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HomeProduct name list3,4-(Methylenedioxy)aniline

3,4-(Methylenedioxy)aniline

Synonym(s):5-Amino-1,3-benzodioxole

  • CAS NO.:14268-66-7
  • Empirical Formula: C7H7NO2
  • Molecular Weight: 137.14
  • MDL number: MFCD00005832
  • EINECS: 238-161-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:57
3,4-(Methylenedioxy)aniline Structural

What is 3,4-(Methylenedioxy)aniline?

Chemical properties

dark brown to black low melting solid

The Uses of 3,4-(Methylenedioxy)aniline

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.
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.]

Properties of 3,4-(Methylenedioxy)aniline

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 for 3,4-(Methylenedioxy)aniline

Signal word Warning
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H302:Acute toxicity,oral
H312:Acute toxicity,dermal
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H331:Acute toxicity,inhalation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for 3,4-(Methylenedioxy)aniline

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