Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetone at 0 - 20℃; | 98% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 2h; | 98% |
With N-Bromosuccinimide In acetonitrile at 20℃; for 2h; | 98% |
2-aminopyridine
A
5-bromo-2-pyridylamine
B
2-amino-3,5-dibromopyridine
Conditions | Yield |
---|---|
With tetra-N-butylammonium tribromide In chloroform at 20℃; for 0.0333333h; other reagent: tetraphenylphosphonium tribromide; | A 98% B 2% |
With N-Bromosuccinimide; lithium perchlorate; silica gel In dichloromethane at 20℃; for 0.0833333h; | A 90% B 10% |
With bromine In ethanol at 20℃; | A 76% B 12% |
2-aminopyridine
A
5-bromo-2-pyridylamine
B
2-amino-4,6-dibromopyridine
Conditions | Yield |
---|---|
With tetra-N-butylammonium tribromide In chloroform for 0.0333333h; Ambient temperature; | A 98% B 2% |
5-bromo2-nitropyridine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With tetrahydroxydiboron; 5%-palladium/activated carbon; water In acetonitrile at 50℃; for 24h; | 96% |
With potassium borohydride; TPGS-750-M In tetrahydrofuran; water at 20℃; for 20h; Inert atmosphere; | 91% |
With potassium tert-butylate; isopropyl alcohol; bis(pinacol)diborane at 110℃; for 2h; | 90% |
5-bromo-N,N-bis[(4-methoxyphenyl)methyl]pyridin-2-amine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 5h; | 90% |
pent-4-ynenitrile
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With hydrogen bromide; bromine; sodium hydroxide In dichloromethane; water at 30 - 45℃; | 89.9% |
5-bromo-2-nitraminopyridine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With 50percent aq. HPO2 for 5h; Heating; | 88% |
2-[(N,N-dibenzyl)amino]-5-bromopyridine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 0.5h; | 87% |
Conditions | Yield |
---|---|
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction; | 86% |
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; | 86% |
With ammonia; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 180℃; for 2h; |
pyridinium N-<2'-(3',5'-dibromopyridyl)>aminide
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With zinc In acetic acid for 29h; Ambient temperature; | 75% |
pyridinium N-<2'-(5'-bromopyridyl)>aminide
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With triethylammonium formate; platinum on activated charcoal In acetonitrile for 4h; Heating; | 63% |
With acetic acid; zinc |
5-bromo-1-(difluoromethyl)pyridin-2(1H)-imine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With potassium hydroxide at 100℃; for 2h; | 63% |
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 30℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction; | A 50% B 25% |
(E)-5-bromo-2-((4-chlorophenyl)diazenyl)pyridine
A
5-bromo-2-pyridylamine
B
N1-(5-bromopyridin-2-yl)-5-chlorobenzene-1,2-diamine
Conditions | Yield |
---|---|
Stage #1: (E)-5-bromo-2-((4-chlorophenyl)diazenyl)pyridine With trimethylsilyl iodide In hexane at 0 - 20℃; for 8h; Benzidine Rearrangement; Stage #2: With hydrogenchloride; tin(ll) chloride In ethanol; water at 110℃; for 2h; Benzidine Rearrangement; | A 40% B 37% |
5-bromo2-nitropyridine
A
5-bromo-2-pyridylamine
B
6-nitropyridin-3-ylamine
Conditions | Yield |
---|---|
With ammonium hydroxide at 150℃; |
5,6-dibromopyridin-2-ylamine
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
Hydrogenation; |
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
With potassium hydroxide; bromine |
pyridine-2-carboxylic acid amide
bromine
A
2-aminopyridine
B
5-bromo-2-pyridylamine
C
2-amino-3,5-dibromopyridine
5-bromo2-nitropyridine
ethanol
ammonia
A
5-bromo-2-pyridylamine
B
6-nitropyridin-3-ylamine
Conditions | Yield |
---|---|
at 150℃; |
5-bromo2-nitropyridine
A
5-bromo-2-pyridylamine
B
6-nitropyridin-3-ylamine
Conditions | Yield |
---|---|
at 150℃; |
N-(5-bromopyridin-2-yl)-3-oxobutanamide
sulfuric acid
A
5-bromo-2-pyridylamine
B
7- bromo-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
Conditions | Yield |
---|---|
With copper(I) oxide; ammonia at 60℃; for 40h; |
(pyridin-1-iumyl)[(pyridin-2-yl)aminide]
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Br2 / CH2Cl2 / 0 °C 2: Zn, acetic acid View Scheme |
N’-(5-bromopyridin-2-yl)-N,N-dimethylformimidamide
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / 1 h / 140 °C / Microwave irradiation; Inert atmosphere; Sealed tube 2: ammonium acetate View Scheme |
Conditions | Yield |
---|---|
With ammonium acetate |
Conditions | Yield |
---|---|
Stage #1: N-(2-pyridyl)acetamide With bromine at 20 - 50℃; for 2.5h; Stage #2: With sodium hydroxide In water for 0.5h; Temperature; | 14.1 g |
5-bromo-2-pyridylamine
Conditions | Yield |
---|---|
Stage #1: pyridine-2-ylcarbamic acid With bromine at 20 - 50℃; for 2.5h; Stage #2: With sodium hydroxide In water for 0.5h; Temperature; | 14.1 g |
5-bromo-2-pyridylamine
p-toluenesulfonyl chloride
N-(5-bromopyridin-2-yl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With pyridine at 0 - 90℃; | 100% |
With pyridine at 0 - 90℃; | 100% |
With pyridine at 20 - 90℃; for 24h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2-chloroethanal; 5-bromo-2-pyridylamine In ethanol; water for 3h; Reflux; Stage #2: With sodium hydrogencarbonate In water | 100% |
In ethanol; water at 80℃; for 15h; | 100% |
In ethanol for 6h; Reflux; | 98% |
5-bromo-2-pyridylamine
ethyl (2-chloroaceto)acetate
ethyl 2-(6-bromoimidazo[1,2-a]pyridin-2-yl)acetate
Conditions | Yield |
---|---|
In ethanol for 4h; Reflux; Inert atmosphere; | 100% |
In toluene Reflux; | 24% |
In toluene at 115℃; for 18h; | |
In ethanol Heating / reflux; |
5-bromo-2-pyridylamine
Ethoxycarbonyl isothiocyanate
ethyl [(5-bromopyridin-2-yl)carbamothioyl]carbamate
Conditions | Yield |
---|---|
In dichloromethane at 5 - 20℃; for 16.25h; | 100% |
In dichloromethane at 5 - 20℃; for 16.25h; | 100% |
In 1,4-dioxane at 25℃; for 18h; Inert atmosphere; | 100% |
5-bromo-2-pyridylamine
tert-Butyl acrylate
(E)-tert-butyl 3-(6-aminopyridin-3-yl)acrylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide; propiononitrile at 100℃; for 20h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 50℃; | 100% |
With sodium hydride In tetrahydrofuran at 50℃; Reflux; |
Conditions | Yield |
---|---|
In dichloromethane at 0 - 15℃; for 48h; | 100% |
In dichloromethane at 0 - 15℃; for 48h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 100% |
5-bromo-2-pyridylamine
2-nitroamino-4-bromopyridine
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at -8℃; for 0.333333h; | 99.2% |
5-bromo-2-pyridylamine
acetic anhydride
N-(5-bromopyridin-2-yl)acetamide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Industrial scale; | 99.04% |
at 80℃; for 24h; | 97% |
With pyridine In tetrahydrofuran at 20℃; | 92% |
5-bromo-2-pyridylamine
1-Hydroxymethyl-1H-benzotriazole
Benzotriazol-1-ylmethyl-(5-bromo-pyridin-2-yl)-amine
Conditions | Yield |
---|---|
In ethanol for 5h; Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide at 20℃; for 3h; | 99% |
With cellulose sulfuric acid In methanol at 20℃; for 2h; | 98% |
With sulfuric acid; silica gel In methanol at 20℃; for 3h; | 97% |
5-bromo-2-pyridylamine
bis(pinacol)diborane
2-aminopyridine-5-boronic acid pinacol ester
Conditions | Yield |
---|---|
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 80℃; for 16h; Temperature; Solvent; Inert atmosphere; | 99% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; | 75% |
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere; | 62% |
5-bromo-2-pyridylamine
2,5-hexanedione
5-bromo-2-(2,5-dimethyl-pyrrol-1-yl)-pyridine
Conditions | Yield |
---|---|
In toluene for 14h; Reflux; Dean-Stark; Inert atmosphere; | 99% |
With toluene-4-sulfonic acid In toluene for 14h; Heating / reflux; | 92% |
toluene-4-sulfonic acid In toluene for 14h; Heating / reflux; Dean Stark conditions; | 92% |
5-bromo-2-pyridylamine
N,N-dimethyl-formamide dimethyl acetal
N’-(5-bromopyridin-2-yl)-N,N-dimethylformimidamide
Conditions | Yield |
---|---|
In methanol at 70℃; for 16h; | 99% |
In methanol at 70℃; for 6h; | 82% |
In N,N-dimethyl-formamide at 130℃; for 12h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; hexane at 20℃; for 75h; Heating / reflux; | 99% |
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; hexane at 20℃; for 75h; Heating / reflux; | 99% |
5-bromo-2-pyridylamine
phenyl chloroformate
phenyl (5-bromopyridin-2-yl)carbamate
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 0 - 20℃; for 1h; Concentration; | 99% |
With pyridine In dichloromethane at 0℃; | 91.5% |
With pyridine In dichloromethane at 5℃; | 90% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h; | 59% |
5-bromo-2-pyridylamine
ethyl Bromopyruvate
ethyl 6-bromoimidazo<1,2-a>pyridine-2-carboxylate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 12h; | 98% |
With magnesium sulfate In 1,4-dioxane at 80℃; for 18h; | 93% |
Stage #1: 5-bromo-2-pyridylamine; ethyl Bromopyruvate In 1,2-dimethoxyethane for 5h; Stage #2: In ethanol Reflux; | 87% |
5-bromo-2-pyridylamine
N,N-dimethyl-formamide dimethyl acetal
(E)-N’-(5-bromopyridin-2-yl)-N,N-dimethylformamidine
Conditions | Yield |
---|---|
In methanol at 70℃; for 6h; Inert atmosphere; | 98% |
In isopropyl alcohol at 80℃; | 75% |
In methanol Heating; | 73% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; acetonitrile at 90℃; for 16h; | 98% |
With [(t-Bu)3PH]BF4; palladium diacetate; sodium hydroxide In water; butan-1-ol at 25℃; for 0.25h; Suzuki Coupling; Inert atmosphere; Glovebox; | 94% |
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In methanol; toluene for 12h; Suzuki reaction; Heating; | 92% |
Conditions | Yield |
---|---|
With 1-n-butyl-3-methylimidazolim bromide at 20℃; for 3h; | 98% |
With sulfuric acid; silica gel In methanol at 20℃; for 3h; | 98% |
With cellulose sulfuric acid In methanol at 20℃; for 2h; | 98% |
5-bromo-2-pyridylamine
N,N-dimethylacetamide dimethyl acetal
Conditions | Yield |
---|---|
In methanol at 80℃; for 16h; | 98% |
In methanol at 80℃; for 16h; | 98% |
With N,N-dimethyl-formamide at 130℃; for 12h; | |
In N,N-dimethyl-formamide at 130℃; for 12h; |
Conditions | Yield |
---|---|
Stage #1: 5-bromo-2-pyridylamine; 3-bromo-1,1,1-trifluoroacetone With potassium carbonate In ethanol for 24h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water | 98% |
With potassium carbonate In ethanol for 2h; Reflux; | 91% |
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene at 20℃; for 24h; Suzuki Coupling; Heating / reflux; | 98% |
5-bromo-2-pyridylamine
oxalyl dichloride
3,4,5-trimethoxy-2-nitrobenzoic acid
Conditions | Yield |
---|---|
With pyridine In hexane; dichloromethane; ethyl acetate | 98% |
With pyridine In hexane; dichloromethane; ethyl acetate | 98% |
5-bromo-2-pyridylamine
3,4,5-trimethoxy-2-nitrobenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5-trimethoxy-2-nitrobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: 5-bromo-2-pyridylamine With pyridine In dichloromethane at 20℃; | 98% |
5-bromo-2-pyridylamine
alpha-(3-methylphenoxy)acetophenone
Conditions | Yield |
---|---|
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h; | 98% |
The IUPAC name of 2-Amino-5-bromopyridine is 5-bromopyridin-2-amine. With the CAS registry number 1072-97-5 and EINECS 214-019-9, it is also named as 2-Pyridinamine, 5-bromo-. The product's categories are Compounds of Pyridine; Fine Chemical & Intermediates;Amines; Blocks; Bromides; Pyridines; Pyridine; Pyridine Derivative; Pyridines, Pyrimidines, Purines and Pteredines; Organic Acids; Bromopyridines; Halopyridines; Heterocyclic Building Blocks; Amino-pyridine Series; Organohalides. It is light yellow crystal which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.98; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.93; (4)ACD/LogD (pH 7.4): 1.98; (5)ACD/BCF (pH 5.5): 16.6; (6)ACD/BCF (pH 7.4): 18.92; (7)ACD/KOC (pH 5.5): 250.42; (8)ACD/KOC (pH 7.4): 285.41; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.636; (13)Molar Refractivity: 36.27 cm3; (14)Molar Volume: 101.1 cm3; (15)Polarizability: 14.37×10-24 cm3; (16)Surface Tension: 56.9 dyne/cm; (17)Enthalpy of Vaporization: 46.75 kJ/mol; (18)Vapour Pressure: 0.0643 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 171.963611; (21)MonoIsotopic Mass: 171.963611; (22)Topological Polar Surface Area: 38.9; (23)Heavy Atom Count: 8; (24)Complexity: 76.8.
Preparation of 2-Amino-5-bromopyridine: It can be obtained by pyridin-2-ylamine. This reaction needs reagent NBS and solvent acetonitrile at temperature of 20 °C. The reaction time is 17 hours. The yield is 93%.
Uses of 2-Amino-5-bromopyridine: It is used to produce drugs and other fine chemicals. It also can react with benzotriazol-1-yl-methanol to get benzotriazol-1-ylmethyl-(5-bromo-pyridin-2-yl)-amine. This reaction needs solvent ethanol at ambient temperature. The reaction time is 5 hours. The yield is 99%.
When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.
People can use the following data to convert to the molecule structure.
1. SMILES:Brc1cnc(N)cc1
2. InChI:InChI=1/C5H5BrN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)
3. InChIKey:WGOLHUGPTDEKCF-UHFFFAOYAB
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