2,6-Diaminopyridine

Description

2,6-Diaminopyridine is an important organic reagent with a wide range of uses. It can be used for fluorescence detection, 2,6-Diaminopyridine fluorescence method for the determination of certain aromatic primary amines. It can also be used to prepare 2,6-Diaminopyridine imprinted core-shell nanoparticles. A new method for the detection of diaminopyridine derivatives using molecularly imprinted electrochemical sensors has been established, which has been applied to the detection of 2,6-Diaminopyridine in hair dyes with good sensitivity and selectivity.

Chemical properties

Off-white crystal powder/granuale

Description

2,6-Diaminopyridine functions as a reagent in chemical synthesis. It acts as a building block in the formation of various organic compounds, particularly in the production of agrochemicals, and specialty chemicals.

The Uses of 2,6-Diaminopyridine

2,6-Diaminopyridine, used as a pharmaceutical intermediate and a hair dye coupler in oxidation/permanent formulations.

Preparation

In a 600 mL autoclave equipped with a gas entrapment stirrer, a solution of 5 g CuI in 120 g aqueous ammonia (30% NH3 by weight) was added and mixed with 77 g ammonium acetate and 60 g of 2, 6-dichloropyridine. After purging with nitrogen, 24 g of liquid ammonia was added resulting in a pressure of about 150 psi (1.03 MPa). Subsequently, the reaction mixture was heated to 150°C for 8 h under stirring. Throughout the reaction, the pressure decreased from an initial pressure of 680 psi (4.69 MPa) to 450 psi (3.10 MPa). The reaction mixture was allowed to cool to room temperature, and the pressure was brought back to atmospheric pressure. Finally, 2,6-Diaminopyridine was obtained after purification.

Mechanism of action

The mechanism of action involves its ability to participate in nucleophilic substitution reactions, where it can undergo substitution with other functional groups to form new chemical bonds. Its role in chemical synthesis involves its interaction at the molecular level, where it can facilitate the formation of specific chemical structures through its reactivity with other compounds.

Safety Profile

Poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Toxicity evaluation

2,6-Diaminopyridine was not mutagenic in Salmonella typhimurium strain TA98 in the presence or absence of nonharman at 200 μg/plate. The mutagenicity of this compound was not enhanced by rodent liver S-9 (Sugimura et al., 1982).
In another study, it was not mutagenic in S. typhimurium strain TA98 without rodent liver S-9. However, it was mutagenic in the presence of rodent liver S-9 (Takahashi & Ono, 1993). 
This compound was not mutagenic in S. typhimurium strains TA98, TA100, and TA1535 in the presence or absence of rodent liver S-9 (JETOC, 1997; Takahashi & Ono, 1993)
It was mutagenic in S. typhimurium strain TA1537 in the presence or absence of rodent liver S-9 (JETOC, 1997).
2,6-Diaminopyridine was not mutagenic in Escherichia coli strain WP2 uvrA in the presence or absence of rodent liver S-9 (JETOC, 1997).