Tetronic acid supplier | CasNO.4971-56-6

Name
TETRONIC ACID
EINECS 225-617-4
CAS No. 4971-56-6
Article Data22
CAS DataBase
Density 1.375 g/cm³
Solubility
Melting Point 139-140 °C (dec.)
Formula C₄H₄O₃
Boiling Point 324.3 °C at 760 mmHg
Molecular Weight 100.074
Flash Point 151.1 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Acetoaceticacid, 4-hydroxy-, g-lactone (7CI);Butanoic acid, 4-hydroxy-3-oxo-, g-lactone;Tetrahydrofuran-2,4-dione;Tetrahydrofuran-3,5-dione;
PSA 43.37000
LogP -0.49760

Synthetic route

: 638-07-3
ethyl (2-chloroaceto)acetate

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With potassium acetate; acetic acid at 80 - 90℃; for 12h;	45%

: 1192-50-3
3-bromo-furan-2,4-dione

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With sodium carbonate Behandeln mit Natriumamalgam unter Einleiten von Kohlendioxyd und anschliessend Behandeln mit Schwefelsaeure;
With sodium carbonate anschliessend Hydrierung an Palladium/Kohle;

: 1192-50-3
3-bromo-furan-2,4-dione

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 167644-70-4
[3,3']bifuryl-2,4,2',4'-tetraone

Conditions

Conditions	Yield
With sodium amalgam

: 64-17-5
ethanol

: 2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 67-64-1
acetone

...Expand

: 36717-62-1
2,4-dioxo-tetrahydro-furan-3-carboxylic acid ethyl ester

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide Ansaeuern mit wss. Salzsaeure;

: 22273-65-0
4-(phenylamino)furan-2(5H)-one

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 62-53-3
aniline

Conditions

Conditions	Yield
With water at 25℃; Rate constant; Mechanism;

4-oxo-2-imino-tetrahydrofuran-carboxylic acid-(3): 4-oxo-2-imino-tetrahydrofuran-carboxylic acid-(3)

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With sulfuric acid

: 2,4-dioxo-tetrahydro-furan-3-carboxylic acid methyl ester

aqueous-methanolic NaOH-solution: aqueous-methanolic NaOH-solution

: 4971-56-6
tetrahydrofuran-2,4-dione

barium salt of/the/ tetronic acid α-carboxylic acid: barium salt of/the/ tetronic acid α-carboxylic acid

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With sulfuric acid

: 96-32-2
bromoacetic acid methyl ester

magnesium compound of bromoacetic acid benzyl ester: magnesium compound of bromoacetic acid benzyl ester

: 4971-56-6
tetrahydrofuran-2,4-dione

: 3-bromo-3-chloro-furan-2,4-dione

sodium amalgam: sodium amalgam

: 4971-56-6
tetrahydrofuran-2,4-dione

tetronic acid α-carboxylic acid methyl ester: tetronic acid α-carboxylic acid methyl ester

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With sodium hydroxide

: 7647-01-0
hydrogenchloride

: furan-2,4-dione-4-oxime

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 7803-49-8
hydroxylamine

...Expand

: 4-hydroxy-2-iodo-acetoacetic acid-lactone

acidified potassium iodide solution: acidified potassium iodide solution

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 7553-56-2
iodine

...Expand

: 7647-01-0
hydrogenchloride

: 63464-79-9
4-hydroxy-3-phenylimino-butyric acid-lactone

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 62-53-3
aniline

...Expand

: 7647-01-0
hydrogenchloride

: 114187-91-6
furan-2,4-dione-4-phenylhydrazone

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 100-63-0
phenylhydrazine

...Expand

: 2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane

alkalies: alkalies

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 67-64-1
acetone

...Expand

: 2,2-bis-(2,4-dioxo-tetrahydro-[3]furyl)-propane

alkaline earth carbonates: alkaline earth carbonates

A: 4971-56-6
tetrahydrofuran-2,4-dione

B: 67-64-1
acetone

...Expand

: 1192-50-3
3-bromo-furan-2,4-dione

sodium amalgam: sodium amalgam

A: 4971-56-6
tetrahydrofuran-2,4-dione

B anhydrotetronic acid: anhydrotetronic acid

...Expand

: 7664-93-9
sulfuric acid

: 2-imino-4-oxo-tetrahydro-furan-3-carboxylic acid

A: 4971-56-6
tetrahydrofuran-2,4-dione

B tetronic acid α-carboxylic acid: tetronic acid α-carboxylic acid

...Expand

: 13176-46-0
4-bromoethyl acetoacetate

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With potassium acetate; acetic acid In dichloromethane at 80 - 85℃; for 5h;

: 67354-35-2
ethyl 4-(tert-butoxy)-3-oxobutanoate

: 4971-56-6
tetrahydrofuran-2,4-dione

Conditions

Conditions	Yield
With hydrogenchloride In acetic acid at 20 - 30℃; for 1h;
With hydrogenchloride; acetic acid at 20℃; for 3h;

: 4971-56-6
tetrahydrofuran-2,4-dione

: 102-96-5
(2-nitroethenyl)benzene

: 3-(2-nitro-1-phenylethyl)furan-2,4(3H,5H)-dione

Conditions

Conditions	Yield
at 20℃; Michael addition; Neat (no solvent); Grinding; optical yield given as %de; diastereoselective reaction;	99%

: 4971-56-6
tetrahydrofuran-2,4-dione

: 98-59-9
p-toluenesulfonyl chloride

: 471931-08-5
4-(p-toluenesulfonyloxy)-2(5H)-furanone

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	98%

: 4971-56-6
tetrahydrofuran-2,4-dione

: 18940-21-1
5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one

: 104-88-1
4-chlorobenzaldehyde

: 9-(4-chloro-phenyl)-6,6-dimethyl-4-phenyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4-b]quinoline-1,8-dione

Conditions

Conditions	Yield
With acetic acid at 100℃; for 0.133333h; microwave irradiation;	98%
In acetic acid at 100℃; for 0.133333h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 36646-78-3
3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

: 459-57-4
4-fluorobenzaldehyde

: C26H24FNO3

Conditions

Conditions	Yield
In acetic acid at 100℃; for 0.116667h; microwave irradiation;	98%

...Expand

: 3-(cyclopropylamino)-5,5-dimethylcyclohex-2-enone

: 4971-56-6
tetrahydrofuran-2,4-dione

: 459-57-4
4-fluorobenzaldehyde

: C22H22FNO3

Conditions

Conditions	Yield
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1122-91-4
4-bromo-benzaldehyde

: 91-59-8
naphthalen-2-ylamine

: C21H14BrNO2

Conditions

Conditions	Yield
In water at 100℃; for 0.116667h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 100-52-7
benzaldehyde

: 106-49-0
p-toluidine

: C18H15NO2

Conditions

Conditions	Yield
In water at 100℃; for 0.0666667h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 623-27-8
terephthalaldehyde,

: 1,4-bis(3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one-4-yl)benzene

Conditions

Conditions	Yield
With ethylene glycol at 100℃; for 0.0125h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 626-19-7
Isophthalaldehyde

: 1,3-bis(3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridin-5-one-4-yl)benzene

Conditions

Conditions	Yield
With ethylene glycol at 100℃; for 0.0125h; microwave irradiation;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 104-88-1
4-chlorobenzaldehyde

: 1049682-27-0
4-(4-chlorophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 25h;	98%
In water at 100℃; for 0.0333333h; microwave irradiation;	96%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	96%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 555-16-8
4-nitrobenzaldehdye

: 1049682-33-8
4-(4-nitrophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one

Conditions

Conditions	Yield
In water at 100℃; for 0.0333333h; microwave irradiation;	98%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 3h;	87%
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 30h;	80%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 1122-91-4
4-bromo-benzaldehyde

: 1049682-29-2
4-(4-bromophenyl)-3-methyl-1-phenyl-1,7-dihydro-5H-furo[3,4-b]pyrazolo[4,3-e]pyridine-5-one

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	98%
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 20h;	97%
In water at 100℃; for 0.0166667h; microwave irradiation;	95%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1131-18-6
1-Phenyl-3-methyl-5-aminopyrazole

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 1173933-04-4
3-methyl-4-(3,4-dimethoxyphenyl)-1-phenyl-1H-furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 9h;	98%
With 1-n-butyl-3-methylimidazolim bromide at 95℃; for 2h;	91%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 106-40-1
4-bromo-aniline

: 1100695-03-1
4-((4-bromophenyl)amino)furan-2(5H)-one

Conditions

Conditions	Yield
In acetonitrile for 0.666667h; Solvent; Temperature; Microwave irradiation; Reflux;	98%
In 1,4-dioxane at 20℃;

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1118-61-2
3-Aminocrotononitrile

: 587-04-2
3-Chlorobenzaldehyde

: 100-63-0
phenylhydrazine

: 1016225-37-8
C21H16ClN3O2

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: m-Chlorobenzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1118-61-2
3-Aminocrotononitrile

: 555-16-8
4-nitrobenzaldehdye

: 100-63-0
phenylhydrazine

: 1016225-38-9
C21H16N4O4

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-nitrobenzaldehdye at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1118-61-2
3-Aminocrotononitrile

: 100-52-7
benzaldehyde

: 100-63-0
phenylhydrazine

: 1190990-97-6
C21H17N3O2

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: benzaldehyde at 70℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Ionic liquid; Green chemistry;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1118-61-2
3-Aminocrotononitrile

: 104-87-0
4-methyl-benzaldehyde

: 100-63-0
phenylhydrazine

: 1016225-30-1
C22H19N3O2

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-methyl-benzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1118-61-2
3-Aminocrotononitrile

: 123-08-0
4-hydroxy-benzaldehyde

: 100-63-0
phenylhydrazine

: 1016225-32-3
C21H17N3O3

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran-2,4-dione; 3-Aminocrotononitrile; phenylhydrazine With aluminum potassium sulfate dodecahydrate at 70℃; for 0.0833333h; Ionic liquid; Green chemistry; Stage #2: 4-hydroxy-benzaldehyde at 70℃; for 0.25h; Ionic liquid; Green chemistry;	98%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1159372-20-9
(2-amino-5-chlorophenyl)(phenyl)methanol

: 867068-08-4
C17H12ClNO2

Conditions

Conditions	Yield
With zinc(II) chloride In toluene for 0.333333h; Microwave irradiation; Sealed tube; Heating;	98%

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1023303-72-1
1,1-diethyl (2R,3S)-2-formyl-3-phenylcyclopropane-1,1-dicarboxylate

: diethyl (2R,3S)-2-((4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl)methyl)-3-phenylcyclopropane-1,1-dicarboxylate

Conditions

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In dichloromethane at 25℃; for 0.5h; diastereoselective reaction;	98%

: 4971-56-6
tetrahydrofuran-2,4-dione

: 36646-78-3
3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

: 99-61-6
3-nitro-benzaldehyde

: 6,6-dimethyl-9-(3-nitro-phenyl)-4-p-tolyl-5,6,7,9-tetrahydro-3H,4H-furo[3,4-b]quinoline-1,8-dione

Conditions

Conditions	Yield
With acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 882-07-5
2-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)amino)acetic acid

: 99-61-6
3-nitro-benzaldehyde

: [6,6-dimethyl-9-(3-nitro-phenyl)-1,8-dioxo-3,5,6,7,8,9-hexahydro-1H-furo[3,4-b]quinolin-4-yl]-acetic acid

Conditions

Conditions	Yield
With acetic acid at 100℃; for 0.116667h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.116667h; microwave irradiation;	97%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 36646-78-3
3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

: 123-11-5
4-methoxy-benzaldehyde

: 9-(4-methoxyphenyl)-6,6-dimethyl-4-p-tolyl-5,6,7,9-tetrahydrofuro[3,4-b]quinoline-1,8(3H,4H)-dione

Conditions

Conditions	Yield
With acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
In acetic acid at 100℃; for 0.0833333h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 2h;	94%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 36646-78-3
3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

: 100-52-7
benzaldehyde

: C26H25NO3

Conditions

Conditions	Yield
In acetic acid at 100℃; for 0.133333h; microwave irradiation;	97%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 36646-74-9
3-(p-tolylamino)cyclohex-2-en-1-one

: 1122-91-4
4-bromo-benzaldehyde

: C24H20BrNO3

Conditions

Conditions	Yield
In acetic acid at 100℃; for 0.0666667h; microwave irradiation;	97%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 1122-91-4
4-bromo-benzaldehyde

: 62-53-3
aniline

: C17H12BrNO2

Conditions

Conditions	Yield
In water at 100℃; for 0.0833333h; microwave irradiation;	97%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 99-61-6
3-nitro-benzaldehyde

: 106-49-0
p-toluidine

: 7-methyl-9-(3-nitrophenyl)-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one

Conditions

Conditions	Yield
In water at 100℃; for 0.116667h; microwave irradiation;	97%

...Expand

: 98-03-3
thiophene-2-carbaldehyde

: 4971-56-6
tetrahydrofuran-2,4-dione

: 134-32-7
1-amino-naphthalene

: C19H13NO2S

Conditions

Conditions	Yield
In water at 100℃; for 0.1h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 0.5h; regioselective reaction;	93%

...Expand

: 4971-56-6
tetrahydrofuran-2,4-dione

: 104-88-1
4-chlorobenzaldehyde

: 134-32-7
1-amino-naphthalene

: C21H14ClNO2

Conditions

Conditions	Yield
In water at 100℃; for 0.0666667h; microwave irradiation;	97%
With L-proline In ethanol at 80℃; for 1h; regioselective reaction;	92%

...Expand

Tetronic acid Specification

The CAS registry number of 2,4(3H,5H)-Furandione is 4971-56-6. Its EINECS registry number is 225-617-4. The IUPAC name is 2-hydroxy-2H-furan-5-one. In addition, the molecular formula is C₄H₄O₃ and the molecular weight is 100.07. It is also called tetrahydrofuran-2,4-dione. What's more, it should be stored in sealed container, and put in a cool and dry place.

Physical properties about 2,4(3H,5H)-Furandione are: (1)ACD/LogP: -2.03; (2)ACD/LogD (pH 5.5): -2.03; (3)ACD/LogD (pH 7.4): -2.03; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1.87; (7)ACD/KOC (pH 7.4): 1.87; (8)#H bond acceptors: 3; (9)Polar Surface Area: 43.37 Å²; (10)Index of Refraction: 1.47; (11)Molar Refractivity: 20.31 cm³; (12)Molar Volume: 72.7 cm³; (13)Polarizability: 8.05 ×10^-24cm³; (14)Surface Tension: 47.7 dyne/cm; (15)Density: 1.375 g/cm³; (16)Flash Point: 151.1 °C; (17)Enthalpy of Vaporization: 56.63 kJ/mol; (18)Boiling Point: 324.3 °C at 760 mmHg; (19)Vapour Pressure: 0.000248 mmHg at 25 °C.

Uses of 2,4(3H,5H)-Furandione: it can react with 2-amino-benzaldehyde to get 3H-furo[3,4-b]quinolin-1-one. This reaction will need solvent ethanol. The yield is about 80% with ambient temperature.

2,4(3H,5H)-Furandione can react with 2-amino-benzaldehyde to get 3H-furo[3,4-b]quinolin-1-one

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1COC(=O)C1
(2)InChI: InChI=1/C4H4O3/c5-3-1-4(6)7-2-3/h1-2H2
(3)InChIKey: JCGNDDUYTRNOFT-UHFFFAOYAI

Product Name

TETRONIC ACID

Synthetic route

Tetronic acid Specification

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