| Identification | More | [Name]
5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER | [CAS]
29682-15-3 | [Synonyms]
5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
METHYL 5-BROMO-2-PYRIDINECARBOXYLATE
METHYL 5-BROMOPICOLINATE
METHYL 5-BROMOPYRIDINE-2-CARBOXYLATE
Methyl 5-bromopyridine-2-carboxylate, 98+% | [EINECS(EC#)]
681-695-3 | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD04112493 | [Molecular Weight]
216.03 | [MOL File]
29682-15-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
101-103°C | [Boiling point ]
290.9±20.0 °C(Predicted) | [density ]
1.579±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
-0.67±0.10(Predicted) | [color ]
White to Almost white | [Water Solubility ]
Soluble in water. | [InChI]
InChI=1S/C7H6BrNO2/c1-11-7(10)6-3-2-5(8)4-9-6/h2-4H,1H3 | [InChIKey]
JEURNBCYNWNADN-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)=NC=C(Br)C=C1 | [CAS DataBase Reference]
29682-15-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37:Wear suitable gloves . | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Uses]
Methyl 5-bromopyridine-2-carboxylate is used as an organic chemical synthesis intermediate. | [Synthesis]
Example 89 - Preparation of Intermediate 25: The synthesis of Intermediate 25 followed the following general procedure. To a solution of 5-bromopyridine-2-carboxylic acid (50.0 g, 0.247 mol, 1.0 eq.) in anhydrous methanol (400 mL) cooled to 0 °C was added thionyl chloride (107.0 mL, 2.47 mol, 10.0 eq.) dropwise. The reaction mixture was slowly warmed to room temperature and subsequently heated at 50 °C for 12 hours. The reaction process was monitored by thin layer chromatography (TLC) and liquid chromatography-mass spectrometry (LC-MS). After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give a white solid residue. The residue was slowly quenched with saturated sodium bicarbonate solution and the white solid was collected by filtration to afford the target product methyl 5-bromopyridine-2-carboxylate (43.0 g, 80% yield). The product was characterized by mass spectrometry (m/z 216.14) and nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, DMSO): δ 8.86 (d, J=1.9 Hz, 1H), 8.28 (dd, J=8.4,2.4 Hz, 1H), 8.00 (d, J=8.4 Hz, 1H), 3.89 (s, 3H) ppm. | [References]
[1] Patent: WO2018/126072, 2018, A1. Location in patent: Paragraph 0246; 0247
[2] Patent: WO2012/76898, 2012, A1. Location in patent: Page/Page column 64-65
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 22, p. 4780 - 4784
[4] Patent: WO2016/44662, 2016, A1. Location in patent: Paragraph 00379-00380
[5] Patent: CN103360407, 2016, B. Location in patent: Paragraph 0135-0137 |
|
|