116119-01-8

Basic information

• Product Name: 1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester
• Synonyms: 1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester;Methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate;Methyl 3,4-Methylenedioxy-5-hydroxybenzoate;7-Hydroxy-1,3-benzodioxole-5-carboxylic Acid Methyl Ester;methyl 7-hydroxy-1,3-benzodioxole-5-carboxylate
• CAS NO: 116119-01-8
• Molecular Formula: C₉H₈O₅
• Molecular Weight: 196
• Mol File: 116119-01-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: CDCl3, DCM, Ethanol, Ethyl Acetate,
• CAS DataBase Reference: 1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester(116119-01-8)
• EPA Substance Registry System: 1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester(116119-01-8)

Safety Data

• Hazardous Substances Data: 116119-01-8(Hazardous Substances Data)

Usage

Description

1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester is an organic compound that serves as an intermediate in the synthesis of natural dihydrostilbenes. These dihydrostilbenes exhibit significant cytotoxicity towards human cancer cell lines, making this compound a valuable component in the development of potential anticancer agents.

Uses

Used in Pharmaceutical Industry:
1,3-Benzodioxole-5-carboxylic acid, 7-hydroxy-, methyl ester is used as an intermediate in the synthesis of natural dihydrostilbenes for their significant cytotoxicity towards human cancer cell lines. This makes it a promising candidate for the development of novel anticancer drugs and therapies.

Synthetic route

methyl 7-(benzyloxy)benzo[d][1,3]dioxole-5-carboxylate (142531-43-9) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
With titanium tetrachloride In chloroform at 20℃; for 12h;	90%
With titanium tetrachloride In chloroform at 20℃; for 12h;	90%
With palladium 10% on activated carbon; hydrogen In ethanol

diiodomethane (75-11-6) + methyl galloate (99-24-1) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
With potassium carbonate; copper(II) oxide In N,N-dimethyl-formamide at 130℃; for 5h; Inert atmosphere;	60%
Stage #1: methyl galloate With sulfuric acid In methanol for 12h; Reflux; Stage #2: diiodomethane With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	58%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 40h;	49%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 1.5h;	37%
With potassium carbonate In N,N-dimethyl-formamide

methyl galloate (99-24-1) + 1,2-dibromomethane (74-95-3) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
With potassium hydrogencarbonate In dimethyl sulfoxide at 60℃; for 1.5h; Inert atmosphere;	55%

7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid + methanol (67-56-1) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
With hydrogenchloride
With sulfuric acid In water Inert atmosphere; Sealed tube; Reflux;

7-benzyloxy-2-ethoxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / hydrochloric acid / methanol; H2O / 2 h / 20 °C 2: 90 percent / potassium fluoride / dimethylformamide / 110 °C 3: 90 percent / TiCl4 / CHCl3 / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; water 2: palladium 10% on activated carbon; hydrogen / ethanol View Scheme

3,4,5-trihydroxybenzoic acid (149-91-7) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 100 percent / sulfuric acid / 6 h / Heating 2: 98.5 percent / Amberlyst 15E / benzene / 18 h / Heating 3: 100 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C 4: 100 percent / hydrochloric acid / methanol; H2O / 2 h / 20 °C 5: 90 percent / potassium fluoride / dimethylformamide / 110 °C 6: 90 percent / TiCl4 / CHCl3 / 12 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: sulfuric acid / Reflux 2: Amberlist 15E 3: potassium carbonate / N,N-dimethyl-formamide 4: hydrogenchloride; water 5: palladium 10% on activated carbon; hydrogen / ethanol View Scheme

methyl galloate (99-24-1) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 98.5 percent / Amberlyst 15E / benzene / 18 h / Heating 2: 100 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C 3: 100 percent / hydrochloric acid / methanol; H2O / 2 h / 20 °C 4: 90 percent / potassium fluoride / dimethylformamide / 110 °C 5: 90 percent / TiCl4 / CHCl3 / 12 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: Amberlist 15E 2: potassium carbonate / N,N-dimethyl-formamide 3: hydrogenchloride; water 4: palladium 10% on activated carbon; hydrogen / ethanol View Scheme

methyl 3-(benzyloxy)-4,5-dihydroxybenzoate (79831-86-0) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / potassium fluoride / dimethylformamide / 110 °C 2: 90 percent / TiCl4 / CHCl3 / 12 h / 20 °C View Scheme

2-ethoxy-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester (526221-05-6) → methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C 2: 100 percent / hydrochloric acid / methanol; H2O / 2 h / 20 °C 3: 90 percent / potassium fluoride / dimethylformamide / 110 °C 4: 90 percent / TiCl4 / CHCl3 / 12 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: hydrogenchloride; water 3: palladium 10% on activated carbon; hydrogen / ethanol View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 2-bromo-3-hydroxy-4,5-methylenedioxybenzoate (848772-89-4)

Conditions	Yield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 10h;	95%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 10h;	95%
With N-Bromosuccinimide In tetrahydrofuran at 25℃; for 1h; regioselective reaction;	85%
With N-Bromosuccinimide In tetrahydrofuran at 20℃;	79%

homoalylic alcohol (627-27-0) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 7-(but-3-en-1-yloxy)benzo[d][1,3]dioxole-5-carboxylate

Conditions	Yield
Stage #1: homoalylic alcohol; methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: In tetrahydrofuran at 23℃; for 12h; Inert atmosphere;	92%

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) + 1,3-dibromo-2-phenylsulfonylpropane → 7-(2-Benzenesulfonyl-allyloxy)-benzo[1,3]dioxole-5-carboxylic acid methyl ester (219500-47-7)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 20℃; for 12h; Alkylation;	87%
With potassium carbonate In acetone Ambient temperature;	85%

dimethyl sulfate (77-78-1) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate (22934-58-3)

Conditions	Yield
Stage #1: methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate With sodium hydroxide In ethanol at 0 - 20℃; Inert atmosphere; Stage #2: dimethyl sulfate In ethanol for 5h; Inert atmosphere; Reflux;	87%
With potassium carbonate In N,N-dimethyl-formamide

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) + methyl iodide (74-88-4) → methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate (22934-58-3)

Conditions	Yield
Stage #1: methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: methyl iodide In dimethyl sulfoxide for 44h;	84%

4-picolylchloride hydrochloride (1822-51-1) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 7-(pyridin-4-ylmethoxy)benzo[d][1,3]dioxole-5-carboxylate

Conditions	Yield
With potassium carbonate In acetonitrile at 60℃;	78%

4-fluorobenzaldehyde (459-57-4) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 3-(4-formylphenoxy)-4,5-(methylenedioxy)benzoate (157096-83-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 155 - 160℃; for 4h;	72%

benzyl bromide (100-39-0) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 7-(benzyloxy)benzo[d][1,3]dioxole-5-carboxylate (142531-43-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 1.5h; Ambient temperature;	68%

(1-cyclohexenyl)methanol (4845-04-9) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 7-(cyclohex-1-en-1-ylmethoxy)benzo[d][1,3]dioxole-5-carboxylate

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere;	57%

2,4-dichlorophenylethyl alcohol (81156-68-5) + methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 7-[2-(2,4-dichloro-phenyl)-ethoxy]-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Conditions	Yield
With PPh3-polystyrene; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;
With PPh3-polystyrene; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction;

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 7-[2-(2,4-Dichloro-phenyl)-ethoxy]-benzo[1,3]dioxole-5-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: DEAD; PPh3-polystyrene / tetrahydrofuran / 16 h / 20 °C 2: aq. NaOH / dioxane / 1 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: DEAD; PPh3-polystyrene / tetrahydrofuran / 20 °C 2: aq. NaOH / dioxane / 60 °C View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 7-[2-(2,4-Dichloro-Phenyl)-Ethoxy]-Benzo[1,3]Dioxole-5-Carboxylic Acid (3,4,5,6-Tetrahydro-2H-[1,4']Bipyridinyl-4-Ylmethyl)-Amide

Conditions	Yield
Multi-step reaction with 3 steps 1: DEAD; PPh3-polystyrene / tetrahydrofuran / 16 h / 20 °C 2: aq. NaOH / dioxane / 1 h / 60 °C 3: TOTU; N-ethylmorpholine / dimethylformamide View Scheme
Multi-step reaction with 3 steps 1: DEAD; PPh3-polystyrene / tetrahydrofuran / 20 °C 2: aq. NaOH / dioxane / 60 °C 3: TOTU; N-ethylmorpholine / dimethylformamide View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl 2-bromo-3-benzyloxy-4,5-methylenedioxybenzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 1,3-dibromo-5,5-dimethylhydantoin / CHCl3 / 10 h / 20 °C 2: 100 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → methyl-6-bromo-7-methoxybenzo [d] [1, 3] dioxole-5-carboxylate (81474-47-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / 1,3-dibromo-5,5-dimethylhydantoin / CHCl3 / 10 h / 20 °C 2: 95 percent / potassium carbonate / dimethylformamide / 12 h / 70 °C View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / tetrahydrofuran / 1 h / 25 °C 2: potassium carbonate / N,N-dimethyl-formamide; acetone / 5 h / 20 °C / Inert atmosphere; Reflux View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 6-Allyl-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester (219500-46-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C 3: K2CO3 / acetone / Heating 4: 86 percent / Na-Hg / methanol; ethyl acetate / 12 h / -20 °C View Scheme
Multi-step reaction with 4 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 5-Allyl-6-(1-hydroxy-1-methyl-ethyl)-benzo[1,3]dioxol-4-ol (219500-50-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C 3: K2CO3 / acetone / Heating 4: 86 percent / Na-Hg / methanol; ethyl acetate / 12 h / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h / -78 - 0 °C View Scheme
Multi-step reaction with 5 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 6-Allyl-7-(1,1-dimethyl-prop-2-ynyloxy)-benzo[1,3]dioxol-5-ol (219500-52-4)

Conditions	Yield
Multi-step reaction with 7 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C 3: K2CO3 / acetone / Heating 4: 86 percent / Na-Hg / methanol; ethyl acetate / 12 h / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h / -78 - 0 °C 6: DBU; CuCl2*H2O / acetonitrile / 24 h / 20 °C 7: 85 percent / H2SO4; aq. H2O2 / CH2Cl2 / 0.17 h / 0 °C View Scheme
Multi-step reaction with 7 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h 6: 73 percent / KI, K2CO3 / acetone / 48 h / 60 °C 7: 85 percent / H2O2, H2SO4 / CH2Cl2 / 0.17 h View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 2-[6-Allyl-7-(1,1-dimethyl-prop-2-ynyloxy)-benzo[1,3]dioxol-5-yl]-propan-2-ol (219500-51-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C 3: K2CO3 / acetone / Heating 4: 86 percent / Na-Hg / methanol; ethyl acetate / 12 h / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h / -78 - 0 °C 6: DBU; CuCl2*H2O / acetonitrile / 24 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating 4: 87 percent / Na-Hg / methanol; ethyl acetate / -20 °C 5: 90 percent / LiBr / tetrahydrofuran / 12 h 6: 73 percent / KI, K2CO3 / acetone / 48 h / 60 °C View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 6-(2-Benzenesulfonyl-allyl)-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester (219500-48-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C View Scheme
Multi-step reaction with 2 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C View Scheme

methyl 7-hydroxybenzo[d][1,3]dioxole-5-carboxylate (116119-01-8) → 7-Benzenesulfonyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-h]chromene-5-carboxylic acid methyl ester (219500-49-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / K2CO3; KI / acetone / 12 h / 20 °C 2: toluene / 12 h / 165 °C 3: K2CO3 / acetone / Heating View Scheme
Multi-step reaction with 3 steps 1: 85 percent / K2CO3 / acetone / Ambient temperature 2: 94 percent / 12 h / 165 °C 3: 95 percent / K2CO3 / acetone / Heating View Scheme

Upstream product

• 99-24-1 methyl galloate 
• 74-95-3 1,1-dibromomethane 
• 149-91-7 3,4,5-trihydroxybenzoic acid 
• 482627-94-1 7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid 
• 67-56-1 methanol 
• 142531-43-9 methyl 7-(benzyloxy)benzo[d][1,3]dioxole-5-carboxylate 
• 75-11-6 diiodomethane 
• 526221-05-6 2-ethoxy-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 79831-86-0 methyl 3-(benzyloxy)-4,5-dihydroxybenzoate 

Downstream Products

• 219500-48-8 6-(2-Benzenesulfonyl-allyl)-7-hydroxy-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 219500-49-9 7-Benzenesulfonyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-h]chromene-5-carboxylic acid methyl ester 
• 292073-83-7 [6-Allyl-7-(1,1-dimethyl-allyloxy)-benzo[1,3]dioxol-5-yloxy]-tert-butyl-diphenyl-silane 
• 292073-82-6 [6-Allyl-7-(1,1-dimethyl-prop-2-ynyloxy)-benzo[1,3]dioxol-5-yloxy]-tert-butyl-diphenyl-silane 
• 22934-58-3 methyl 7-methoxybenzo[d][1,3]dioxole-5-carboxylate 
• 22934-59-4 (7-methoxybenzo[d][1,3]dioxol-5-yl)methanol 
• 109893-05-2 methyl 6-amino-7-methoxy-1,3-benzodioxole-5-carboxylate 
• 157096-84-9 methyl 3-<4-(dimethoxymethyl)phenoxy>-4,5-(methylenedioxy)benzoate 
• 157096-85-0 3-<4-(dimethoxymethyl)phenoxy>-4,5-(methylenedioxy)benzyl alcohol 
• 157096-86-1 3-<4-(dimethoxymethyl)phenoxy>-4,5-(methylenedioxy)benzaldehyde 

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