13296-69-0

Basic information

• Product Name: 2-BROMO-BENZENE-1,4-DIAMINE
• Synonyms: 2-BROMO-BENZENE-1,4-DIAMINE;2-Bromo-1,4-benzenediamine;2-Bromo-1,4-phenylenediamine;2-Bromo-4-aminoaniline
• CAS NO: 13296-69-0
• Molecular Formula: C₆H₇BrN₂
• Molecular Weight: 187.04
• Product Categories: pharmacetical
• Mol File: 13296-69-0.mol

Chemical Properties

• Boiling Point: 303.7°Cat760mmHg
• Flash Point: 137.5°C
• Appearance: /
• Density: 1.697g/cm³
• Vapor Pressure: 0.000916mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2-BROMO-BENZENE-1,4-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-BENZENE-1,4-DIAMINE(13296-69-0)
• EPA Substance Registry System: 2-BROMO-BENZENE-1,4-DIAMINE(13296-69-0)

Safety Data

• Hazardous Substances Data: 13296-69-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BROMO-BENZENE-1,4-DIAMINE is used as a key intermediate in the production of pharmaceuticals, contributing to the synthesis of various medicinal compounds due to its unique chemical structure and reactivity.
Used in Dye Industry:
In the dye industry, 2-BROMO-BENZENE-1,4-DIAMINE is employed as a precursor for the synthesis of dyes, leveraging its chemical properties to create a range of colorants for different applications.
Used in Chemical Reactions:
2-BROMO-BENZENE-1,4-DIAMINE is utilized as a reagent in various chemical reactions, facilitating the formation of new compounds and aiding in the advancement of chemical research and development.
Used in Organic Synthesis:
As a building block in organic synthesis, 2-BROMO-BENZENE-1,4-DIAMINE is used to construct complex organic molecules, playing a crucial role in the creation of novel chemical entities with potential applications in various fields.
It is important to handle 2-BROMO-BENZENE-1,4-DIAMINE with care, as it can be harmful if inhaled or ingested, and can cause skin and eye irritation upon contact. Proper safety measures should be taken during its use to minimize potential health risks.

InChI:InChI=1/C6H7BrN2/c7-5-3-4(8)1-2-6(5)9/h1-3H,8-9H2

Synthetic route

2,6-dibromo-4-nitroaniline (827-94-1) → 2-bromo-p-phenylenediamine (13296-69-0)

Conditions	Yield
With ammonium chloride; zinc In ethanol for 12h; Heating;	67%

2-bromo-4-nitroaniline (13296-94-1) → 2-bromo-p-phenylenediamine (13296-69-0)

Conditions	Yield
With hydrogenchloride; tin
With hydrogenchloride; tin(ll) chloride
With hydrogenchloride; iron In ethanol for 1h; Heating;

hydrogenchloride (7647-01-0) + N'-(2-bromo-4-nitro-phenyl)-N-phenyl-diazene-N-oxide + tin → 2-bromo-p-phenylenediamine (13296-69-0) + aniline (62-53-3)

4-nitro-aniline (100-01-6) → 2-bromo-p-phenylenediamine (13296-69-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid; bromine 2: tin (II)-chloride; concentrated hydrochloric acid View Scheme

2-bromo-p-phenylenediamine (13296-69-0) + acetic anhydride (108-24-7) → N,N'-(bromo-p-phenylene)-bis-acetamide (57045-90-6)

Conditions	Yield
With pyridine at 20℃; for 2h;	96%

2-bromo-p-phenylenediamine (13296-69-0) + allyl bromide (106-95-6) → N,N-diallyl-2-bromo-4-(N,N-diallylamino)aniline

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide for 3h; Heating;	70%

2-bromo-p-phenylenediamine (13296-69-0) + dimethyl sulfate (77-78-1) → 2-bromo-N,N,N',N'-tetramethyl-p-phenylenediamine

Conditions	Yield
With sodium hydrogencarbonate	65%

2-bromo-p-phenylenediamine (13296-69-0) + 2-trimethylsilanyl-ethanesulfonyl chloride (106018-85-3) → 2-trimethylsilanyl-ethanesulfonic acid [2-bromo-4-(2-trimethylsilanyl-ethanesulfonylamino)-phenyl]-amide (487047-44-9)

Conditions	Yield
With pyridine at 20℃;	64%

2-bromo-p-phenylenediamine (13296-69-0) + benzenesulfenyl chloride (931-59-9) → 2-bromo-N,N'-bisphenylthiobenzoquinone diimide

Conditions	Yield
With pyridine In dichloromethane	33%

2-bromo-p-phenylenediamine (13296-69-0) → N,N'-(bromo-p-phenylene)-bis-benzamide (19627-56-6)

hydrogenchloride (7647-01-0) + 2-bromo-p-phenylenediamine (13296-69-0) + tin (II)-chloride → bromine (7726-95-6)

Conditions	Yield
Geschwindigkeit;

2-bromo-p-phenylenediamine (13296-69-0) → (Z)-4-(2,5-Bis-acetylamino-phenyl)-but-3-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / pyridine / 2 h / 20 °C 2: tetrakis(triphenylphosphine)palladium(0); 2,6-di-tert-butyl-4-methylphenol / toluene / 7 h / Heating View Scheme

2-bromo-p-phenylenediamine (13296-69-0) → (E)-4-(2,5-Bis-acetylamino-phenyl)-but-3-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / pyridine / 2 h / 20 °C 2: tetrakis(triphenylphosphine)palladium(0); 2,6-di-tert-butyl-4-methylphenol / toluene / 7 h / Heating View Scheme

2-bromo-p-phenylenediamine (13296-69-0) → (Z)-4-[2,5-Bis-(2-trimethylsilanyl-ethanesulfonylamino)-phenyl]-but-3-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / pyridine / 20 °C 2: tetrakis(triphenylphosiphine)palladium(0); 2,6-di-tert-butyl-4-methylphenol / toluene / 12 h / Heating View Scheme

2-bromo-p-phenylenediamine (13296-69-0) → (E)-4-[2,5-Bis-(2-trimethylsilanyl-ethanesulfonylamino)-phenyl]-but-3-enoic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / pyridine / 20 °C 2: tetrakis(triphenylphosiphine)palladium(0); 2,6-di-tert-butyl-4-methylphenol / toluene / 12 h / Heating View Scheme

2-bromo-p-phenylenediamine (13296-69-0) → 2-phenylthio-N,N'-bisphenylthio-benzoquinone diimide

Conditions	Yield
Multi-step reaction with 2 steps 1: 33 percent / pyridine / CH2Cl2 2: 1.) NaOEt / 1.) EtOH, 2.) EtOH, benzene, reflux, 5 h View Scheme

2-bromo-p-phenylenediamine (13296-69-0) + triethyl phosphite (122-52-1) → (2,5-diaminophenyl)-phosphonic acid diethyl ester (1126651-91-9)

Conditions	Yield
With palladium diacetate In acetonitrile at 160℃; for 0.5h; Microwave irradiation;

2-bromo-p-phenylenediamine (13296-69-0) → C23H35N4O4P

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate / acetonitrile / 0.5 h / 160 °C / Microwave irradiation 2: trimethylaluminum / 1,4-dioxane / 3 h / 80 °C View Scheme

Upstream product

• 13296-94-1 2-bromo-4-nitroaniline 
• 7647-01-0 hydrogenchloride 
• 100-01-6 4-nitro-aniline 
• 827-94-1 2,6-dibromo-4-nitroaniline 

Downstream Products

• 19627-56-6 N,N'-(bromo-p-phenylene)-bis-benzamide 
• 57045-90-6 N,N'-(bromo-p-phenylene)-bis-acetamide 
• 7726-95-6 bromine 
• 487047-44-9 2-trimethylsilanyl-ethanesulfonic acid [2-bromo-4-(2-trimethylsilanyl-ethanesulfonylamino)-phenyl]-amide 
• 1126651-91-9 (2,5-diaminophenyl)-phosphonic acid diethyl ester 

Relevant articles and documents

Investigation of 2,6-disubstituted N,N,N′,N′-tetramethyl-p-phenylenediamines as precursors/building blocks for molecular magnets

The synthesis of 2,6-disubstituted N,N,N′,N′-tetramethyl-p-phenylenediamines (R = Cl, Br, I, CN, or C≡CSi(CH3)3), potential precursors/building blocks for molecular magnets, is presented. In addition to standard methods (1

Synthesis of polysubstituted indoles and indolines by means of zirconocene-stabilized benzyne complexes

The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.