4-Bromo-2,6-diaminopyridine supplier

Name
4-Bromo-2,6-diaminopyridine
EINECS -0
CAS No. 329974-09-6
Article Data8
CAS DataBase
Density 1.818 g/cm³
Solubility
Melting Point 126 °C
Formula C₅H₆BrN₃
Boiling Point 352.697 °C at 760 mmHg
Molecular Weight 188.027
Flash Point 167.105 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2,6-Diamino-4-bromopyridine;4-Bromo-2,6-diaminopyridine;4-bromopyridine-2,6-diamine;
PSA 64.93000
LogP 2.17090

Synthetic route

: 410534-47-3
(4-bromo-6-tert-butoxycarbonylamino-pyridin-2-yl)-carbamic acid tert-butyl ester

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane	74%
With trifluoroacetic acid In toluene for 2h; Reflux;	209 mg

: 329974-10-9
4-bromo-pyridine-2,6-dicarbonyl diazide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-dicarbonyl diazide With tert-butyl alcohol Heating; Stage #2: With trifluoroacetic acid In dichloromethane	74%

: N,N'-dibenzyl-4-bromo-1-oxypyridine-2,6-diamine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With sulfuric acid at 40℃; for 1.5h;	68.5%

: 1310-73-2
sodium hydroxide

: 76-05-1
trifluoroacetic acid

: 329974-10-9
4-bromo-pyridine-2,6-dicarbonyl diazide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-dicarbonyl diazide In toluene; tert-butyl alcohol for 12h; Heating / reflux; Stage #2: trifluoroacetic acid In toluene for 2h; Heating / reflux; Stage #3: sodium hydroxide In diethyl ether; water	67%

...Expand

: 4-bromo-1-oxypyridine-2,6-diamine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With iron; acetic acid In water at 100℃; for 2h;	59.4%

: 2408-70-0
2,4,6-tribromopyridine

A: 39771-34-1
4-amino-2,6-dibromopyridine

B: 329974-09-6
4-bromo-pyridine-2,6-diamine

C: 2,4-diamino-6-bromopyridine

Conditions

Conditions	Yield
With ammonia In water	A n/a B 25% C n/a

...Expand

: 2408-70-0
2,4,6-tribromopyridine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With ammonium hydroxide at 200℃;

: 668992-72-1
4-bromopyridine-2,6-biscarbonamide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With potassium hydroxide; bromine for 4h; Hofmann rearrangement; Heating;
With bromine; potassium hydroxide at 0 - 90℃; for 2.5h;

: 1206250-19-2
C5H4BrClN2

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
With ammonia

: 626-05-1
2,6-Dibromopyridine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale 2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 4: toluene / 2 h / 70 °C 5: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 5 steps 1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale 2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 4: potassium carbonate / toluene / 21 h / 110 °C 5: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 5 steps 1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale 2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 4: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube 5: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 5 steps 1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale 2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 4: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube 5: iron; acetic acid / water / 2 h / 100 °C View Scheme

: 25373-69-7
2,6-dibromopyridin N-oxide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 3: toluene / 2 h / 70 °C 4: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 3: potassium carbonate / toluene / 21 h / 110 °C 4: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 3: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube 4: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 4 steps 1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale 2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 3: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube 4: iron; acetic acid / water / 2 h / 100 °C View Scheme

: 98027-81-7
2,6-dibromo-4-nitro-pyridine 1-oxide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 2: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube 3: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 2: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube 3: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 2: toluene / 2 h / 70 °C 3: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 3 steps 1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C 2: potassium carbonate / toluene / 21 h / 110 °C 3: sulfuric acid / 1.5 h / 40 °C View Scheme

: 2,4,6-tribromopyridine-1-oxide hydrobromide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube 2: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube 2: iron; acetic acid / water / 2 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / toluene / 21 h / 110 °C 2: sulfuric acid / 1.5 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: toluene / 2 h / 70 °C 2: sulfuric acid / 1.5 h / 40 °C View Scheme

: 138-60-3
chelidamic acid

: 329974-09-6
4-bromo-pyridine-2,6-diamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: phosphorus pentabromide / 3 h / 80 °C 1.2: 1 h / -10 °C 2.1: ammonia / methanol / 2 h / 20 °C 3.1: bromine; potassium hydroxide / 2.5 h / 0 - 90 °C View Scheme

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 106-47-8
4-chloro-aniline

: (E)-4-bromo-3-((4-chlorophenyl)diazenyl)pyridine-2,6-diamine

Conditions

Conditions	Yield
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: 4-bromo-pyridine-2,6-diamine In water for 1.5h;	99%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: 4-bromo-pyridine-2,6-diamine In water for 1.5h;	99%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: 4-bromo-pyridine-2,6-diamine With urea In water for 1.5h; Stage #3: With sodium acetate In water	99%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 638-29-9
n-valeryl chloride

: 662164-82-1
2,6-di-n-butylamino-4-bromo-pyridine

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 1.5h;	97%
With triethylamine In dichloromethane at 20℃; for 1.5h;	69.2%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 75-36-5
acetyl chloride

: 662164-81-0
N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 25h; Inert atmosphere;	97%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 141-75-3
butyryl chloride

: N,N'-(4-bromopyridine-2,6-diyl)dibutyramide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	95%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 79-03-8
propionyl chloride

: 4-bromo-2,6-dipropamidopyridine

Conditions

Conditions	Yield
With triethylamine In dichloromethane	90%

: 1121-60-4
pyridine-2-carbaldehyde

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 329972-51-2
7-bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	79%
With potassium hydroxide; mesitylenesulfonylhydroxylamine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 70-23-5
ethyl Bromopyruvate

: 865604-77-9
ethyl 5-amino-7-bromo-imidazo[1,2-a]pyridine-2-carboxylate

Conditions

Conditions	Yield
In ethanol for 3h; Heating / reflux;	75%
In ethanol for 5h; Reflux;

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 97-72-3
2-Methylpropionic anhydride

: N,N'-(4-bromopyridine-2,6-diyl)bis(2-methylpropanamide)

Conditions

Conditions	Yield
With pyridine at 0℃; for 2h; Reflux;	75%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 264144-59-4
(Z)-1-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolan-2’-yl)-1,2-diphenylethene

: (E)-4-(1,2-diphenylvinyl)pyridine-2,6-diamine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 70℃; for 16h;	75%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 108-24-7
acetic anhydride

: 662164-81-0
N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide

Conditions

Conditions	Yield
In pyridine at 20℃; for 10h;	68%
With pyridine at 20℃; for 10h;	68%
With pyridine	68%
With pyridine at 20℃; Inert atmosphere;	61%
Stage #1: 4-bromo-pyridine-2,6-diamine; acetic anhydride With sulfuric acid In water for 72h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 7065-46-5
3,3-dimethylbutanoic acid chloride

: N-(6-amino-4-bromopyridin-2-yl)-3,3-dimethylbutanamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;	68%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 13734-31-1
(S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid

: tert-butyl N-{1-[(6-amino-4-bromopyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate

Conditions

Conditions	Yield
Stage #1: (S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; Stage #2: 4-bromo-pyridine-2,6-diamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; for 72h;	67%
Stage #1: (S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Cooling with ice; Stage #2: 4-bromo-pyridine-2,6-diamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; for 72h;	67%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 1129-28-8
3-methoxycarbonylbenzyl bromide

: methyl 3-((2,6-diaminopyridin-4-yl)methyl)benzoate

Conditions

Conditions	Yield
Stage #1: 3-methoxycarbonylbenzyl bromide With chloro-trimethyl-silane; zinc In tetrahydrofuran; ethylene dibromide at 20℃; for 1h; Negishi Coupling; Inert atmosphere; Stage #2: 4-bromo-pyridine-2,6-diamine With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate at 20℃; Negishi Coupling;	63.9%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 766-80-3
1-bromomethyl-3-chlorobenzene

: 4-(3-chlorobenzyl)pyridine-2,6-diamine

Conditions

Conditions	Yield
Stage #1: 1-bromomethyl-3-chlorobenzene With chloro-trimethyl-silane; zinc In tetrahydrofuran; ethylene dibromide at 20℃; for 0.5h; Negishi Coupling; Inert atmosphere; Stage #2: 4-bromo-pyridine-2,6-diamine With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate at 20℃;	58.6%

: 35087-46-8
2-methoxythiophene-5-carbaldehyde

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 329972-48-7
7-bromo-2-(5-methoxythiophen-2-yl)[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	56%
With potassium hydroxide; mesitylenesulfonylhydroxylamine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 151169-75-4
3,4-dichlophenylboronic acid

: 329974-12-1
4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine

Conditions

Conditions	Yield
With sodium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) In 1,2-dimethoxyethane at 80℃; for 17h;	52%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 100-39-0
benzyl bromide

: 1204589-47-8
4-bromo-N,N,N',N'-tetrabenzyl-2,6-diaminopyridine

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-diamine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;	47%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 214360-67-5
2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 1309365-48-7
4-(3,4,5-trimethoxyphenyl)pyridine-2,6-diamine hydrochloride

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-diamine; 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane With caesium carbonate In methanol at 100℃; for 18h; Suzuki coupling; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol	44%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 24424-99-5
di-tert-butyl dicarbonate

: di-tert-butyl (4-bromopyridine-2,6-diyl)bis((tert-butoxycarbonyl)carbamate)

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 70℃; Inert atmosphere;	43%

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 100-52-7
benzaldehyde

: 329974-11-0
7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	39%

: 1310-58-3
potassium hydroxide

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 100-52-7
benzaldehyde

: 329974-11-0
7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-diamine With mesitylenesulfonylhydroxylamine In methanol at -5℃; for 0.25h; Stage #2: benzaldehyde In methanol for 0.5h; Stage #3: potassium hydroxide	39%

...Expand

: 98-03-3
thiophene-2-carbaldehyde

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 329972-33-0
7-bromo-2-thiophen-2-yl[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	37%
With potassium hydroxide; mesitylenesulfonylhydroxylamine

: 98-01-1
furfural

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 329972-27-2
7-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	36%
With potassium hydroxide; mesitylenesulfonylhydroxylamine

: 620-02-0
5-Methylfurfural

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 329972-28-3
7-bromo-2-(5-methylfuran-2-yl)[1,2,4 ]triazolo[1,5-a]pyridin-5-ylamine

Conditions

Conditions	Yield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine	35%
With potassium hydroxide; mesitylenesulfonylhydroxylamine

: 329974-09-6
4-bromo-pyridine-2,6-diamine

: 74427-22-8
2,2-difluoroethyl triflate

: 1158784-72-5
4-bromo-N-(2,2-difluoro-ethyl)-pyridine-2,6-diamine

Conditions

Conditions	Yield
Stage #1: 4-bromo-pyridine-2,6-diamine With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Stage #2: 2,2-difluoroethyl triflate In tetrahydrofuran at 25℃; for 18h;	32%

4-Bromo-2,6-diaminopyridine Chemical Properties

Empirical Formula: C₅H₆BrN₃
Molecular Weight: 188.0252
Polar Surface Area: 64.93 Å²
Index of Refraction: 1.712
Molar Refractivity: 40.507 cm³
Molar Volume: 103.402 cm³
Polarizability: 16.058 ×10^-24cm³
Surface Tension: 74.301 dyne/cm
Density: 1.818 g/cm³
Flash Point: 167.105 °C
Enthalpy of Vaporization: 59.754 kJ/mol
Boiling Point: 352.697 °C at 760 mmHg
The Cas Register Number of 2,6-Pyridinediamine,4-bromo- is 329974-09-6.The chemical synonyms of 2,6-Pyridinediamine,4-bromo-(CAS NO.329974-09-6) are 4-Bromopyridine-2,6-diamine .The molecular structure of 2,6-Pyridinediamine,4-bromo- (CAS NO.329974-09-6) is
.

4-Bromo-2,6-diaminopyridine Uses

2,6-Pyridinediamine,4-bromo- (CAS NO.329974-09-6) is used in organic synthesis .

Product Name

4-Bromo-2,6-diaminopyridine

Synthetic route

4-Bromo-2,6-diaminopyridine Chemical Properties

4-Bromo-2,6-diaminopyridine Uses

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