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| CAS No.: | 34160-40-2 |
|---|---|
| Name: | 6-Bromopyridine-2-carbaldehyde |
| Molecular Structure: | |
|
|
|
| Formula: | C6H4BrNO |
| Molecular Weight: | 186.008 |
| Synonyms: | Picolinaldehyde,6-bromo- (8CI);2-Bromo-6-formylpyridine;2-Bromopyridine-6-carboxaldehyde;2-Bromopyridyl-6-carboxaldehyde;2-Formyl-6-bromopyridine;6-Bromo-2-formylpyridine;6-Bromo-2-pyridinecarbaldehyde;6-Bromo-2-pyridinecarboxaldehyde;6-Bromopicolylaldehyde;6-Bromopyridine-2-aldehyde;Bromo-2-pyridinecarboxaldehyde; |
| EINECS: | -0 |
| Density: | 1.683 g/cm3 |
| Melting Point: | 81-85 °C(lit.) |
| Boiling Point: | 248.2 °C at 760 mmHg |
| Flash Point: | 103.9 °C |
| Solubility: | Soluble in dichloromethane, ether, ethyl acetate and methanol. Insoluble in water. |
| Appearance: | Light yellow flakes |
| Hazard Symbols: |
 Xn,  Xi,  F
|
| Risk Codes: | 36/37/38-20/21/22-10 |
| Safety: | 26-36-36/37/39-16 |
| PSA: | 29.96000 |
| LogP: | 1.65660 |
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- 852475-26-4MC1568
- 33674-96-3
2-bromo-6-(hydroxymethyl)pyridine
- 34160-40-2
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; |
- 626-05-1
2,6-Dibromopyridine
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 34160-40-2
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% |
- 626-05-1
2,6-Dibromopyridine
- 109-72-8, 29786-93-4
n-butyllithium
- 693-04-9
butyl magnesium bromide
- 34160-40-2
6-bromo-2-pyridinecarbaldehyde
| Conditions | Yield |
|---|---|
| With acetic acid In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene | 95% |
- 109-04-6
2-bromo-pyridine
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 34160-40-2
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% |
- 82315-66-0
2-bromo-6-(dibromomethyl) pyridine
- 34160-40-2
6-bromo-2-pyridinecarbaldehyde
| Conditions | Yield |
|---|---|
| With calcium carbonate In water for 8h; Heating; | 86% |
- 626-05-1
2,6-Dibromopyridine
- 1068-55-9
isopropylmagnesium chloride
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
A
- 5431-44-7
2,6-Pyridinedicarboxaldehyde
B
- 34160-40-2
6-bromo-2-pyridinecarbaldehyde
C
- 153646-83-4
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% |
- 5315-25-3
2-bromo-6-methylpyridine
- 34160-40-2
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 |
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 34160-40-2
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% |
- 626-05-1
2,6-Dibromopyridine
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
A
- 5431-44-7
2,6-Pyridinedicarboxaldehyde
B
- 34160-40-2
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% |
- 37709-60-7
2-(6-bromopyridinyl)lithium
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 34160-40-2
6-bromo-2-pyridinecarbaldehyde
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -75℃; for 0.25h; Yield given; |
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Chemistry
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
Uses
6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is a useful synthetic intermediate.
Safety Profile
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
Specification
6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is also called 6-Bromopyridine-2-carbaldehyde ; 6-Bromo-2-formylpyridine ; 6-Bromopyridine-2-barboxaldehyde .