| Identification | More | [Name]
Methyl 5-bromonicotinate | [CAS]
29681-44-5 | [Synonyms]
5-BROMO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER
5-BROMO NICOTINIC ACID METHYL ESTER
5-BROMOPYRIDINE-3-CARBOXYLIC ACID METHYL ESTER
BUTTPARK 37\04-20
METHYL 3-BROMO-5-PYRIDINECARBOXYLATE
METHYL 5-BROMONICOTINATE
METHYL 5-BROMOPYRIDINE-3-CARBOXYLATE
5-Bromonictinic acid ethyl ester
5-BROMONICOTIC ACID METHYL ESTER
5-Bromonicotinic acid methyl ester, 5-Bromopyridine-3-carboxylic acid methyl ester, Methyl 5-bromonicotinate
3-(Methoxycarbonyl)-5-bromopyridine | [EINECS(EC#)]
627-974-5 | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD00173668 | [Molecular Weight]
216.03 | [MOL File]
29681-44-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white powder | [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 Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H315-H318-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
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 .
S39:Wear eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white powder | [Uses]
Substrate used in a microwave-assisted, palladium-catalyzed arylation of acetone as its TMS enol ether. | [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 |
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