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M59203

Sigma-Aldrich

Methyl nicotinate

99%

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Synonym(s):
Nicotinic acid methyl ester
Empirical Formula (Hill Notation):
C7H7NO2
CAS Number:
93-60-7
Molecular Weight:
137.14
Beilstein:
113951
EC Number:
202-261-8
MDL number:
MFCD00006388
PubChem Substance ID:
24897056
NACRES:
NA.22

biological source

synthetic

Quality Level

100

Assay

99%

form

powder or crystals (possibly with chunks)

color

white to faint yellow

bp

204 °C (lit.)

mp

42-44 °C (lit.)

SMILES string

COC(=O)c1cccnc1

InChI

1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3

InChI key

YNBADRVTZLEFNH-UHFFFAOYSA-N

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General description

Methyl nicotinate (or nicotinic acid methyl ester) is used as a rubefacient for the relief of pains in muscles, tendons, and joints. It is also used in food as a flavoring agent.

Application

Methyl nicotinate can be employed as a precursor in the synthesis:
  • Di-3-pyridyl ketone ligand, which is used in the preparation of silver(I) complexes for the derivation of coordination polymeric chains.
  • 5-arylnicotinates , ±-sesbanine , and 1,4-dihydropyridine derivatives.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of 3, 5-diacyl-4-phenyl-1, 4-dihydropyridines
Bennasar M-L, et al.
Tetrahedron Letters, 39(50), 9275-9278 (1998)
Helical and zigzag coordination polymeric chains derived from di-3-pyridyl ketone and silver (I) salts
Chen X-D and Mak Thomas CW
Journal of Molecular Structure, 743(1-3), 1-6 (2005)
A facile synthesis of ? -sesbanine via γ-addition of ketene silyl acetal with quaternized methyl nicotinate
Wada M, et al.
Tetrahedron Letters, 26(27), 3267-3270 (1985)
Topical antirheumatic agents as hydroxyl radical scavengers
Billany MR, et al.
International Journal of Pharmaceutics, 124(2), 279-283 (1995)
A general synthesis of 5-arylnicotinates
Thompson WJ and Gaudino J
The Journal of Organic Chemistry, 49(26), 5237-5243 (1984)
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