| Identification | More | [Name]
6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER | [CAS]
26218-75-7 | [Synonyms]
6-BROMO-2-PYRIDINE CARBOXYLIC ACID METHYL ESTER
6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
METHYL 6-BROMO-2-PYRIDINECARBOXYLATE
METHYL 6-BROMOPICOLINATE
METHYL 6-BROMOPYRIDINE-2-CARBOXYLATE
RARECHEM AL BF 0899
Methyl 6-Bromoyridine-2-carboxylate
Methyl 6-bromopyridine-2-carboxylate 98%
Methyl 6-bromo-2-pyridinecarboxylate, Methyl 6-bromopicolinate
Methyl-6-bromopyridine-2-carboxylate ,97% | [EINECS(EC#)]
627-687-5 | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD06203934 | [Molecular Weight]
216.03 | [MOL File]
26218-75-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
92-96 °C(lit.)
| [Boiling point ]
289.7±20.0 °C(Predicted) | [density ]
1.579±0.06 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder or Needles | [pka]
-1.03±0.10(Predicted) | [color ]
White to pale pink to pale brown to yellow | [Detection Methods]
HPLC,NMR | [InChI]
InChI=1S/C7H6BrNO2/c1-11-7(10)5-3-2-4-6(8)9-5/h2-4H,1H3 | [InChIKey]
SGNCOKUHMXLGAH-UHFFFAOYSA-N | [SMILES]
C1(C(OC)=O)=NC(Br)=CC=C1 | [CAS DataBase Reference]
26218-75-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Harmful/Irritant/Keep Cold | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white solid | [Uses]
Methyl 6-bromopicolinate, also known as Methyl 6-bromopyridine-2-carboxylate, is a halogenated pyridine derivative that can be used in esterolysis reactions to form 6-Bromopicolinic acid.It can also be used in substitution reactions or cross-couplings to synthesise other pyridine compounds. | [Synthesis]
The general procedure for the synthesis of methyl 6-bromo-2-pyridinecarboxylate from methanol and 6-bromo-2-pyridinecarboxylic acid is as follows:
1. 6-bromo-2-pyridine carboxylic acid (6.000 g) was dissolved in methanol (180 mL) containing concentrated hydrochloric acid and heated to reflux.
2. Sulfuric acid (2 mL) was added and the reaction continued to reflux for 4 hours.
3. Upon completion of the reaction, the reaction mixture was cooled to about 0°C and concentrated.
4. Ammonia (4.8 mL) was added to the concentrated mixture.
5. The resulting solution was evaporated to give a white solid residue. 6.
6. The white solid was dissolved in a solvent mixture of dichloromethane (100 mL) and brine (100 mL), and the organic layer was separated with sufficient shaking.
7. The organic layer was dried with magnesium sulfate and the solvent was evaporated to give the white solid product methyl 6-bromo-2-pyridinecarboxylate (6.300 g, 98% yield).
Product characterization data: 1H NMR (400 MHz, CDCl3) δ 4.00 (3H, s), 7.66-7.74 (2H, m), 8.07-8.13 (1H, m). | [References]
[1] Patent: WO2003/84917, 2003, A1. Location in patent: Page/Page column 26
[2] Journal of Agricultural and Food Chemistry, 2016, vol. 64, # 18, p. 3533 - 3537
[3] Patent: WO2017/9798, 2017, A1. Location in patent: Page/Page column 92
[4] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 722 - 748
[5] Inorganic Chemistry, 2018, vol. 57, # 13, p. 7512 - 7515 |
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