326-59-0

Basic information

• Product Name: BENZO[1,3]DIOXOL-5-YL-ACETIC ACID METHYL ESTER
• Synonyms: BENZO[1,3]DIOXOL-5-YL-ACETIC ACID METHYL ESTER;ASISCHEM D13375;1,3-Benzodioxole-5-acetic Acid Methyl Ester;Methyl 2-(2H-1,3-benzodioxol-5-yl)acetate;[3,4-(Methylenedioxy)phenyl]acetic Acid Methyl Ester;Methyl (3,4-Methylenedioxyphenyl)acetate;Methyl 1,3-Benzodioxole-5-acetate;Methyl 4,5-(Methylenedioxy)phenylacetate
• CAS NO: 326-59-0
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.184
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 326-59-0.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 278.3℃
• Flash Point: 120.0℃
• Appearance: /
• Density: 1.265
• Vapor Pressure: 0.00431mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• CAS DataBase Reference: BENZO[1,3]DIOXOL-5-YL-ACETIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[1,3]DIOXOL-5-YL-ACETIC ACID METHYL ESTER(326-59-0)
• EPA Substance Registry System: BENZO[1,3]DIOXOL-5-YL-ACETIC ACID METHYL ESTER(326-59-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 326-59-0(Hazardous Substances Data)

Usage

Uses

Methyl 1,3-benzodioxol-5-ylacetate is a reagent used to prepare pharmaceutically active Benzodioxole derivatives.

InChI:InChI=1/C10H10O4/c1-12-10(11)5-7-2-3-8-9(4-7)14-6-13-8/h2-4H,5-6H2,1H3

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + 1,3-benzodioxole-5-acetic acid (2861-28-1) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
In 1,4-dioxane; diethyl ether	100%

methanol (67-56-1) + 1,3-benzodioxole-5-acetic acid (2861-28-1) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With acetyl chloride In various solvent(s)	100%
With oxalyl dichloride at 0℃;	95%
With oxalyl dichloride at 0℃; for 0.5h;	95%

acetyl chloride (75-36-5) + 3,4-methylenedioxyphenylacetonitrile (4439-02-5) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
In methanol at 0℃; for 8h;	95%

methanol (67-56-1) + benzo[1,3]dioxol-5-yl-acetaldehyde (6543-34-6) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With potassium hydroxide; ozone at -78℃; for 3h;	86%

1,3-benzodioxole-5-acetic acid (2861-28-1) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With sulfuric acid In methanol	86%
With sulfuric acid; sodium hydrogencarbonate In methanol

methanol (67-56-1) + piperonol (495-76-1) + carbon monoxide (201230-82-2) + carbonic acid dimethyl ester (616-38-6) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With palladium(II) trifluoroacetate; 1,3-bis-(diphenylphosphino)propane at 135℃; under 15001.5 Torr; for 24h; Autoclave; Green chemistry;	83%

methanol (67-56-1) + 1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With sulfuric acid; trimethyl orthoformate at 20℃; for 0.333333h;	77%

dichloromethane (75-09-2) + 2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide for 3h; Heating;	55%
With cesium fluoride In N,N-dimethyl-formamide at 90℃; for 12h;

methanol (67-56-1) + homopiperonylic acid → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With hydrogenchloride

3,4-dihydroxyphenylacetate (102-32-9) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / conc. H2SO4 / 3 h / Heating 2: 55 percent / CsF / dimethylformamide / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Heating / reflux 2: cesium fluoride / N,N-dimethyl-formamide / 12 h / 90 °C View Scheme

1-allyl-3,4-methylenedioxybenzene (94-59-7) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) O3/O2, 2.) Zn, CH3COOH / 1.) CH3COOH, 0 deg C, 2.) 0 deg C, 2 h 2: 75 percent / Jones reagent / acetone / 0 °C 3: 100 percent / dioxane; diethyl ether View Scheme

benzo[1,3]dioxol-5-yl-acetaldehyde (6543-34-6) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Jones reagent / acetone / 0 °C 2: 100 percent / dioxane; diethyl ether View Scheme

1,3-benzodioxole-5-acetic acid (2861-28-1) + methyl iodide (74-88-4) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + bromo(3,4-methylenedioxyphenyl)-acetic acid methyl ester (158692-25-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide
With caesium carbonate In N,N-dimethyl-formamide

1,3-benzodioxole-5-acetic acid (2861-28-1) + sodium hydrogencarbonate (144-55-8) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With TSOH In methanol

methanol (67-56-1) + 3-(1,3 benzodioxol-5-yl)propionic acid (2815-95-4) → benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0)

Conditions	Yield
With sulfuric acid at 90℃; for 24h;

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
Stage #1: benzo[1,3]dioxol-5-yl-acetic acid methyl ester With potassium hydroxide; water In methanol for 3h; Heating / reflux; Stage #2: With hydrogenchloride In water pH=1;	99%
With 20percent aq. KOH In methanol for 3h; Heating;	97%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 2-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dithiolan-2-yl)-ethylamine (134993-17-2) → N-<2-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dithiolan-2-yl)-ethyl>-(3,4-methylenedioxyphenyl)acetamide (134993-18-3)

Conditions	Yield
at 150℃; for 16h;	93%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium; tetrafluoroborate (41948-92-9) → Benzo[1,3]dioxol-5-yl-[1-methyl-pyrrolidin-(2E)-ylidene]-acetic acid methyl ester (103740-43-8, 103740-54-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran for 1h; Ambient temperature;	91%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + C9H16NO3(1+)*BF4(1-) → Benzo[1,3]dioxol-5-yl-[1-methoxycarbonylmethyl-pyrrolidin-(2E)-ylidene]-acetic acid methyl ester (103740-46-1, 103740-57-4)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran for 1h; Ambient temperature;	90%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 4-methoxy-benzoyl chloride (100-07-2) → methyl 2-[2-(4-methoxybenzoyl)-4,5-methylenedioxyphenyl]acetate (197369-11-2)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 20℃; for 12h; Acylation; Friedel-Crafts acylation;	89%
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature;	27%
With tin(IV) chloride In dichloromethane	27%
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 13h;
With tin(IV) chloride In dichloromethane

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + methyl iodide (74-88-4) → methyl 2-(3,4-methylenedioxyphenyl)propionate (126934-94-9)

Conditions	Yield
Stage #1: benzo[1,3]dioxol-5-yl-acetic acid methyl ester With potassium hydride In tetrahydrofuran at -70℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at -70 - 20℃; for 16h;	86.8%
Stage #1: benzo[1,3]dioxol-5-yl-acetic acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	77.6%
Stage #1: benzo[1,3]dioxol-5-yl-acetic acid methyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at -78℃;	77.6%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + ethyl iodide (75-03-6) → methyl 2-(3,4-methylenedioxyphenyl)butyrate (148149-44-4)

Conditions	Yield
Stage #1: benzo[1,3]dioxol-5-yl-acetic acid methyl ester With potassium hydride In tetrahydrofuran at -70℃; for 0.5h; Stage #2: ethyl iodide In tetrahydrofuran at -70 - 20℃; Further stages.;	85%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → methyl (6-bromobenzo<1,3>dioxol-5-yl)acetate (51665-84-0)

Conditions	Yield
With bromine; acetic acid for 0.5h; Ambient temperature;	84%
With bromine In acetic acid	84%
With bromine In acetic acid at 20℃; for 0.5h;	84%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → methyl α-diazo-α-(benzo[1,3]dioxol-5-yl)acetate (172795-73-2)

Conditions	Yield
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;	84%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere;	45%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere;	34%

4-acetoxybenzoyl chloride (27914-73-4) + benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → [6-(4-Acetoxy-benzoyl)-benzo[1,3]dioxol-5-yl]-acetic acid methyl ester (207238-96-8)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 20℃; for 12h; Acylation; Friedel-Crafts acylation;	83%
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 13h;

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + benzoyl chloride (98-88-4) → 2-benzoyl-4,5-(methylenedioxy)-phenyl acetic acid methyl ester (132813-95-7)

Conditions	Yield
With tin(IV) chloride In dichloromethane at 20℃; for 12h; Acylation; Friedel-Crafts acylation;	81%
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature;	48%
With tin(IV) chloride; sodium hydrogencarbonate In dichloromethane	48%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + acetic acid (64-19-7) → Methyl 2-acetyl-4,5-methylenedioxyphenylacetate (87722-77-8)

Conditions	Yield
With perchloric acid In various solvent(s) for 48h; Ambient temperature;	78%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 3-nitrobenzoic acid (121-92-6) → methyl 4,5-methylenedioxy-2-(3-nitrobenzoyl)phenylacetate

Conditions	Yield
With phosphorus pentoxide In 1,2-dichloro-ethane	77%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + C10H20NO3(1+)*BF4(1-) → Benzo[1,3]dioxol-5-yl-[1-(2,2-dimethoxy-ethyl)-pyrrolidin-(2E)-ylidene]-acetic acid methyl ester (103740-45-0, 103740-56-3)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran for 1h; Ambient temperature;	75%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + acrylonitrile (107-13-1) → 2-Benzo[1,3]dioxol-5-yl-4-cyano-butyric acid methyl ester (96422-65-0)

Conditions	Yield
	74%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 2-Aminophenyl disulfide (1141-88-4) → 2-Benzo[1,3]dioxol-5-yl-4H-benzo[1,4]thiazin-3-one (131602-97-6) + 2-amino-benzenethiol (137-07-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 100℃; for 0.333333h;	A 73% B n/a

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + propionic acid (802294-64-0) → methyl 5-(1-oxopropyl)-1,3-benzodioxol-6-ylacetate (87722-78-9)

Conditions	Yield
With perchloric acid In various solvent(s) for 48h; Ambient temperature;	72%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 3-Trifluoroacetyl-aminobenzoyl chloride (207238-93-5) → {6-[3-(2,2,2-Trifluoro-acetylamino)-benzoyl]-benzo[1,3]dioxol-5-yl}-acetic acid methyl ester

Conditions	Yield
With tin(IV) chloride In dichloromethane at 20℃; for 12h; Acylation; Friedel-Crafts acylation;	72%
With tin(IV) chloride In dichloromethane at 0 - 20℃; for 13h;

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + ortho-chlorobenzoic acid (118-91-2) → methyl 2-[6-(2-chlorobenzoyl)-2H-1,3-benzodioxole-5-yl]acetate

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 20℃; for 18h;	71%
With phosphorus pentoxide In dichloromethane at 20℃;

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 3-chlorobenzoate (535-80-8) → methyl 2-[6-(3-chlorobenzoyl)-2H-1,3-benzodioxole-5-yl]acetate

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 20℃; for 18h;	70%
With phosphorus pentoxide In dichloromethane at 20℃;

methanol (67-56-1) + benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) → methyl 2-(3,4-methylenedioxyphenyl)propionate (126934-94-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium tert-butylate; 1,2-bis-(diphenylphosphino)ethane at 150℃; for 48h; Inert atmosphere;	69%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 4-methoxybenzoic acid (100-09-4) → methyl 2-[2-(4-methoxybenzoyl)-4,5-methylenedioxyphenyl]acetate (197369-11-2)

Conditions	Yield
With phosphorus pentoxide In dichloromethane at 20℃; for 16h;	64%

benzo[1,3]dioxol-5-yl-acetic acid methyl ester (326-59-0) + 4-fluorobenzoyl chloride (403-43-0) → methyl 2-(4-fluorobenzoyl)-4,5-methylenedioxyphenylacetate (197369-12-3)

Conditions	Yield
With tin(IV) chloride In dichloromethane for 24h; Ambient temperature;	63%
With tin(IV) chloride In dichloromethane	63%
With tin(IV) chloride In dichloromethane at 20℃; for 12h; Acylation; Friedel-Crafts acylation;	50%
With tin(IV) chloride In dichloromethane

Upstream product

• 186581-53-3 diazomethane 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 67-56-1 methanol 
• 75-36-5 acetyl chloride 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 74-88-4 methyl iodide 
• 144-55-8 sodium hydrogencarbonate 
• 2815-95-4 3-(1,3 benzodioxol-5-yl)propionic acid 
• 495-76-1 piperonol 
• 201230-82-2 carbon monoxide 
• 616-38-6 carbonic acid dimethyl ester 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 102-32-9 3,4-dihydroxyphenylacetate 

Downstream Products

• 129483-24-5 methyl cis-2-nitrocyclohexyl-(3,4-methylenedioxyphenyl)acetate 
• 129483-24-5 methyl trans-2-nitrocyclohexyl-(3,4-methylenedioxyphenyl)acetate 
• 155004-78-7 methyl 3,4-methylenedioxy-6-(3',4',5'-trimethoxybenzoyl)phenylacetate 
• 134993-18-3 N-<2-(3,4-dimethoxyphenyl)-2-(2-methyl-1,3-dithiolan-2-yl)-ethyl>-(3,4-methylenedioxyphenyl)acetamide 
• 103740-44-9 Benzo[1,3]dioxol-5-yl-[1-(2-benzyloxy-ethyl)-pyrrolidin-(2E)-ylidene]-acetic acid methyl ester 
• 132813-95-7 2-benzoyl-4,5-(methylenedioxy)-phenyl acetic acid methyl ester 
• 131602-97-6 2-Benzo[1,3]dioxol-5-yl-4H-benzo[1,4]thiazin-3-one 
• 137-07-5 2-amino-benzenethiol 
• 623944-58-1 6-(4-chlorobenzoyl)-1,3-benzodioxole-5-acetic acid methyl ester 
• 1003857-16-6 methyl 3-(3,5-dimethoxyphenyl)-2-(3,4-methylenedioxyphenyl)-3-oxopropionate 
• 6845-81-4 3,4-methylenedioxyphenylacetyl chloride 
• 347378-55-6 5-benzyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-45-4 5-benzyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-50-1 (S)-N-[2-(3,4-methylenedioxyphenyl)ethyl]-1-phenylethanolamine 

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