6951-08-2

Usage

Uses

Used in Perfume and Soap Production:
1,3-Benzodioxole-5-carboxylic acid ethyl ester is used as a key ingredient in the production of perfumes and soaps, providing a unique and pleasant scent.
Used in Pharmaceutical and Agrochemical Synthesis:
Safrole is used as a starting material in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and agricultural products.
Used in Flavoring Agents (Historically):
1,3-Benzodioxole-5-carboxylic acid ethyl ester was historically used as a flavoring agent in food and beverages, enhancing the taste and aroma of these products.
Note: Due to the potential health risks and legal restrictions associated with safrole, its use in flavoring agents has been significantly reduced or discontinued in many countries.

InChI:InChI=1/C10H10O4/c1-2-12-10(11)7-3-4-8-9(5-7)14-6-13-8/h3-5H,2,6H2,1H3

Upstream product

• 94-53-1 Piperonylic acid 
• 64-17-5 ethanol 
• 274-09-9 Methylenedioxybenzene 
• 509-14-8 tetranitromethane 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 1609-47-8 diethyl dicarbonate 
• 1906-57-6 potassium monoethyl oxalate 
• 120-57-0 piperonal 
• 124156-21-4 ethyl (4-methoxyphenylimino)acetate 
• 94839-07-3 3,4-(methylenedioxy)-benzeneboronic acid 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 15226-74-1 dicobalt octacarbonyl 
• 109586-40-5 1,3-dihydroisobenzofuran-5-yl trifluoromethanesulfonate 

Downstream Products

• 26036-40-8 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropane-1,3-dione 
• 96220-14-3 3-benzo[1,3]dioxol-5-yl-3-oxo-propionitrile 
• 68233-51-2 1-benzo[1,3]dioxol-5-yl-2-phenyl-2-pyridin-2-yl-ethanone 
• 89084-30-0 2-diphenylphosphinoyl-1-(3,4-methylenedioxyphenyl)propan-1-one 
• 356560-89-9 1-(benzo[1,3]dioxol-5-yl)-2-(6-methylpyridin-2-yl)ethanone 
• 102124-73-2 α,α,α-trifluoro-3,4-methylenedioxyacetophenone 
• 63698-52-2 2-mercapto-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 876552-72-6 2-benzylthio-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 67572-46-7 2-((ethoxycarbonyl)methylthio)-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole 
• 4421-09-4 piperonylonitrile 
• 78266-84-9 1-Benzo[1,3]dioxol-5-yl-2-(diphenyl-phosphinoyl)-propan-1-ol 
• 78266-84-9 1-Benzo[1,3]dioxol-5-yl-2-(diphenyl-phosphinoyl)-propan-1-ol 
• 15777-84-1 N-methylbenzo[d][1,3]dioxole-5-carboxamide 

Relevant academic research and scientific papers

Metal-Free Oxidative Esterification of Ketones and Potassium Xanthates: Selective Synthesis of α-Ketoesters and Esters

A novel and efficient oxidative esterification for the selective synthesis of α-ketoesters and esters has been developed under metal-free conditions. In the protocol, various α-ketoesters and esters are available in high yields from commercially available ketones and potassium xanthates. Mechanistic studies have proven that potassium xanthate not only promotes oxidative esterification but also provides an alkoxy moiety for the reaction, which involves the cleavage and reconstruction of C-O bonds.

A heterocyclic compound and use thereof

The invention discloses a compound of a general formula I and application of the compound serving as a plant disease-resistance activator. In the formula, a substituent group R1 and 0-3 substituent groups R2 exist on the 4th, 5th, 6th and 7th sites; R1 is independently selected from -R3OOH, -R4OOR5, -R6OH and -R7-O-R8; R2 is independently selected from C1-C6 alkyl, C1-6 halogenated alkyl, C1-C6 alkoxy, C1-C6 halogenated alkoxy, hydroxyl, halogen, nitro, amino and C1-C6 alkylamino; R3, R4, R5, R6, R7 and R8 are independently selected from C1-C6 alkyl and C1-6 halogenated alkyl. The compound induces plants to generate disease resistance so as to inhibit pathogens instead of directly killing or inhibiting the pathogens. The compound has the advantages of systematicness, durability, broad spectrum, high safety and the like, so the amount of highly toxic pesticides can be reduced, and the compound is environmentally friendly and has huge industrialized and commercial prospects and market values.

Accessing N-Acyl Azoles via Oxoammonium Salt-Mediated Oxidative Amidation

An operationally simple, robust, metal-free approach to the synthesis of N-acyl azoles from both alcohols and aldehydes is described. Oxidative amidation is facilitated by a commercially available organic oxidant (4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and proceeds under very mild conditions for an array of structurally diverse substrates. Tandem reactions of these activated amides, such as transamidation and esterification, enable further elaboration. Also, the spent oxidant can be recovered and used to regenerate the oxoammonium salt.

SO2F2-Mediated One-Pot Synthesis of Aryl Carboxylic Acids and Esters from Phenols through a Pd-Catalyzed Insertion of Carbon Monoxide

A one-pot Pd-catalyzed carbonylation of phenols into their corresponding aryl carboxylic acids and esters through the insertion of carbon monoxide has been developed. This procedure offers a direct synthesis of aryl carboxylic acids and esters from inexpensive and abundant starting materials (phenols, SO2F2 and CO) under mild conditions. This method tolerates a broad range of functional groups and is also applicable for the modification of complicated natural products.

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co2(CO)8] has been developed. Besides acting as carbon monoxide (CO) source, Co2(CO)8enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd-Co(CO)4] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates). (Figure presented.).

Cu(ii)-catalyzed esterification reaction via aerobic oxidative cleavage of C(CO)-C(alkyl) bonds

A novel Cu(ii)-catalyzed aerobic oxidative esterification of simple ketones for the synthesis of esters has been developed with wide functional group tolerance. This process is assumed to go through a tandem sequence consisting of α-oxygenation/esterification/nucleophilic addition/C-C bond cleavage and carbon dioxide is released as the only byproduct.

Synthesis, characterization and urease inhibiting derivatives of 5-(3,4-Methylenedioxyphenyl)-1,3,4-Oxadiazol-2-thiol

In the present work, the urease inhibition activity of 1,3,4-oxadiazole bearing molecules was evaluated and were found to be potential inhibitors. 3,4-(Methylenedioxy)benzoic acid (1) was employed to synthesize 5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazol-2-thiol (4) via a series of steps. It was further stepped to yield S-substituted-5-(3,4-methylenedioxyphenyl)-1,3,4-oxadiazole derivatives (6a-h) on reaction with alkyl/aralkyl halides (5a-h) in DMF using LiH as an activator. All the synthesized compounds were well supported by IR, 1H NMR and EIMS spectral analysis. The enzyme inhibition activity against urease enzyme showed these molecules as potent inhibitors of this enzyme.

Correlation of the rates of solvolysis of electron-rich benzoyl chloride using the extended Grunwald-Wistein equation

The solvolysis rate constants of piperonyloyl chloride (1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale, YCl solvent ionizing scale, and I aromatic ring parameter with sensitivity values of 0.30 ± 0.05, 0.71 ± 0.02, and 0.60 ± 0.04 for l, m, and h, respectively. The solvent kinetic isotope effect values (SKIE, kMeOH/kMeOD and k 50%MeOD-50%D2O) of 1.16 and 1.12 were also in accord with the values for the SN1 mechanism and/or the dissociative SN2 mechanism. The product selectivity values (S) for solvolysis of 1 in alcohol/water mixtures were in the range of 0.5 to 1.9, which is also consistent with the proposed unimolecular ionization mechanism.

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. The Royal Society of Chemistry.

Oxidative esterification of aldehydes with alcohols and phenols in air

Nucleophilic carbene-catalysed oxidative esterification of aldehydes with alcohols and phenols without additional oxidant under an air atmosphere has been achieved, which provides a metal-free new methodology for the oxidative esterification of aldehydes.