25462-61-7

Basic information

• Product Name: 2,5-Dibromo-1,4-phenylenediamine
• Synonyms: 2,5-Dibromo-1,4-benzenediamine;2,5-Dibromo-1,4-phenylenediamine;1,4-BenzenediaMine, 2,5-dibroMo-;1,4-Diamino-2,5-dibromobenzene;2,5-Dibromo-p-phenylenediamine;2,5-dibromobenzene-1,4-diamine
• CAS NO: 25462-61-7
• Molecular Formula: C₆H₆Br₂N₂
• Molecular Weight: 265.93
• Mol File: 25462-61-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 187-188℃
• Boiling Point: 332.9±37.0 °C(Predicted)
• Appearance: /
• Density: 2.104
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 3.02±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dibromo-1,4-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromo-1,4-phenylenediamine(25462-61-7)
• EPA Substance Registry System: 2,5-Dibromo-1,4-phenylenediamine(25462-61-7)

Safety Data

• Hazardous Substances Data: 25462-61-7(Hazardous Substances Data)

Usage

General Description

2,5-Dibromo-1,4-phenylenediamine is a chemical compound that is commonly used as an intermediate in the production of dyes and pigments. It is a dark gray to black crystalline solid that is insoluble in water. The compound is often utilized in hair dyes and cosmetics as a coloring agent, as well as in the manufacturing of photographic developers and rubber antioxidants. However, 2,5-Dibromo-1,4-phenylenediamine is known to be a skin and eye irritant, and prolonged exposure to the substance can cause dermatitis and allergic reactions. It is important to handle this chemical with caution and follow proper safety protocols when using it in industrial and commercial applications.

Synthetic route

2-acetamido-5-amino-p-dibromobenzene → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
With methanol; sodium hydroxide at 80℃; for 6h; Temperature;	90.84%

2,5-dibromo-4-nitroaniline (25462-68-4) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
With hydrogenchloride; tin In ethanol; water at 0 - 20℃; for 16h; Inert atmosphere;	88%
With hydrogenchloride; tin In ethanol; water at 20℃; for 12h; Inert atmosphere;	66%

1,4-dibromo-2,5-bisnitrobenzene (18908-08-2) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
With hydrogenchloride; tin

N-(2,5-dibromo-4-nitrophenyl)acetamide (25462-67-3) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride In ethanol Heating; Yield given;
Multi-step reaction with 2 steps 1: hydrogenchloride; water / 32 h / Reflux 2: hydrogenchloride; tin / water; ethanol / 12 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 41 h / Reflux; Inert atmosphere 2: hydrogenchloride; tin / water; ethanol / 16 h / 0 - 20 °C / Inert atmosphere View Scheme

hydrogenchloride (7647-01-0) + 1,4-dibromo-2,5-bisnitrobenzene (18908-08-2) + tin → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

2,5-dibromo-p-phenylenediamine; dihydrochloride → hydrogenchloride (7647-01-0) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
beim Erhitzen;

1.4-dibromobenzene (106-37-6) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: tin; hydrochloric acid View Scheme
Multi-step reaction with 6 steps 1: nitric acid; sulfuric acid / dichloromethane / 40 °C / Cooling with ice 2: tin(II) chloride dihdyrate / ethanol / 4 h / 80 °C 3: triethylamine / ethyl acetate / 2 h / 70 °C 4: nitric acid; sulfuric acid / 0.67 h / 30 °C 5: acetic acid; iron / 2 h / 100 °C 6: sodium hydroxide; methanol / 6 h / 80 °C View Scheme

N-(2,5-dibromophenyl)acetamide (25462-66-2) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / water / 2 h / 10 °C / Cooling with ice 2: hydrogenchloride; water / 32 h / Reflux 3: hydrogenchloride; tin / water; ethanol / 12 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid; nitric acid / water / 2 h / 6 °C / Inert atmosphere 2: hydrogenchloride / water / 41 h / Reflux; Inert atmosphere 3: hydrogenchloride; tin / water; ethanol / 16 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: nitric acid; sulfuric acid / 0.67 h / 30 °C 2: acetic acid; iron / 2 h / 100 °C 3: sodium hydroxide; methanol / 6 h / 80 °C View Scheme

2,5-dibromoaniline (3638-73-1) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: water / 12 h / Reflux; Inert atmosphere 2: sulfuric acid; nitric acid / water / 2 h / 6 °C / Inert atmosphere 3: hydrogenchloride / water / 41 h / Reflux; Inert atmosphere 4: hydrogenchloride; tin / water; ethanol / 16 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: triethylamine / ethyl acetate / 2 h / 70 °C 2: nitric acid; sulfuric acid / 0.67 h / 30 °C 3: acetic acid; iron / 2 h / 100 °C 4: sodium hydroxide; methanol / 6 h / 80 °C View Scheme

1,4-dibromo-2-nitrobenzene (3460-18-2) → 2,5-dibromo-1,4-phenylenediamine (25462-61-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: tin(II) chloride dihdyrate / ethanol / 4 h / 80 °C 2: triethylamine / ethyl acetate / 2 h / 70 °C 3: nitric acid; sulfuric acid / 0.67 h / 30 °C 4: acetic acid; iron / 2 h / 100 °C 5: sodium hydroxide; methanol / 6 h / 80 °C View Scheme

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + trimethylsilylacetylene (1066-54-2) → 2,5-bis(trimethylsilylethynyl)-1,4-phenylenediamine

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine at 80℃; for 26h; Inert atmosphere;	98%
With copper diacetate; triphenylphosphine; palladium dichloride In triethylamine at 85℃; for 8h; Inert atmosphere;	60%

Thien-3-ylboronic acid (6165-69-1) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-di(thiophen-3-yl)benzene-1,4-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 80℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;	91%

7-(bromomethyl)pentadecane (52997-43-0) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → C38H70Br2N2

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 7-(bromomethyl)pentadecane In tetrahydrofuran; hexane at 40℃; Inert atmosphere;	85%

9-(iodomethyl)nonadecane (1043023-53-5) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → C46H86Br2N2

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃;	84.6%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + benzenesulfenyl chloride (931-59-9) → 2,5-dibromo-N,N'-bisphenylthio-benzoquinone diimine

Conditions	Yield
With pyridine In dichloromethane	83%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene (476004-80-5) → 2,5-bis(5-methylthiophen-2-yl)benzene-1,4-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; XPhos In tetrahydrofuran; water at 80℃; Suzuki Coupling; Inert atmosphere;	82.1%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 1,4-dibromo-2,5-bisnitrobenzene (18908-08-2)

Conditions	Yield
With trifluoroacetyl peroxide In dichloromethane at -5 - 5℃; for 6h;	80%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + ((2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthra[2,3-b]thiophene-5,10-diyl)bis (ethyne-2,1-diyl))bis(triisopropylsilane) → 2,5-(5,10-bis((triisopropylsilyl)ethynyl)anthra[2,3-b]thiophen-2-yl)benzene-1,4-diamine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Darkness;	74%

pyridine-2-carbaldehyde (1121-60-4) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-dibromo-N,N-bis(pyridine-2-ylmethylene)benzene-1,4-diamine (1574359-42-4)

Conditions	Yield
In ethanol for 2h; Reflux;	73%

1-bromo-hexane (111-25-1) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-dibromo-N1,N4-dihexylbenzene-1,4-diamine

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Schlenk technique; Stage #2: 1-bromo-hexane In tetrahydrofuran at 0 - 40℃; for 14h; Schlenk technique;	70%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + N-methylaniline (100-61-8) → 1-(2,5-dibromo-4-aminophenyl)-3-methyl-3-phenyltriazene

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine With hydrogenchloride In acetonitrile at 20℃; Stage #2: With sodium nitrite In water; acetonitrile at 0℃; Stage #3: N-methylaniline at 0 - 20℃; pH=< 7 - < 8;	69%

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-hexylthiophene (917985-54-7) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-bis(5-hexyl-2-thienyl)-1,4-phenylenediamine

Conditions	Yield
Stage #1: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-hexylthiophene; 2,5-dibromo-1,4-phenylenediamine With caesium carbonate In ethanol; water; toluene for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	66%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water; toluene at 80℃; Suzuki Coupling; Schlenk technique; Inert atmosphere;	66%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + phenylacetylene (536-74-3) → 2,6-diphenyl-1,5-dihydropyrrolo[2,3-f]indole (620987-20-4)

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine; phenylacetylene With (1,10-phenanthroline)bis(triphenylphosphine)copper(I) nitrate; caesium carbonate In toluene at 110℃; for 24h; Inert atmosphere; Stage #2: With sodium butanolate In toluene at 110℃; for 2h; Inert atmosphere;	64%

1-bromo-octane (111-83-1) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-dibromo-N1,N4-dioctylbenzene-1,4-diamine

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Reflux; Stage #2: 1-bromo-octane In tetrahydrofuran; mineral oil at 20℃; for 15h; Inert atmosphere; Reflux;	64%

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-propylthiophene + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-bis(5-propyl-2-thienyl)-1,4-phenylenediamine

Conditions	Yield
Stage #1: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-propylthiophene; 2,5-dibromo-1,4-phenylenediamine With caesium carbonate In ethanol; water; toluene for 0.75h; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	63%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water; toluene at 80℃; Schlenk technique; Inert atmosphere;	63%

fur-2-ylboronic acid (13331-23-2) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-bis(2-furanyl)-1,4-phenylenediamine

Conditions	Yield
Stage #1: fur-2-ylboronic acid; 2,5-dibromo-1,4-phenylenediamine With caesium carbonate In ethanol; water; toluene for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	60%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water; toluene at 80℃; Suzuki Coupling; Schlenk technique; Inert atmosphere;

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + propionaldehyde (123-38-6) → C12H6Br2N2

Conditions	Yield
With hydrogenchloride In water for 12h; Inert atmosphere; Reflux;	59.6%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + 2-thiopheneboronic acid pinacol ester (193978-23-3) → 2,5-bis(2-thienyl)-1,4-phenylenediamine

Conditions	Yield
Stage #1: 2,5-dibromo-1,4-phenylenediamine; 2-thiopheneboronic acid pinacol ester With caesium carbonate In ethanol; water; toluene for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	59%
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	59%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + 3,5-dimethoxyphenylboronic acid (192182-54-0) → 3,3’’,5,5’’-tetramethoxy-1,1’:4’,1’-terphenyl-2’,5’-diamine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran at 80℃; for 15h; Inert atmosphere;	39%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + p-tert-butyl benzoyl chloride (1710-98-1) → N,N'-(2,5-dibromo-1,4-phenylene)bis(4-(tertbutyl)benzamide)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃;	31.9%
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h;	31.9%

benzo[b]thiophene-2-boronic acid (98437-23-1) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-bis(2-benzothienyl)-1,4-phenylenediamine

Conditions	Yield
Stage #1: benzo[b]thiophene-2-boronic acid; 2,5-dibromo-1,4-phenylenediamine With caesium carbonate In ethanol; water; toluene for 0.666667h; Inert atmosphere; Schlenk technique; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In ethanol; water; toluene at 80℃; Suzuki Coupling; Inert atmosphere; Schlenk technique;	14%

benzo[b]thiophene-2-boronic acid (98437-23-1) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-bis(2-benzothienyl)-1,4-phenylenediamine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; water; toluene at 80℃; Suzuki Coupling; Schlenk technique; Inert atmosphere;	14%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + phenylacetylene (536-74-3) → 1,4-diamino-2,5-bis(phenylethynyl)benzene (1141727-55-0)

Conditions	Yield
With copper diacetate; triphenylphosphine; palladium dichloride In triethylamine at 85℃; for 8h; Inert atmosphere;	13%

2,5-dibromo-1,4-phenylenediamine (25462-61-7) → 2,5-dibromo-1,4-benzoquinone (1633-14-3)

Conditions	Yield
Oxydation;

di-tert-butyl dicarbonate (24424-99-5) + 2,5-dibromo-1,4-phenylenediamine (25462-61-7) → di(tert‐butyl) (2,5‐dibromo‐1,4‐phenylene)dicarbamate (159624-12-1)

Conditions	Yield
With sodium hydride 1.) THF, reflux, 0.5 h, 2.) THF, reflux, 14 h; Yield given. Multistep reaction;

2,5-dibromo-1,4-phenylenediamine (25462-61-7) + chromic acid mixture → 2,5-dibromo-1,4-benzoquinone (1633-14-3)

Upstream product

• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 3638-73-1 2,5-dibromoaniline 
• 25462-68-4 2,5-dibromo-4-nitroaniline 
• 25462-66-2 N-(2,5-dibromophenyl)acetamide 
• 106-37-6 1.4-dibromobenzene 
• 7647-01-0 hydrogenchloride 
• 18908-08-2 1,4-dibromo-2,5-dinitro-benzene 
• 25462-67-3 N-(2,5-dibromo-4-nitrophenyl)acetamide 

Downstream Products

• 1633-14-3 2,5-dibromo-1,4-benzoquinone 
• 1574359-42-4 2,5-dibromo-N,N-bis(pyridine-2-ylmethylene)benzene-1,4-diamine 
• 1141727-54-9 2,5-diethynyl-1,4-phenylenediamine 
• 18908-08-2 1,4-dibromo-2,5-dinitro-benzene 
• 620987-20-4 2,6-diphenyl-1,5-dihydropyrrolo[2,3-f]indole 

Relevant articles and documents

Synthetic method of 2,5-dibromo-p-phenylenediamine

The invention discloses a synthetic method of 2,5-dibromo-p-phenylenediamine. According to the method, the 2,5-dibromo-p-phenylenediamine is synthesized from a compound shown as I, namely, p-dibromobenzene serving as a starting material. By adopting the synthetic method of the 2,5-dibromo-p-phenylenediamine disclosed by the invention, the 2,5-dibromo-p-phenylenediamine can be effectively synthesized. Moreover, the synthetic method has the advantages of high synthesis efficiency, safe production, simple process operation, short production period and the like, so that the method is more suitablefor large-scale and industrialized production of the 2,5-dibromo-p-phenylenediamine.

Synthesis of bromine- or aryl-substituted ditopic Schiff base ligands and their bimetallic iron(II) complexes: Electronic and magnetic properties

Syntheses of three new ditopic Schiff base ligands bearing bromine, phenyl or 2-thienyl substituents are described. Bimetallic iron(II) complexes were prepared from these ligands and were characterized. Electrochemical measurements suggest no measurable electronic coupling between the metal ions in each complex. Variable temperature magnetic susceptibility measurements indicate gradual spin-crossover is operative in the complexes studied, with the low-spin state as the ground state in all cases. Density functional theory calculations corroborate these experimental observations. Attempts to electropolymerize the 2-thienyl-substituted complexes were not successful.