5-Bromo-2-methoxypyridine Chemical Properties

Boiling point:

80 °C/12 mmHg (lit.)

Density 

1.453 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.555(lit.)

Flash point:

205 °F

storage temp. 

Inert atmosphere,Room Temperature

pka

1.04±0.10(Predicted)

form 

Liquid

Specific Gravity

1.453

color 

Clear colorless to slightly yellow

BRN 

115150

InChI

InChI=1S/C6H6BrNO/c1-9-6-3-2-5(7)4-8-6/h2-4H,1H3

InChIKey

XADICJHFELMBGX-UHFFFAOYSA-N

SMILES

C1(OC)=NC=C(Br)C=C1

LogP

0.952

CAS DataBase Reference

13472-85-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromo-2-methoxypyridine Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

A building block for the β-alanine moiety of an α_vβ₃ antagonist and for the synthesis of a potent and selective somatostatin sst₃ receptor antagonist.

Uses

5-Bromo-2-methoxypyridine is used as a ligand for central nicotinic acetylcholine receptor. Also used in a novel synthetic approach to anti-HIV active integrase inhibitors.

Synthesis

Step 1. 2,5-dibromopyridine (5.5 g, 23.2 mmol) and sodium methanolate (3.76 g, 69.6 mmol) were dissolved in methanol (60 mL), and the mixture was placed in a sealed reaction vessel and heated to react for 42 hours at 70 °C. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the light yellow oily product 5-bromo-2-methoxypyridine (4.1 g, 95% yield). Thin layer chromatography (TLC) analytical conditions: 10% ethyl acetate/90% hexane, Rf value of 0.57.

References

[1] Patent: US2002/65296, 2002, A1
[2] Patent: US2004/102636, 2004, A1
[3] Patent: EP1042305, 2005, B1. Location in patent: Page/Page column 32-33
[4] Tetrahedron, 1985, vol. 41, # 7, p. 1373 - 1384
[5] Patent: EP1308441, 2003, A1

5-Bromo-2-methoxypyridine(13472-85-0)Related Product Information

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