ChemicalBook CAS DataBase List 1,5-Naphthalenediamine

1,5-Naphthalenediamine synthesis

13synthesis methods

Product Name:1,5-Naphthalenediamine
CAS Number:2243-62-1
Molecular formula:C10H10N2
Molecular Weight:158.2

The 1979 estimated production volume was 50,000 kg in Germany and Japan. The major use of the compound is for the manufacture of 1,5-naphthalene diisocyanate and in the production of polyurethane elastomers.
The potential for exposure to 1,5-naphthalenediamine may be greatest for workers involved in the manufacture of 1,5- naphthalene diisocyanate, which is known to hydrolyze readily to 1,5-naphthalenediamine upon contact with water.

83-55-6 Synthesis

83-55-6
171 suppliers
$34.39/25g

2243-62-1
280 suppliers
$6.00/5g

Yield:2243-62-1 93.6%

Reaction Conditions:

with ammonium hydrogen sulfite;ammonia in diethylene glycol dimethyl ether;water at 150; for 6 h;

Steps:

9 EXAMPLE 9 Amination of 5-amino-1-naphthol
In an autoclave was placed 8.0 g (0.05 moles) of 5-amino-1-naphthol, 10.2 g of 50% ammonium-hydrogensulfite aqueous solution, 30.4 g of 28% aqueous ammonia (0.5 moles of ammonia), and 25.0 g of diglyme, and the reaction was carried out at 150 C. for 6 hours. After the reaction mixture was cooled, the contents were dissolved in DMF. Quantification by HPLC indicated that the remaining content of 5-amino-1-naphthol, i.e., the starting material, was 6.2% and the yield of 1,5-diaminonaphthalene was 93.6% (selectivity 99.8%).

References:

Mitsui Chemicals, Inc. US2004/143137, 2004, A1 Location in patent:Page 5