4182-80-3

Basic information

• Product Name: N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine
• Synonyms: N,N,N',N'-tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine;1,4-Benzenediamine, N,N,N,N-tetrakis4-(dibutylamino)phenyl-;N,N,N',N'-Tetrakis(4-dibutylaminophenyl)-1,4-phenylenediamine;N,N,N',N'-Tetrakis(4-dibutylaminophenyl)-p-phenylenediamine;N,N,N',N'tetrakis(p-n-butylaminophenyl)-p-phenylenediamine;N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]-1,4-benzenediamine;1-N,1-N-dibutyl-4-N-[4-[4-(dibutylamino)-N-[4-(dibutylamino)phenyl]anilino]phenyl]-4-N-[4-(dibutylamino)phenyl]benzene-1,4-diamine;dibutyl-[4-[4-(dibutylamino)-N-[4-[4-(dibutylamino)-N-[4-(dibutylamino)phenyl]anilino]phenyl]anilino]phenyl]amine
• CAS NO: 4182-80-3
• Molecular Formula: C₆₂H₉₂N₆
• Molecular Weight: 921.43
• EINECS: 224-057-8
• Mol File: 4182-80-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 92-94 °C
• Boiling Point: 916.7 °C at 760 mmHg
• Flash Point: 340.7 °C
• Appearance: /
• Density: 1.023
• Storage Temp.: 2-8°C
• PKA: 7.53±0.32(Predicted)
• CAS DataBase Reference: N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine(4182-80-3)
• EPA Substance Registry System: N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine(4182-80-3)

Safety Data

• Hazardous Substances Data: 4182-80-3(Hazardous Substances Data)

Usage

General Description

N,N,N',N'-Tetrakis[4-(dibutylamino)phenyl]benzene-1,4-diamine, also known as Barium butaxate, is a chemical compound commonly used as an antioxidant in rubber and plastic materials. It is a member of the diphenylamine compound class. It acts as a stabilizer by preventing oxidation and degradation of the materials it is used in. This chemical has low toxicity and is considered safe for use in these applications. However, its widespread use has led to some concern about its potential environmental impact and human health effects. Therefore, caution should still be taken when handling and using this compound.

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 
• 53358-54-6 1-bromo-4-(N,N-dibutyl)aniline 
• 106-50-3 1,4-phenylenediamine 
• 109-65-9 1-bromo-butane 

Downstream Products

• 88358-74-1 C₆₂H₉₂N₆⁽²⁺⁾*2ClO₄^(1-) 

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