| Identification | More | [Name]
6-Bromopyridine-2-carbaldehyde | [CAS]
34160-40-2 | [Synonyms]
2-BROMO-6-FORMYLPYRIDINE
2-BROMOPYRIDINE-6-CARBOXALDEHYDE
6-BROMO-2-FORMYLPYRIDINE
6-BROMO-2-PYRIDINE CARBOXALDEHYDE
6-BROMOPYRIDINE-2-CARBALDEHYDE
6-BROMOPYRIDINE-2-CARBOXALDEHYDE
6-bromopyridine-2-barboxaldehyde
6-BROMO-PYRIDINE CARBOXALDEHYDE
2-Bromopyridinecarboxaldehyde
6-BROMO-2-PYRIDINE CARBOXALDEHYDE 6-BROMO-PYRIDINE-2-CARBALDEHYDE | [EINECS(EC#)]
608-952-4 | [Molecular Formula]
C6H4BrNO | [MDL Number]
MFCD02683546 | [Molecular Weight]
186.01 | [MOL File]
34160-40-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow Flakes | [Melting point ]
81-85 °C(lit.)
| [Boiling point ]
248.2±20.0 °C(Predicted) | [density ]
1.683±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Chloroform (Sparingly), Dichloromethane, Ether, Ethyl Acetate, Methanol (Slightl | [form ]
Powder | [pka]
1.00±0.10(Predicted) | [color ]
White to beige or pale brown | [Water Solubility ]
Soluble in dichloromethane, ether, ethyl acetate and methanol. Insoluble in water. | [Sensitive ]
Air Sensitive | [Usage]
A useful synthetic intermediate | [Detection Methods]
HPLC | [BRN ]
1524300 | [InChI]
InChI=1S/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H | [InChIKey]
QWFHFNGMCPMOCD-UHFFFAOYSA-N | [SMILES]
C1(C=O)=NC(Br)=CC=C1 | [CAS DataBase Reference]
34160-40-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn,F | [Risk Statements ]
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 ]
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-No smoking . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow Flakes | [Uses]
6-Bromopyridine-2-carbaldehyde can be a useful synthetic intermediate.
| [Uses]
6-Bromopyridine-2-carboxaldehyde is used in the study of a rhodium-catalyzed, reductive aldol coupling with divinyl ketones leading to syn ?-hydroxyenones. It is also used as a building block for Tris[(pyridyl)methyl]amine ligands. | [General Description]
6-Bromo-2-pyridinecarboxaldehyde is a pyridine derivative. It participates in the synthesis of meso-substituted trans-A2B2-porphyrin. | [Synthesis]
To a 12 L three-necked flask equipped with a mechanical stirrer, addition funnel, nitrogen inlet and thermocouple sleeve was added n-butyllithium (BuLi, 619 mL, 1.55 mol). Anhydrous toluene (750 mL) was then added and the reaction system was cooled to -15 °C in an ice/methanol bath. Butylmagnesium chloride (BuMgCl, 387 mL, 0.774 mol) was added slowly over a period of 30 to 45 minutes, with the rate of addition being controlled so that the reaction temperature did not exceed 0°C. A fine white to gray suspension was formed during the reaction. The suspension was continued to be stirred at -15 °C for 30 min. During this time, 2,6-dibromopyridine (500 g, 2.11 mol) was dissolved in anhydrous toluene (3 L), which was slightly heated if necessary to promote dissolution. After stirring is complete, the 2,6-dibromopyridine solution is transferred to a dosing funnel and slowly added dropwise to the reaction flask at a rate not exceeding -5 °C (about 1.5 h). After the dropwise addition was completed, stirring of the reaction mixture was continued for 45 minutes. A small amount of the reaction solution was quenched in 20% aqueous citric acid and the extent of metal exchange was analyzed by 1H NMR and TLC (25% ethyl acetate/heptane).
Toluene (750 mL) and N,N-dimethylformamide (DMF, 250 mL) were added to another 12 L three-necked flask equipped with a mechanical stirrer, nitrogen inlet, and thermocouple cannula and cooled to -15 °C in an ice/methanol bath. The initial reaction solution was transferred to the toluene/DMF mixture through a cannula at a rate not exceeding 5°C. After the transfer was complete, the reaction mixture was stirred for 45 minutes and the completion of the reaction was confirmed by TLC. The reaction solution was transferred to a partition funnel containing 4 L of water and citric acid (1 kg), stirred for 15 min and left to stratify. The organic layer was washed sequentially with 4 L of water and 4 L of saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to afford the intermediate 6-bromopyridine-2-carbaldehyde as an off-white to yellow solid (355.7 g, 90% yield). | [References]
[1] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6775 - 6786
[2] Tetrahedron Letters, 2001, vol. 42, # 29, p. 4841 - 4844
[3] Organic Letters, 2004, vol. 6, # 12, p. 1887 - 1890
[4] Dalton Transactions, 2017, vol. 46, # 18, p. 5955 - 5964
[5] Patent: US2009/82573, 2009, A1. Location in patent: Page/Page column 15 |
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