| Identification | Back Directory | [Name]
METHYL 6-FORMYLNICOTINATE | [CAS]
10165-86-3 | [Synonyms]
METHYL 6-FORMYLNICOTINATE
methyl 2-formylpyridine-5-carboxylate
Methyl 6-formylpyridine-3-carboxylate
6-Formylpyridine-3-carboxylic acid methyl ester
3-Pyridinecarboxylic acid, 6-forMyl-, Methyl ester | [Molecular Formula]
C8H7NO3 | [MDL Number]
MFCD08275010 | [MOL File]
10165-86-3.mol | [Molecular Weight]
165.15 |
| Chemical Properties | Back Directory | [Melting point ]
115-116.7 °C | [Boiling point ]
273℃ | [density ]
1.249 | [Fp ]
119℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
1.68±0.10(Predicted) | [color ]
Yellow to brown | [InChI]
InChI=1S/C8H7NO3/c1-12-8(11)6-2-3-7(5-10)9-4-6/h2-5H,1H3 | [InChIKey]
BZOWIADSJYMJJJ-UHFFFAOYSA-N | [SMILES]
C1=NC(C=O)=CC=C1C(OC)=O |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
37/38-41 | [Safety Statements ]
26-39-36 | [WGK Germany ]
WGK 3 | [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 | [Synthesis Reference(s)]
Tetrahedron, 64, p. 688, 2008 DOI: 10.1016/j.tet.2007.11.030 | [Synthesis]
General procedure for the synthesis of methyl 6-formylnicotinate from methyl 6-hydroxymethylnicotinate: a mixture of methyl 6-hydroxymethylnicotinate (7 g, 37 mmol) and manganese dioxide (32.3 g, 372 mmol) in dichloromethane (200 mL) was stirred and reacted for 4 hours at 20°C. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford methyl 6-formylnicotinate (6 g, 97% yield). Mass spectral data: MS-ESI (m/z): 166.2 ([M + H]+) (LC-MS method C; retention time: 0.36 min). | [References]
[1] Patent: WO2014/114185, 2014, A1. Location in patent: Page/Page column 126
[2] Patent: US2014/206681, 2014, A1. Location in patent: Paragraph 0782
[3] Molecules, 2014, vol. 19, # 1, p. 102 - 121
[4] Patent: CN104418811, 2017, B. Location in patent: Paragraph 0234-0236
[5] Tetrahedron Letters, 2006, vol. 47, # 39, p. 7025 - 7029 |
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