol. Reaction with diketene or acetic acid ester creates the acetoacetate; thermal reaction leads to...

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Pigment Yellow 16

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20040. The compound is obtained via acetoacetylation of o-tolidine using diketene. The resulting bisacetoacetylated compound is coupled with two equiv of...

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Penem

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II. Synthesis of 3-acetyl-2-azetidinones by (2 + 2) cycloaddition of diketene and Schiff bases". Chemical & Pharmaceutical Bulletin. 40 (5): 1094–7....

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List of UN numbers 2501 to 2600

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2519 ? (UN No. no longer in use) UN 2520 3 Cyclooctadienes UN 2521 6.1 Diketene, inhibited UN 2522 6.1 2-Dimethylaminoethyl methacrylate UN 2523 ? (UN...

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Alkenylsuccinic anhydrides

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of the cyclic carboxylic anhydride structure in the ASA compared to the diketene structure in AKD. This is accompanied by the much faster hydrolysis in...

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Streptomyces fimbriatus

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new metabolite from Streptomyces Fimbriatus via asymmetric reaction of diketene with 2,4-hexadienal promoted by chiral Schiff base-titanium alkoxide complexes"...

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Danheiser benzannulation

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intermediates cannot be isolated due to their high reactivity to form diketenes. These rearrangements are performed in the presence of unsaturated compounds...

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