3,4-(Methylenedioxy)aniline Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3,4-(Methylenedioxy)aniline Chemical Properties,Usage,Production

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.]