3-BROMO-4-FORMYLPYRIDINE Chemical Properties

Melting point:

81-82 °C(lit.)

Boiling point:

246.2±20.0 °C(Predicted)

Density 

1.683±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetonitrile (Slightly), Chloroform (Slightly)

form 

Solid

pka

0.90±0.18(Predicted)

color 

Light Brown

InChIKey

NOBDKWLIAQKADB-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/38-43

Safety Statements 

26-36/37

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

3-BROMO-4-FORMYLPYRIDINE Usage And Synthesis

Chemical Properties

Off-white solid

Uses

3-Bromo-4-pyridinecarboxaldehyde acts as a reagent in the synthesis of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles agonists which interact with the G-protein-coupled bile acid receptor 1 (TGR5) inducing insulin secretion which may be used as a potential treatment for diabetus mellitus.

Synthesis

Diisopropylamine (27.6 g, 273.0 mmol) was dissolved in tetrahydrofuran (300 mL) under nitrogen protection and cooled to -78 °C. A tetrahydrofuran solution of n-butyllithium (91 mL, 228.0 mmol, 2.5 M) was slowly added dropwise and stirred at -78 °C for 1 hour. Subsequently, 3-bromopyridine (30.0 g, 190.0 mmol) was added dropwise and stirring was continued at -78 °C for 20 min. Next, N,N-dimethylformamide (55.0 g, 760.0 mmol) was added dropwise and stirred at -78 °C for 1 hour. After completion of the reaction, the mixture was slowly warmed to room temperature and the reaction was quenched with saturated aqueous ammonium chloride solution (150 mL). The aqueous layer was extracted with ethyl acetate (200 mL x 3), and the organic layers were combined and concentrated in vacuum. The residue was purified by silica gel column chromatography to afford 3-bromopyridine-4-aldehyde (12.0 g, 34.0% yield). The product was confirmed by 1H NMR (400 MHz, CD3OD): δ 10.37 (s, 1H), 8.91 (s, 1H), 8.80-8.61 (m, 1H), 7.78-7.63 (m, 1H).LCMS (m/z): 187.0 (M + 1).

References

[1] Tetrahedron, 2000, vol. 56, # 3, p. 397 - 406
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3146 - 3151
[3] Patent: WO2015/200677, 2015, A2. Location in patent: Paragraph 00504; 00505
[4] Tetrahedron Letters, 1983, vol. 24, # 32, p. 3291 - 3294
[5] Synthesis, 1999, # 2, p. 306 - 311

3-BROMO-4-FORMYLPYRIDINE(70201-43-3)Related Product Information

• 3-BROMO-2-FORMYLPYRIDINE
• 4-Bromo-3-formylpyridine hyrdobromide salt
• 2-FORMYL-5-BROMOPYRIDINE / 5-BROMO-2-FORMYLPYRIDINE,5-BROMO-2-FORMYLPYRIDINE,5-Bromo-2-formylpyridine, 5-Bromo-2-picolinaldehyde
• 6-BROMO-2-FORMYLPYRIDINE,2-BROMO-6-FORMYLPYRIDINE
• 2-Bromopyridine-3-carboxaldehyde, 2-Bromo-3-formylpyridine,2-BROMO-3-FORMYLPYRIDINE
• 2-BROMO-4-FORMYLPYRIDINE
• 5-Bromo-3-formylpyridine
• 5-BROMO-3-METHYL-2-PYRIDINECARBALDEHYDE
• 2-BROMO-5-FORMYLPYRIDINE,2-BROMO-5-FORMYLPYRIDINE97+%
• ,5-Dihydro-5-methyl-6-[4-(4-oxo-1(4H)-pyridinyl)phenyl]-1,2,4-triazin-3(2H)-one
• 4-BROMO-3-FORMYLPYRIDINE