482-83-7

Basic information

• Product Name: 6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN
• Synonyms: DALBERGIN;6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN;6-Hydroxy-7-methoxy-4-phenylcoumarin ,99%;4-Phenyl-6-hydroxy-7-methoxy-2H-1-benzopyran-2-one;6-Hydroxy-7-methoxy-4-phenyl-2H-1-benzopyran-2-one;6-hydroxy-7-methoxy-4-phenyl-chromen-2-one;6-hydroxy-7-methoxy-4-phenylchromen-2-one;6-Hydroxy-7-methoxy-4-phenyl-2H-chromen-2-one
• CAS NO: 482-83-7
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Product Categories: Coumarins
• Mol File: 482-83-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 210°C
• Boiling Point: 489°Cat760mmHg
• Flash Point: 187.5°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 3.47E-10mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.85±0.20(Predicted)
• CAS DataBase Reference: 6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN(482-83-7)
• EPA Substance Registry System: 6-HYDROXY-7-METHOXY-4-PHENYLCOUMARIN(482-83-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/37
• Safety Statements: 26-36-24/25
• Hazardous Substances Data: 482-83-7(Hazardous Substances Data)

Usage

Chemical Properties

Brown powder

InChI:InChI=1/C16H12O4/c1-19-15-9-14-12(7-13(15)17)11(8-16(18)20-14)10-5-3-2-4-6-10/h2-9,17H,1H3

Synthetic route

C15H18O7 (1092835-49-8) + phenylboronic acid (98-80-6) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Stage #1: C15H18O7; phenylboronic acid With copper (I) acetate In methanol at 28℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In methanol for 6h; Inert atmosphere; Reflux;	92%

O-benzyldalbergin (934815-44-8) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With cyclohexene; palladium dihydroxide In ethanol Heating;	87%

methoxyhydroquinone (824-46-4) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With sulfuric acid Pechmann Condensation;	70%

1-methyl-4-nitrosobenzene (623-11-0) + 7-methoxy-4-phenyl-2H-chromen-2-one (2555-31-9) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Behandeln der Reaktionsloesung mit Kaliumperoxodisulfat und anschliessendes Erwaermen mit wss. Salzsaeure;

7-methoxy-4-phenyl-2H-chromen-2-one (2555-31-9) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With sodium hydroxide; dipotassium peroxodisulfate anschliessend erwaermen mit Natriumsulfit und wss. Salzsaeure;

nordalbergin (482-82-6) + dimethyl sulfate (77-78-1) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With sodium hydrogencarbonate; acetone

6,7-dimethoxy-4-phenyl-2H-chromen-2-one (1857-05-2) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With hydrogen bromide; acetic acid
With hydrogen iodide; acetic anhydride

C17H18O3 (934815-36-8) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: 61 percent / ZnO / 20 °C 2: 88 percent / tert-BuOK 3: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 4: 77 percent / DDQ / dioxane / 1 h / 20 °C 5: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

C24H22O4 (934815-37-9) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / tert-BuOK 2: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 3: 77 percent / DDQ / dioxane / 1 h / 20 °C 4: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

C25H24O3 (934815-38-0) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 2: 77 percent / DDQ / dioxane / 1 h / 20 °C 3: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

C23H20O3 (934815-40-4) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / DDQ / dioxane / 1 h / 20 °C 2: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

3-methoxy-4-(phenylmethoxy)benzaldehyde (2426-87-1) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: m-CPBA / CH2Cl2 / 12 h 1.2: 92 percent / NaOH / methanol; H2O / 3 h 2.1: 98 percent / K2CO3 / acetone / 8 h / Heating 3.1: 61 percent / ZnO / 20 °C 4.1: 88 percent / tert-BuOK 5.1: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 6.1: 77 percent / DDQ / dioxane / 1 h / 20 °C 7.1: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

4-benzyloxy-3-methoxyphenol (40232-88-0) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / K2CO3 / acetone / 8 h / Heating 2: 61 percent / ZnO / 20 °C 3: 88 percent / tert-BuOK 4: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 5: 77 percent / DDQ / dioxane / 1 h / 20 °C 6: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

vanillin (121-33-5) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions

Yield

Multi-step reaction with 8 steps 1.1: 98 percent / K2CO3 / acetone / 5 h / Heating 2.1: m-CPBA / CH2Cl2 / 12 h 2.2: 92 percent / NaOH / methanol; H2O / 3 h 3.1: 98 percent / K2CO3 / acetone / 8 h / Heating 4.1: 61 percent / ZnO / 20 °C 5.1: 88 percent / tert-BuOK 6.1: 96 percent / Grubbs' catalyst (II) / CH2Cl2 / 8 h / 20 °C 7.1: 77 percent / DDQ / dioxane / 1 h / 20 °C 8.1: 87 percent / cyclohexene / Pd(OH)2/C / ethanol / Heating View Scheme

7-hydroxy-4-phenylcoumarin (2555-30-8) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution; potassium peroxo disulfate / anschliessend erwaermen mit Natriumsulfit und wss. Salzsaeure 2: acetone; sodium hydrogencarbonate View Scheme

2-hydroxy-4,5-dimethoxybenzophenone (36896-99-8) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / 170 °C 2: aqueous hydriodic acid; acetic acid anhydride View Scheme

nordalbergin (482-82-6) + methyl iodide (74-88-4) → 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 30℃; for 1.5h;	410 mg

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + 1-Bromo-2-chloroethane (107-04-0) → 6-(2-chloroethoxy)-7-methoxy-4-phenyl-2H-chromen-2-one

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 4h;	94%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + methyl iodide (74-88-4) → 6,7-dimethoxy-4-phenyl-2H-chromen-2-one (1857-05-2)

Conditions	Yield
With potassium carbonate In acetone at 40℃; for 4h;	92%

1,5-dibromo-pentane (111-24-0) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 6-(5-bromopentyloxy)-7-methoxy-4-phenyl-2H-chromen-2-one

Conditions	Yield
With potassium carbonate In acetone at 40℃;	89%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + 1,3-dibromo-propane (109-64-8) → 6-(3-bromopropoxy)-7-methoxy-4-phenyl-2H-chromen-2-one

Conditions	Yield
With potassium carbonate In acetone at 40℃;	86%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + acetyl chloride (75-36-5) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl acetate (59057-75-9)

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 6h;	86%

(E)-2-methylbut-2-enoyl chloride (35660-94-7) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl (E)-2-methylbut-2-enoate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 6h;	82%

6-bromohexanoyl chloride (22809-37-6) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl 6-bromohexanoate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 8h;	81%

2-thienylacetic acid chloride (39098-97-0) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl 2-(thiophen-2-yl)acetate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 7h;	80%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 5,8-diketo-7-methoxy-4-phenylcoumarin (21128-04-1) + 5,6-diketo-7-methoxy-4-phenylcoumarin (124092-97-3)

Conditions	Yield
With (PhSeO)2O In dichloromethane for 18h; Product distribution; Ambient temperature; oxidation of 4-arylcoumarins with benzeneseleninic anhydride;	A 2% B 76.5%
With (PhSeO)2O In dichloromethane for 18h; Ambient temperature;	A 2% B 76.5%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + 4-chlorobenzoyl chloride (586-75-4) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl 4-bromobenzoate

Conditions	Yield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 6h;	74%

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + epichlorohydrin (106-89-8) → 7-methoxy-6-(oxiran-2-ylmethoxy)-4-phenyl-2H-chromen-2-one

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 6h;	68%

diethyl sulfate (64-67-5) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → 6-ethoxy-7-methoxy-4-phenyl-coumarin (110060-74-7)

Conditions	Yield
With potassium carbonate; acetone

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + acetic anhydride (108-24-7) → 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl acetate (59057-75-9)

Conditions	Yield
With sodium acetate

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + benzoyl chloride (98-88-4) → 6-benzoyloxy-7-methoxy-4-phenyl-coumarin

Conditions	Yield
With pyridine

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) → dalbergin

Conditions	Yield
With ethanol; sodium anschliessendes Behandeln mit wss. Salzsaeure;

6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + dimethyl sulfate (77-78-1) → 6,7-dimethoxy-4-phenyl-2H-chromen-2-one (1857-05-2)

Conditions	Yield
With potassium carbonate

chloroform (67-66-3) + 6-Hydroxy-7-methoxy-4-phenyl-coumarin (482-83-7) + bromine (7726-95-6) → compound C16H8Br6O4

Upstream product

• 36896-99-8 2-hydroxy-4,5-dimethoxybenzophenone 
• 482-82-6 nordalbergin 
• 74-88-4 methyl iodide 
• 1092835-49-8 C₁₅H₁₈O₇ 
• 98-80-6 phenylboronic acid 
• 2555-30-8 7-hydroxy-4-phenylcoumarin 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 934815-40-4 C₂₃H₂₀O₃ 
• 934815-38-0 C₂₅H₂₄O₃ 
• 934815-37-9 C₂₄H₂₂O₄ 
• 934815-36-8 C₁₇H₁₈O₃ 
• 934815-44-8 O-benzyldalbergin 
• 1857-05-2 6,7-dimethoxy-4-phenyl-2H-chromen-2-one 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1857-05-2 6,7-dimethoxy-4-phenyl-2H-chromen-2-one 
• 21128-04-1 5,8-diketo-7-methoxy-4-phenylcoumarin 
• 124092-97-3 5,6-diketo-7-methoxy-4-phenylcoumarin 
• 59057-75-9 7-methoxy-2-oxo-4-phenyl-2H-chromen-6-yl acetate 

Relevant articles and documents

High-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin

The invention provides a high-selectivity preparation method for 7-methoxy-6/8-hydroxy coumarin and belongs to the field of synthesis of natural medicines. The method comprises the steps of subjecting a catechol coumarin compound to a high-selectivity methylation reaction with a methylation reagent in a proper base catalyst added organic reaction system, so as to obtain a 7-hydroxyl mono-methylate, wherein the mole ratio of a base to the catechol coumarin compound is (2.0 to 7.0): 1, the mole ratio of the methylation reagent to the catechol coumarin compound is (1.0 to 3.0): 1, the temperature of the organic reaction system is 0 DEG C to 30 DEG C, and the reaction time is 1.0 to 5.0 hours. The method has the characteristics of simplicity in operation, moderate conditions, good selectivity, high yield and the like and can be applied to the preparation of mono-methylates of coumarin catechols with different types of substituents.

Synthesis of 4-arylcoumarins via Cu-catalyzed hydroarylation with arylboronic acids

(Chemical Equation Presented) In the presence of 2-4 mol % of CuOAc, methyl phenylpropiolates having a MOM-protected hydroxy group at the ortho position underwent hydroarylation with various arylboronic acids in MeOH at ambient temperature, resulting in the formation of 4-arylcoumarins in high yields after the acidic workup. This method was effectively used for the synthesis of biologically active natural and artificial compounds.