4-Hydroxy-6-methyl-2-pyrone supplier

Name
4-Hydroxy-6-methyl-2-pyrone
EINECS 211-619-2
CAS No. 675-10-5
Article Data43
CAS DataBase
Density 1.348 g/cm³
Solubility 8.60 g/L (20 °C) in water
Melting Point 188-190 °C (dec.)(lit.)
Formula C₆H₆O₃
Boiling Point 239.074 °C at 760 mmHg
Molecular Weight 126.112
Flash Point 108.677 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2H-Pyran-2-one,4-hydroxy-6-methyl-;Sorbicacid, 3,5-dihydroxy-, d-lactone (6CI,7CI);Triacetic acid lactone;4-Hydroxy-6-methyl-2H-pyran-2-one;4-Hydroxy-6-methyl-a-pyrone;4-Hydroxy-6-methylpyran-2-one;6-Methyl-4-hydroxy-2-pyrone;NSC 34625;
PSA 50.44000
LogP 0.65380

Synthetic route

: 771-03-9
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With sulfuric acid In water at 130℃; for 0.216667h; Flow reactor;	96%
With sulfuric acid at 130℃; for 0.25h;	90%
With sulfuric acid at 130℃; for 0.25h; Cooling with ice;	89%

: 2140-49-0
3,5-dioxohexanoic acid

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With trifluoroacetic acid; trifluoroacetic anhydride for 0.5h; Heating;	94%
With 1,1'-carbonyldiimidazole In diethyl ether at 0℃; for 2h; Yield given;

: 130473-38-0
2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
In toluene at 100℃; for 0.5h;	92%
In toluene for 0.166667h; Heating;	66%
In toluene Reflux;

: 84257-12-5
2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
In 1,4-dioxane for 2h; Heating;	89%

: 771-03-9
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 3265-58-5
2,6-dimethyl-4-oxopyran-3-carboxylic acid

Conditions

Conditions	Yield
With sulfuric acid In water at 130℃; for 0.25h; Temperature; Flow reactor;	A 81% B 6 %Spectr.

: 4-Hydroxy-6-trimethylsilanylmethyl-pyran-2-one

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;	80%

: 143456-22-8
2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
In toluene Heating;	76%

: 13735-81-4
1-styrenyloxytrimethylsilane

: 1663-67-8
malonoyl dichloride

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
	67%

: 4188-63-0
isopropenyl isopropyl ether

: 1663-67-8
malonoyl dichloride

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 64507-45-5
Phloroglucinmonoisopropylether

Conditions

Conditions	Yield
In diethyl ether	A 24% B 65%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 520-45-6
Dehydracetic acid

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
In sulfuric acid; water at 120℃; for 1.5h; Deacetylation;	60%

: 108-24-7
acetic anhydride

: 2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 7118-95-8
N-(5-methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-acetamide

Conditions

Conditions	Yield
With zinc(II) chloride at 23 - 25℃; for 72h;	A 30% B 57%

...Expand

: 108-24-7
acetic anhydride

: 75843-20-8
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 13053-83-3
N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide

Conditions

Conditions	Yield
for 0.166667h; Heating;	A 50% B 55%

...Expand

: 123-62-6
propionic acid anhydride

: 2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-propionamide

Conditions

Conditions	Yield
With zinc(II) chloride at 23 - 25℃; for 45h;	A n/a B 54%

...Expand

: 123-62-6
propionic acid anhydride

: 75843-20-8
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone

A: 25958-41-2
N-(5-methyl-1,3,4-thiadiazol-2-yl)-propionamide

B: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
at 120 - 130℃; for 0.25h;	A 53% B 45%

...Expand

: 116-11-0
2-Methoxypropene

: 1663-67-8
malonoyl dichloride

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 2174-64-3
5-methoxyresorcinol

Conditions

Conditions	Yield
In diethyl ether	A 43% B 52%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 771-03-9
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

C: 7159-68-4
5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine

Conditions

Conditions	Yield
In ethanol; acetic acid for 2.41667h; Heating;	A 20% B n/a C 44%

...Expand

: 926-66-9
2-ethoxyprop-1-ene

: 1663-67-8
malonoyl dichloride

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 28334-98-7
Phloroglucinmonoethylether

Conditions

Conditions	Yield
In diethyl ether	A 42% B 43%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 771-03-9
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 29736-80-9
3,5-dioxohexanoic acid methyl ester

C: 105-45-3
acetoacetic acid methyl ester

Conditions

Conditions	Yield
With sodium methylate In methanol; benzene for 18h; Heating;	A 7% B 18% C 16%

...Expand

: 908094-04-2
phenyldiazomethane

: 93338-99-9
4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: meso-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

: (+/-)-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

Conditions

Conditions	Yield
Multistep reaction. Yields of byproduct given;

...Expand

: 29736-80-9
3,5-dioxohexanoic acid methyl ester

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With sulfuric acid at 80℃;

α-acetyl-allene-α.γ-dicarboxylic acid ester: α-acetyl-allene-α.γ-dicarboxylic acid ester

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With hydrogenchloride
With potassium hydroxide

: 72-89-9
acetylcoenzyme A

: 524-14-1
S-(hydrogen malonyl)coenzyme A

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
With 6-hydroxymellein synthase from carrot root cells; sodium chloride; Coenzyme A; NADPH In water at 37℃; pH=6.0; Enzyme kinetics; Further Variations:; Reagents; pH-values;
With 2-pyrone synthase

: 72-89-9
S-acetyl coenzyme A

: malonyl coenzyme A

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 10310-07-3
4-hydroxy-6-(2-oxopropyl)pyran-2-one

Conditions

Conditions	Yield
With type III polyketide synthase RppA from S. griseus; 2-hydroxyethanethiol In various solvent(s) at 37℃; for 2h; pH=7.5;	A 1 % Turnov. B 5 % Turnov.

...Expand

: 33176-11-3
2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / MeONa / benzene / 18 h / Heating 2: conc. H2SO4 / 80 °C View Scheme

: 123-54-6
acetylacetone

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) butyl-lithium, di-isopropylamine / 1.) THF, hexane, -78 deg C, 30 min; 2.) THF, hexane, up to RT 2: 94 percent / trifluoroacetic acid, trifluoroacetic anhydride / 0.5 h / Heating View Scheme

: 26567-75-9
acetylacetone enol

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: N,N'-carbonyldiimidazole (CDI) / diethyl ether / 2 h / 0 °C View Scheme

: 72-89-9
acetylcoenzyme A

: 524-14-1
S-(hydrogen malonyl)coenzyme A

A: 6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one

B: 675-10-5
4-hydroxy-6-methyl-2-pyron

C: 10310-07-3
4-hydroxy-6-(2-oxopropyl)pyran-2-one

D: 83095-25-4
4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone

Conditions

Conditions	Yield
Stage #1: acetylcoenzyme A; S-(hydrogen malonyl)coenzyme A With recombinant N-His-tagged hexaketide synthase of Drosophyllum lusitanicum Link at 30℃; for 1h; pH=7.0; aq. buffer; Enzymatic reaction; Stage #2: Acidic aq. solution;

...Expand

: 524-14-1
S-(hydrogen malonyl)coenzyme A

A: 675-10-5
4-hydroxy-6-methyl-2-pyron

B: 21534-03-2
(E)-4-hydroxy-6-(prop-1-en-1-yl)-2H-pyran-2-one

C: 1187429-74-8
C10H10O3

D: 676579-01-4
1,3E,5E,7E,9E,11E,13E-pentadecaheptaene

E: 1187429-75-9
C12H12O3

F: 1187429-73-7
(3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one

G: 1187429-71-5
3-oxohexadeca-4,6,8,10,12,14-hexaenoic acid

Conditions

Conditions	Yield
With calicheamicin polyketide synthase CalE8; calicheamicin thioesterase CalE7; NADPH In glycerol at 24℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction;

...Expand

: 136801-79-1
6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

: 675-10-5
4-hydroxy-6-methyl-2-pyron

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Dess-Martin periodane / 20 °C 2: toluene / Reflux View Scheme
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C 2: toluene / 0.5 h / 100 °C View Scheme

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 64-19-7
acetic acid

: 771-03-9
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene Reflux;	100%
With dmap; dicyclohexyl-carbodiimide In toluene at 100℃; for 2h;	86.4%
With dmap; dicyclohexyl-carbodiimide In toluene at 20 - 100℃;

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 27751-97-9
4-hydroxy-6-methyl-tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
palladium 10% on activated carbon In butan-1-ol at 49.84℃; under 15514.9 Torr; for 8h; Product distribution / selectivity;	99.4%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 123-11-5
4-methoxy-benzaldehyde

: 82420-03-9
3,3’-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 9h;	99%
With nano Fe3O4 supported carbamoylsulfamic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 1h; Reagent/catalyst; Green chemistry;	96%
With piperidine; acetic acid In ethanol at 60℃; for 2.5h;	95%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 75-07-0
acetaldehyde

: 92405-61-3
1,1-bis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethane

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol for 24h; Ambient temperature;	99%
In chloroform at 40℃; for 16h;	60%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 1192-88-7
1-cyclohexene-1-carboxaldehyde

: 194796-93-5
3-Methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;	99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%
With L-proline In ethyl acetate at 70℃; for 24h;	76%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 67-64-1
acetone

: 672-89-9
4-methoxy-6-methyl-2H-pyran-2-one

Conditions

Conditions	Yield
With potassium carbonate In various solvent(s) for 8h; Methylation; Heating;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 123-73-9
trans-Crotonaldehyde

: 92405-72-6
2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%
With piperidine; acetic anhydride In ethyl acetate at -10 - 85℃;	66%
Stage #1: trans-Crotonaldehyde With piperidine; acetic anhydride In ethyl acetate at -10 - 85℃; Stage #2: 4-hydroxy-6-methyl-2-pyron In ethyl acetate at 85℃; Further stages.;	66%
With piperdinium acetate; sodium sulfate In ethyl acetate at 80 - 90℃; for 18h;

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 107-86-8
3,3-dimethyl acrylaldehyde

: 220633-52-3
2,2,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;	99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%
In neat (no solvent) at 20 - 120℃; for 10h; Microwave irradiation; Green chemistry;	94%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 488-17-5
3-methylbenzene-1,2-diol

: 7,8-dihydroxy-3,6-dimethyl-1H-pyrano[4,3-b]benzofuran-1-one

Conditions

Conditions	Yield
With Trametes versicolor laccase; oxygen In acetate buffer at 20℃; for 3.5h; pH=4.37;	99%
With laccase from Trametes versicolor at 20℃; for 3h; pH=4.4; aq. acetate buffer; Enzymatic reaction; regioselective reaction;	99%
With sodium acetate; potassium hexacyanoferrate(III) In water	80%
With sodium acetate In water Electrochemical reaction;	67%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 123-73-9
crotonaldehyde

: 92405-72-6
2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;	99%
With 4 A molecular sieve In dichloromethane	53%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 931-59-9
benzenesulfenyl chloride

: 53603-21-7
4-hydroxy-6-methyl-3-(phenylsulfanyl)-2H-pyran-2-one

Conditions

Conditions	Yield
With hydrogenchloride In benzene	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 1115-11-3
2-methyl-2-pentenal

: 2,3,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;	99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 5392-40-5
(E/Z)-3,7-dimethyl-2,6-octadienal

: 2,7-dimethyl-2-(4-methyl-pent-3-enyl)-2H-pyrano[4,3-b]pyran-5-one

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;	99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 90-59-5
3,5-Dibromosalicylaldehyde

: 98253-83-9
6,8-dibromo-3-acetoacetylcoumarin

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 90℃; for 4h;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 2548-87-0, 20664-46-4, 2363-89-5
2-octen-1-al

: 1198426-98-0
C14H18O3

Conditions

Conditions	Yield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 107969-78-8
methyl benzylidenepyruvate

: (R)-methyl 2-hydroxy-7-methyl-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

Conditions

Conditions	Yield
With C29H29F6N3OS In diethyl ether at 20℃; for 1h; Michael addition; optical yield given as %ee; enantioselective reaction;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 42393-11-3
methyl (E)-2-oxo-4-(4-chlorophenyl)but-3-enoate

: (R)-methyl 4-(4-chlorophenyl)-2-hydroxy-7-methyl-5-oxo-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

Conditions

Conditions	Yield
With C29H29F6N3OS In diethyl ether at 20℃; for 1h; Michael addition; optical yield given as %ee; enantioselective reaction;	99%

: 504-29-0
2-aminopyridine

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9
pyrimidine-2,4,5,6(1H,3H)-tetraone

: 1367747-80-5
2-aminopyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions

Conditions	Yield
In chloroform for 5h; Reflux;	99%

...Expand

: 504-29-0
2-aminopyridine

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 2757-85-9
1,3-dimethylalloxan

: 1367748-29-5
2-aminopyridinium 3-(5-hydroxy-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions

Conditions	Yield
In chloroform for 18h; Reflux;	99%

...Expand

: 1603-41-4
(5-methyl-pyridin-2-yl)amine

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9
pyrimidine-2,4,5,6(1H,3H)-tetraone

: 1367748-08-0
2-amino-5-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions

Conditions	Yield
In chloroform for 5h; Reflux;	99%

...Expand

: 1603-40-3
3-methylpyridin-2-ylamine

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9
pyrimidine-2,4,5,6(1H,3H)-tetraone

: 1367748-01-3
2-amino-3-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions

Conditions	Yield
In chloroform for 3h; Reflux;	99%

...Expand

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 143693-24-7
(R/S)-1,2-Butandiol-1-<(4-methylbenzol)sulfonat>

: 1642145-05-8
4-[1-(4-toluenesulfonyloxy)but-2-yloxy]-6-methyl-2-pyrone

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 25℃; Mitsunobu Displacement; Inert atmosphere;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 998-40-3
tributylphosphine

: 1761-61-1
5-bromosalicyclaldehyde

: 3-((5-bromo-2-hydroxyphenyl)(tributylphosphonio)methyl)-6-methyl-2-oxo-2H-pyran-4-olate

Conditions

Conditions	Yield
With pyrrolidine; benzoic acid In tetrahydrofuran at 30℃; for 5h; Schlenk technique; Inert atmosphere;	99%

...Expand

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: N-(4-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)pivalamide

: N-(4-(7-methyl-5-oxo-2,4-diphenyl-2H,5H-pyrano[4,3-b]pyran-2-yl)phenyl)pivalamide

Conditions

Conditions	Yield
With diphenyl hydrogen phosphate In dichloromethane at 20℃; for 2h;	99%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 2446-83-5
di-isopropyl azodicarboxylate

: 136984-23-1
1-tert-butyldimethylsilyloxy-2-hydroxybutane

: 1259313-03-5
4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone

Conditions

Conditions	Yield
Stage #1: 4-hydroxy-6-methyl-2-pyron; 1-tert-butyldimethylsilyloxy-2-hydroxybutane With triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	98.4%

...Expand

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 136984-23-1
1-tert-butyldimethylsilyloxy-2-hydroxybutane

: 1259313-03-5
4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 25℃; Mitsunobu Displacement; Inert atmosphere;	98.4%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 99-61-6
3-nitro-benzaldehyde

: 132559-96-7
3,3'-((3-nitrophenyl)methylene)bis(4-hydroxy-6-methyl-2H-pyran-2-one)

Conditions

Conditions	Yield
With nano Fe3O4 supported 2-carbamoylhydrazine-1-sulfonic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 0.666667h; Reagent/catalyst; Green chemistry;	98%
With sodium dodecyl-sulfate In water at 90℃; for 6h;	93%
With Fe3O4(at)SiO2/(CH2)3-[imidazolium-SO3H]Cl at 90℃; for 0.416667h; Green chemistry;	91%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 100-52-7
benzaldehyde

: 16929-83-2
4,4'-dihydroxy-6,6'-dimethyl-3,3'-(phenylmethylene)bis(pyran)-2,2'-dione

Conditions

Conditions	Yield
With piperidine; acetic acid In ethanol for 2h;	98%
With nano Fe3O4 supported carbamoylsulfamic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 0.266667h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Green chemistry;	95%
With Fe3O4(at)SiO2/(CH2)3-[imidazolium-SO3H]Cl at 90℃; for 0.25h; Green chemistry;	94%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 90-02-8
salicylaldehyde

: 13252-79-4
(1-(2-oxo-2H-chromen-3-yl)butane-1,3-dione)

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 90℃; for 4h;	98%
With β‐cyclodextrin In water at 70℃; for 0.5h; Green chemistry;	97%
molecular sieve In ethanol for 0.166667h; Heating;	89%

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 100-46-9
benzylamine

: 84259-92-7
(Z)-N-benzyl-5-(benzylamino)-3-oxohex-4-enamide

Conditions

Conditions	Yield
In ethanol for 4h; Reflux;	98%
In methanol for 1h; Heating; 1/1 proportion;

4-Hydroxy-6-methyl-2-pyrone Chemical Properties

Molecular Structure of Triacetic acid lactone (CAS NO.675-10-5):

IUPAC Name: 2-Hydroxy-6-methylpyran-4-one
Canonical SMILES: CC1=CC(=O)C=C(O1)O
InChI: InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,8H,1H3
InChIKey: OOKCZXGEYPSNIM-UHFFFAOYSA-N
Molecular Weight: 126.11004 [g/mol]
Molecular Formula: C₆H₆O₃
XLogP3: -0.4
H-Bond Donor: 1
H-Bond Acceptor: 3
EINECS: 211-619-2
Product Categories: API intermediates
Appearance: white to light yellow crystal powder
Melting Point: 188-190 °C (dec.)(lit.)
Water Solubility: 8.60 g/L (20 °C )
Index of Refraction: 1.561
Molar Refractivity: 30.292 cm³
Molar Volume: 93.546 cm³
Surface Tension: 51.792 dyne/cm
Density: 1.348 g/cm³
Flash Point: 108.677 °C
Enthalpy of Vaporization: 55.315 kJ/mol
Boiling Point: 239.074 °C at 760 mmHg
Vapour Pressure: 0.007 mmHg at 25 °C
Classification Code: Drug / Therapeutic Agent; TSCA Flag P [A commenced PMN (Premanufacture Notice) substance]

4-Hydroxy-6-methyl-2-pyrone Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	subcutaneous	3200mg/kg (3200mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 128, Pg. 126, 1960.

4-Hydroxy-6-methyl-2-pyrone Consensus Reports

Reported in EPA TSCA Inventory.

4-Hydroxy-6-methyl-2-pyrone Safety Profile

Safety Information of Triacetic acid lactone (CAS NO.675-10-5):
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UQ1000000
Hazard Note: Irritant

4-Hydroxy-6-methyl-2-pyrone Specification

Triacetic acid lactone (CAS NO.675-10-5), its Synonyms are 4-Hydroxy-6-methyl-2H-pyran-2-one ; 6-Methyl-4-hydroxypyron-(2) ; 2H-Pyran-2-one, 4-hydroxy-6-methyl- ; 4-Hydroxy-6-methyl-2-pyrone ; 4-Hydroxy-6-methylpyran-4-one .

Product Name

4-Hydroxy-6-methyl-2-pyrone

Synthetic route

4-Hydroxy-6-methyl-2-pyrone Chemical Properties

4-Hydroxy-6-methyl-2-pyrone Toxicity Data With Reference

4-Hydroxy-6-methyl-2-pyrone Consensus Reports

4-Hydroxy-6-methyl-2-pyrone Safety Profile

4-Hydroxy-6-methyl-2-pyrone Specification

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