13067-19-1

Basic information

• Product Name: 3',4'-METHYLENEDIOXYACETANILIDE
• Synonyms: N-(1,3-Benzodioxol-5-yl)acetamide;n-1,3-benzodioxol-5-yl-acetamid;n-1,3-benzodioxol-5-ylacetamide;TIMTEC-BB SBB007866;N-(benzo[d][1,3]dioxol-5-yl)acetamide;N-Benzo[1,3]dioxol-5-yl-acetamide;3',4'-METHYLENEDIOXYACETANILIDE;3',4-METHYLENEDIOXYACETANILIDE
• CAS NO: 13067-19-1
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Mol File: 13067-19-1.mol

Chemical Properties

• Boiling Point: 367.4 °C at 760 mmHg
• Flash Point: 176 °C
• Appearance: /
• Density: 1.34 g/cm³
• CAS DataBase Reference: 3',4'-METHYLENEDIOXYACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3',4'-METHYLENEDIOXYACETANILIDE(13067-19-1)
• EPA Substance Registry System: 3',4'-METHYLENEDIOXYACETANILIDE(13067-19-1)

Safety Data

• Hazardous Substances Data: 13067-19-1(Hazardous Substances Data)

Usage

Uses

Used in Illicit Drug Preparations:
3',4'-METHYLENEDIOXYACETANILIDE is used as a psychoactive substance in illicit drug preparations for its stimulating and hallucinogenic effects. However, it is important to note that the use of MDAA in this context is illegal and associated with significant health risks and adverse effects.
It should be emphasized that the use of MDAA is strictly prohibited due to its classification as a Schedule I controlled substance, and the information provided is for educational purposes only, not to encourage or endorse its use.

Upstream product

• 108-24-7 acetic anhydride 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 75-36-5 acetyl chloride 
• 917-61-3 sodium isocyanate 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 562-90-3 tetraacetoxysilane 
• 14040-11-0 tungsten hexacarbonyl 
• 2620-44-2 5-nitro-1,3-benzodioxole 
• 616-38-6 carbonic acid dimethyl ester 
• 62681-68-9 1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 
• 62681-68-9 (E)-1-(benzo[d][1,3]dioxol-5-yl)ethan-1-one oxime 

Downstream Products

• 78881-21-7 4-amino-3-methylbenzonitrile 
• 149809-25-6 2'-(acetylamino)-2-chloro-4',5'-(methylenedioxy)acetophenone 
• 332382-81-7 6-chloro-[1,3]dioxolo[4,5-g]quinoline-7-carbaldehyde 
• 243133-76-8 2-benzoyl-4,5-(methylenedioxy)acetanilide 
• 81864-14-4 N-(6-Nitrobenzo[d][1,3]dioxol-5-yl)acetamide 
• 99185-29-2 6-Acetamino-piperonylsaeure 
• 1332835-67-2 1-(6,7-diphenyl-5H-[1,3]dioxolo[4,5-f]indol-5-yl)ethanone 
• 1000802-34-5 6-iodobenzo[d][1,3]dioxol-5-amine 
• 1462270-91-2 6-acetamidobenzo[d][1,3]dioxol-5-yl 4-chlorobenzoate 
• 1462270-93-4 6-acetamidobenzo[d][1,3]dioxol-4-yl 4-chlorobenzoate 

Relevant articles and documents

Synthesis and biological evaluation of 10,11-methylenedioxy-14- azacamptothecin

10,11-Methylenedioxy-14-azacamptothecin, a potent analogue of the antitumor agent camptothecin (CPT), has been prepared via a key condensation between AB and DE ring precursors. The biological testing of this compound validated a strategy for modulation of the off-rate of camptothecin analogues from the topoisomerase-DNA-CPT ternary complex via structural modification.

Synthesis and bio-evaluation of novel quinolino-stilbene derivatives as potential anticancer agents

A series of 25 novel quinolino-stilbene derivatives were designed, synthesized and evaluated for their potential as anticancer agents. Three of them not only displayed quite potent antiproliferative activity with IC50 values 50 values in the range of 4-10 μM, and the rest was moderately active or inactive. One of these viz. 3-[E-(4-fluorostyryl)]-2-chloroquinoline (compound 7B) caused substantial DNA damage and arrested cell cycle in S phase. Interestingly, 7B was very active against MDA-MB468 (IC50 = 0.12 μM), but not against other cell lines examined. Compound 3-[Z-(3-(trifluoromethyl)styryl)]-2-chloroquinoline (12A), the most effective against all cancer cell lines examined, caused prolonged cell cycle arrest at mitosis and eventually apoptosis. Data from an in vitro study showed that compound 12A inhibited microtubule polymerization in a similar fashion to nocodazole. Further study using in silico molecular modeling revealed that 12A causes the impediment of microtubule polymerization by binding to tubulin at the same cavity where podophyllotoxin binds.

A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds

Dimethyl carbonate (DMC), an environment-friendly compound prepared from CO2, shows diverse reactivities. In this communication, an efficient procedure using DMC as both a C1 building block and solvent in the aminocarbonylation reaction with nitro compounds has been developed. W(CO)6acts both a CO source and a reductant here.

Preparation method of acetamide compound

The invention discloses a preparation method of an acetamide compound, the preparation method comprises the following steps: reacting tetracarbonyl dichloride rhodium, 1, 3-bis (diphenylphosphine) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 DEG C for 24 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound. According to the preparation method, dimethyl carbonate serves as a C1 source and also serves as a green solvent, operation is easy, reaction starting raw materials are low in price and easy to obtain, the tolerance range of substrate functional groups is wide, and reaction efficiency is high. Various acetamide compounds can be synthesized according to actual needs, so that the practicability of the method is widened while the operation is convenient.

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.

A Novel Difluoroacetic Acid Derivatives Compound, and Composition Comprising the Same

The present invention relates to a novel difluoroacetic acid derivative compound and a composition for various uses containing the same, wherein the difluoroacetic acid derivative compound can not only act as an agonist activating one among PPARandalpha;, andbeta; or andgamma;, but also can exhibit double efficacy or triple efficacy. Therefore, the difluoroacetic acid derivative compound can more effectively prevent, alleviate or treat metabolic diseases in which PPARs involves, and further exhibits whitening and wrinkle alleviation activity, and anti-inflammatory and antioxidant effects, thereby being able to be usefully utilized as various compositions.COPYRIGHT KIPO 2020

CHEMICAL ENTITIES, PHARMACEUTICAL FORMULATIONS, AND METHODS FOR TREATING FIBROSIS

Disclosed herein are chemical entities, or pharmaceutically acceptable salts thereof, for treating fibrosis, including pulmonary fibrosis, such as idiopathic pulmonary fibrosis. Also disclosed herein are pharmaceutical formulations for treating fibrosis, the pharmaceutical formulations including one or more of the foregoing chemical entities and one or more pharmaceutically acceptable excipients, carriers, vehicles, or a combination thereof. Also disclosed herein are packaged pharmaceutical formulations for treating fibrosis, the packaged pharmaceutical formulations including one of the foregoing pharmaceutical formulations and instructions for using the pharmaceutical formulation to treat a patient having fibrosis or susceptible to fibrosis. Also disclosed herein is a method for treating fibrosis, the method including administering one of the foregoing pharmaceutical formulations.

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement

A metal-free and redox-neutral method for Beckmann rearrangement employing inexpensive and readily available SO2F2 gas is described. The reported transformation proceeds at ambient temperature and is compatible with a wide range of sterically and electronically diverse aromatic, heteroaromatic, aliphatic and lignin-like oximes providing amides in good to excellent yields. The reaction proceeds through the formation of an imidoyl fluoride intermediate that can also be used for the synthesis of amidines.