Methyl 5-bromonicotinate
Synonym(s):5-Bromonicotinic acid methyl ester;5-Bromopyridine-3-carboxylic acid methyl ester;Methyl 5-bromonicotinate
- CAS NO.:29681-44-5
- Empirical Formula: C7H6BrNO2
- Molecular Weight: 216.03
- MDL number: MFCD00173668
- EINECS: 627-974-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-16 18:29:06
What is Methyl 5-bromonicotinate?
Chemical properties
white powder
The Uses of Methyl 5-bromonicotinate
A substrate used in a microwave-assisted, palladium-catalyzed arylation of acetone as its TMS enol ether.
What are the applications of Application
Methyl 5-bromonicotinate could be used to synthesize Pyridine alkaloids from Rubiaceae with various organometallic reagents by palladium-catalyzed cross-coupling reactions. This compound is a derivative of 5-bromonicotinic acid (BrnicH) which has been widely used in the last decade to obtain MOF materials with unique luminescence, magnetism, catalysis, and adsorption through assembling with lanthanide ions and transition metal ions, such as Cu(II), Co(II), Cd(II), Zn(II), and Pb(II)[1-2].
Synthesis
To an ice-cooled suspension of 5-bromo nicotinic acid (1.6g, 7.9 mmol) in diethyl ether (20ml), a solution of diazomethane in diethyl ether was added dropwise with stirring until the mixture remained yellow. The mixture was stirred for additional 15min (hood!), and the volatile compounds were removed by distillation in vaeuo. Finally, Methyl 5-bromonicotinate was obtained after purification[2].
References
[1] WENJIE LI . Syntheses, crystal structures, and properties of new metal–5-bromonicotinate coordination polymers[J]. Journal of Solid State Chemistry, 2015. DOI:10.1016/j.jssc.2015.01.002.
[2] Bracher, F., Papke, T. Total syntheses and antimicrobial activities of pyridine alkaloids from Rubiaceae. Monatsh Chem 126, 805–809 (1995). https://doi.org/10.1007/BF00807174
Properties of Methyl 5-bromonicotinate
Melting point: | 96-100 °C |
Boiling point: | 241.7±20.0 °C(Predicted) |
Density | 1.579±0.06 g/cm3(Predicted) |
storage temp. | Inert atmosphere,Room Temperature |
solubility | Chloroform (Slightly), Methanol (Slightly) |
pka | 0.84±0.20(Predicted) |
color | White |
Water Solubility | Slightly soluble in water. |
InChI | InChI=1S/C7H6BrNO2/c1-11-7(10)5-2-6(8)4-9-3-5/h2-4H,1H3 |
CAS DataBase Reference | 29681-44-5(CAS DataBase Reference) |
Safety information for Methyl 5-bromonicotinate
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Methyl 5-bromonicotinate
InChIKey | AAJZXPWBILCHAW-UHFFFAOYSA-N |
SMILES | C1=NC=C(Br)C=C1C(OC)=O |
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