2861-28-1

Basic information

• Product Name: 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID
• Synonyms: (1,3-BENZODIOXOL-5-YL)ACETIC ACID;1,3-BENZODIOXOLE-5-ACETIC ACID;3,4-METHYLENDIOXYPHENYLACETIC ACID;3,4-(METHYLENEDIOXY)PHENYLACETIC ACID;ASISCHEM D13365;HOMOPIPERONYLIC ACID;TIMTEC-BB SBB000212;RARECHEM AL BO 0211
• CAS NO: 2861-28-1
• Molecular Formula: C₉H₈O₄
• Molecular Weight: 180.16
• EINECS: 220-679-9
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Organic acids;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2861-28-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 125-129 °C(lit.)
• Boiling Point: 272.96°C (rough estimate)
• Flash Point: 142.4 °C
• Appearance: Beite to pale yellow/Micro-Crystalline Powder
• Density: 1.2933 (rough estimate)
• Vapor Pressure: 3.29E-05mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.31±0.10(Predicted)
• Water Solubility: Soluble in water (partly), ethanol, and methanol.
• BRN: 177739
• CAS DataBase Reference: 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID(2861-28-1)
• EPA Substance Registry System: 3,4-(METHYLENEDIOXY)PHENYLACETIC ACID(2861-28-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2861-28-1(Hazardous Substances Data)

Usage

Description

3,4-(Methylenedioxy)phenylacetic acid, also known as Homopiperonylic acid, is a 1,3-benzodioxole derivative characterized by its beige to pale yellow micro-crystalline powder form. It has been evaluated for its standard molar energy of combustion in oxygen, indicating its potential as a compound of interest in various applications.

Uses

Used in Pharmaceutical Industry:
3,4-(Methylenedioxy)phenylacetic acid is used as an organic intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to serve as a building block in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3,4-(Methylenedioxy)phenylacetic acid is utilized as a key intermediate in the production of a range of chemical compounds. Its versatility in reacting with other molecules makes it a valuable component in creating diverse chemical products.
Used in Research and Development:
3,4-(Methylenedioxy)phenylacetic acid is also employed in research and development settings, where its properties and reactivity are studied to understand its potential applications in various scientific and industrial domains. This includes exploring its use in the creation of new materials, catalysts, and other specialized compounds.

InChI:InChI=1/C9H8O4/c10-9(11)4-6-1-2-7-8(3-6)13-5-12-7/h1-3H,4-5H2,(H,10,11)/p-1

Synthetic route

3,4-methylenedioxyphenylacetonitrile (4439-02-5) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With sodium hydroxide In methanol Hydrolysis;	100%

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%

3,4-(methylenedioxy)mandelic acid (27738-46-1) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With phosphonic Acid; methanesulfonic acid; sodium iodide In water at 40℃; for 48h; Inert atmosphere;	98.4%

((E)-2-Benzo[1,3]dioxol-5-yl-1-dimethylamino-vinyl)-phosphonic acid diethyl ester (79054-42-5) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With hydrogen bromide at 100℃; for 0.166667h;	95%
With water; hydrogen bromide at 100℃; for 0.166667h; Inert atmosphere;	95%

C18H18O6 → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With sodium hypochlorite In acetonitrile at 20℃; for 3.5h;	88%

(benzo[1,3]dioxol-5-yl)acetic acid ethyl ester (26664-86-8) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 1.5h; Ambient temperature;	87%

benzo[1,3]dioxol-5-yl-acetaldehyde (6543-34-6) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With jones reagent In acetone at 0℃;	75%

carbon dioxide (124-38-9) + 1-(benzo[d][1,3]dioxol-5-yl)-N,N,N-trimethylmethanammonium iodide (112101-21-0) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions

Yield

Stage #1: carbon dioxide; N,N,N-trimethyl-(3',4'-methylenedioxyphenyl)methylammonium iodide With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; nickel(II) bromide diethylene glycol dimethyl ether In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 72h; Schlenk technique; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; Schlenk technique; chemoselective reaction;

70%

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With potassium permanganate; tetradecyldimethylbenzylammonium chloride dihydrate; acetic acid In water; acetone; benzene for 72h; cooling;	58%
With permanganate(VII) ion
Multi-step reaction with 2 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 View Scheme

benzo[1,3]dioxol-5-yl-oxo-acetic acid (62396-98-9) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
Stage #1: benzo[1,3]dioxol-5-yl-oxo-acetic acid With hydrazine hydrate; potassium hydroxide at 0 - 110℃; Stage #2: With hydrogenchloride at 0℃; pH=3 - 4;	45%

1-allyl-3,4-methylenedioxybenzene (94-59-7) → Piperonylic acid (94-53-1) + 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With potassium permanganate; acetic acid

1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5) → Piperonylic acid (94-53-1) + 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With sodium hypobromide

β-(benzo[1,3]dioxol-5-yl)pyruvic acid (884-18-4) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With dihydrogen peroxide

((E)-2-Benzo[1,3]dioxol-5-yl-1-dimethylamino-vinyl)-phosphonic acid diethyl ester (79054-42-5) → 1,3-benzodioxole-5-acetic acid (2861-28-1) + ((E)-2-Benzo[1,3]dioxol-5-yl-1-hydroxy-vinyl)-phosphonic acid diethyl ester (79054-52-7) + (2-Benzo[1,3]dioxol-5-yl-acetyl)-phosphonic acid diethyl ester (79054-51-6) + phosphonic acid diethyl ester (762-04-9)

Conditions	Yield
With hydrogenchloride Product distribution; Ambient temperature; effect of concentration of HCl, of reaction time and temperature;

1-((Z)-2-Benzo[1,3]dioxol-5-yl-1-methoxy-vinyl)-1H-benzotriazole → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With hydrogenchloride; zinc dibromide 1.) 1,4-dioxane, reflux, 1 h, 2.) 1,4-dioxane, reflux, 4 h; Yield given. Multistep reaction;

((E)-2-Benzo[1,3]dioxol-5-yl-1-piperidin-1-yl-vinyl)-phosphonic acid diethyl ester → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With hydrogenchloride for 0.5h; Heating; Yield given;

α'-nitro-α-<3.4-methylenedioxy-phenyl>-acetone → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With potassium permanganate

3.4-methylenedioxy-mandelic acid → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With hydrogen bromide; acetic acid Behandeln des Reaktionsprodukts mit Zink und Salzsaeure;

(E)-3-(benzo[d][1,3]dioxol-5-yl)-2-cyanoacrylic acid (49711-55-9) + aqueous alkaline sodium hypochlorite solution → 1,3-benzodioxole-5-acetic acid (2861-28-1)

homopiperonylic acid nitrile → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With potassium hydroxide

1-(1,3-benzodioxol-5-yl)-2-propanone (4676-39-5) + sodium hypobromite → Piperonylic acid (94-53-1) + 1,3-benzodioxole-5-acetic acid (2861-28-1)

1-allyl-3,4-methylenedioxybenzene (94-59-7) → 1,3-benzodioxole-5-acetic acid (2861-28-1) + homopiperonal

Conditions	Yield
With water; benzene bei der Ozonisation;

safrole glycol → 1,3-benzodioxole-5-acetic acid (2861-28-1) + piperonal; piperonylic acid

Conditions	Yield
With potassium permanganate

3,4-methylenedioxyphenylacetonitrile (4439-02-5) → (1,3-benzodioxol-5-ylmethyl)-amide (5661-47-2) + 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
With potassium phosphate buffer; lyophilized Zea mays nitrilase ZmNIT2 EC 3.5.5.1 In water at 30℃; for 14h; pH=7.15; Title compound not separated from byproducts;

3,4-dihydroxyphenylacetate (102-32-9) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 97 percent / conc. H2SO4 / 3 h / Heating 2: 55 percent / CsF / dimethylformamide / 3 h / Heating 3: 97 percent / 20percent aq. KOH / methanol / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sulfuric acid / 3 h / Heating / reflux 2.1: cesium fluoride / N,N-dimethyl-formamide / 12 h / 90 °C 3.1: potassium hydroxide; water / methanol / 3 h / Heating / reflux 3.2: pH 1 View Scheme

2-(3,4-dihydroxyphenyl)acetic acid methyl ester (25379-88-8) → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / CsF / dimethylformamide / 3 h / Heating 2: 97 percent / 20percent aq. KOH / methanol / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: cesium fluoride / N,N-dimethyl-formamide / 12 h / 90 °C 2.1: potassium hydroxide; water / methanol / 3 h / Heating / reflux 2.2: pH 1 View Scheme

piperonal (120-57-0) + hydrogen sulfide remaining ammonium polysulfide → 1,3-benzodioxole-5-acetic acid (2861-28-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, cyclohexane, -78 deg C, 1 h, 2.) THF, cyclohexane, a) -78 deg C, 1 h, b) from -78 deg C to RT, overnight 2: 1.) ZnBr2, 2.) aq. HCl / 1.) 1,4-dioxane, reflux, 1 h, 2.) 1,4-dioxane, reflux, 4 h View Scheme

piperonal (120-57-0) + alkali → 1,3-benzodioxole-5-acetic acid (2861-28-1) + piperonal; piperonylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: 76 percent / NaOH / 3 h / 80 °C 2: 90 percent / copper(II) chloride dihydrate, HCl / 23 h / Heating 3: 87 percent / 1N NaOH / tetrahydrofuran / 1.5 h / Ambient temperature View Scheme

2-(3,4-methylenedioxyphenyl)-1-(methylsulfinyl)-1-(methylthio)ethylene (35453-09-9) → 1,3-benzodioxole-5-acetic acid (2861-28-1) + piperonal; piperonylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / copper(II) chloride dihydrate, HCl / 23 h / Heating 2: 87 percent / 1N NaOH / tetrahydrofuran / 1.5 h / Ambient temperature View Scheme

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%

1,3-benzodioxole-5-acetic acid (2861-28-1) → 3,4-methylenedioxyphenylacetyl chloride (6845-81-4)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In toluene at 20℃; for 1h; Inert atmosphere;	100%
With oxalyl dichloride In N,N-dimethyl-formamide; toluene at 20℃; for 1h;	97%
With thionyl chloride In dichloromethane for 1h; Heating;

1,3-benzodioxole-5-acetic acid (2861-28-1) → 3,4-methylenedioxyphenethyl alcohol (6006-82-2)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 25 - 30℃; for 1.25h;	100%
With sodium tetrahydroborate; iodine	100%
With borane tetrahydrofuran In tetrahydrofuran at 0 - 20℃; for 1h;	98%

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%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 2-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dimethoxyphenethyl)acetamide (42971-27-7)

Conditions	Yield
With 1,1'-carbonyldiimidazole In tetrahydrofuran	99%
Stage #1: 1,3-benzodioxole-5-acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 3.5h; Inert atmosphere; Stage #2: 2-(3,4-dimethoxyphenyl)-ethylamine In tetrahydrofuran at 0 - 20℃; for 15.5h; Inert atmosphere;	80%
at 190 - 210℃; for 2h;	73%

1,3-benzodioxole-5-acetic acid (2861-28-1) → (6-bromobenzo[1,3]dioxol-5-yl)acetic acid (5470-14-4)

Conditions	Yield
With bromine In chloroform at 20℃; for 2h;	99%
With bromine; acetic acid at 23℃; for 18h;	97%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	92%

1,3-benzodioxole-5-acetic acid (2861-28-1) + phenethylamine (64-04-0) → 2-(2H-1,3-benzodioxol-5-yl)-N-(2-phenylethyl)acetamide (1427329-53-0)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 2-(2-(trifluoromethyl)phenyl)ethan-1-amine (774-18-5) → 2-(2H-1,3-benzodioxol-5-yl)-N-{2-[2-(trifluoromethyl)phenyl]ethyl}acetamide (1427329-55-2)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	99%

BH3.THF + 1,3-benzodioxole-5-acetic acid (2861-28-1) → 3,4-methylenedioxyphenethyl alcohol (6006-82-2)

Conditions	Yield
In tetrahydrofuran; water	98%

BH3THF + 1,3-benzodioxole-5-acetic acid (2861-28-1) → 3,4-methylenedioxyphenethyl alcohol (6006-82-2)

Conditions	Yield
In tetrahydrofuran; water	98%
In tetrahydrofuran; water	98%
In tetrahydrofuran; water	98%

BH3 THF + 1,3-benzodioxole-5-acetic acid (2861-28-1) → 3,4-methylenedioxyphenethyl alcohol (6006-82-2)

Conditions	Yield
In tetrahydrofuran; water	98%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 4-Methoxyphenethylamine (55-81-2) → 2-(2H-1,3-benzodioxol-5-yl)-N-[2-(4-methoxyphenyl)ethyl]acetamide (1395084-65-7)

Conditions	Yield
In neat (no solvent) at 150℃; for 0.5h; Microwave irradiation;	98%
In 5,5-dimethyl-1,3-cyclohexadiene for 16h; Reflux; Inert atmosphere;	80%

N-hydroxyphthalimide (524-38-9) + 1,3-benzodioxole-5-acetic acid (2861-28-1) → 1,3-dioxoisoindolin-2-yl 2-(benzo[d][1,3]dioxol-5-yl)acetate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In tetrahydrofuran at 20℃; Inert atmosphere;	96%
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.5h;	83%

1,3-benzodioxole-5-acetic acid (2861-28-1) + N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamine hydrochloride (80376-85-8) → 2-Benzo[1,3]dioxol-5-yl-N-methyl-N-(1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-acetamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 18h; Ambient temperature;	95%

ethyl bromide (74-96-4) + 1,3-benzodioxole-5-acetic acid (2861-28-1) → (benzo[1,3]dioxol-5-yl)acetic acid ethyl ester (26664-86-8)

Conditions	Yield
With tetradecyl(trihexyl)phosphonium bistriflamide; N-ethyl-N,N-diisopropylamine at 30℃;	95%
With tetradecyl(trihexyl)phosphonium bistriflimide; N-ethyl-N,N-diisopropylamine at 30℃; for 12h;	95%

1,3-benzodioxole-5-acetic acid (2861-28-1) + isopropyl bromide (75-26-3) → isopropyl 2-(3,4-methylenedioxyphenyl)acetate

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Reflux;	95%
With tetradecyl(trihexyl)phosphonium bistriflamide; N-ethyl-N,N-diisopropylamine at 40℃;	93%
With tetradecyl(trihexyl)phosphonium bistriflimide; N-ethyl-N,N-diisopropylamine at 40℃; for 12h;	93%

1,3-benzodioxole-5-acetic acid (2861-28-1) + pivaloyl chloride (3282-30-2) → 2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride (250261-64-4)

Conditions	Yield
With triethylamine In diethyl ether at -78 - 0℃; for 1h; Substitution;	94%
With triethylamine In diethyl ether at -78℃; for 1h;	80%
With triethylamine In diethyl ether at -78 - 0℃; Acylation;

1-(3-phenylpropyl)piperazine (55455-92-0) + 1,3-benzodioxole-5-acetic acid (2861-28-1) → 2-(3,4-methylenedioxy)phenyl-1-(4-(3-phenylpropyl)piperazin-1-yl)ethanone

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;	94%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → benzo[1,3]dioxol-5-ylacetic acid 8-(3,4-dimethoxyphenyl)naphtho[2,3-d][1,3]dioxol-6-yl ester

Conditions	Yield
Stage #1: 1,3-benzodioxole-5-acetic acid With phosphoric acid; trifluoroacetic anhydride In acetonitrile at 25℃; for 0.5h; Stage #2: 1-(3,4-dimethoxyphenyl)ethanone In acetonitrile at 25 - 80℃; for 20h;	93%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 5-Nitrosalicylaldehyde (97-51-8) → 3-(1,3-benzodioxol-5-yl)-6-nitro-2H-chromen-2-one (753470-29-0)

Conditions	Yield
With potassium acetate In acetic anhydride for 49h; Perkin-Oglialoro reaction; Heating;	91%
With potassium acetate; acetic anhydride Heating;	30%

1,3-benzodioxole-5-acetic acid (2861-28-1) + ammonium chloride → 3,4-methylenedioxyphenethyl alcohol (6006-82-2)

Conditions	Yield
	90%
	90%
	90%

1,3-benzodioxole-5-acetic acid (2861-28-1) + Benzoylformic acid (611-73-4) → BPD (213481-12-0)

Conditions	Yield
With acetic anhydride for 3h; Heating / reflux;	90%
With acetic anhydride Reflux;

1,3-benzodioxole-5-acetic acid (2861-28-1) → (1,3-benzodioxol-5-ylmethyl)-amide (5661-47-2)

Conditions	Yield
With 1H-imidazole; urea In octane at 120℃; for 24h; Reagent/catalyst;	90%
Stage #1: 1,3-benzodioxole-5-acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With ammonia; ammonium chloride In methanol; dichloromethane; N,N-dimethyl-formamide for 2h;

1,3-benzodioxole-5-acetic acid (2861-28-1) + para-methanesulfonylbenzaldehyde (5398-77-6) → C17H14O6S (1430809-12-3)

Conditions	Yield
With potassium acetate; acetic anhydride at 100℃; for 19h; Perkin Carboxylic Acid Synthesis;	89%

1,3-benzodioxole-5-acetic acid (2861-28-1) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → 5-(3,4,5-trimethoxyphenyl)-5,8-dihydro[1,3]dioxolo[4,5-g]isochromen-7-one

Conditions	Yield
Stage #1: 1,3-benzodioxole-5-acetic acid With trifluoroacetic anhydride In acetonitrile at 25℃; for 0.166667h; Green chemistry; Stage #2: 3,4,5-trimethoxy-benzaldehyde In acetonitrile at 25℃; for 10h; Green chemistry;	88%
Stage #1: 1,3-benzodioxole-5-acetic acid With trifluoroacetic anhydride In acetonitrile at 25℃; for 0.166667h; Pictet-Spengler Synthesis; Stage #2: 3,4,5-trimethoxy-benzaldehyde In acetonitrile at 25℃; for 10h; Pictet-Spengler Synthesis;

Upstream product

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 884-18-4 β-(benzo[1,3]dioxol-5-yl)pyruvic acid 
• 26664-86-8 (benzo[1,3]dioxol-5-yl)acetic acid ethyl ester 
• 79054-42-5 ((E)-2-Benzo[1,3]dioxol-5-yl-1-dimethylamino-vinyl)-phosphonic acid diethyl ester 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 
• 49711-55-9 (E)-3-(benzo[d][1,3]dioxol-5-yl)-2-cyanoacrylic acid 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 25379-88-8 2-(3,4-dihydroxyphenyl)acetic acid methyl ester 
• 120-57-0 piperonal 
• 35453-09-9 2-(3,4-methylenedioxyphenyl)-1-(methylsulfinyl)-1-(methylthio)ethylene 
• 62396-98-9 benzo[1,3]dioxol-5-yl-oxo-acetic acid 

Downstream Products

• 550-73-2 5-benzo[1,3]dioxol-5-ylmethyl-7-methyl-[1,3]dioxolo[4,5-g]isoquinoline 
• 132727-19-6 3,4-methylenedioxy-2'-nitro-cis-stilbene-α-carboxylic acid 
• 120-57-0 piperonal 
• 94-53-1 Piperonylic acid 
• 621-37-4 m-hydroxyphenylacetic acid 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 
• 34140-20-0 6,7-(methylenedioxy)isochroman-3-one 
• 101038-23-7 2-Benzo[1,3]dioxol-5-yl-1-(7-benzyloxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone 
• 108937-11-7 2-Benzo[1,3]dioxol-5-yl-N-[2-(2-benzyloxy-3-methoxy-phenyl)-ethyl]-acetamide 
• 78423-43-5 trans-2-Chloro-α-(3',4'-methylenedioxyphenyl)cinnamic acid 
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• 130609-98-2 2-Benzo[1,3]dioxol-5-yl-N-methyl-N-((1S,2R)-2-pyrrolidin-1-yl-cyclohexyl)-acetamide 
• 130553-93-4 2-Benzo[1,3]dioxol-5-yl-N-methyl-N-((1R,2S)-2-pyrrolidin-1-yl-cyclohexyl)-acetamide 

Relevant articles and documents

Synthesis and antitumour evaluation of peptidyl-like derivatives containing the 1,3-benzodioxole system

In the scope of a research program aiming at the synthesis and pharmacological evaluation of novel possible antitumour prototype compounds, we described in this paper the synthesis of peptidyl-like derivatives containing the 1,3-benzodioxole system. The proliferation inhibitors tested against tumour cell lines identified the derivatives tyrosine (4f) and lysine (4g) as the most active among them, presenting IC50 values in micromolar range and are more active than Safrole. For the study on the embryonic development, Safrole did not show any selectivity in this latter assay, which indicates that Safrole acts as a 'cell cycle-nonspecific' inhibitory agent. However, compound 4f presented a fair antimitotic effect, mainly on third cleavage and blastulae stages (38% and 1.7% of normal development, at 10 μg/mL), suggesting a time-dependent activity and a 'cell cycle-specific' agent action. Neither derivatives revealed hemolytic action in assay with mouse erythrocytes.

Iodide-catalyzed reductions: Development of a synthesis of phenylacetic acids

A new convenient and scalable synthesis of phenylacetic acids has been developed via the iodide catalyzed reduction of mandelic acids. The procedure relies on in situ generation of hydroiodic acid from catalytic sodium iodide, employing phosphorus acid as the stoichiometric reductant.

Development of a one-pot method for the homologation of aldehydes to carboxylic acids

A highly efficient method is described for the one-carbon homologation of aldehydes to carboxylic acid derivatives employing the reaction of a 1,1-bis-dimethylphosphonate derivative with the aldehyde and controlled acid hydrolysis of the derived α-phosphonoenamine intermediate.