Introduction：Basic information about Methyl 5-bromonicotinate CAS 29681-44-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Methyl 5-bromonicotinate Basic information
| Product Name: | Methyl 5-bromonicotinate |
| Synonyms: | 5-BROMO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER;5-BROMOPYRIDINE-3-CARBOXYLIC ACID METHYL ESTER;5-BROMO NICOTINIC ACID METHYL ESTER;METHYL 5-BROMONICOTINATE;METHYL 5-BROMOPYRIDINE-3-CARBOXYLATE;METHYL 3-BROMO-5-PYRIDINECARBOXYLATE;BUTTPARK 37\04-20;5-Bromonictinic acid ethyl ester |
| CAS: | 29681-44-5 |
| MF: | C7H6BrNO2 |
| MW: | 216.03 |
| EINECS: | 627-974-5 |
| Product Categories: | blocks;Bromides;Carboxes;Pyridines |
| Mol File: | 29681-44-5.mol |
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Methyl 5-bromonicotinate Chemical Properties
| 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) |
| form | solid |
| 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 |
| InChIKey | AAJZXPWBILCHAW-UHFFFAOYSA-N |
| SMILES | C1=NC=C(Br)C=C1C(OC)=O |
| CAS DataBase Reference | 29681-44-5(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 37/38-41-36/37/38 |
| Safety Statements | 26-39-37/39 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
Methyl 5-bromonicotinate Usage And Synthesis
| Chemical Properties | white powder |
| Uses | A substrate used in a microwave-assisted, palladium-catalyzed arylation of acetone as its TMS enol ether. |
| 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 |
Methyl 5-bromonicotinate Preparation Products And Raw materials
| Raw materials | 5-Bromonicotinic acid-->Methanol-->Iodomethane |
| Preparation Products | 2-(5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)propan-2-ol-->3-BroMo-5-(prop-1-en-2-yl)pyridine-->METHYL 5-METHYLNICOTINATE-->5-Bromo-3-pyridinemethanol-->Methyl 5-aminopyridine-3-carboxylate-->methyl 5-(4-(trifluoromethyl)phenyl)pyridine-3-carboxylate-->methyl 5-(3-(trifluoromethyl)phenyl)pyridine-3-carboxylate-->methyl 5-(pyridin-4-yl)pyridine-3-carboxylate-->5-Bromonicotinic acid |
