3,4-(Methylenedioxy)aniline Chemical Properties

Melting point:

39-41 °C(lit.)

Boiling point:

144 °C16 mm Hg(lit.)

Density 

1.2528 (rough estimate)

refractive index 

1.5030 (estimate)

Flash point:

289 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.78±0.20(Predicted)

form 

Low Melting Solid

color 

Dark brown to black

Water Solubility 

slightly soluble

Sensitive 

Air & Light Sensitive

BRN 

4919

CAS DataBase Reference

14268-66-7(CAS DataBase Reference)

NIST Chemistry Reference

1,3-Benzodioxol-5-amine(14268-66-7)

EPA Substance Registry System

1,3-Benzodioxol-5-amine (14268-66-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

HS Code 

29329970

MSDS

• Language:English Provider:3,4-(Methylenedioxy)aniline
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3,4-(Methylenedioxy)aniline Usage And Synthesis

Chemical Properties

dark brown to black low melting solid

Uses

3,4-(Methylenedioxy)aniline is an pharmaceutically important aniline derivative. It undergoes N-alkylation with cyclic secondary alkylamines in the presence of Shvo catalyst to yield N-arylpyrrolidines. 3,4-(Methylenedioxy)aniline was used in the synthesis of γ-glutamylanilides.

Synthesis

A 10mL-sealed tube was charged with 5-bromobenzo[d][1,3]dioxole (1mmol), CuI (19mg, 0.1mmol), and DMEDA (13mg/16μL, 0.15mmol) in NH4OH (1.5mL, 27% NH3 in H2O) and DMSO (0.5mL). The tube was flushed with Ar gas before being capped. The solution was stirred at 130°C or 110°C for the given times. The resulting suspension was cooled to room temperature, and saturated aqueous Na2SO4 solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL×3). The organic layer was separated, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography to give 3,4-(Methylenedioxy)aniline.

Purification Methods

Crystallise the base from pet ether and/or distil it in a vacuum. The hydrochloride has m 198o(dec). [Sonn & Benirschke Chem Ber 54 1734 1921, Beilstein 19 H 328, 19 II 341, 19 III/IV 4056.]

3,4-(Methylenedioxy)aniline(14268-66-7)Related Product Information

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