ChemicalBook CAS DataBase List p-Phenylenediamine

p-Phenylenediamine synthesis

14synthesis methods

Product Name:p-Phenylenediamine
CAS Number:106-50-3
Molecular formula:C6H8N2
Molecular Weight:108.14

1516-60-5 Synthesis

1516-60-5
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106-50-3
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Yield:106-50-3 100%

Reaction Conditions:

Stage #1: 4-nitrophenyl azidewith hydrazine hydrate at 135; for 3 h;
Stage #2: with potassium hydroxide at 135; for 24 h;

Steps:

Benzene 1,4-diamine (4)

General procedure: The corresponding substrate (1 mmol) was dissolved in 2 mL of distilled hydrazine hydrate. The mixture was stirred for 3 h in a sealed pressure tube placed in an oil bath at 135 °C. The reaction was then allowed to reach room temperature and KOH (5 mmol) was added. The mixture was allowed to react overnight at 135 °C. It was then extracted with a mixture of DCM and isopropanol 80:20 and washed with water (3x30 mL) and the organic solvent was evaporated to give a residue that was purified by silica gel column chromatography, eluting with hexane:ethylacetate (1:1) to yield the desired products.

References:

Diez-Cecilia, Elena;Kelly, Brendan;Rozas, Isabel [Tetrahedron Letters,2011,vol. 52,# 50,p. 6702 - 6704] Location in patent:supporting information; experimental part

106-40-1 Synthesis