27738-39-2

Basic information

• Product Name: 3,4-METHYLENEDIOXYBENZYLIDENE ANILINE
• Synonyms: TIMTEC-BB SBB007839;PIPERONYLIDENE ANILINE;N-[(E)-1,3-BENZODIOXOL-5-YLMETHYLIDENE]-N-PHENYLAMINE;N-[(E)-1,3-BENZODIOXOL-5-YLMETHYLIDENE]ANILINE;3,4-METHYLENEDIOXYBENZYLIDENE ANILINE;N-Piperonylideneaniline
• CAS NO: 27738-39-2
• Molecular Formula: C₁₄H₁₁NO₂
• Molecular Weight: 225.24
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 27738-39-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 86 °C
• Boiling Point: 363.5°Cat760mmHg
• Flash Point: 141.1°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 3.75E-05mmHg at 25°C
• Refractive Index: 1.602
• PKA: 3.78±0.20(Predicted)
• CAS DataBase Reference: 3,4-METHYLENEDIOXYBENZYLIDENE ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-METHYLENEDIOXYBENZYLIDENE ANILINE(27738-39-2)
• EPA Substance Registry System: 3,4-METHYLENEDIOXYBENZYLIDENE ANILINE(27738-39-2)

Safety Data

• Hazardous Substances Data: 27738-39-2(Hazardous Substances Data)

Usage

General Description

3,4-Methylenedioxybenzylidene aniline, also known as MDBA, is a chemical compound that belongs to the class of benzylidene anilines. It is commonly used as an intermediate in the synthesis of various pharmaceuticals and dyes. MDBA is also known for its potential use as a precursor for the synthesis of psychoactive substances, such as designer drugs.

InChI:InChI=1/C14H11NO2/c1-2-4-12(5-3-1)15-9-11-6-7-13-14(8-11)17-10-16-13/h1-9H,10H2/b15-9+

Upstream product

• 120-57-0 piperonal 
• 62-53-3 aniline 
• 495-76-1 piperonol 
• 98-95-3 nitrobenzene 

Downstream Products

• 3526-42-9 N-(benzo[d][1,3]dioxol-5-ylmethyl)benzenamine 
• 36797-61-2 2t-benzo[1,3]dioxol-5-yl-5-oxo-1-phenyl-pyrrolidine-3r-carboxylic acid 
• 16226-81-6 4-benzo[1,3]dioxol-5-yl-2,6-dioxo-5-phenyl-[1,3,5]triazinane-1,3-disulfonic acid bis-(2,6-dimethyl-phenyl) ester 
• 125112-34-7 diethyl cis-<3-(3,4-methylenedioxyphenyl)-1-phenyl-2-aziridinyl>phosphonate 
• 112383-83-2 4-Benzo[1,3]dioxol-5-yl-3,3-bis-ethylsulfanyl-1-phenyl-azetidin-2-one 
• 135508-99-5 (3S,4R)-4-Benzo[1,3]dioxol-5-yl-3-(2-isopropyl-5-methyl-phenoxy)-1-phenyl-azetidin-2-one 
• 94612-51-8 13d 
• 75638-35-6 α-(phenylamino)-1,3-benzodioxole-5-acetonitrile 
• 135508-98-4 (3S,4R)-3-(4-Allyl-2-methoxy-phenoxy)-4-benzo[1,3]dioxol-5-yl-1-phenyl-azetidin-2-one 
• 135508-92-8 (3S,4R)-4-Benzo[1,3]dioxol-5-yl-3-phenoxy-1-phenyl-azetidin-2-one 
• 29874-34-8 2-(benzo[d][1,3]dioxol-5-ylmethylene)-1H-indene-1,3(2H)-dione 
• 64499-60-1 N-phenyl-piperonylamidine 
• 62-53-3 aniline 

Relevant articles and documents

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Arene diruthenium(II)-mediated synthesis of imines from alcohols and amines under aerobic condition

The utility and selectivity of the newly synthesized dinuclear arene Ru(II) complex were demonstrated towards the synthesis of imines from coupling of alcohols and amines in the aerobic condition. Analytical and various spectral methods have been used to establish the unprecedented formation of the new thiolato-bridged dinuclear ruthenium complex. The molecular structure of the titled complex was evidenced with aid of X-ray crystallographic technique. A wide range of imines were obtained in good-to-excellent yields up to 98% and water as the by-product through an acceptorless dehydrogenative coupling of alcohols with amines. The catalytic reaction operated a concise atom economical without any oxidant with 1 mol% of the catalyst load. Further, the role of base, solvent and catalyst loading of the coupling reaction has been investigated. A plausible mechanism has been described and was found to proceed via the formation of an aldehyde intermediate. Short synthesis of antibacterial drug N-(salicylidene)-2-hydroxyaniline illustrated the utility of the present protocol.

Polyoxometalate catalyzed imine synthesis: Investigation of mechanistic pathways

The syntheses of imines by oxidative coupling of primary alcohols and amines were achieved by using 2 molpercent polyoxometalate (POM) Na12[WZn3(H2O)2(ZnW9O34)2] (Zn–WZn3) catalyst in the presence of t-BuOK and di-oxygen with excellent conversion (up to 100percent) and selectivity (up to 100percent). Non-noble metal-based POM catalyst in the presence of base represents a new reaction protocol for the selective synthesis of imine from both aromatic and aliphatic primary amines with functional group tolerance. Control experiment shows the formation of di-oxygen bind Zn–WZn3 activated species. The electron-density of POM is mostly situated on the surface oxygen atoms of W–O–W bonds which can engage the alcoholic OH group and helps for the imine selectivity in the second step of imine synthesis.