| Identification | Back Directory | [Name]
methyl 6-(bromomethyl)nicotinate | [CAS]
131803-48-0 | [Synonyms]
methyl 6-(bromomethyl)nicotinate
6-Bromomethyl-nicotinic acid methyl ester
3-Pyridinecarboxylic acid, 6-(broMoMethyl)-
Methyl 2-(bromomethyl)pyridine-5-carboxylate
6-Bromomethylpyridin-3-carboxylic acid methyl ester
6-(bromomethyl)-3-pyridinecarboxylic acid methyl ester
3-Pyridinecarboxylic acid, 6-(bromomethyl)-, methyl ester | [Molecular Formula]
C8H8BrNO2 | [MDL Number]
MFCD10566280 | [MOL File]
131803-48-0.mol | [Molecular Weight]
230.06 |
| Chemical Properties | Back Directory | [Boiling point ]
284.9±30.0℃ (760 Torr) | [density ]
1.533±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
126.1±24.6℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
1.40±0.22(Predicted) | [color ]
OFF WHITE | [InChI]
InChI=1S/C8H8BrNO2/c1-12-8(11)6-2-3-7(4-9)10-5-6/h2-3,5H,4H2,1H3 | [InChIKey]
IRQSKJQDKUAART-UHFFFAOYSA-N | [SMILES]
C1=NC(CBr)=CC=C1C(OC)=O |
| Hazard Information | Back Directory | [Uses]
methyl 6-(bromomethyl)nicotinate is an organic reagent mainly used in chemical and scientific laboratory research. | [Synthesis]
methyl 6-(bromomethyl)nicotinate is synthesised using methyl 6-methylnicotinate as a raw material by chemical reaction. The specific synthesis steps are as follows:
0.471 g (1.0 equivalent) of N-bromosuccinimide and 64 mg (0.1 equivalent) of benzoyl peroxide are added to a solution of 0.4 g of the product obtained in the preceding Stage 1 in 15 ml of carbon tetrachloride. The solution is brought to reflux for 6 hours, then filtered and evaporated under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate: 95/5) to produce 0.262 g of the expected product. [ Yield: 43percent MS: MH+ 231].
 | [References]
[1] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5074 - 5077
[2] Journal of the American Chemical Society, 2002, vol. 124, # 21, p. 6009 - 6019
[3] Tetrahedron Asymmetry, 1990, vol. 1, # 9, p. 571 - 574
[4] Patent: US2004/72871, 2004, A1. Location in patent: Page/Page column 19-20
[5] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5005 - 5022 |
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