Conditions | Yield |
---|---|
at 350℃; under 3.8 Torr; | 80% |
Conditions | Yield |
---|---|
In tetrachloromethane at 90 - 95℃; for 1h; | A n/a B 77% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydride In tetrahydrofuran; paraffin for 1h; Heating; | 60% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trifluoroacetic anhydride In dichloromethane at 20℃; for 6h; | 42% |
1,1,2,2-tetramethoxyethylene
2,2,6-trimethyl-4H-1,3-dioxin-4-one
A
2,3-dihydro-2,2,3,3-tetramethoxy-6-methyl-4H-pyran-4-one
B
Dehydracetic acid
Conditions | Yield |
---|---|
In xylene for 0.666667h; Heating; | A 38% B n/a |
2,2,6-trimethyl-4H-1,3-dioxin-4-one
1-phenylbutan-1,3-dione
A
3-benzoyl-2,6-dimethyl-4-pyrone
B
Dehydracetic acid
Conditions | Yield |
---|---|
at 120 - 130℃; for 4h; | A 36% B 0.49 g |
Conditions | Yield |
---|---|
Stage #1: acetic acid; benzene With trifluoroacetic anhydride In dichloromethane at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h; | A 36% B 18% |
Creatinine
acetyl chloride
A
N-(1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)acetamide
B
Dehydracetic acid
Conditions | Yield |
---|---|
A 25% B 10% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 4h; Ambient temperature; | A n/a B 15.6% C 22.4% |
2-methylene-4,4,5,5-tetramethyl-1,3-dioxolane
acetic anhydride
A
Essigsaeure-2-hydroxy-1,1,2-trimethylpropylester
B
Dehydracetic acid
Conditions | Yield |
---|---|
With dmap; water 1) 80 - 90 deg C, 2h, 2) 2h; Yield given. Multistep reaction; | A 15% B n/a |
With dmap; water 1) 80 - 90 deg C, 2h, 2) 2h; Yield given. Multistep reaction; | A n/a B 0.07 g |
Conditions | Yield |
---|---|
at 20℃; | 12% |
2-amino-1H-imidazol-4(5H)-one
acetyl chloride
A
1-acetylhydantoin
B
Dehydracetic acid
Conditions | Yield |
---|---|
A 9% B 10% |
Conditions | Yield |
---|---|
A 9% B 10% |
2-amino-5-phenyl-4-oxazolinone
acetyl chloride
A
Dehydracetic acid
B
2-acetamido-5-phenyl-4-oxazolinone
Conditions | Yield |
---|---|
With triethylamine In benzene from 0-5 deg C to boiling point; | A 10% B 5% |
With triethylamine In benzene for 5h; from 0-5 deg C to biling point; | A 10% B 5% |
1,4-dioxane
pyridine
Ketene
A
2-methyl-10a,11-dihydro-pyrano[2,3-b]quinolizine-4,5-dione
B
Dehydracetic acid
pyridine
4-methyleneoxetan-2-one
acetylacetone
Dehydracetic acid
Conditions | Yield |
---|---|
es erfolgt Polymerisation; |
4-methyleneoxetan-2-one
diethyl ether
A
1,1-diphenylethanol
B
acetophenone
C
Dehydracetic acid
Conditions | Yield |
---|---|
With 4-methyl-morpholine; pyridine; triethylamine Reagens 4: Natriumaethylat oder Natriumbutylat; | |
With basicene catalysts |
Conditions | Yield |
---|---|
With basicene catalysts | |
With 4-methyl-morpholine; pyridine; triethylamine Reagens 4: Natriumaethylat oder Natriumbutylat; |
4-methyleneoxetan-2-one
A
3,9-Diacetyl-4,5,10-trimethyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-2,8-dion
B
Dehydracetic acid
Conditions | Yield |
---|---|
With sodium phenoxide; benzene |
Conditions | Yield |
---|---|
With aluminium trichloride; nitrobenzene |
carbon suboxide
A
1,3,5-triacetyl-2,4,6-trihydroxybenzene
B
Dehydracetic acid
Conditions | Yield |
---|---|
beim Erhitzen im Vakuum; |
Conditions | Yield |
---|---|
bei der Destillation; | |
bei der Destillation unter gewoehnlichem Druck; |
3-acetoxy-crotonic acid ethyl ester
A
ethyl acetoacetate
B
ethyl acetate
C
Dehydracetic acid
Conditions | Yield |
---|---|
at 233℃; |
Conditions | Yield |
---|---|
With lead(IV) acetate; acetic acid |
Dehydracetic acid
2,6-dimethylpyridin-4-ol
Conditions | Yield |
---|---|
With ammonia In water at 120℃; for 0.333333h; Microwave irradiation; | 100% |
With ammonia In water at 120℃; for 0.333333h; Microwave irradiation; | 100% |
With ammonia In water at 120℃; for 0.333333h; microwave irradiation; | 100% |
Conditions | Yield |
---|---|
In tert-butyl methyl ether at 20℃; for 8h; | 100% |
Conditions | Yield |
---|---|
In ethanol; water 40-50°C, 3-4 h; pptn. on cooling, ppt. filtration off, washing (ethanol, ether), vaccum drying (over silica gel); elem. anal.; | 98% |
Dehydracetic acid
3-acetyl-5,6-dihydro-4-hydroxy-6-methyl-2-pyrone
Conditions | Yield |
---|---|
With pyridine; hydrogen; palladium on activated charcoal In benzene under 3102.9 Torr; for 40h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 95% |
4-chlorobenzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-[(2E)-(4-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 95% |
Conditions | Yield |
---|---|
In ethanol for 4h; Reflux; | 95% |
Conditions | Yield |
---|---|
In ethanol; water 40-50°C, 3-4 h; pptn. on cooling, ppt. filtration off, washing (ethanol, ether), vaccum drying (over silica gel); elem. anal.; | 94% |
4-nitrobenzaldehdye
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-nitrobenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 94% |
Conditions | Yield |
---|---|
In methanol mixt. Mn(OAc)2*4H2O and ligand in MeOH was refluxed for 5 h; solid was filtered, washed with MeOH, dried under vac. overnight; elem. anal.; | 93% |
3-Chlorobenzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-[(2E)-(3-chlorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 93% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating; | 92% |
Conditions | Yield |
---|---|
In benzene for 2h; Condensation; Isomerization; Heating; | 92% |
Conditions | Yield |
---|---|
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.; | 92% |
4-bromo-benzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-[ (2E)-(4-bromobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 92% |
4-fluorobenzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-[(2E)-(4-fluorobenzylidene)hydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 91% |
4-methoxy-6-methyl-5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5-ol
Dehydracetic acid
Conditions | Yield |
---|---|
In methanol at 25℃; diastereoselective reaction; | 91% |
Conditions | Yield |
---|---|
With magnesium at 85℃; | 90% |
With magnesium for 16h; Reflux; | 81% |
With magnesium for 10h; Heating; | 80% |
With magnesium methanolate for 8h; Heating; | 75% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating; | 90% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol for 4h; Heating; | 90% |
Conditions | Yield |
---|---|
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.; | 90% |
N-isocyaniminotriphenylphosphorane
3-methoxy-benzaldehyde
Dehydracetic acid
(2Z)-2,3-dihydro-3-hydroxy-2-[(2E)-(3-methoxybenzylidene)hydrazinylidene]-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 90% |
4-methyl-benzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-[(2E)-(4-methylbenzylidene)hydrazinylidene]-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 90% |
Conditions | Yield |
---|---|
In methanol for 4h; Reflux; | 90% |
Dehydracetic acid
3-Ethyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
Conditions | Yield |
---|---|
With hydrogenchloride; sodium cyanoborohydride In tetrahydrofuran | 89% |
With triethylsilane; lithium perchlorate; trifluoroacetic acid Reduction; | 83% |
With methanol; platinum Hydrogenation; |
Conditions | Yield |
---|---|
In ethanol metal acetate dissoln. in soln. of acid, N-compd. addn., stirring and heating (50°C); elem. anal.; | 89% |
pyridine-4-carbaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2,3-dihydro-3-hydroxy-3,6-dimethyl-2-{[ (2E)-(pyridin-4-yl)methylidene]hydrazinylidene}-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 89% |
benzaldehyde
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-[(2E)-benzylidenehydrazinylidene]-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 89% |
Conditions | Yield |
---|---|
With sodium methylate In methanol for 2h; Condensation; Isomerization; Heating; | 88% |
furfural
N-isocyaniminotriphenylphosphorane
Dehydracetic acid
(2Z)-2-{[(2E)-(furan-2-yl)methylidene]hydrazinylidene}-2,3-dihydro-3-hydroxy-3,6-dimethyl-4H-furo[3,2-c]pyran-4-one
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 4h; | 88% |
IUPAC Name: 3-Acetyl-6-methylpyran-2,4-dione
Canonical SMILES: CC1=CC(=O)C(C(=O)O1)C(=O)C
InChI: InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
InChIKey: PGRHXDWITVMQBC-UHFFFAOYSA-N
Molecular formula: C8H8O4
Molecular Weight: 168.15
EINECS: 212-227-4
Melting point: 111-113 °C(lit.)
Boiling Point: 332.6 °C at 760 mmHg
Flash Point: 150.6 °C
Index of Refraction: 1.489
Molar Refractivity: 38.43 cm3
Molar Volume: 133 cm3
Surface Tension: 41.9 dyne/cm
Density: 1.264 g/cm3
Enthalpy of Vaporization: 57.54 kJ/mol
Vapour Pressure: 0.000144 mmHg at 25 °C
storage temp.: 0-6 °C
Stability: Stable. Incompatible with oxidizing agents, bases, reducing agents.
Appearance: white to light yellow crystal powder
Classification Code of Methylacetopyronone (CAS NO.520-45-6): Agricultural Chemical; Fungicide, bactericide, wood preservativ ; Tumor data
Methylacetopyronone (CAS NO.520-45-6) is a pyrone derivative used as a fungicide and bactericide. It is used to reduce pickle bloating as a preservative for squash and strawberries. The sodium salt, sodium dehydroacetate, is often used in place of dehydroacetic acid because of its greater solubility in water. Industrially, it is also used as a plasticizer in a variety of synthetic resins.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 1186mg/kg (1186mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 98, 1950. | |
mouse | LD50 | oral | 1330mg/kg (1330mg/kg) | Shokuhin Eiseigaku Zasshi. Food Hygiene Journal. Vol. 12, Pg. 520, 1971. | |
rabbit | LDLo | skin | 5gm/kg (5000mg/kg) | Journal of the American College of Toxicology. Vol. 4(3), Pg. 123, 1985. | |
rat | LD50 | oral | 500mg/kg (500mg/kg) | World Review of Pest Control. Vol. 9, Pg. 119, 1970. |
Reported in EPA TSCA Inventory.
Poison by ingestion. Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Combustible when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xn
Risk Statements:
R22: Harmful if swallowed
Safety Statements:
S22: Do not breathe dust
WGK Germany: 1
RTECS: UP8050000
Methylacetopyronone (CAS NO.520-45-6), its Synonyms are 2H-Pyran-2,4(3H)-dione, 3-acetyl-6-methyl- ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione, ion(1-), ; Dehydroacetic Acid ; 3-Acety;-6-methylpyran-2,4(3H)-dione ; 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one ; 3-Acetyl-6-methyl-2,4-pyrandione ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione ; 3-Acetyl-6-methyl-2H-pyran-2,4(3H)-dione. enol form ; 3-Acetyl-6-methyldihydropyrandione-2,4 ; 2-Acetyl-5-hydroxy-3-oxo-4-hexenoic acid, delta-lactone .
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