2187-88-4

Usage

Uses

Used in Dye Production:
1,4,5,8-Naphthalenetetramine is used as a chemical intermediate for the production of dyes. Its aromatic amine structure allows for the synthesis of various dye compounds, contributing to the coloration of textiles and other materials.
Used in Polymer Synthesis:
1,4,5,8-Naphthalenetetramine is used as a building block in the synthesis of polymers. The presence of multiple amine groups facilitates the formation of polymer chains, which can be utilized in various applications such as plastics, coatings, and adhesives.

Synthetic route

1,4,5,8-tetranitronaphthalene (4793-98-0) → 1,4,5,8-tetra(amino)naphthalene (2187-88-4)

Conditions	Yield
With tin(ll) chloride In hydrogenchloride; ethanol at 40℃; for 2.5h;	82%

Nitroethane (79-24-3) + 1,4,5,8-tetra(amino)naphthalene (2187-88-4) → 2,7-dimethylpyrimido[4,5,6-gh]perimidine (2187-86-2)

Conditions	Yield
With polyphosphoric acid at 110℃; for 3h;	78%

1-nitro-1-phenylmethane (622-42-4) + 1,4,5,8-tetra(amino)naphthalene (2187-88-4) → 2,7-diphenylpyrimido[4,5,6-gh]perimidine (2608-35-7)

Conditions	Yield
With polyphosphoric acid at 150℃; for 8h;	63%

nitromethane (75-52-5) + 1,4,5,8-tetra(amino)naphthalene (2187-88-4) → pyrimido[4,5,6-gh]perimidine (194-10-5)

Conditions	Yield
With polyphosphoric acid at 100℃; for 14h;	56%

1,4,5,8-tetra(amino)naphthalene (2187-88-4) → naphtho<1,8-cd:5,4-c'd'>bis<1,2,6>thia(SIV)diazine (65989-13-1)

Conditions	Yield
With 1-piperidinosulfenyl chloride In diethyl ether at -20℃;	25%

1,4,5,8-tetra(amino)naphthalene (2187-88-4) + dimethyl sulfate (77-78-1) → 1,4,5,8-Tetrakis(dimethylamino)naphthalene (134180-29-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 25 - 60℃;	14%

1,4,5,8-tetra(amino)naphthalene (2187-88-4) + tris(dimethylamino)-bromophosphonium bromide → tris(dimethylamino)iminophosphorane hydrobromide (83978-10-3) + 1,6-bis(dimethylamino)-2,5,7,10-tetraazo-1,6λ5-diphosphapyrene (1301606-11-0)

Conditions	Yield
Stage #1: 1,4,5,8-tetra(amino)naphthalene; tris(dimethylamino)-bromophosphonium bromide With triethylamine In chlorobenzene at 20℃; for 72h; Inert atmosphere; Stage #2: With sodium hexamethyldisilazane In chlorobenzene; toluene for 24h; Inert atmosphere;	A n/a B 2.14%

Upstream product

• 4793-98-0 1,4,5,8-tetranitronaphthalene 

Downstream Products

• 2608-35-7 2,7-diphenylpyrimido[4,5,6-gh]perimidine 

Relevant academic research and scientific papers

Conjugated perimidine corrosion inhibitor and preparation method thereof

The invention discloses a conjugated perimidine corrosion inhibitor and a preparation method thereof. The preparation method comprises the following steps: carrying out acylation and cyclization reaction on 1,4,5,8-tetraminonaphthalene and substituted benzoic acid to obtain dialkyl phenyl perimidine; and 2) performing quaternization reaction on the dialkyl phenyl perimidine and hydrobromic acid to prepare a conjugated perimidine corrosion inhibitor. According to the invention, the conjugated perimidine corrosion inhibitor is high in conjugation degree of molecules, can form a large pi bond to be adsorbed on a metal surface in a planar configuration, is strong in adhesive force, greatly improves the corrosion inhibition rate, can be used as a copper and iron corrosion inhibitor, and has a good corrosion inhibition effect.

peri-naphthalenediamines: XXXIV. 1,4,5,8-Tetrakis(dimethylamino)naphthalene: Alternative approaches to synthesis

New methods were proposed for synthesizing 1,4,5,8-tetrakis(dimethylamino)naphthalene with an overall yield of 4 to 12% to replace the known procedure ensuring an overall yield of 2%. Catalytic hydrogenation was shown to be inapplicable for preparation of polyaminonaphthalenes from nitro compounds having 3 or 4 nitro gruops in the α-positions. Nucleophilic amination of 1,5-dinitronaphthalene in the system NH2OH/NaOH/MeOH yields 1-amino-4-nitronaphthalene. The nitration of 1,5-bis(p-tolylsulfonylamino)-naphthalene leads to formation of 2,6-dinitro rather than 4,8-dinitro derivative, as it was believed formerly. This was confirmed by transformation of the latter into 1,2,5,6-tetrakis(dimethylamino)naphthalene. 3-Nitro, 2,6-dinitro, 2,6-diamino, and 2,4,6,8-tetranitro derivatives of 1,5-bis(dimethylamino)naphthalene, nitro and amino derivatives of 1,4,5-tris(dimethylamino)naphthalene, and 4,5-diamino-1,8-bis(methylamino)naphthalene were synthesized. By treatment with perchloric acid 1,4,5,8-tetrakis(dimethylamino)naphthalene was oxidized to 2,3-dihydroperimidinium salt.