tert-butyl 5-bromopyridine-2-carboxylate
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
In hexafluoropropan-2-ol at 100℃; for 3h; Microwave irradiation; | 95% |
methyl 5-bromopicolinate
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 15h; | 90% |
With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; | |
With sodium hydroxide In water at 20℃; for 12h; |
Conditions | Yield |
---|---|
With n-butyllithium In hexane; toluene at -75℃; for 2h; | 64% |
Stage #1: 2,5-dibromopyridine With n-butyllithium In toluene at -78℃; for 2h; Stage #2: carbon dioxide In toluene at -78℃; for 1h; Stage #3: With hydrogenchloride In water; toluene | 47% |
Stage #1: 2,5-dibromopyridine With n-butyllithium In toluene at -78℃; for 2h; Stage #2: carbon dioxide In toluene at -78℃; for 1h; | 47% |
2-Cyano-5-bromopyridine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water Reflux; | 64% |
With hydrogenchloride for 24h; Heating; | |
Stage #1: 2-Cyano-5-bromopyridine With potassium hydroxide; ethanol; water at 80℃; for 24h; Stage #2: With hydrogenchloride; water pH=4; |
5-bromo-2-methylpyridine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With potassium permanganate In water at 80℃; | 39% |
With potassium permanganate | |
With potassium permanganate; water at 100℃; for 6h; | |
With potassium permanganate Heating; |
5-amino-pyridine-2-carboxylic acid
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With hydrogen sulfide; hydrogen bromide; urea; copper(I) bromide; sodium nitrite 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux; Yield given. Multistep reaction; |
5-nitro-pyridin-2-ylamine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) 48 percent HBr, Br2; 2.) NaNO2 / 1) 30-40 deg C; 2) -5 deg C, H2O; 10-15 Deg C, 90 min.; 3) 40 deg C. 15 min 2: dimethylsulfoxide / 0.08 h / 180 °C 3: 54 percent / HCl / 1.5 h / Heating 4: 70 percent / H2S, 25 percent NH3 5: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme |
2-bromo-5-nitropyridine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dimethylsulfoxide / 0.08 h / 180 °C 2: 54 percent / HCl / 1.5 h / Heating 3: 70 percent / H2S, 25 percent NH3 4: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme |
5-nitropyridine-2-carbonitrile
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 54 percent / HCl / 1.5 h / Heating 2: 70 percent / H2S, 25 percent NH3 3: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme |
5-nitropicolinic acid
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / H2S, 25 percent NH3 2: 1) 24 percent HBr, NaNO2, urea; 2) CuBr, 48 percent HBr, H2S / 1) H2O, 0 deg C, 5 min; 0 deg C, 10 min; 2) 0 deg C, 10 min; reflux View Scheme |
5-Amino-2-methylpyridine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 2: aqueous KMnO4 View Scheme |
6-methylnicotinamide
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaOCl; aqueous KOH 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme |
ethyl 6-methylnicotinate
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aqueous NH3 2: NaOCl; aqueous KOH 3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 4: aqueous KMnO4 View Scheme | |
Multi-step reaction with 6 steps 1: N2H4+H2O 2: KNO2; aqueous HCl 4: aqueous KOH 5: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 6: aqueous KMnO4 View Scheme |
6-methylpyridine-3-carbohydrazide
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: KNO2; aqueous HCl 3: aqueous KOH 4: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 5: aqueous KMnO4 View Scheme |
6-methyl-nicotinoyl azide
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: aqueous KOH 3: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 4: aqueous KMnO4 View Scheme |
(6-methyl-[3]pyridyl)-carbamic acid ethyl ester
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous KOH 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme |
1,3-bis(6-methylpyridin-3-yl)urea
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: concentrated aqueous HCl / 130 °C 2: aqueous sulfuric acid; potassium nitrite / anschliessend Behandeln mit Kupfer(I)-bromid 3: aqueous KMnO4 View Scheme |
C6H3BrNO2(1-)*Na(1+)
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With water; acetic acid at 25℃; for 16h; |
5-bromo-pyridine-2-carbaldehyde
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Stage #1: 5-bromo-pyridine-2-carbaldehyde With potassium permanganate; sodium carbonate In water at 10 - 20℃; Stage #2: With hydrogenchloride In water pH=2 - 4; | |
With 1,4-dithio-D,L-threitol; recombinant aldehyde dehydrogenase from Escherichia coli; water‐forming NADH oxidase from Streptococcus mutans; NAD In aq. phosphate buffer at 40℃; for 4h; pH=8.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; chemoselective reaction; |
2,5-dibromopyridine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: trimethylsilylmethyllithium / toluene / 0.5 h / -78 - 0 °C 1.2: 3 h 1.3: 18 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 15 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: trimethylsilylmethyllithium / toluene / 0.5 h / -78 - 0 °C 1.2: 3 h 1.3: 18 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran / 15 h / 0 - 20 °C View Scheme |
5-bromo-pyridine-2-carboxylic acid ethyl ester
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 15h; |
5-bromoisonicotinic acid
ethanol
5-bromo-pyridine-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 18h; | 100% |
With sulfuric acid at 75℃; for 2h; | 86% |
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 2h; Heating / reflux; Stage #2: ethanol In toluene Heating / reflux; Stage #3: With sodium carbonate In water; toluene pH=8; | 28% |
5-bromoisonicotinic acid
5-bromopyridine-2-carbonyl chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; | 100% |
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 2h; | 99% |
With thionyl chloride for 2h; Inert atmosphere; Reflux; | 93% |
5-bromoisonicotinic acid
5-bromo-2-carboxypyridin-1-ium-1-olate
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct; trifluoroacetic anhydride In acetonitrile at 0℃; for 4.5h; Stage #2: With sodium thiosulfate In water; acetonitrile at 0℃; for 0.166667h; | 100% |
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct; trifluoroacetic anhydride In acetonitrile at 0℃; for 4.5h; Stage #2: With sodium thiosulfate In water; acetonitrile for 0.166667h; | |
With dihydrogen peroxide; urea; trifluoroacetic anhydride In acetonitrile at 0℃; for 0.5h; | 19.6 g |
With dihydrogen peroxide; urea; trifluoroacetic anhydride In acetonitrile at 0℃; for 0.5h; | 19.6 g |
Stage #1: 5-bromoisonicotinic acid With urea hydrogen peroxide adduct In acetonitrile at 0℃; for 0.333333h; Stage #2: With trifluoroacetic anhydride In acetonitrile at 20℃; |
5-bromoisonicotinic acid
tert-butyl 4-[6-(dimethoxyboryl)-4H-1,3-benzodioxin-2-yl]piperidine-1-carboxylate
5-{2-[1-(tert-butoxycarbonyl)piperidin-4-yl]-4H-1,3-benzodioxin-6-yl}pyridine-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; acetonitrile at 160℃; for 0.333333h; Irradiation; | 100% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Inert atmosphere; | 100% |
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: ethyl 2-(furan-2-yl)-5-(trifluoromethyl)piperidine-3-carboxylate With triethylamine In dichloromethane at 0 - 20℃; | 99% |
5-bromoisonicotinic acid
2,3,4,5,6-pentafluorophenol
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; | 98% |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 96% |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h; | 96% |
Conditions | Yield |
---|---|
With thionyl chloride at -78 - 20℃; for 16.1667h; | 95% |
5-bromoisonicotinic acid
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 20℃; | 95% |
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 25h; Inert atmosphere; | 95% |
5-bromoisonicotinic acid
tri-n-butyl(vinyl)tin
5-vinylpyridine-2-carboxylic acid
Conditions | Yield |
---|---|
bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20 - 100℃; Inert atmosphere; | 94.5% |
5-bromoisonicotinic acid
1-ethynyl-3-fluoro-benzene
5-(3-fluoro-phenylethynyl)-pyridine-2-carboxylic acid
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Sonogashira Cross-Coupling; Microwave irradiation; | 94% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Microwave irradiation; | 71% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine In N,N-dimethyl-formamide at 90℃; for 0.75h; Sonogashira Cross-Coupling; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 93.3% |
5-bromoisonicotinic acid
2-methoxyethylamine
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid; 2-methoxyethylamine With pyridine In dichloromethane at 0℃; for 0.166667h; Stage #2: With trichlorophosphate In dichloromethane at 0 - 20℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 4h; Inert atmosphere; | 93% |
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 22℃; for 17h; Inert atmosphere; | 93% |
5-bromoisonicotinic acid
5-bromo-2-pyridinecarboxamide
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 80℃; for 1h; Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 1.5h; | 92.4% |
With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; | 73% |
Stage #1: 5-bromoisonicotinic acid With thionyl chloride; N,N-dimethyl-formamide In tetrahydrofuran at 0 - 23℃; for 1h; Stage #2: With ammonia In tetrahydrofuran; water at 0℃; for 0.5h; | 50% |
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 3h; Reflux; Stage #2: With ammonia In tetrahydrofuran; water at 20℃; Cooling with ice; | |
Stage #1: 5-bromoisonicotinic acid With thionyl chloride for 3h; Reflux; Stage #2: With ammonia In tetrahydrofuran; water Cooling with ice; | 43 g |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 70℃; for 6h; | 92% |
Stage #1: methanol; 5-bromoisonicotinic acid With thionyl chloride at 20℃; for 3h; Reflux; Stage #2: With sodium hydrogencarbonate pH=7; | 86.9% |
With sulfuric acid for 117h; Reflux; | 86% |
5-bromoisonicotinic acid
tert-butylamine
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h; | 92% |
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h; | 92% |
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h; | 92% |
5-bromoisonicotinic acid
dimethyl amine
5-bromo-2-(N,N-dimethylaminocarbonyl)pyridine
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Stage #2: dimethyl amine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 3h; | 91.7% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 18h; | |
With oxalyl dichloride In dichloromethane at 0 - 40℃; for 1h; | |
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h; Stage #2: dimethyl amine In dichloromethane at 0 - 20℃; for 3h; | |
Stage #1: 5-bromoisonicotinic acid With oxalyl dichloride In dichloromethane at 40℃; for 1h; Stage #2: dimethyl amine With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; |
5-bromoisonicotinic acid
methoxycarbonylmethylamine
methyl (5-bromopyridine-2-carbonyl)glycinate
Conditions | Yield |
---|---|
With thionyl chloride; N-ethyl-N,N-diisopropylamine | 90% |
5-bromoisonicotinic acid
N,N-diethylethylenediamine
5-bromo-N-(2-(diethylamino)ethyl)picolinamide
Conditions | Yield |
---|---|
Stage #1: 5-bromoisonicotinic acid With O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 3h; Stage #2: N,N-diethylethylenediamine In N,N-dimethyl-formamide at 20℃; for 2h; | 90% |
4-ethylpiperazine
5-bromoisonicotinic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; | 89% |
1-(2-hydroxyethyl)piperazine
5-bromoisonicotinic acid
(5-bromopyridin-2-yl)(4-hydroxyethylpiperazin-1-yl)methanone
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; | 88% |
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; | 65% |
5-bromoisonicotinic acid
cyclobutylamine
5-bromo-N-cyclobutylpicolinamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; | 88% |
Molecular structure of 5-Bromopyridine-2-carboxylic acid (CAS NO.30766-11-1) is:
IUPAC Name: 5-bromopyridine-2-carboxylic acid
Molecular Weight: 202.00546 [g/mol]
Molecular Formula: C6H4BrNO2
XLogP3-AA: 1.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Melting Point: 173-175 °C
Index of Refraction: 1.616
Molar Refractivity: 38.96 cm3
Molar Volume: 111.3 cm3
Surface Tension: 63.2 dyne/cm
Density: 1.813 g/cm3
Flash Point: 147 °C
Enthalpy of Vaporization: 59.23 kJ/mol
Boiling Point: 319.5 °C at 760 mmHg
Vapour Pressure: 0.000141 mmHg at 25°C
Product Categories: blocks;Bromides; Carboxes; Pyridines; Pyridine;Pyridines, Pyrimidines, Purines and Pteredines; pharmacetical; Carboxylic Acids; Pyridine Series; Carboxy; Organohalides; Bromopyridines; Halopyridines; Carboxylic Acids
Safty information about 5-Bromopyridine-2-carboxylic acid (CAS NO.30766-11-1) is:
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazard Note: Irritant
HazardClass: IRRITANT
5-Bromopyridine-2-carboxylic acid , its cas register number is 30766-11-1. It also can be called Picolinic acid, 5-bromo- (6CI,8CI) ; 5-Bromo-2-picolinicacid ; 5-Bromo-2-pyridinecarboxylic acid ; 5-Bromopicolinic acid ; 5-Bromopyridine-2-carboxylic acid ; 5-bromo-2-pyridine carboxlic acid .It is a white cryst.
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