2-bromo-pyridine
N,N-dimethyl-formamide
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-bromo-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h; Further stages.; | 85% |
Stage #1: 2-bromo-pyridine With lithium diisopropyl amide In tetrahydrofuran at -50℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran for 1h; Temperature; Reagent/catalyst; | 78% |
Stage #1: 2-bromo-pyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 4h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; | 75% |
(2-bromopyrid-3-yl)methanol
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide for 1.5h; Ambient temperature; | 83% |
With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide at 20℃; for 1.5h; | 80% |
2-bromo-3-(dibromomethyl)-pyridine
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With calcium carbonate In water for 8h; Heating; | 83% |
With calcium carbonate In water for 14h; Reflux; | 78% |
With water; calcium carbonate at 100℃; for 7h; | 60% |
Conditions | Yield |
---|---|
With lithium | 42% |
2-bromo-pyridine
formic acid ethyl ester
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-bromo-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Stage #2: formic acid ethyl ester In tetrahydrofuran at -78℃; for 1h; Stage #3: With water; ammonium chloride In tetrahydrofuran at -30℃; | 11% |
2,6-Dibromopyridine
N,N-dimethyl-formamide
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
2,4-dibromopyridine
N,N-dimethyl-formamide
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
2,5-dibromopyridine
N,N-dimethyl-formamide
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
C9H8BrNO4
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 2: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C View Scheme |
2-bromo-3-picoline
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 98 percent / KMnO4; H2O / 20 h / Heating 2: Et3N / benzene / 1 h / 20 °C 3: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 4: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 83 percent / N-bromosuccinimide; benzoylperoxyde / CCl4 / 4 h / Heating 2: 83 percent / CaCO3 / H2O / 8 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 70 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 83 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / dichloromethane / 4 h / 80 °C / Inert atmosphere 2: calcium carbonate; water / 7 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 2: calcium carbonate / water / 14 h / Reflux View Scheme |
2-bromonicotinic acid
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Et3N / benzene / 1 h / 20 °C 2: 1.03 g / LiAlH4 / tetrahydrofuran / 0.5 h / -78 °C 3: 80 percent / N,N'-dicyclohexylcarbodiimide; H3PO4; DMSO / 1.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 83 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme |
3-methylpyridin-2-ylamine
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: HBr; Br2 / H2O / 0.83 h / -20 °C 1.2: NaNO2 / H2O / 2.5 h / -20 °C 2.1: 83 percent / N-bromosuccinimide; benzoylperoxyde / CCl4 / 4 h / Heating 3.1: 83 percent / CaCO3 / H2O / 8 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 88 percent / NaNO2, Br2, 48percent HBr / 5 °C 2: 70 percent / KMnO4 / H2O / Heating 3: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 4: 83 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme |
2,3-dibromopyridine
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) t-BuLi, i-Pr2NH, 2.) Br2 / 1.) THF, -60 deg C, 2.) -70 deg C, 4 h View Scheme |
2-bromo-pyridine
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; water; N,N-dimethyl-formamide | |
With ammonium chloride; lithium diisopropyl amide In tetrahydrofuran; N-methyl-acetamide |
2-bromopyridine-3-carboxaldehyde
2-bromonicotinic acid
Conditions | Yield |
---|---|
With potassium permanganate In water Ambient temperature; | 100% |
With potassium permanganate In water for 2h; Ambient temperature; | 98% |
2-bromopyridine-3-carboxaldehyde
(2-bromopyrid-3-yl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; water In tetrahydrofuran at 20℃; for 2h; | 100% |
With methanol; sodium tetrahydroborate at 0 - 25℃; for 2h; | 90.2% |
With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; | 69% |
2-bromopyridine-3-carboxaldehyde
phenylhydrazine
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 160℃; for 0.166667h; microwave irradiation; | 100% |
With acetic acid In ethanol for 2h; Reflux; |
Conditions | Yield |
---|---|
Stage #1: 2-bromopyridine-3-carboxaldehyde; malononitrile With piperidine In methanol at 20℃; Stage #2: ethyl acetoacetate With piperidine In methanol at 20℃; for 0.333333h; | 100% |
3-methoxyphenylboronic acid
2-bromopyridine-3-carboxaldehyde
2-(3-methoxyphenyl)nicotinaldehyde
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 17h; Heating / reflux; | 100% |
2-bromopyridine-3-carboxaldehyde
4-methoxyphenylacetylen
2-(4-methoxyphenylethynyl)pyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 50℃; for 3h; | 99% |
Stage #1: 2-bromopyridine-3-carboxaldehyde; 4-methoxyphenylacetylen With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; for 4h; Sonogashira Cross-Coupling; Inert atmosphere; | 61% |
With bis(triphenylphosphine)palladium(II) dichloride; triethylamine In acetonitrile for 70h; Sonogashira Cross-Coupling; | |
Stage #1: 2-bromopyridine-3-carboxaldehyde; 4-methoxyphenylacetylen With trans-bis(triphenylphosphine)palladium dichloride; triethylamine at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With copper(l) iodide at 50℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With magnesium sulfate In tetrahydrofuran at 100℃; for 0.25h; Microwave irradiation; | 99% |
2-bromopyridine-3-carboxaldehyde
orthoformic acid triethyl ester
2-bromo-3-(diethoxymethyl)pyridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol for 6h; Reflux; | 98% |
With ammonium chloride In ethanol for 15h; Heating; | |
With toluene-4-sulfonic acid In ethanol for 6h; Reflux; |
2-bromopyridine-3-carboxaldehyde
1,2-diamino-benzene
2-(2-bromopyridin-3-yl)-1H-benzimidazole
Conditions | Yield |
---|---|
With ammonium chloride In methanol at 20℃; for 8h; | 98% |
2-bromopyridine-3-carboxaldehyde
(S)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
With titanium(IV) tetraethanolate In tetrahydrofuran at 23℃; for 12h; Inert atmosphere; | 98% |
4-methoxyphenylboronic acid
2-bromopyridine-3-carboxaldehyde
2-(4-methoxyphenyl)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; | 98% |
2-bromopyridine-3-carboxaldehyde
Methyltriphenylphosphonium bromide
2-bromo-3-vinylpyridine
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 14h; Wittig reaction; | 97% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 2-bromopyridine-3-carboxaldehyde In tetrahydrofuran at 0 - 20℃; | 89% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Wittig reaction; Inert atmosphere; Stage #2: 2-bromopyridine-3-carboxaldehyde In tetrahydrofuran at 0 - 20℃; for 72h; Wittig reaction; Inert atmosphere; | 89% |
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 0.5h; Wittig Olefination; Stage #2: 2-bromopyridine-3-carboxaldehyde In tetrahydrofuran at 0 - 20℃; for 72h; Wittig Olefination; | 89% |
3-butene-1-amine
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-butene-1-amine; 2-bromopyridine-3-carboxaldehyde With magnesium sulfate In dichloromethane Stage #2: With sodium tetrahydroborate In methanol | 97% |
2-bromopyridine-3-carboxaldehyde
phenylacetylene
2-(2-phenylethynyl)pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; Sonogashira reaction; | 96% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 5h; Inert atmosphere; | 94% |
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 70℃; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2-bromopyridine-3-carboxaldehyde; phenylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; Stage #2: tert-butylamine at 20℃; for 24h; Further stages.; | 96% |
methylmagnesium bromide
2-bromopyridine-3-carboxaldehyde
1-(2′-bromo-3′-pyridyl)ethan-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 5℃; | 96% |
In diethyl ether; dibutyl ether at -78 - 0℃; Inert atmosphere; | 87% |
Stage #1: methylmagnesium bromide; 2-bromopyridine-3-carboxaldehyde In tetrahydrofuran at -20 - 0℃; for 0.333333h; Stage #2: With ammonium chloride In tetrahydrofuran; water |
2-bromopyridine-3-carboxaldehyde
(trifluoromethyl)trimethylsilane
1-(2-bromo-3-pyridinyl)-2,2,2-trifluoroethanol
Conditions | Yield |
---|---|
Stage #1: 2-bromopyridine-3-carboxaldehyde; (trifluoromethyl)trimethylsilane In tetrahydrofuran at -70 - 20℃; for 1h; Cooling with methanol-dry ice; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1h; | 96% |
2-bromopyridine-3-carboxaldehyde
1-t-Butoxycarbonylpiperazine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid for 16h; | 95.99% |
n-octyne
2-bromopyridine-3-carboxaldehyde
2-(1-octyn-1-yl)pyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; Sonogashira reaction; | 95% |
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide for 15h; Ambient temperature; | 79% |
Conditions | Yield |
---|---|
Stage #1: n-octyne; 2-bromopyridine-3-carboxaldehyde With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine at 50℃; Stage #2: tert-butylamine at 20℃; for 24h; Further stages.; | 95% |
2-bromopyridine-3-carboxaldehyde
Trimethylenediamine
2-(2-bromopyridin-3-yl)-1,4,5,6-tetrahydropyrimidine
Conditions | Yield |
---|---|
Stage #1: 2-bromopyridine-3-carboxaldehyde; Trimethylenediamine In tert-butyl alcohol at 70℃; for 0.5h; Stage #2: With iodine; potassium carbonate In tert-butyl alcohol at 70℃; for 3h; | 95% |
2-vinylbenzeneboronic acid
2-bromopyridine-3-carboxaldehyde
3-formyl-2-(2-vinylphenyl)pyridine
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; toluene at 100℃; for 17h; Suzuki reaction; Inert atmosphere; | 95% |
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With diethylamino-sulfur trifluoride In dichloromethane at 25℃; for 4h; | 95% |
With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 12.5h; Inert atmosphere; | 33.5% |
2-bromopyridine-3-carboxaldehyde
methylmagnesium chloride
1-(2′-bromo-3′-pyridyl)ethan-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 5℃; for 0.5h; | 95% |
In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
2-bromopyridine-3-carboxaldehyde
tert-butylamine
Conditions | Yield |
---|---|
With water at 25℃; | 94% |
2-bromopyridine-3-carboxaldehyde
(Z)-1,2-di(2-bromopyridin-3-yl)ethene
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 20℃; for 18h; Wittig reaction; | 94% |
Conditions | Yield |
---|---|
With cadmium sulphide In methanol for 0.25h; Reflux; | 94% |
2-bromopyridine-3-carboxaldehyde
ethyl (triphenylphosphoranylidene)acetate
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 8h; Wittig Olefination; | 94% |
In dichloromethane at 0 - 20℃; for 8h; Wittig Olefination; | 94% |
In dichloromethane at 0 - 20℃; Wittig Olefination; |
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 80℃; Suzuki-Miyaura Coupling; Sealed tube; | 94% |
1-Phenyl-2-propyn-1-ol
2-bromopyridine-3-carboxaldehyde
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 4h; Schlenk technique; Inert atmosphere; | 94% |
The 3-Pyridinecarboxaldehyde,2-bromo-, with the CAS registry number 128071-75-0, is also known as 2-Bromo-3-formylpyridine. It belongs to the product categories of Pharmacetical; Aldehydes; Pyridines; Pyridine; Pyridines derivates; Halogenated; Organohalides; Bromopyridines; Halopyridines. This chemical's molecular formula is C6H4BrNO and molecular weight is 186.01. What's more, its systematic name is 2-bromopyridine-3-carbaldehyde. It should be sealed and stored in a cool and dry place. Moreover, it should be ensured that the workshop is well ventilated or equipped with exhaust devices. It is used as an organic reagent and a pharmaceutical intermediate.
Physical properties of 3-Pyridinecarboxaldehyde,2-bromo- are: (1)ACD/LogP: 0.99; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.99; (4)ACD/LogD (pH 7.4): 0.99; (5)ACD/BCF (pH 5.5): 3.33; (6)ACD/BCF (pH 7.4): 3.33; (7)ACD/KOC (pH 5.5): 82.36; (8)ACD/KOC (pH 7.4): 82.36; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 29.96 Å2; (13)Index of Refraction: 1.619; (14)Molar Refractivity: 38.78 cm3; (15)Molar Volume: 110.5 cm3; (16)Polarizability: 15.37×10-24cm3; (17)Surface Tension: 52.1 dyne/cm; (18)Density: 1.683 g/cm3; (19)Flash Point: 115.7 °C; (20)Enthalpy of Vaporization: 50.58 kJ/mol; (21)Boiling Point: 267.7 °C at 760 mmHg; (22)Vapour Pressure: 0.00802 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes and may cause sensitisation by skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves.
You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1cccnc1Br
(2)Std. InChI: InChI=1S/C6H4BrNO/c7-6-5(4-9)2-1-3-8-6/h1-4H
(3)Std. InChIKey: GNFWMEFWZWXLIN-UHFFFAOYSA-N
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