4182-80-3

Usage

Uses

Used in Rubber and Plastic Industry:
N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine is used as an antioxidant for enhancing the durability and stability of rubber and plastic materials. It acts as a stabilizer by preventing the oxidation and degradation processes that can compromise the integrity and performance of these materials over time.
Used in Material Preservation:
N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine is used as a preservative agent to maintain the quality and performance of rubber and plastic materials, ensuring that they remain effective and reliable for their intended applications.
Environmental and Health Considerations:
While N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine is considered safe for use in its intended applications, its widespread use has raised concerns about potential environmental impact and human health effects. Therefore, it is important to handle and use N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine with caution, adhering to safety guidelines and regulations to minimize any adverse effects.

Synthetic route

1-iodo-butane (542-69-8) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80 - 93℃; for 4h;	96%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80 - 93℃; for 4h; Product distribution / selectivity;	96%

1-bromo-butane (109-65-9) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80 - 96℃; for 6h; Product distribution / selectivity;	89%

1-bromo-4-(N,N-dibutyl)aniline (53358-54-6) + 1,4-phenylenediamine (106-50-3) → N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3)

Conditions	Yield
With sodium t-butanolate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 18h;

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) → C62H92N6(2+)*2ClO4(1-)

Conditions	Yield
Stage #1: N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene With Oxone In acetonitrile at 20℃; for 3h; Stage #2: With sodium perchlorate In acetonitrile at 20℃; for 1h; Product distribution / selectivity;	98%
Stage #1: N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene With iron(II) perchlorate hydrate In N,N-dimethyl-formamide at 70℃; for 5h; Inert atmosphere; Stage #2: With caesium hexafluorophosphate at 20℃; Inert atmosphere;	98%
With Oxone; potassium perchlorate In water; ethyl acetate; acetonitrile at 20℃; for 3.5h; Product distribution / selectivity;	95%

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) → C62H92N6(2+)*2F6P(1-)

Conditions	Yield
Stage #1: N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene With silver nitrate In N,N-dimethyl-formamide at 70℃; for 5h; Inert atmosphere; Stage #2: With caesium hexafluorophosphate at 20℃; Inert atmosphere;	96%

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) → C62H92N6(2+)*O4S(2-)

Conditions	Yield
With Oxone; sulfuric acid In water; ethyl acetate; acetonitrile at 20℃; for 3.5h;	92%

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) + lithium bis[1,2-oxalato(2-)-O,O'] borate (244761-29-3) → C62H92N6(2+)*2C4BO8(1-)

Conditions	Yield
Stage #1: N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene With silver nitrate In N,N-dimethyl-formamide at 70℃; for 5h; Inert atmosphere; Stage #2: lithium bis[1,2-oxalato(2-)-O,O'] borate at 20℃; Inert atmosphere;	90%

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) + silver(I) triflimide (189114-61-2) → bis(trifluoromethanesulfone)imidate N,N,N',N'-tetrakis(p-dibutylaminophenyl)-p-phenylene diimmonium

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 3h; Product distribution / selectivity;

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) + 1-[bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene (405074-81-9) → 2C9F11O4S2(1-)*C62H92N6(2+)

Conditions	Yield
With silver nitrate In N,N-dimethyl-formamide at 60℃; for 0.5h;

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) + tris-(trifluoromethanesulfonyl)methane acid (60805-12-1) → 2C4F9O6S3(1-)*C62H92N6(2+)

Conditions	Yield
With silver nitrate In water; N,N-dimethyl-formamide at 60℃; for 0.5h;

N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene (4182-80-3) → bis(hexafluoroantimonate) N,N,N',N'-tetrakis {p-di(n-butyl)aminophenyl}-p-phenylene diimmonium

Conditions	Yield
With silver hexafluoroantimonate In acetonitrile at 60℃; for 3h;

Upstream product

• 542-69-8 1-iodo-butane 
• 3283-07-6 N¹,N¹,N⁴,N⁴-tetrakis(4-aminophenyl)-p-phenylenediamine 
• 109-65-9 1-bromo-butane 
• 53358-54-6 1-bromo-4-(N,N-dibutyl)aniline 
• 106-50-3 1,4-phenylenediamine 

Downstream Products

• 88358-74-1 C₆₂H₉₂N₆⁽²⁺⁾*2ClO₄^(1-) 

Relevant academic research and scientific papers

NEAR-INFRARED ABSORPTIVE COLORING MATTER AND NEAR-INFRARED ABSORPTIVE COMPOSITION

An object of the present invention is to provide a near infrared absorbent dye capable of providing a near infrared shielding filter with excellent transparency as well as high heat resistance and hygrothermal resistance. The near infrared absorbent dye is characterized in that it is made of the amorphous form of diimmonium salt represented by formula (1).

NEAR-INFRARED ABSORBING FILM COMPOSITIONS

A curable liquid formulation containing at least (i) one or more near-infrared absorbing triphenylamine -based dyes, and (ii) one or more casting solvents. The invention is also directed to solid near- infrared absorbing films composed of crosslinked forms of the curable liquid formulation. The invention is also directed to a microelectronic substrate containing a coating of the solid near-infrared absorbing film as well as a method for patterning a photoresist layer coated on a microelectronic substrate in the case where the near-infrared absorbing film is between the microelectronic substrate and a photoresist film.

METHOD FOR PRODUCING POLYANILINE COMPOUND

A method for producing a compound of formula (I), which comprises reducing a compound of formula (II) with a hydrazine compound: wherein R103, R113, R123, R133, R143, R203, R213, R223, R233 and R243 represent a substituent; the other Rs represent H, an aliphatic group or an aromatic group; and n103 to n243 are 0 to 4.

Method of producing near-infrared absorbing dye compound

A method of producing a near-infrared absorbing dye compound, useful for image forming materials, infrared heat-sensitive recording devices, optical film materials, and the like, containing a process of reacting a compound represented by formula (I) with peroxomonosulfuric acid or its salt. wherein R 111 , R 112 , R 121 , R 122 , R 131 , R 132 , R 141 and R 142 each independently represent a hydrogen atom, an aliphatic group or an aromatic group; R 103 , R 113 , R 123 , R 133 and R 143 each independently represent a substituent; and n 103 , n 113 , n 123 , n 133 and n 143 each independently denote an integer from 0 to 4.