3-Methylflavone-8-carboxylic acid supplier

Name
3-Methylflavone-8-carboxylic acid
EINECS 222-425-2
CAS No. 3468-01-7
Article Data5
CAS DataBase
Density 1.336 g/cm³
Solubility
Melting Point 234-236 °C
Formula C₁₇H₁₂O₄
Boiling Point 485.1 °C at 760 mmHg
Molecular Weight 280.28
Flash Point 183.3 °C
Transport Information
Appearance White crystalline solid
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 8-Carboxy-3-methylflavone;3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylicacid;
PSA 67.51000
LogP 3.46660

Synthetic route

: methyl 2-benzoyloxy-3-propionylbenzoate

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Stage #1: methyl 2-benzoyloxy-3-propionylbenzoate With aluminum oxide at 165℃; for 4h; Stage #2: With sodium hydroxide In methanol; water at 75 - 80℃; for 1.5h; Temperature;	88%

: 103085-54-7
8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide In butanone at 90 - 95℃; for 44h;	85%
With nitric acid In benzene Product distribution; Heating; various concentrations of HNO3.;	85%

: 3-methyl-2-phenyl-8-(1-propenyl)-4H-1-benzopyran-4-one

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / NaBr, H2SO4 / acetonitrile; H2O / 2.83 h / 45 °C / electrolysis 2: 1) H2SO4; 2) electrolysis / 1) MeOH, 60 deg C, 40 min; 2) 60 deg C, 48 h. 3: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme
Multi-step reaction with 4 steps 1: 94 percent / NaBr, H2SO4 / acetonitrile; H2O / 2.83 h / 45 °C / electrolysis 2: 94 percent / 10percent H2SO4 / tetrahydrofuran / 11 h / Ambient temperature 3: 91 percent / H2SO4 / methanol / 6 h / Ambient temperature; electrolysis 4: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme
Multi-step reaction with 4 steps 1: 94 percent / NaBr, H2SO4 / acetonitrile; H2O / 2.83 h / 45 °C / electrolysis 2: 94 percent / 10percent H2SO4 / tetrahydrofuran / 11 h / Ambient temperature 3: 74 percent / H2SO4, electrolysis / methanol / 50 °C / other temperatures, other reagent, other solvent. 4: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme

: 103085-50-3
8-(1,2-epoxypropyl)-3-methyl-2-phenyl-4H-1-benzopyran-4-one

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) H2SO4; 2) electrolysis / 1) MeOH, 60 deg C, 40 min; 2) 60 deg C, 48 h. 2: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme
Multi-step reaction with 3 steps 1: 94 percent / 10percent H2SO4 / tetrahydrofuran / 11 h / Ambient temperature 2: 91 percent / H2SO4 / methanol / 6 h / Ambient temperature; electrolysis 3: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme
Multi-step reaction with 3 steps 1: 94 percent / 10percent H2SO4 / tetrahydrofuran / 11 h / Ambient temperature 2: 74 percent / H2SO4, electrolysis / methanol / 50 °C / other temperatures, other reagent, other solvent. 3: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme

: 103085-53-6
8-(1,2-dihydroxypropyl)-3-methyl-2-phenyl-4H-1-benzopyran-4-one

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / H2SO4 / methanol / 6 h / Ambient temperature; electrolysis 2: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme
Multi-step reaction with 2 steps 1: 74 percent / H2SO4, electrolysis / methanol / 50 °C / other temperatures, other reagent, other solvent. 2: 85 percent / HNO3 / benzene / Heating; various concentrations of HNO3. View Scheme

0.5N-KOH: 0.5N-KOH

: 90101-87-4
Methyl 3-methylflavone-8-carboxylate

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
In methanol; water	27.3 g (97.5%)

: flavoxate hydrochloride

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Stage #1: flavoxate hydrochloride With sodium hydroxide for 3h; Reflux; Stage #2: With hydrogenchloride; water

: 119-36-8
methyl salicylate

: 3468-01-7
3-methylflavone-8-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: bromine / dichloromethane / 4 h / 0 - 15 °C 1.2: 2.5 h / 60 - 65 °C 1.3: 1.5 h / 20 °C 2.1: sodium hydroxide / dichloromethane / 0 - 25 °C 3.1: aluminum oxide / 4 h / 165 °C 3.2: 1.5 h / 75 - 80 °C View Scheme

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 2680-03-7
N,N-Dimethylacrylamide

: (E)-N,N-dimethyl-3-(3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)acrylamide

Conditions

Conditions	Yield
With palladium(II) trifluoroacetate; 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; sodium chloride In 1,4-dioxane at 150℃; for 10h; Heck Reaction; Schlenk technique; Inert atmosphere;	94%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 762-04-9
phosphonic acid diethyl ester

: diethyl (3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)phosphonate

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	93%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;	93%

: 1809-19-4
dibutyl hydrogen phosphite

: 3468-01-7
3-methylflavone-8-carboxylic acid

: dibutyl (3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)phosphonate

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;	93%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	91%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 14717-29-4
dicyclohexylphosphine oxide

: 8-(dicyclohexylphosphoryl)-3-methyl-2-phenyl-4H-chromen-4-one

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	83%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;	83%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 3-methyl-2-phenyl-8-(2,2,2-trifluoroacetyl)-4H-chromen-4-one

Conditions

Conditions	Yield
With dmap; cesium fluoride; trifluoroacetic anhydride at 120℃; for 15h; Schlenk technique; Inert atmosphere;	80%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 121-44-8
triethylamine

: 90101-88-5
N,N-diethyl-3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxamide

Conditions

Conditions	Yield
With trifuran-2-yl-phosphane; palladium diacetate; 2,2-dimethylpropanoic anhydride In toluene at 120℃; for 15h; Inert atmosphere;	75%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: N,N,3-trimethyl-4-oxo-2-phenyl-4H-chromene-8-carboxamide

Conditions

Conditions	Yield
With trifuran-2-yl-phosphane; palladium diacetate; 2,2-dimethylpropanoic anhydride In toluene at 150℃; for 15h; Inert atmosphere;	75%

: 578-66-5
8-amino quinoline

: 3468-01-7
3-methylflavone-8-carboxylic acid

: C26H18N2O3

Conditions

Conditions	Yield
Stage #1: 3-methylflavone-8-carboxylic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 8-amino quinoline With triethylamine In dichloromethane at 0 - 45℃; for 12h;	73%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 768-60-5
4-methoxyphenylacetylen

: 8-((4-methoxyphenyl)ethynyl)-3-methyl-2-phenyl-4H-chromen-4-one

Conditions

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; 2,2-dimethylpropanoic anhydride; palladium dichloride In 1,4-dioxane at 150℃; for 16h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	70%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 4559-70-0
Diphenylphosphine oxide

: 8-(diphenylphosphoryl)-3-methyl-2-phenyl-4H-chromen-4-one

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	68%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Inert atmosphere; Schlenk technique;	68%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 172487-18-2
ethyl Phenylphosphinate

: ethyl (3-methyl-4-oxo-2-phenyl-4H-chromen-8-yl)(phenyl)phosphinate

Conditions

Conditions	Yield
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox;	67%
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating;	67%

: 14365-73-2
2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester

: 3468-01-7
3-methylflavone-8-carboxylic acid

: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(3-methyl-4-oxo-2-phenyl-4H-chromene-8-carbonyl)-amino]-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With dmap; benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h;	49%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 5472-49-1
1-(3-chloropropyl)piperidine hydrochloride

: 3-(1-piperidinyl)propyl 2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-8-carboxylate

Conditions

Conditions	Yield
With potassium hydroxide In methanol; isopropyl alcohol for 0.5h; Heating;	32%

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 1-deoxy-1-{[(3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-yl)carbonyl]amino}-β-D-glucopyranuronic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / HOBT; DMAP; DCC / tetrahydrofuran / 12 h / 20 °C 2: 84 percent / LiOH / methanol; tetrahydrofuran; H2O / 0 °C View Scheme

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 151860-17-2
(1α,5α,6α)-3-N-benzyl-6-amino-3-aza-bicyclo[3.1.0]hexane

: (1α,5α,6α)-6N-[3-benzyl-3-azabicyclo [3.1.0]hexyl]-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 4-methyl-morpholine; DMF (N,N-dimethyl-formamide); 1-hydorxy benzotriazole at 0 - 20℃; for 3.5h;

: 134574-95-1
1-aminomethyl-3-benzyl-3-azabicyclo [3.1.0] hexane

: 3468-01-7
3-methylflavone-8-carboxylic acid

: N-[3-benzyl-3-azabicyclo [3.1.0]hexyl-1-aminomethyl]-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxamide

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 4-methyl-morpholine; DMF (N,N-dimethyl-formamide); benzotriazol-1-ol at 0 - 20℃; for 3.5h;

: N-(3-chloropropyl)-2-(3,4-dimethoxyphenyl)-N-methyl-ethylamine hydrochloride

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 153240-51-8
8-{3-[2-(3,4-Dimethoxyphenyl)-N-methylethylamino]propoxycarbonyl}-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; potassium carbonate In N-methyl-acetamide; ethanol; water; isopropyl alcohol

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 21279-77-6
1-(2-methoxyphenyl)-4-(3-chloropropyl)piperazine

: Rec 15/2667 dihydrochloride

Conditions

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; ethanol
With potassium carbonate In N-methyl-acetamide; ethanol

: 90101-87-4
Methyl 3-methylflavone-8-carboxylate

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 100859-97-0
piperidinoethyl chloride

: flavoxate hydrochloride

Conditions

Conditions	Yield
With sodium In N-hydroxyethylpiperidine; benzene

...Expand

: 110-89-4
piperidine

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 556-52-5
oxiranyl-methanol

: 86433-56-9
oxiranemethyl 2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-8-carboxylate

: 2-hydroxy-3-(1-piperidinyl)propyl 2-phenyl-3-methyl-4-oxo-4H-1-benzopyran-8-carboxylate

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile; benzene

...Expand

: 54151-70-1
1-(2-aminoisopropyl)-piperidine

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 541-41-3
chloroformic acid ethyl ester

: 92606-55-8
N-[2-(1-Piperidyl)propyl]-3-methylflavone-8-carboxamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran

...Expand

quinoline-S: quinoline-S

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 51950-71-1
3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride

: sodium hydrogensulfite

: 103085-54-7
8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran

Conditions

Conditions	Yield
With thionyl chloride; palladium In 5,5-dimethyl-1,3-cyclohexadiene; water

...Expand

: 7154-73-6
1-(2-aminoethyl)pyrrolidine

: 3468-01-7
3-methylflavone-8-carboxylic acid

: 51950-71-1
3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carbonyl chloride

: N-[2-(pyrrolidin-1-yl)ethyl]-3-methylflavone-8-carboxamide

Conditions

Conditions	Yield
With hydrogenchloride; thionyl chloride In benzene

...Expand

3-Methylflavone-8-carboxylic acid Specification

The 3-Methylflavone-8-carboxylic acid, with the CAS registry number 3468-01-7, is also known as 8-Carboxy-3-methylflavone. It belongs to the product categories of Pharmaceutical Raw Materials; Pharmaceutical Material and Intermeidates; Di-substituted Flavones; All Inhibitors; Inhibitors; Heterocycles; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals. Its EINECS registry number is 222-425-2. This chemical's molecular formula is C₁₇H₁₂O₄ and molecular weight is 280.27. What's more, its IUPAC name is called 3-Methyl-4-oxo-2-phenylchromene-8-carboxylic acid. It is the main active metabolite of flavoxate hydrochloride in human.

Physical properties about 3-Methylflavone-8-carboxylic acid are: (1)ACD/LogP: 3.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.94; (4)ACD/LogD (pH 7.4): 0.33; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.42; (8)ACD/KOC (pH 7.4): 1.35; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 52.6 Å²; (13)Index of Refraction: 1.642; (14)Molar Refractivity: 75.84 cm³; (15)Molar Volume: 209.7 cm³; (16)Surface Tension: 55.4 dyne/cm; (17)Density: 1.335 g/cm³; (18)Flash Point: 183.3 °C; (19)Enthalpy of Vaporization: 79.05 kJ/mol; (20)Boiling Point: 485.1 °C at 760 mmHg; (21)Vapour Pressure: 3.2E-10 mmHg at 25 °C.

Preparation of 3-Methylflavone-8-carboxylic acid: this chemical can be prepared by 8-Formyl-3-methyl-2-phenyl-4H-1-benzopyran-4-one. This reaction needs reagent H₂O₂ and solvent butan-2-one at temperature of 90 - 95 °C. The reaction time is 44 hours. The yield is 85 %.

3-Methylflavone-8-carboxylic acid can be prepared by 8-Formyl-3-methyl-2-phenyl-4H-1-benzopyran-4-one.

Uses of 3-Methylflavone-8-carboxylic acid: it is used to produce other chemicals. For example, it can react with 1-(3-Chloro-propyl)-piperidine; hydrochloride to get 3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid 3-piperidin-1-yl-propyl ester. The reaction occurs with reagent KOH, solvents methanol, propan-2-ol and other condition of heating for 30 min. The yield is 32 %.

3-Methylflavone-8-carboxylic acid can react with 1-(3-Chloro-propyl)-piperidine; hydrochloride to get 3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid 3-piperidin-1-yl-propyl ester.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)c3cccc1c3O/C(=C(\C1=O)C)c2ccccc2
(2) InChI: InChI=1S/C17H12O4/c1-10-14(18)12-8-5-9-13(17(19)20)16(12)21-15(10)11-6-3-2-4-7-11/h2-9H,1H3,(H,19,20)
(3) InChIKey: KMMBBZOSQNLLMN-UHFFFAOYSA-N

Product Name

3-Methylflavone-8-carboxylic acid

Synthetic route

3-Methylflavone-8-carboxylic acid Specification

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