methyl 6-(bromomethyl)nicotinate Chemical Properties

Boiling point:

284.9±30.0℃ (760 Torr)

Density 

1.533±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

126.1±24.6℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.40±0.22(Predicted)

form 

solid

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

Safety Information

HazardClass 

IRRITANT

HS Code 

29333990

methyl 6-(bromomethyl)nicotinate Usage And Synthesis

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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