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p-Phenylenediamine (PPD) is an artificial dye commonly used in the tattoo and dye industry, often added to henna for color enhancement. Studies highlight its potential harmfulness, as its degradation under conditions like UV irradiation and electrochemical perturbations can produce harmful byproducts, raising concerns about its safety compared to natural dyes like henna. Additionally, PPD serves as a chemical intermediate in various synthesis processes, including the formation of corrosion-inhibiting trimers and radiopharmaceutical complexes. Its widespread use underscores the need for careful handling due to its reactivity and potential toxicity.

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  • 106-50-3 Structure
  • Basic information

    1. Product Name: p-Phenylenediamine
    2. Synonyms: 1,4-Benzenediamine;1,4-Phenylenediamine;4-Phenylenediamine;CI 76060;p-Phenylenediamine;1,4-Diaminobenzene;4-Aminoaniline;6PPD;AI3-00710;BASF ursol D;Benzofur D;C.I. 76060;C.I. Developer 13;C.I. Oxidation Base 10;CCRIS 509;Fenylenodwuamina;Fouramine D;Paraphenylenediamine;Pelagol D;p-Aminoaniline;p-Benzenediamine;p-Diaminobenzene;p-Fenylendiamin;p-Phenyldiamine;p-Phenylenediamine;1,4-Benzenediamine;Phenylenediamine, para-;p-Phenylenediamine;
    3. CAS NO:106-50-3
    4. Molecular Formula: C6H8N2
    5. Molecular Weight: 108.1411
    6. EINECS: 203-404-7
    7. Product Categories: Chemistry;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;VARIOUSAMINE;Intermediates of Dyes and Pigments;1,4-Benzenediamine;Fluorescent;Fine Chemicals;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Environmental;amine series
    8. Mol File: 106-50-3.mol
  • Chemical Properties

    1. Melting Point: 138-143℃
    2. Boiling Point: 267.4 °C at 760 mmHg
    3. Flash Point: 135.9 °C
    4. Appearance: white to light purple solid
    5. Density: 1.15 g/cm3
    6. Vapor Density: 3.7 (vs air)
    7. Vapor Pressure: 0.00817mmHg at 25°C
    8. Refractive Index: 1.66
    9. Storage Temp.: 2-8°C
    10. Solubility: Soluble in alcohol, chloroform, ether and hot benzene.
    11. PKA: 4.17(at 25℃)
    12. Water Solubility: 47 g/L (25℃)
    13. Stability: Stable, but oxidizes when exposed to air. Incompatible with oxidizing agents. Store under inert atmosphere.
    14. Merck: 14,7285
    15. BRN: 742029
    16. CAS DataBase Reference: p-Phenylenediamine(CAS DataBase Reference)
    17. NIST Chemistry Reference: p-Phenylenediamine(106-50-3)
    18. EPA Substance Registry System: p-Phenylenediamine(106-50-3)
  • Safety Data

    1. Hazard Codes:  T:Toxic;
    2. Statements: R23/24/25:; R36:; R43:; R50/53:;
    3. Safety Statements: S28A:; S36/37:; S45:; S60:; S61:;
    4. RIDADR: UN 1673 6.1/PG 3
    5. WGK Germany: 3
    6. RTECS: SS8050000
    7. F: 8-10-23
    8. TSCA: Yes
    9. HazardClass: 6.1
    10. PackingGroup: III
    11. Hazardous Substances Data: 106-50-3(Hazardous Substances Data)

106-50-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 106-50-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 106-50:
(5*1)+(4*0)+(3*6)+(2*5)+(1*0)=33
33 % 10 = 3
So 106-50-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2

106-50-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (P0170)  1,4-Phenylenediamine  >98.0%(GC)(T)

  • 106-50-3

  • 25g

  • 80.00CNY

  • Detail
  • TCI America

  • (P0170)  1,4-Phenylenediamine  >98.0%(GC)(T)

  • 106-50-3

  • 250g

  • 206.00CNY

  • Detail
  • Alfa Aesar

  • (A15680)  p-Phenylenediamine, 97%   

  • 106-50-3

  • 250g

  • 314.0CNY

  • Detail
  • Alfa Aesar

  • (A15680)  p-Phenylenediamine, 97%   

  • 106-50-3

  • 1000g

  • 795.0CNY

  • Detail
  • Alfa Aesar

  • (A15680)  p-Phenylenediamine, 97%   

  • 106-50-3

  • 5000g

  • 3502.0CNY

  • Detail
  • Supelco

  • (48298)  p-Phenylenediaminesolution  certified reference material, 2000 μg/mL in methylene chloride

  • 106-50-3

  • 000000000000048298

  • 443.43CNY

  • Detail
  • Aldrich

  • (78429)  p-Phenylenediamine  ≥99.0% (GC/NT)

  • 106-50-3

  • 78429-100G

  • 1,633.32CNY

  • Detail
  • Aldrich

  • (78429)  p-Phenylenediamine  ≥99.0% (GC/NT)

  • 106-50-3

  • 78429-250G

  • 3,433.95CNY

  • Detail
  • Aldrich

  • (695106)  p-Phenylenediamine  sublimed, ≥99%

  • 106-50-3

  • 695106-1G

  • 1,028.43CNY

  • Detail
  • Aldrich

  • (695106)  p-Phenylenediamine  sublimed, ≥99%

  • 106-50-3

  • 695106-5G

  • 3,422.25CNY

  • Detail

106-50-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-phenylenediamine

1.2 Other means of identification

Product number -
Other names p-Phenylenediamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. p-Phenylenediamine is primarily used as a dye intermediate and as a dye (e.g., hair dyes and dyes used for dyeing furs), as well as a photographic developing agent and a chemical intermediate. p-Phenylenediamine is also used as a vulcanization accelerator and as an antioxidant in rubber compounds.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-50-3 SDS

106-50-3Synthetic route

para-dinitrobenzene
100-25-4

para-dinitrobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 50℃; for 0.0833333h; Green chemistry;100%
With hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h; chemoselective reaction;100%
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 3h; Sonication; chemoselective reaction;99%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: 4-nitrophenyl azide With hydrazine hydrate at 135℃; for 3h;
Stage #2: With potassium hydroxide at 135℃; for 24h;
100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 5h;94%
With hydrogenchloride; tin
4-nitro-aniline
100-01-6

4-nitro-aniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With palladium diacetate; carbon monoxide; triphenylphosphine In water; acetic acid at 56℃; under 532 Torr; for 11h;100%
With triethylsilane; palladium dichloride In ethanol at 20℃; for 1h; Inert atmosphere;100%
With 10% palladium on activated charcoal; hydrogen for 2h;100%
p-nitrophenyl isocyanide
1984-23-2

p-nitrophenyl isocyanide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;100%
nitrobenzene
98-95-3

nitrobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: nitrobenzene With Oxalamide; tetramethyl ammoniumhydroxide; ammonia In dimethyl sulfoxide at 100℃; under 18751.9 Torr; for 7h; Autoclave;
Stage #2: With 5%-palladium/activated carbon; hydrogen In methanol at 55℃; under 9000.9 Torr; for 4h; Reagent/catalyst; Autoclave;
99.1%
Multi-step reaction with 2 steps
1: urea, monosodium salt; urea / dimethyl sulfoxide / 2 h / 90 °C
2: 5%-palladium/activated carbon; hydrogen / ethanol / 80 °C / 15001.5 - 22502.3 Torr
View Scheme
N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);99%
With ammonium iodide; hydrazine at 50℃; for 12h;99%
With ammonium iodide; hydrazine hydrate at 50℃; for 12h; Inert atmosphere; Sealed tube;99%
4-azidoaniline
14860-64-1

4-azidoaniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 2h; Concentration; Temperature; Time; Inert atmosphere;99%
With zinc In methanol at 20℃; for 5h;95%
With hydrazine hydrate In ethanol at 20℃; chemoselective reaction;90%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;99%
With ammonia; C16H16N2O2*0.8Ni*0.2Cu at 85℃; under 1500.15 Torr; for 8.5h; Autoclave; Inert atmosphere;92%
Multi-step reaction with 2 steps
1: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C
2: copper(ll) sulfate pentahydrate; sodium L-ascorbate; potassium carbonate; ammonium hydroxide / dimethyl sulfoxide; glycerol / 8 h / 100 °C
View Scheme
para-diiodobenzene
624-38-4

para-diiodobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;99%
With ammonia at 20℃; Reagent/catalyst; Temperature;97%
With [10%-Pd/Al2O3]; ammonia at 250℃; Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere;
para-dinitrobenzene
100-25-4

para-dinitrobenzene

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube; chemoselective reaction;98%
Multi-step reaction with 2 steps
1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C
2: hydrogenchloride; water / methanol / 1 h / 20 °C
View Scheme
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;97%
With acetamidine hydrochloride; caesium carbonate; L-proline; copper(l) iodide In N,N-dimethyl-formamide at 120℃; for 10h;94%
With copper(l) iodide; ammonia; potassium carbonate In water; dimethyl sulfoxide at 100℃; for 12h;93%
N-(tert-butoxycarbonyl)-1,4-phenylenediamine
71026-66-9

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
In various solvent(s) at 150℃; for 0.5h; microwave irradiation;97%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;97%
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;97%
With 2,2,2-trifluoroethanol at 150℃; for 3h; Product distribution / selectivity; Microwave irradiation;93%
1,4-diazidobenzene
2294-47-5

1,4-diazidobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.166667h; Ambient temperature;96%
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;92%
1,4-Benzochinondioxim
105-11-3, 6133-83-1, 6421-98-3

1,4-Benzochinondioxim

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate at 20℃; for 0.0333333h; neat (no solvent, solid phase);96%
With iron oxide; zirconium(IV) chloride; sodium cyanoborohydride In neat (no solvent) at 20℃; for 0.0833333h;94%
p-benzoquinone dioxime
105-11-3, 6133-83-1, 6421-98-3

p-benzoquinone dioxime

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With (pyridine)(tetrahydroborato)zinc In tetrahydrofuran for 1h; Heating;95%
With fermenting. yeast
With hydrogenchloride; tin(ll) chloride
aniline yellow
60-09-3

aniline yellow

A

aniline
62-53-3

aniline

B

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.0833333h;A 95%
B 93%
With hydrazine hydrate; aluminium In ethanol Heating;A 94%
B 93%
With ammonium acetate; zinc In methanol at 20℃; for 0.05h;A n/a
B 93%
C12H8Cl6N2O6

C12H8Cl6N2O6

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With acetic acid; zinc In water at 0℃; for 0.5h;95%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With [Zn(BH4)2(py)] In tetrahydrofuran for 3.1h; Heating;94%
With mineral acid durch elektrolytische Reduktion;
With hydrogenchloride; tin
N,N,N',N'-tetrakis(trimethylsilyl)-1,4-phenylenediamine
25811-68-1

N,N,N',N'-tetrakis(trimethylsilyl)-1,4-phenylenediamine

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1h;94%
With hydrogenchloride In diethyl ether
aniline yellow
60-09-3

aniline yellow

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With ammonium formate; nickel In methanol at 20℃; for 0.0833333h;93%
With hydrazine hydrate In ethanol Heating;93%
With water; zinc
4-Aminoazobenzene
60-09-3

4-Aminoazobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With nickel; hydrazinium monoformate In methanol for 0.0833333h; Heating;93%
4-bromo-aniline
106-40-1

4-bromo-aniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With ammonium hydroxide; trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In neat (no solvent) at 80℃; for 7h;93%
With ammonium hydroxide; (2-methylacetatobenzyl)triphenylphosphonium hexabromodipalladate(II) at 60℃; for 5h;92%
With ammonium hydroxide; bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium] hexabromodipalladate(II) In neat (no solvent) at 60℃; for 5h;90%
terephthalamide
3010-82-0

terephthalamide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With water; chlorine; sodium hydroxide at 5 - 80℃; for 4.5h; Reagent/catalyst; Hofmann Rearrangement;93%
N,N-dibenzyl-4-nitroaniline
65052-89-3

N,N-dibenzyl-4-nitroaniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;93%
benzyl 4-(nitro)phenylcarbamate
53821-12-8

benzyl 4-(nitro)phenylcarbamate

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 5h;92%
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;86%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With ammonium hydroxide; copper(II) ferrite at 150℃; under 31503.2 - 36003.6 Torr; for 10h; Catalytic behavior; Pressure; Temperature; Autoclave;91.7%
With copper(l) iodide; 2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol); ammonia at 150℃; under 31503.2 Torr; for 10h; Reagent/catalyst; Temperature; Pressure; Autoclave;90.6%
With ammonium hydroxide; 1,10-Phenanthroline; copper(I) bromide at 150℃; under 45004.5 Torr; for 0.00555556h; Reagent/catalyst; Temperature; Pressure;90.6%
4-Azidoaniline hydrochloride

4-Azidoaniline hydrochloride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;90%
p-dinitrosobenzene
105-12-4

p-dinitrosobenzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With Saccharomyces cerevisiae BY In methanol at 20℃; pH=7.0; aq. buffer; Enzymatic reaction;90%
benzaldehyde
100-52-7

benzaldehyde

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N,N'-dibenzylidene-benzene-1,4-diamine
797-20-6

N,N'-dibenzylidene-benzene-1,4-diamine

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
In chloroform at 20℃; Inert atmosphere;82%
With sodium hydrogen sulfate; silica gel for 0.0666667h; microwave irradiation;78%
salicylaldehyde
90-02-8

salicylaldehyde

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

2,2'-{(1E,1'E)-[1,4-phenylenebis(azanylylidene)]bis(methanylylidene)}diphenol
119643-02-6

2,2'-{(1E,1'E)-[1,4-phenylenebis(azanylylidene)]bis(methanylylidene)}diphenol

Conditions
ConditionsYield
In methanol for 0.5h; Reflux;100%
In ethanol for 2h; Heating;88%
With tin(II) chloride dihdyrate In dichloromethane at 20℃; for 6h;87.7%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N,N'-ditosyl-p-phenylenediamine
41595-29-3

N,N'-ditosyl-p-phenylenediamine

Conditions
ConditionsYield
With pyridine for 2h; Reflux;100%
With triethylamine In dichloromethane at 4℃;100%
With sodium hydroxide In diethyl ether at 0 - 20℃;90%
With pyridine In tetrahydrofuran at 40℃; for 2h;74%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N-(tert-butoxycarbonyl)-1,4-phenylenediamine
71026-66-9

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃;100%
With glycerol at 20℃; for 0.333333h; Green chemistry; chemoselective reaction;97%
In dichloromethane at 20℃; for 18h; Cooling with ice;97%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.78 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.78 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.67 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.67 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.69 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.69 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.65 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.65 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.44 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.44 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

2,4-diamino-(n-hexadecyloxy)benzene
137819-03-5

2,4-diamino-(n-hexadecyloxy)benzene

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 0.27 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

soluble polyimide, inherent viscosity: 0.27 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine; 2,4-diamino-(n-hexadecyloxy)benzene

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

soluble polyimide, inherent viscosity: 1.42 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine

soluble polyimide, inherent viscosity: 1.42 dl/g; monomer(s): 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride; p-phenylenediamine

Conditions
ConditionsYield
With isoquinoline In various solvent(s) at 70 - 200℃;100%
4-hexylbenzoyl chloride
50606-95-6

4-hexylbenzoyl chloride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

N-(4-aminophenyl)-4-hexylbenzamide
1055298-70-8

N-(4-aminophenyl)-4-hexylbenzamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 17h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

di(tert‐butyl) 1,4‐phenylenedicarbamate
121680-23-7

di(tert‐butyl) 1,4‐phenylenedicarbamate

Conditions
ConditionsYield
With 1,4-disulfopiperazine-1,4-diium chloride In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;100%
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.333333h;98%
Stage #1: 1,4-phenylenediamine With caesium carbonate In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 70℃; Schlenk technique;
90%
With triethylamine In dichloromethane at 20℃;51%
With guanidine hydrochloride In ethanol at 40℃; for 8h;
C50H30N4NiO4
1443978-57-1

C50H30N4NiO4

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C56H34N6NiO2
1443978-66-2

C56H34N6NiO2

Conditions
ConditionsYield
Stage #1: C50H30N4NiO4 With 1,2,4-Trichlorobenzene for 1h; Molecular sieve; Reflux;
Stage #2: 1,4-phenylenediamine In pyridine at 220℃; for 16h;
100%
4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester
77716-16-6

4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C17H22N4O3

C17H22N4O3

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃; for 2h;100%
C44H47N3O5

C44H47N3O5

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C50H53N5O4

C50H53N5O4

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide; toluene at 150℃; Inert atmosphere;100%
Pyromellitic dianhydride
89-32-7

Pyromellitic dianhydride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C10H6O8*C6H8N2

C10H6O8*C6H8N2

Conditions
ConditionsYield
Stage #1: Pyromellitic dianhydride In water at 80℃; for 1h; Inert atmosphere;
Stage #2: 1,4-phenylenediamine In water at 80℃; for 4h; Inert atmosphere;
100%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

benzene-1,4-diamine hydrochloride
624-18-0

benzene-1,4-diamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; methanol for 0.166667h;100%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

C6H8N2*(x)ClH

C6H8N2*(x)ClH

Conditions
ConditionsYield
With hydrogenchloride; tetrabutylammomium bromide In N,N-dimethyl-formamide at 10℃; for 2.5h; Temperature; Reagent/catalyst;99.5%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

benzyl alcohol
100-51-6

benzyl alcohol

N1,N4-dibenzylbenzene-1,4-diamine
10368-25-9

N1,N4-dibenzylbenzene-1,4-diamine

Conditions
ConditionsYield
With [((5-Me)PyNPPh2)IrACHTUNGTRENUNG(cod)]; potassium tert-butylate In diethylene glycol dimethyl ether at 70℃; for 48h; Inert atmosphere;99%
With C41H36AsClN3OPRuS; potassium hydroxide In toluene at 100℃; for 12h;91%
at 120℃; for 48h; Molecular sieve; Green chemistry;78%
dodecyl isocyanate
4202-38-4

dodecyl isocyanate

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

1-amino-4-(3-dodecylureido)benzene

1-amino-4-(3-dodecylureido)benzene

Conditions
ConditionsYield
In dichloromethane for 1h;99%
1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

2',2'-(1,4-phenylene)bis(1,3-diisopropylguanidine)

2',2'-(1,4-phenylene)bis(1,3-diisopropylguanidine)

Conditions
ConditionsYield
With C80H124Cl2N8Nd2O2 In tetrahydrofuran at 60℃; for 0.5h; Reagent/catalyst; Temperature; Time; Schlenk technique; Inert atmosphere; Glovebox;99%
With [Li(THF)(DME)]3La[μ-η2η1(iPrN)2C(NC6H4p-Cl)]3 at 25℃; for 2h; Inert atmosphere;98%
[(Me3Si)2N]3Yb(μ-Cl)Li(THF)3 In tetrahydrofuran at 60℃; for 4h;97%
phthalic anhydride
85-44-9

phthalic anhydride

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

cis-1,2,3,6-tetrahydrophthalic anhydride
935-79-5

cis-1,2,3,6-tetrahydrophthalic anhydride

N-{4-[((1S,6R)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenyl}-phthalamic acid

N-{4-[((1S,6R)-6-Carboxy-cyclohex-3-enecarbonyl)-amino]-phenyl}-phthalamic acid

Conditions
ConditionsYield
In acetone at 20℃; for 12h;99%

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106-50-3Relevant articles and documents

Silver nanoparticles supported on P, Se-codoped g-C3N4 nanosheet as a novel heterogeneous catalyst for reduction of nitroaromatics to their corresponding amines

Elhampour, Ali,Heravi, Majid M.,Nemati, Firouzeh,Piri, Mohadese

, (2021)

P, Se-codoped g-C3N4 (PSeCN) nanosheet was in situ prepared by facile thermal polymerization of melamine, phosphonitrilic chloride trimer, and selenium black powder as the precursors. It was found as a suitable support for the immobilization of silver nanoparticles (Ag NPs). The prepared nanocatalyst was fully characterized via standard analysis methods including EDX, ICP-OES, XRD, FT-IR, SEM, TEM, and BET. This PSeCN/Ag nanocatalyst with a higher specific surface area compared with CN, showed excellent catalytic activity towards the reduction of several nitroaromatic compounds using sodium borohydride (NaBH4) in short reaction times with high efficiency and good selectivity in water as a green solvent. Significantly, the above-mentioned nanocomposite could be reused six times without appreciable loss of its catalytic activity.

Bakers' yeast-catalyzed ring opening of benzofuroxans: An efficient green synthesis of aryl-1,2-diamines

Borah, Harsha N.,Prajapati, Dipak,Boruah, Romesh C.

, p. 267 - 272 (2009)

A simple and inexpensive method for the reductive cleavage of N-O bond of benzofuroxans with bakers' yeast under nonfermenting condition in aqueous media was achieved. The procedure gives excellent yields of aryl-1,2-diamines. Copyright Taylor & Francis Group, LLC.

Radical reactions in aqueous medium using (Me3Si)3SiH

Postigo, Al,Kopsov, Sergey,Ferreri, Carla,Chatgilialoglu, Chryssostomos

, p. 5159 - 5162 (2007)

(Chemical Equation Presented) (Me3Si)3SiH was used as a successful reagent in a variety of radical-based transformations in water. The system comprising substrate, silane, and initiator (ACCN) mixed in aqueous medium at 100°C worked well for both hydrophilic and hydrophobic substrates, with the only variation that an amphiphilic thiol was also needed in case of the water-soluble compounds.

Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper

Dai, Xingchao,He, Dongcheng,Li, Teng,Shi, Feng,Wang, Hongli,Wang, Tao,Wang, Xinzhi

, p. 397 - 406 (2021)

Based on the experimental and DFT calculation results, here for the first time we built preferential adsorption sites for nitroarenes by modification of the supported Cu catalysts surface with 1,10-phenathroline (1,10-phen), by which the yield of aniline via reduction of nitroarene is enhanced three times. Moreover, a macromolecular layer was in-situ generated on supported Cu catalysts to form a stable macromolecule modified supported Cu catalyst, i.e., CuAlOx-M. By applying the CuAlOx-M, a wide variety of nitroarene substrates react smoothly to afford the desired products in up to > 99% yield with > 99% selectivity. The method tolerates a variety of functional groups, including halides, ketone, amide, and C = C bond moieties. The excellent catalytic performance of the CuAlOx-M can be attributed to that the 1,10-phen modification benefits the preferential adsorption of nitrobenzene and slightly weakens adsorption of aniline on the supported nano-Cu surface.

The Solvent Effect on the Electro-oxidation of 1,4-Phenylenediamine. The Influence of the Solvent Reorientation Dynamics on the One-electron Transfer Rate

Opallo, Marcin

, p. 339 - 348 (1986)

The one-electron electro-oxidation of 1,4-phenylenediamine to the corresponding radical cation has been studied by cyclic voltammetry at a Pt electrode in perchlorate solutions in a wide range of aprotic and hydrogenbonded solvents.A linear relationship between the redox potential of this system and the donor number of a given solvent has been found.It has been shown that the dynamics of solvent reorientation strongly affects the heterogeneous electron transfer rate in the studied case: an almost linear relationship between the standard rate constant and the reciprocal of the longitudinal dielectric relaxation time of a given solvent has been found.It has been suggested that the solvent dynamics affects the rate of the analogous homogeneous electron-transfer reaction.

Visible-light-induced photocatalytic hydrogenation of 4-nitroaniline over In2S3 photocatalyst in water

Wu, Weiming,Lin, Rui,Shen, Lijuan,Liang, Ruowen,Yuan, Rusheng,Wu, Ling

, p. 1 - 4 (2013)

Photocatalytic hydrogenation of 4-nitroaniline over the In 2S3 photocatalyst was investigated in water under visible light irradiation (λ ≥ 420 nm). After 90 min of visible light irradiation, 100% of 4-nitroaniline could be reduced t

Application of silica-supported Fe–Cu nanoparticles in the selective hydrogenation of p-dinitrobenzene to p-phenylenediamine

Shesterkina,Shuvalova,Kirichenko,Strelkova,Nissenbaum,Kapustin,Kustov

, p. 201 - 204 (2017)

Supported bimetallic Fe–Cu/SiO2 materials are synthesized, and their catalytic activity in hydrogenation of dinitrobenzene to phenylenediamine at 145–180°С and 1.3 MPa hydrogen pressure is studied for the first time. The best results (89% selectivity toward p-phenylenediamine at complete conversion of p-dinitrobenzene) are obtained for the sample synthesized via co-deposition with subsequent calcination at 300°С. The sample contains 7% iron and 3% copper. The formation of separate phases of metal oxides (for the catalysts prepared by impregnation) and mixed bimetallic oxide phases (in case of co-deposition procedure) in calcined samples is revealed via thermoprogrammed reduction with hydrogen.

Preparation and characterization of Ni/mZSM-5 zeolite with a hierarchical pore structure by using KIT-6 as silica template: An efficient bi-functional catalyst for the reduction of nitro aromatic compounds

Mazaheri, Omid,Kalbasi, Roozbeh Javad

, p. 34398 - 34414 (2015)

Ni/mZSM-5 and Ni/H-mZSM-5 were synthesized as hierarchical (micro/meso porous) ZSM-5 zeolites by an indirect template method for the first time. The resulting zeolite materials exhibited significantly enhanced diffusional properties in comparison to purely microporous zeolite materials. The structural and morphological characterization of the prepared catalysts was investigated using XRD, BET, atomic absorption spectroscopy, FT-IR, 27Al-MAS NMR, SEM, TEM, XPS and DRS-UV techniques. These hierarchical zeolites were used as acid-metal bi-functional heterogeneous catalysts for hydride transfer in the reduction of nitro aromatic compounds. In these reactions, NaBH4 was used as a reducing agent. Excellent yields at room temperature and very short reaction times in aqueous media conditions were obtained. Reusability experiments showed the excellent stability of Ni/mZSM-5 and Ni/H-mMZSM-5 and the catalysts could be reused 7 times without much loss of activity in reduction of nitro aromatic compounds. Surprisingly, the acid form of Ni/H-mZSM-5 showed much higher activity than that of Ni/mZSM-5. High yield, short reaction time, green solvent (water), room temperature, no by-product, the easy reusability of catalysts and the low amounts of catalyst required are some of the advantages of these catalysts.

A simple and convenient method for the reduction of nitroarenes

Ravi Kanth,Venkat Reddy,Rama Rao,Maitraie,Narsaiah,Shanthan Rao

, p. 2849 - 2853 (2002)

A variety of nitroarenes such as simple, electron rich and electron poor were reduced on A12O3 support in presence of sodium hydrogen sulphide under microwave condition to give the corresponding aromatic amines in high yields. It is found that the substituents at different positions on nitrobenzene have no influence except 2d on the rate of reaction and yields of product.

Supported polymer magnets with high catalytic performance in the green reduction of nitroaromatic compounds

Safari,Gandomi-Ravandi,Haghighi

, p. 31514 - 31525 (2016)

Magnetic Fe3O4 nanoparticles (MNPs) were prepared by a simple co-precipitation method using molar ratios of Fe2+:Fe3+ = 1:2 in ammonia solution, and subsequently were modified with tetraethyl orthosilicate (TEOS

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