3283-07-6

Basic information

• Product Name: N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine
• Synonyms: n,n,n',n'-tetrakis(p-aminophenyl)-p-phenylenediamine;n,n,n',n'-tetrakis(4-aminophenyl)-1,4-benzenediamine;N,N,N',N'-TETRAKIS(4-AMINOPHENYL)-1,4-PHENYLENEDIAMINE;N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-phenylenediamine 98%;N,N,N',N'-Tetra(p-aminophenyl)-p-phenylenediamine;4,4',4'',4'''-(1,4-Phenylene)bis(nitrilo)tetrakisaniline;4,4',4'',4'''-(p-Phenylenebisnitrilo)tetrakisaniline;4,4',4'',4'''-[(1,4-Phenylene)bisnitrilo]tetrakisaniline
• CAS NO: 3283-07-6
• Molecular Formula: C₃₀H₂₈N₆
• Molecular Weight: 472.58
• Mol File: 3283-07-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: >300°C
• Boiling Point: 765.6 °C at 760 mmHg
• Flash Point: 409.3 °C
• Appearance: /
• Density: 1.309
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in DMSO, DMF Insoluble in methanol & water
• PKA: 6.85±0.10(Predicted)
• CAS DataBase Reference: N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine(3283-07-6)
• EPA Substance Registry System: N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine(3283-07-6)

Safety Data

• Statements: 20/21/22
• Safety Statements: 22-36/37/39
• Hazardous Substances Data: 3283-07-6(Hazardous Substances Data)

Usage

Description

N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine, also known as Rubrene, is an organic compound with a unique molecular structure featuring four aminophenyl groups attached to a central benzene ring. This structure endows it with specific chemical and physical properties, making it suitable for various applications in different industries.

Uses

Used in Electronics Industry:
N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine is used as a composition and solution for temporary bonding in the electronics industry. Its unique molecular structure allows for the formation of strong, yet reversible, bonds between electronic components during the manufacturing process. This temporary bonding is crucial for protecting sensitive components and ensuring the integrity of the final product.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine serves as a key intermediate or building block for the development of more complex organic compounds. Its multiple reactive sites, the amino groups, facilitate the formation of various chemical bonds, making it a versatile component in the synthesis of advanced materials and pharmaceuticals.
Used in Research and Development:
Due to its unique structure and properties, N,N,N',N'-Tetrakis(4-aminophenyl)-1,4-benzenediamine is also utilized in research and development for the study of molecular interactions, electronic properties, and potential applications in various fields. Its use in research helps to advance the understanding of its potential benefits and limitations, paving the way for future innovations and applications.

Synthetic route

N1,N1,N4,N4-tetrakis(4-nitrophenyl)-p-phenylenediamine (3283-05-4) → N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6)

Conditions	Yield
With iron(III) chloride; iron(III) oxide; pyrographite; hydrazine In water; N-methylpyrrolidine N-oxide at 100 - 110℃; for 6h; Product distribution / selectivity;	99%
With hydrazine; iron(III) chloride; pyrographite In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 100 - 110℃; for 6h;	98%
With iron(III) chloride; pyrographite; hydrazine In 1-methyl-pyrrolidin-2-one; water; isopropyl alcohol at 100 - 110℃; for 6h; Product distribution / selectivity;	98%

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%

2,5-dimethyl-1,4-benzenedicarboxaldehyde (7044-92-0) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → C66H60N6

Conditions	Yield
In ethanol; dichloromethane for 5h; Reflux;	94%

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%

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + acrylic acid (79-10-7) → C54H60N6O16

Conditions	Yield
at 40 - 50℃;	87%

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + 2,5-dimethoxyterephthalaldehyde (7310-97-6) → C66H60N6O8

Conditions	Yield
In ethanol; dichloromethane for 5h; Reflux;	80%

4-Chlorobutyronitrile (628-20-6) + n-Butyl chloride (109-69-3) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → C62H71N13

Conditions	Yield
With potassium carbonate; potassium iodide at 90 - 130℃; for 4h;

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + iodomethylbenzene (620-05-3) → N,N,N',N'-tetrakis(p-dibenzylaminophenyl)-p-phenylenediamine

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 120℃; for 10h;

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + acrylic acid (79-10-7) → C54H52N6O16(8-)*8Na(1+) + C54H56N6O16(4-)*4Na(1+)

Conditions	Yield
Stage #1: N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine; acrylic acid at 50 - 60℃; for 4h; Stage #2: With sodium hydrogencarbonate In water for 1h;

silver hexafluoroantimonate + 4-Chlorobutyronitrile (628-20-6) + n-Butyl chloride (109-69-3) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → C62H71N13

Conditions	Yield
Stage #1: 4-Chlorobutyronitrile; n-Butyl chloride; N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine With potassium carbonate; potassium iodide at 90 - 130℃; for 4h; Stage #2: silver hexafluoroantimonate In DMF (N,N-dimethyl-formamide) at 60℃; for 0.5h;

cyclohexylmethyl iodide (5469-33-0) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → N,N,N',N'-tetrakis{p-di(cyclohexylmethyl)aminophenyl}-p-phenylenediamine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 10h;

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → N,N,N',N'-tetrakis{p-(cyclohexylmethyl)(n-propyl)aminophenyl}-p-phenylenediamine

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene / 5 h / 80 °C 2: hydrogen / palladium on activated charcoal / toluene / 2 h / 20 °C 3: potassium carbonate / toluene / 6 h / 120 °C View Scheme

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → C58H76N6

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 5 h / 80 °C 2: hydrogen / palladium on activated charcoal / toluene / 2 h / 20 °C View Scheme

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + cyclohexanecarbaldehyde (2043-61-0) → C58H68N6

Conditions	Yield
In toluene at 80℃; for 5h;

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → N,N,N',N'-tetrakis{p-(cyclohexylmethyl)(n-propyl)aminophenyl}-p-phenylenediimmonium hexafluorophosphate

Conditions	Yield
Multi-step reaction with 4 steps 1: toluene / 5 h / 80 °C 2: hydrogen / palladium on activated charcoal / toluene / 2 h / 20 °C 3: potassium carbonate / toluene / 6 h / 120 °C 4: silver(I) hexafluorophosphate / acetonitrile / 3 h / 60 °C View Scheme

Isobutyl bromide (78-77-3) + N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) → (N,N,N’,N’-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine) (485831-34-3)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; sodium hydrogencarbonate at 80℃; for 9.5h;

N1,N1,N4,N4-tetrakis(4-aminophenyl)-p-phenylenediamine (3283-07-6) + 1,4-dichlorobutane (110-56-5) → C46H52N6

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 120℃; for 10h;

Upstream product

• 3283-05-4 N¹,N¹,N⁴,N⁴-tetrakis(4-nitrophenyl)-p-phenylenediamine 

Downstream Products

• 4182-80-3 N,N,N’,N’-tetrakis[p-di(butyl)aminophenyl]-p-phenylene 
• 485831-34-3 (N,N,N’,N’-tetrakis(p-diisobutylaminophenyl)-p-phenylenediamine) 

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