Conditions | Yield |
---|---|
With titanium tetrachloride; sodium iodide In acetonitrile at 30℃; for 0.0833333h; | 91% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 31℃; for 16h; Sealed tube; Irradiation; | 89% |
With sodium hydroxide; thiourea S,S-dioxide In ethanol at 80 - 85℃; for 2h; | 81% |
Conditions | Yield |
---|---|
With thionyl chloride; sulfuric acid; bromine at 130℃; for 10h; Temperature; | 82% |
With tetrachloromethane; N-Bromosuccinimide; aluminium trichloride Behandeln des Reaktionsgemisches mit wss. Salzsaeure; |
4-amino-3,5-dibromopyridine
3,5-dibromopyridine
Conditions | Yield |
---|---|
With trifluoroacetic acid; isopentyl nitrite In tetrahydrofuran at 70℃; for 7h; | 78% |
3,5-dibromo-4-pyridinesulfonic acid
3,5-dibromopyridine
Conditions | Yield |
---|---|
With nickel In ethanol for 4h; Reflux; | 48.54% |
3,5-dibromopyridine
Conditions | Yield |
---|---|
Heating; | 4% |
Conditions | Yield |
---|---|
With bromine; aluminium trichloride at 100℃; for 5h; Product distribution; various ratios pyridine:bromine, various Lewis catalysts, various temperatures; | |
With bromine at 300℃; Leiten ueber Bimsstein oder ueber mit Kupfer(I)-bromid impraegnierten Bimsstein; | |
With bromine at 300℃; Leiten ueber mit Kupfer(I)-bromid oder Eisen(II)-bromid impraegnierten Bimsstein; | |
With bromine at 300℃; Leiten ueber Bimsstein; |
Conditions | Yield |
---|---|
With bromine at 120 - 130℃; |
Conditions | Yield |
---|---|
With bromine at 170℃; |
Conditions | Yield |
---|---|
With bromine at 180℃; im Rohr; |
Conditions | Yield |
---|---|
With bromine; acetic acid at 60 - 65℃; Abdestillieren des Eisessigs und Erhitzen des Rueckstandes auf 230-250grad; |
Pyridine hydrobromide
3,5-dibromopyridine
Conditions | Yield |
---|---|
With bromine; acetic acid at 60 - 65℃; Abdestillieren des Eisessigs und Erhitzen des Rueckstandes auf 230-250grad; |
Conditions | Yield |
---|---|
With bromine | |
With bromine anschliessend Erhitzen bis auf 200grad; | |
With bromine; mercury dichloride at 215℃; |
3-bromopyridine hydrochloride
3,5-dibromopyridine
Conditions | Yield |
---|---|
With water; bromine at 230 - 250℃; im Rohr; |
Conditions | Yield |
---|---|
at 250℃; |
3,5-dibromopyridine
dibromo-3,4 pyridine
pentan-3-one
A
3-Bromopyridine
B
3,5-dibromopyridine
C
4-bromopyridin
D
bromo-3 (ethyl-1 propanol-1)-5 pyridine
Conditions | Yield |
---|---|
With n-butyllithium 1.) THF, hexane -60 deg C, 15 min, 2.) -60 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given; |
dibromo-3,4 pyridine
A
3-Bromopyridine
B
3,5-dibromopyridine
C
4-bromopyridin
Conditions | Yield |
---|---|
With n-butyllithium; ethanol 1.) THF, hexane -60 deg C, 15 min, 2.) -60 deg C, 15 min then -40 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
at 180℃; |
Conditions | Yield |
---|---|
at 120 - 130℃; im Rohr; |
Conditions | Yield |
---|---|
at 170℃; |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With methyllithium; calcium carbonate |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With bromine at 165℃; |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With water; bromine at 200 - 210℃; im Rohr; |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With bromine; acetic acid |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With hydrogenchloride at 200 - 210℃; |
N-Ethoxycarbonylpiperidine
bromine
A
piperidine
B
pyridine
C
3,5-dibromopyridine
pyridine
hydrogenchloride
bromine
A
3-Bromopyridine
B
3,5-dibromopyridine
pyridine
sulfuric acid
bromine
A
3-Bromopyridine
B
3,5-dibromopyridine
pyridine
hydrogenchloride
water
bromine
A
3-Bromopyridine
B
3,5-dibromopyridine
Conditions | Yield |
---|---|
at 200 - 210℃; |
3,5-dibromopyridine
ethanol
carbon monoxide
diethyl 3,5-pyridinedicarboxylate
Conditions | Yield |
---|---|
With triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; under 5171.5 Torr; for 3h; | 100% |
3,5-dibromopyridine
Conditions | Yield |
---|---|
With trimethoxonium tetrafluoroborate In nitromethane at 0 - 20℃; Inert atmosphere; | 100% |
3,5-dibromopyridine
borane-THF
Conditions | Yield |
---|---|
Stage #1: borane-THF; tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane In dichloromethane at 60℃; for 8h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: 3,5-dibromopyridine In dichloromethane for 0.0833333h; Glovebox; Inert atmosphere; Sealed tube; | 100% |
3,5-dibromopyridine
1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine; 1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one With potassium carbonate In water; butan-1-ol for 0.0833333h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In water; butan-1-ol at 70℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; trifluoroacetic acid at 60℃; under 3750.38 Torr; Temperature; | 99.7% |
With phthalic anhydride; urea-hydrogen peroxide In acetonitrile for 2h; Ambient temperature; | 96% |
With bis-trimethylsilanyl peroxide; per-rhenic acid In dichloromethane; water at 24℃; for 24h; | 88% |
Conditions | Yield |
---|---|
Stage #1: thiophenol With sodium hydride Metallation; Stage #2: 3,5-dibromopyridine In N,N-dimethyl-formamide at 90℃; for 2h; Substitution; Further stages.; | 99% |
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3,5-dibromopyridine In N,N-dimethyl-formamide at 130℃; for 6.5h; |
3,5-dibromopyridine
1-benzenesulfonyl-6-methoxy-2-tributylstannyl-1H-indole
1-benzenesulfonyl-2-(5-bromo-pyridin-3-yl)-6-methoxy-1H-indole
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 100℃; for 0.333333h; Stille cross-coupling; Inert atmosphere; Microwave irradiation; | 99% |
3,5-dibromopyridine
2-(5-bromopyridin-3-yl)benzo[d]oxazole
C29H17N5O2
Conditions | Yield |
---|---|
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 85℃; for 16h; Inert atmosphere; | 99% |
3,5-dibromopyridine
p-tolylboronic pinacol ester
3,5-bis(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; | 99% |
3,5-dibromopyridine
bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II)
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 99% |
3,5-dibromopyridine
3-bromo-5-iodopyridine
Conditions | Yield |
---|---|
With iodine; isopropylmagnesium chloride In tetrahydrofuran at -10 - -5℃; for 0.0833333h; | 98% |
Stage #1: 3,5-dibromopyridine With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 18h; Inert atmosphere; chemoselective reaction; | 65% |
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 25℃; for 2h; Stage #2: With iodine In tetrahydrofuran at -75 - 25℃; | 61% |
With iodine; isopropylmagnesium chloride In tetrahydrofuran at -78 - 20℃; for 2h; | 58% |
Multi-step reaction with 2 steps 1: CuSO4; methanol; NH3 / 140 °C 2: sodium nitrite; aqueous hydrochloric acid; potassium iodide / Diazotization View Scheme |
3,5-dibromopyridine
4-methoxyphenylboronic acid
3,5-bis-(4-methoxyphenyl)-pyridine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 14h; Suzuki crosscoupling; Heating; | 98% |
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate In acetonitrile at 110℃; for 1h; Suzuki Coupling; Inert atmosphere; |
Conditions | Yield |
---|---|
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior; | 98% |
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h; | 97% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine; pivalaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine; 2-methylphenyl aldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine; benzaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent; | 97% |
3,5-dibromopyridine
4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide
3,5-diphenylpyridine
Conditions | Yield |
---|---|
With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)] In ethanol; water at 90℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry; | 96% |
3,5-dibromopyridine
1-(1-methyl-piperidin-4-yl)-piperazine
Conditions | Yield |
---|---|
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 4h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior; | 96% |
Conditions | Yield |
---|---|
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h; | 95% |
With ammonium hydroxide; copper(II) sulfate at 130℃; | |
With ammonium hydroxide; copper; copper(II) sulfate at 130℃; for 14h; Substitution; Amination; |
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -78℃; for 2h; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃; | 95% |
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Grignard reaction; Stage #2: benzaldehyde at 20℃; for 2h; Alkylation; | 76% |
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; Substitution; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 18h; Substitution; | 76% |
3,5-dibromopyridine
3,5-diiodopyridine
Conditions | Yield |
---|---|
With copper(l) iodide; N,N-diethylethylenediamine; sodium iodide In 1,4-dioxane at 120℃; for 18h; Schlenk technique; | 95% |
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 20h; Schlenk technique; | 86% |
Stage #1: 3,5-dibromopyridine With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 18h; Inert atmosphere; chemoselective reaction; | 85% |
3,5-dibromopyridine
C31H19N3O2
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate; copper(II) sulfate for 24h; Reflux; | 95% |
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 72h; Inert atmosphere; | 50% |
3,5-dibromopyridine
tri(p-tolyl)bismuth
3,5-bis(4-methylphenyl)pyridine
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1.5h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With 1,3-di-tert-butyl-2-(neopentyloxy)-2,3-dihydro-1H-1,3,2-diazaphosphole In diethyl ether at 20℃; for 12h; | 95% |
3,5-dibromopyridine
tris(4-methoxyphenyl)bismuth
3,5-bis-(4-methoxyphenyl)-pyridine
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1.5h; Schlenk technique; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
In DMF (N,N-dimethyl-formamide) at 20 - 70℃; | 93% |
In methanol; DMF (N,N-dimethyl-formamide) at 70℃; | 93% |
In methanol at 130℃; for 24h; | 92% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -10℃; for 0.25h; Stage #2: allyl bromide In tetrahydrofuran at 0℃; for 1h; | 93% |
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -15 - -10℃; for 0.25h; Stage #2: allyl bromide In tetrahydrofuran at -10℃; for 1h; Product distribution / selectivity; | 93% |
3,5-dibromopyridine
3-methoxyphenylboronic acid
3,5-bis-(3-methoxyphenyl)-pyridine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 14h; Suzuki crosscoupling; Heating; | 93% |
Molecular Structure of 3,5-Dibromopyridine (CAS NO.625-92-3):
IUPAC Name: 3,5-Dibromopyridine
Canonical SMILES: C1=C(C=NC=C1Br)Br
InChI: InChI=1S/C5H3Br2N/c6-4-1-5(7)3-8-2-4/h1-3H
InChIKey: SOSPMXMEOFGPIM-UHFFFAOYSA-N
Molecular Weight: 236.89202 [g/mol]
Molecular Formula: C5H3Br2N
XLogP3-AA: 2.2
H-Bond Donor: 0
H-Bond Acceptor: 1
EINECS: 210-916-4
Index of Refraction: 1.607
Molar Refractivity: 39.72 cm3
Molar Volume: 115 cm3
Surface Tension: 47.7 dyne/cm
Density: 2.059 g/cm3
Flash Point: 84.3 °C
Enthalpy of Vaporization: 43.98 kJ/mol
Boiling Point: 222 °C at 760 mmHg
Vapour Pressure: 0.155 mmHg at 25 °C
Appearance: Light-Yellow Solid
Melting Point: 110-115 °C(lit.)
Product Categories: blocks; Bromides; Pyridines; Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivates; API intermediates; Halogenated; Organohalides; Aromatics Compounds; Bromopyridines; Halopyridines; Aromatics; Bases & Related Reagents; Nucleotides; Halogenated Heterocycles; Heterocyclic Building Blocks; C5Heterocyclic Building Blocks; Brominated heterocyclic series
3,5-Dibromopyridine (CAS NO.625-92-3) is used as a kind of intermediates in medicine.
Safety Information of 3,5-Dibromopyridine (CAS NO.625-92-3):
Hazard Codes: Xn,Xi
Risk Statements: 36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT
3,5-Dibromopyridine (CAS NO.625-92-3), its Synonyms are Pyridine, 3,5-dibromo- ; 3,5-Dibromo pyridine .
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