112776-37-1

Basic information

• Product Name: 3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE
• Synonyms: N-(3,4-METHYLENEDIOXYBENZYLIDENE)BENZYLAMINE;3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE;N-Benzylidene-3,4-(methylenedioxy)benzylamine, 98+%;3,4-Methylenedioxybenzylidinebenzylamine, 98+%;N-Benzylidene-3,4-(methylenedioxy)benzylamine
• CAS NO: 112776-37-1
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.27
• Mol File: 112776-37-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 69.5-70 °C(lit.)
• Boiling Point: 308.4°Cat760mmHg
• Flash Point: 140.3°C
• Appearance: /Powder
• Density: g/cm³
• Vapor Pressure: 0.00124mmHg at 25°C
• PKA: 4.45±0.50(Predicted)
• CAS DataBase Reference: 3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE(112776-37-1)
• EPA Substance Registry System: 3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE(112776-37-1)

Safety Data

• Hazard Codes: T,N
• Statements: 25-37/38-41-51/53
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 112776-37-1(Hazardous Substances Data)

Usage

General Description

3,4-METHYLENEDIOXYBENZYLIDINEBENZYLAMINE, also known as MDA, is a psychoactive chemical compound that belongs to the phenethylamine class of drugs. It is closely related to MDMA, also known as ecstasy, and is known for its empathogenic and hallucinogenic effects. MDA acts as a serotonin-norepinephrine-dopamine releasing agent and reuptake inhibitor, leading to increased levels of these neurotransmitters in the brain. It is commonly used recreationally for its euphoric and psychedelic effects, but it also carries potential risks and can have negative effects on health and mental well-being. Due to its psychoactive properties, MDA is classified as a controlled substance in many countries and is illegal to manufacture, distribute, or possess without proper authorization.

InChI:InChI=1/C9H10NO2P/c13-5-10-4-7-1-2-8-9(3-7)12-6-11-8/h1-3,5H,4,6,13H2/b10-5+

Upstream product

• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 20747-42-6 piperonal-(Z)-oxime 

Downstream Products

• 1023023-78-0 3-(benzo[d][1,3]dioxol-5-ylmethyl)-2-phenylthiazolidin-4-one 
• 1235889-67-4 (2R,5R)-dimethyl 1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(4-methoxyphenyl)-2-phenylpyrrolidine-3,3-dicarboxylate 
• 112776-46-2 N-Benzo[1,3]dioxol-5-ylmethyl-2-chloro-2-phenyl-acetamide 
• 112776-49-5 8-Phenyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquinolin-7-one 
• 135509-04-5 (3R,4S)-3-(4-Allyl-2-methoxy-phenoxy)-1-benzo[1,3]dioxol-5-ylmethyl-4-phenyl-azetidin-2-one 
• 135508-93-9 1-Benzo[1,3]dioxol-5-ylmethyl-3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-phenyl-azetidin-2-one 
• 135509-03-4 (3R,4S)-1-Benzo[1,3]dioxol-5-ylmethyl-3-(2-isopropyl-5-methyl-phenoxy)-4-phenyl-azetidin-2-one 
• 112776-42-8 1-Benzo[1,3]dioxol-5-ylmethyl-2,2-dichloro-3-phenyl-aziridine 

Relevant articles and documents

Synthesis of chromeno[3,4-b]piperazines by an enol-ugi/reduction/cyclization sequence

Keto piperazines and aminocoumarins are privileged building blocks for the construction of geometrically constrained peptides and therefore valuable structures in drug discovery. Combining these two heterocycles provides unique rigid polycyclic peptidomimetics with drug-like properties including many points of diversity that could be modulated to interact with different biological receptors. This work describes an efficient multicomponent approach to condensed chromenopiperazines based on the novel enol-Ugi reaction. Importantly, this strategy involves the first reported post-condensation transformation of an enol-Ugi adduct.

Synthesis of polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a one-pot (Ugi-3CR/aza diels-alder/N-acylation/aromatization/SN2) process. A suitable alternative towards novel Aza-analogues of falipamil

We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology.

Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights

An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor-acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.