96558-78-0

Basic information

• Product Name: 3-BROMO-5-CHLOROPHENYLAMINE
• Synonyms: 3-BROMO-5-CHLOROPHENYLAMINE;3-Bromo-5-chloroaniline;3-BROMO-5-CHLOROPHENYLAMINE, 95+%;3-BROMO-5-CHLOROPHEN;3-broMo-5-chlorobenzenaMine;BenzenaMine,3-broMo-5-chloro-
• CAS NO: 96558-78-0
• Molecular Formula: C₆H₅BrClN
• Molecular Weight: 206.47
• Mol File: 96558-78-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 284.132 °C at 760 mmHg
• Flash Point: 125.639 °C
• Appearance: /
• Density: 1.722 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.47±0.10(Predicted)
• CAS DataBase Reference: 3-BROMO-5-CHLOROPHENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5-CHLOROPHENYLAMINE(96558-78-0)
• EPA Substance Registry System: 3-BROMO-5-CHLOROPHENYLAMINE(96558-78-0)

Safety Data

• Hazard Codes: Xi
• RIDADR: 2018
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 96558-78-0(Hazardous Substances Data)

Usage

Uses

3-Bromo-5-chloroaniline is a reactant in the preparation of triazolophthalazines as inhibitors of diverse bromodomains

Synthetic route

1-bromo-3-chloro-5-nitrobenzene → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
With acetic acid; zinc for 4h;	99%
With sodium sulfide; zinc at 35 - 45℃; for 0.333333h; Temperature;	90%

2,3-dibromo-5-chloroaniline (96558-70-2) → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
With hydrogenchloride; 2H(1+)*2H3N*Cl3Cu(2-) In acetic acid at 90℃; Rate constant; other solvent, other temp., other Cu(I) complex;

5-chloro-3-bromo-1-nitrobenzene → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
With hydrogenchloride; tin

benzenesulfonic acid (98-11-3) → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: nitric acid; manganese(IV) oxide / 0.75 h / 35 °C / 15001.5 Torr 2: N-Bromosuccinimide / 30 °C 3: hydrogenchloride / water / 1 h / 95 °C / 18751.9 Torr 4: acetic acid / 0.75 h / 20 - 25 °C / 15001.5 - 18751.9 Torr 5: zinc; sodium sulfide / 0.33 h / 35 - 45 °C View Scheme

p-nitrobenzenesulfonic acid (138-42-1) → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide / 30 °C 2: hydrogenchloride / water / 1 h / 95 °C / 18751.9 Torr 3: acetic acid / 0.75 h / 20 - 25 °C / 15001.5 - 18751.9 Torr 4: zinc; sodium sulfide / 0.33 h / 35 - 45 °C View Scheme

2-bromo-p-nitrobenzenesulfonic acid → 3-bromo-5-chlorophenylamine (96558-78-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 1 h / 95 °C / 18751.9 Torr 2: acetic acid / 0.75 h / 20 - 25 °C / 15001.5 - 18751.9 Torr 3: zinc; sodium sulfide / 0.33 h / 35 - 45 °C View Scheme

potassium cyclopropyltrifluoroborate (1065010-87-8) + 3-bromo-5-chlorophenylamine (96558-78-0) → 3-chloro-5-cyclopropylaniline

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium tert-butylate In water; toluene at 90℃; for 16h; Inert atmosphere;	92.4%

3-bromo-5-chlorophenylamine (96558-78-0) + 2-chloro-5-(1,1-dioxo-1,2-thiazolidin-2-yl)-3-fluorobenzoic acid → C16H12BrCl2FN2O3S

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 12h;	88.3%

2-amino-6-methyl-4-chloropyrimidine (5600-21-5) + 3-bromo-5-chlorophenylamine (96558-78-0) → N4-(3-bromo-5-chlorophenyl)-6-methylpyrimidine-2,4-diamine

Conditions	Yield
With hydrogenchloride In ethanol; water at 140℃; for 1.5h; Microwave irradiation; Sealed tube;	87%

3-bromo-5-chlorophenylamine (96558-78-0) + 2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (126726-62-3) → 3-chloro-5-(prop-1-en-2-yl)aniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 130℃; for 3h;	82%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	51.1%

3-bromo-5-chlorophenylamine (96558-78-0) + bis(pinacol)diborane (73183-34-3) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1269233-11-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 5h;	81.4%

4,4,5,5-tetramethyl-2-[1-methylprop-1-enyl]-1,3,2-dioxaborolane + 3-bromo-5-chlorophenylamine (96558-78-0) → 3-(but-2-en-2-yl)-5-chloroaniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 130℃; for 12h; Inert atmosphere;	81%

3-bromo-5-chlorophenylamine (96558-78-0) → 3-bromo-5-chloro-benzenesulfonyl chloride

Conditions	Yield
Stage #1: 3-bromo-5-chlorophenylamine With hydrogenchloride; sodium nitrite In water at 0℃; Cooling with ice/salt; Stage #2: With copper(II) choride dihydrate; sulfur dioxide In water; acetic acid at 20℃; Cooling with ice/salt;	78%
Stage #1: 3-bromo-5-chlorophenylamine With hydrogenchloride; sodium nitrite In water at 5℃; Sandmeyer reaction; Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water at 20℃; for 2h; Sandmeyer reaction;
Stage #1: 3-bromo-5-chlorophenylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: With sulfur dioxide; acetic acid; copper(l) chloride In water at 0 - 20℃; for 2h;

4-amino-6-chloro-2-methylpyrimidine (1749-68-4) + 3-bromo-5-chlorophenylamine (96558-78-0) → N4-(3-bromo-5-chlorophenyl)-2-methylpyrimidine-4,6-diamine

Conditions	Yield
With hydrogenchloride In ethanol; water for 18h; Reflux;	75%

3-bromo-5-chlorophenylamine (96558-78-0) + benzyl bromide (100-39-0) → N,N-dibenzyl-3-bromo-5-chloroaniline

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	75%

3-bromo-5-chlorophenylamine (96558-78-0) + 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) → 3-allyl-5-chloroaniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water at 100℃; for 12h; Inert atmosphere;	54.2%

3-bromo-5-chlorophenylamine (96558-78-0) + 4-pyridylboronic acid (1692-15-5) → 3-chloro-5-(pyridin-4-yl)aniline (1426806-67-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere;	53.1%

3-bromo-5-chlorophenylamine (96558-78-0) + methyl 2-chloro-5-(1,1-dioxo-1,2-thiazolidin-2-yl)benzoate → C16H13BrCl2N2O3S

Conditions	Yield
With trimethylaluminum In toluene at 0 - 110℃; for 3h;	52.4%

3-bromo-5-chlorophenylamine (96558-78-0) + 2-tri-n-butylstannylpyridine (17997-47-6) → C11H9ClN2

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 110℃; for 12h; Inert atmosphere;	50.4%

3-bromo-5-chlorophenylamine (96558-78-0) → 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1269233-11-5)

Conditions	Yield
In ethyl acetate	48%

n-propanesulfonyl chloride (10147-36-1) + 3-bromo-5-chlorophenylamine (96558-78-0) → N-(3-bromo-5-chlorophenyl)propane-1-sulfonamide

Conditions	Yield
With pyridine at 20℃; for 48h;	48%

di-tert-butyl dicarbonate (24424-99-5) + 3-bromo-5-chlorophenylamine (96558-78-0) → C11H13BrClNO2

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 40℃; for 12h;	41.1%

2,3-dihydro-2H-furan (1191-99-7) + 3-bromo-5-chlorophenylamine (96558-78-0) → 3-chloro-5-(2,3-dihydrofuran-5-yl)aniline + C10H10ClNO

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere;	A 41.1% B 24.8%

3-bromo-5-chlorophenylamine (96558-78-0) + 2-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene (126689-00-7) → 3-chloro-5-(2-methylprop-1-enyl)aniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 12h; Inert atmosphere;	41%

3-bromo-5-chlorophenylamine (96558-78-0) + allyltributylstanane (24850-33-7) → 3-allyl-5-chloroaniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20 - 85℃; for 16h; Inert atmosphere;	38.7%

3-bromo-5-chlorophenylamine (96558-78-0) → 3-bromo-4,5-dichloroaniline

Conditions	Yield
With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	34%

3-bromo-5-chlorophenylamine (96558-78-0) + pinacol vinylboronate (75927-49-0) → 3-chloro-5-ethenylaniline

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 22h; Inert atmosphere;	24%

3-bromo-5-chlorophenylamine (96558-78-0) → 1-bromo-3-chloro-5-iodobenzene (13101-40-1)

Conditions	Yield
ueber die Diazoverbindung;

3-bromo-5-chlorophenylamine (96558-78-0) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfanilic acid-(3-bromo-5-chloro-anilide)

Conditions	Yield
With pyridine; acetone Erwaermen des Reaktionsprodukts mit wss. Natronlauge;

thiophosgene (463-71-8) + 3-bromo-5-chlorophenylamine (96558-78-0) → C7H3BrClNS

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + 3-bromo-5-chlorophenylamine (96558-78-0) → (S)-tert-butyl 1-(3-bromo-5-chlorophenylamino)-1-oxo-3-phenylpropan-2-ylcarbamate (1240523-63-0)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide for 14h;

morpholine (110-91-8) + 3-bromo-5-chlorophenylamine (96558-78-0) → 3-chloro-5-morpholinoaniline (1259440-76-0)

Conditions	Yield
With lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium(0); 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl In tetrahydrofuran at 65℃; for 2.5h;

4-methyl-1H-imidazole (822-36-6) + 3-bromo-5-chlorophenylamine (96558-78-0) → C10H10ClN3 (1290090-24-2)

Conditions	Yield
With copper(l) iodide; 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere;

Upstream product

• 138-42-1 p-nitrobenzenesulfonic acid 
• 98-11-3 benzenesulfonic acid 
• 219817-43-3 1-bromo-3-chloro-5-nitrobenzene 
• 96558-70-2 2,3-dibromo-5-chloroaniline 

Downstream Products

• 13101-40-1 1-bromo-3-chloro-5-iodobenzene 
• 1049026-36-9 3-bromo-5-chloro-benzenesulfonyl chloride 
• 1261524-60-0 C₆H₅BrClNO₂S 
• 1259440-76-0 3-chloro-5-morpholinoaniline 
• 1426806-67-8 3-chloro-5-(pyridin-4-yl)aniline 

Relevant articles and documents

Synthesis method of 3-cloro-5-bromoaniline

The invention discloses a synthesis method of 3-cloro-5-bromoaniline, and belongs to the technical field of organic synthesis. According to the method, benzenesulfonic acid is used as raw materials; firstly, concentrated nitric acid and a manganese dioxide catalyst are added for generating p-nitrobenzenesulphonic acid; then, NBS is added to generate 2-bromine p-nitrophenyl sulfonic acid; next, HCl is added for generating 2-cloro-6-bromine p-nitrophenyl sulfonic acid; next, a CH3COOH solution is added; benzenesulfonic acid in the 2-cloro-6-bromine p-nitrophenyl sulfonic acid is removed to obtain 3-cloro-5-bromonitrobenzene; finally, reducing Na2S and Zn are added for reduction, so that the 3-cloro-5-bromoaniline prepared by the method is obtained. Examples prove that the synthesis method has the advantages that the preparation is convenient and simple; the environment is protected; no pollution is caused; the equipment investment is low; any pollution does not exist; the yield reaches more than 85 percent.

Copper(I)-Induced Halogen-Hydrogen Exchange of 2-Halogenoanilines

The copper(I)-induced halogen-hydrogen exchange in the 2-position of 2,3-dibromoaniline, 2,3-dibromo-5-methylaniline, 2,3-dibromo-5-chloroaniline and 3-bromo-2-iodoaniline has been studied in acetic acid, ethanol and chlorobenzene media with a hydrochloric acid content of 0.56 mol dm-3.The CuX32- complexes used in the reduction reaction are (CH3Ph3P+)2CuBr32-, (CH3PH3P+)2CuI32-, (NH4+)2CuBr32- and (NH4+)2CuCl32-. (C4H9)4N+ CuCl2- and NH4+ CuBr2- have also been tested in the same media.The reduction rate increases with the size of the Cu(I)-complex.