2-bromo-6-(hydroxymethyl)pyridine
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction; | 98% |
With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide for 1.5h; Ambient temperature; | 89% |
With 1-iodobenzoic acid In dimethyl sulfoxide at 20℃; | |
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 25℃; for 1.5h; | |
With 2-Iodobenzoic acid In dimethyl sulfoxide at 20℃; for 2h; |
2,6-Dibromopyridine
N,N-dimethyl-formamide
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 3.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 0.5h; Further stages.; | 97% |
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 3h; Stage #2: N,N-dimethyl-formamide In toluene at -10 - -5℃; for 1h; Stage #3: With citric acid at 20℃; for 0.166667h; | 95% |
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -70 - 0℃; | 94.2% |
2,6-Dibromopyridine
n-butyllithium
butyl magnesium bromide
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene | 95% |
2-bromo-pyridine
N,N-dimethyl-formamide
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 2.5h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide With zinc chloride*2(tetrahydrofuran) In tetrahydrofuran; hexane at -78 - 40℃; Inert atmosphere; Schlenk technique; | 90.4% |
2-bromo-6-(dibromomethyl) pyridine
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With calcium carbonate In water for 8h; Heating; | 86% |
2,6-Dibromopyridine
isopropylmagnesium chloride
N,N-dimethyl-formamide
A
2,6-Pyridinedicarboxaldehyde
B
6-bromo-2-pyridinecarbaldehyde
C
6-isopropyl-2-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine; isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 5h; Stage #2: N,N-dimethyl-formamide With acetic acid at 0℃; | A 1% B 85% C 6% |
2-bromo-6-methylpyridine
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 16h; | 71% |
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; benzoylperoxide / CCl4 / 4 h / Heating 2: 86 percent / CaCO3 / H2O / 8 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 53 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme | |
Stage #1: 2-bromo-6-methylpyridine With bromine In dichloromethane; water at 10 - 50℃; for 10h; Stage #2: With hexamethylenetetramine In ethanol at 40℃; for 12h; Stage #3: With sulfuric acid; acetic acid In ethanol at 90℃; for 1h; | 62.3 g |
N,N-dimethyl-formamide
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: With n-butyllithium; n-BuMgCl In tetrahydrofuran; H2O; hexane; N,N-dimethyl-formamide; toluene at -10℃; for 0.5h; Stage #2: 2,6-Dibromopyridine In tetrahydrofuran; hexane; toluene at -10℃; for 2.5h; Stage #3: N,N-dimethyl-formamide With citric acid more than 3 stages; | 52% |
2,6-Dibromopyridine
N,N-dimethyl-formamide
A
2,6-Pyridinedicarboxaldehyde
B
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran at -10℃; Stage #2: N,N-dimethyl-formamide at 0℃; | A 43% B 49% |
2-(6-bromopyridinyl)lithium
N,N-dimethyl-formamide
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
In tetrahydrofuran at -75℃; for 0.25h; Yield given; |
2,6-Dibromopyridine
N,N-dimethyl-formamide
A
2-bromo-pyridine
B
6-bromo-2-pyridinecarbaldehyde
C
2,6-dibromo-pyridine-3-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran Further stages.; |
2-Amino-6-methylpyridine
6-bromo-2-pyridinecarbaldehyde
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: 88 percent / N-bromosuccinimide; benzoylperoxide / CCl4 / 4 h / Heating 3.1: 86 percent / CaCO3 / H2O / 8 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 82 percent / NaNO2, Br2, 48percent HBr / 5 °C 2: 53 percent / KMnO4 / H2O / Heating 3: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 4: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme |
2,6-Dibromopyridine
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran / -78 °C 1.3: NaBH4 / tetrahydrofuran / 0 °C 2.1: 1-iodobenzoic acid / dimethylsulfoxide / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: n-BuLi / tetrahydrofuran / -78 °C / addition of 2,6-dibromopyridine to a solution of BuLi 2: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C / addition of 2,6-dibromopyridine into a solution of dilithiopyridine 3: tetrahydrofuran / 0.25 h / -75 °C View Scheme | |
With hydrogenchloride; n-butyllithium In N-methyl-acetamide; hexane | |
With hydrogenchloride | |
With n-butyllithium; acetic acid In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide | 3.33 g (18.0 mmol, 84%) |
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C / addition of 2,6-dibromopyridine into a solution of dilithiopyridine 2: tetrahydrofuran / 0.25 h / -75 °C View Scheme |
6-bromo-pyridine-2-carboxylic acid
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
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: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With n-butyllithium; ammonium chloride In tetrahydrofuran; N,N-dimethyl-formamide |
6-bromo-2-(2,6-diisopropylphenyl)iminopyridine
1-Naphthylboronic acid
A
6-bromo-2-pyridinecarbaldehyde
B
6-(1-naphthyl)-2-[(2,6-diisopropylphenyl)imino]pyridine
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine)palladium (0) In ethanol; water; toluene |
Conditions | Yield |
---|---|
for 6h; Molecular sieve; Reflux; | 100% |
In acetonitrile at 20℃; for 0.166667h; | |
In [D3]acetonitrile at 25℃; for 0.0833333h; Kinetics; Time; |
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With sodium acetate; hydroxylamine sulfate In ethanol at 20℃; for 16h; Inert atmosphere; | 100% |
With hydroxylamine hydrochloride; sodium acetate In ethanol at 90℃; | 99% |
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 16h; | 90% |
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; |
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With potassium phosphate monohydrate; C66H84O10P2Pd In water; ethyl acetate; toluene at 45℃; for 14h; Suzuki-Miyaura Coupling; Inert atmosphere; | 100% |
N-methyl-N-(pyridin-2-yl)hydrazine
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
for 6h; Molecular sieve; Reflux; | 100% |
In [D3]acetonitrile at 25℃; for 0.0833333h; Time; |
3,5-di-tert-butyl-2-methoxyphenyl boronic acid
6-bromo-2-pyridinecarbaldehyde
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 90℃; for 20h; Suzuki Coupling; | 100% |
6-bromo-2-pyridinecarbaldehyde
2-bromo-6-(hydroxymethyl)pyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 1h; | 99% |
With sodium tetrahydroborate In ethanol | 99% |
With methanol; sodium tetrahydroborate In methanol at 0 - 20℃; for 0.5h; | 99% |
6-bromo-2-pyridinecarbaldehyde
trimethyl orthoformate
2-bromo-6-(dimethoxymethyl)pyridin
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol for 4h; Reflux; Inert atmosphere; Schlenk technique; | 99% |
With toluene-4-sulfonic acid In methanol for 4h; Reflux; | 98% |
toluene-4-sulfonic acid In methanol for 1h; Heating; | 96% |
6-bromo-2-pyridinecarbaldehyde
phenylboronic acid
6-phenylpyridine-2-carbaldehyde
Conditions | Yield |
---|---|
With potassium fluoride; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In tetrahydrofuran for 18h; Inert atmosphere; Reflux; | 99% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 120℃; for 6h; Inert atmosphere; | 98% |
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine tetrafluoroborate In 1,4-dioxane; water at 100℃; for 16h; | 94.6% |
6-bromo-2-pyridinecarbaldehyde
4-(N,N-dimethylaminocarbonyl)phenylboronic acid
4-(6-formylpyridin-2-yl)-N,N-dimethylbenzamide
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90℃; for 3h; Inert atmosphere; | 99% |
6-bromo-2-pyridinecarbaldehyde
diethylamine
(6-bromopyridin-2-ylmethyl)diethylamine
Conditions | Yield |
---|---|
Stage #1: 6-bromo-2-pyridinecarbaldehyde; diethylamine In 1,2-dichloro-ethane at 20℃; for 0.0166667h; Inert atmosphere; Schlenk technique; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h; Inert atmosphere; Schlenk technique; | 99% |
With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 20℃; for 2h; | 2.31 g |
propylamine
6-bromo-2-pyridinecarbaldehyde
N-[(6-bromopyridin-2-yl)methyl]propan-1-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In chloroform at 20℃; for 0.75h; | 99% |
6-bromo-2-pyridinecarbaldehyde
phosphorohydrazidic acid diethyl ester
Conditions | Yield |
---|---|
In dichloromethane for 1.5h; Reflux; Dean-Stark; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran at 0℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
In ethanol for 4h; Inert atmosphere; Reflux; | 99% |
6-bromo-2-pyridinecarbaldehyde
2,6-diisopropylbenzenamine
(6-bromo-pyridin-2-yl-methylene)-(2,6-diisopropyl-phenyl)-amine
Conditions | Yield |
---|---|
With formic acid In ethanol for 2 - 3h; Inert atmosphere; Schlenk technique; Reflux; | 98% |
With magnesium sulfate In diethyl ether at 20℃; Inert atmosphere; Schlenk technique; | 98% |
With toluene-4-sulfonic acid In toluene at 70℃; for 12h; Molecular sieve; | 90.5% |
Conditions | Yield |
---|---|
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction; | 98% |
6-bromo-2-pyridinecarbaldehyde
acetic acid
Conditions | Yield |
---|---|
Stage #1: 6-bromo-2-pyridinecarbaldehyde; acetic acid With titanium tetrachloride In dichloromethane at 25℃; for 0.333333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 25℃; Inert atmosphere; stereoselective reaction; | 98% |
6-bromo-2-pyridinecarbaldehyde
2-amino-benzenethiol
Conditions | Yield |
---|---|
In ethanol at 20℃; | 98% |
With amberlite IR-120(H)resin In water at 85℃; Sonication; Microwave irradiation; | 96% |
In water at 60℃; for 1h; Sonication; | 90% |
6-bromo-2-pyridinecarbaldehyde
(Z)-3-bromocyclooct-1-ene
Conditions | Yield |
---|---|
With bismuth; lithium iodide In N,N-dimethyl-formamide at 20℃; for 12h; diastereoselective reaction; | 98% |
6-bromo-2-pyridinecarbaldehyde
2,6-dimethylbenzene boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere; | 97% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; toluene at 80℃; |
6-bromo-2-pyridinecarbaldehyde
2,6-diisopropylbenzenamine
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 97% |
In ethanol for 8h; Reflux; | |
With toluene-4-sulfonic acid In toluene for 0.25h; Reflux; | 23.9 g |
6-bromo-2-pyridinecarbaldehyde
acrylic acid methyl ester
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 7h; Sonication; | 97% |
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 3h; Morita-Baylis-Hillman Alkylation; |
6-bromo-2-pyridinecarbaldehyde
orthoformic acid triethyl ester
2-bromo-6-(diethoxymethyl)pyridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanethiol at 20℃; for 3h; Inert atmosphere; Schlenk technique; | 97% |
With toluene-4-sulfonic acid In ethanol at 20℃; for 3h; Inert atmosphere; Schlenk technique; | 96% |
With toluene-4-sulfonic acid In ethanol Inert atmosphere; Reflux; | 76.5% |
6-bromo-2-pyridinecarbaldehyde
4-Chlorophenylboronic acid
6-(4-chlorophenyl)-2-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With C64H118O20; C54H72NO6PPdS; triethylamine In water at 45℃; for 16h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; | 97% |
With C35H47O3P*C15H16N(1-)*CH3O3S(1-)*Pd(2+); triethylamine In water at 45℃; for 15h; Suzuki-Miyaura Coupling; | 94% |
With TPGS-750-M; palladacycle A; triethylamine In tetrahydrofuran; water at 45℃; for 16h; Inert atmosphere; |
2-amino-5-ethyl-1,3,4-thiadiazole
6-bromo-2-pyridinecarbaldehyde
phosphonic acid diethyl ester
Conditions | Yield |
---|---|
With phospho sulphonic acid In neat (no solvent) for 0.108333h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry; | 96.5% |
6-bromo-2-pyridinecarbaldehyde
ethylene glycol
2-bromo-6-(1,3-dioxolan-2-yl)pyridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene at 100℃; for 24h; Inert atmosphere; Dean-Stark; | 96% |
With toluene-4-sulfonic acid In benzene at 100℃; for 24h; Dean-Stark; Inert atmosphere; | 96% |
With toluene-4-sulfonic acid In toluene at 130℃; for 48h; Inert atmosphere; Dean-Stark; | 95% |
6-bromo-2-pyridinecarbaldehyde
2-methoxyethylamine
N-[(6-bromopyridin-2-yl)methyl]-2-methoxyethaneamine
Conditions | Yield |
---|---|
Stage #1: 6-bromo-2-pyridinecarbaldehyde; 2-methoxyethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Stage #3: With hydrogenchloride; water In dichloromethane pH=4; | 96% |
diethoxyphosphoryl-acetic acid ethyl ester
6-bromo-2-pyridinecarbaldehyde
C10H10BrNO2
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran at 0 - 20℃; Horner-Wadsworth-Emmons reaction; Inert atmosphere; | 96% |
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 15h; Horner-Wadsworth-Emmons Olefination; | 56% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: 6-bromo-2-pyridinecarbaldehyde In tetrahydrofuran; mineral oil at 0 - 20℃; | 56% |
Molecule structure of 6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) :
IUPAC Name: 6-bromopyridine-2-carbaldehyde
Molecular Weight: 186.00606 g/mol
Molecular Formula: C6H4BrNO
Density: 1.683 g/cm3
Melting Point: 81-85 °C(lit.)
Boiling Point: 248.2 °C at 760 mmHg
Flash Point: 103.9 °C
Molar Volume: 110.5 cm3
Polarizability: 15.37*10-24 cm3
Surface Tension: 52.1 dyne/cm
Enthalpy of Vaporization: 48.54 kJ/mol
Vapour Pressure: 0.0246 mmHg at 25 °C
Storage temp.: Refrigerator (+4 °C)
Sensitive: air sensitive
Appreance: light yellow flakes
XLogP3-AA: 1.7
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 184.947626
MonoIsotopic Mass: 184.947626
Topological Polar Surface Area: 30
Heavy Atom Count: 9
Complexity: 107
Canonical SMILES: C1=CC(=NC(=C1)Br)C=O
InChI: InChI=1S/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H
InChIKey: QWFHFNGMCPMOCD-UHFFFAOYSA-N
Product Categories: Pyridine; Aldehydes; Pyridines; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Building Blocks
6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is a useful synthetic intermediate.
Hazard Codes: Xi, Xn, F
Risk Statements: 36/37/38-20/21/22-10
R36/37/38: Irritating to eyes, respiratory system and skin
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R10: Flammable
Safety Statements: 26-36-36/37/39-16
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
S16: Keep away from sources of ignition
WGK Germany: 3
Hazard Note: Irritant
6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is also called 6-Bromopyridine-2-carbaldehyde ; 6-Bromo-2-formylpyridine ; 6-Bromopyridine-2-barboxaldehyde .
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