2-Bromopyridine-5-carbaldehyde Chemical Properties

Melting point:

104-110 °C(lit.)

Boiling point:

284°

Density 

1.683

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in dichloromethane, ether, ethyl acetate and methanol.

form 

Solid

pka

-1.01±0.10(Predicted)

color 

Pale yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C6H4BrNO/c7-6-2-1-5(4-9)3-8-6/h1-4H

InChIKey

PVUKGNBRJFTFNJ-UHFFFAOYSA-N

SMILES

C1=NC(Br)=CC=C1C=O

CAS DataBase Reference

149806-06-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

2-Bromopyridine-5-carbaldehyde Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

A useful synthetic intermediate. 6-Bromonicotinaldehyde is used in wittig reaction. Hydrodehalogenation of 6-bromonicotinaldehyde to produce alcohol.

Uses

2-Bromopyridine-5-carbaldehyde can be a useful synthetic intermediate

Synthesis

General procedure for the synthesis of 2-bromo-5-formylpyridine (Intermediate 1b) from 2-bromo-5-(dibromomethyl)pyridine (Intermediate Ia, 3.650 g, 11.07 mmol): a mixture of Intermediate Ia with calcium carbonate (2.437 g, 24.35 mmol) in water (80 ml) was stirred and reacted for 16 hours at 105 °C. After completion of the reaction, the mixture was cooled to room temperature, diluted with water and extracted twice with ethyl acetate (EtOAc). The organic phases were combined, washed sequentially with water and saturated sodium chloride (NaCl) solution, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give Intermediate 1b (1.890 g, 92% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 10.05 (s, 1H), 8.78 (d, J = 2.2 Hz, 1H), 7.98 (dd, J = 8.2,2.4 Hz, 1H), 7.65 (d, J = 8.2 Hz, 1H).

References

[1] Patent: WO2016/124747, 2016, A1. Location in patent: Page/Page column 58; 59
[2] Patent: US2018/202388, 2018, A1
[3] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[4] Synthesis, 1994, # 1, p. 87 - 92

2-Bromopyridine-5-carbaldehyde(149806-06-4)Related Product Information

• 3-Aminopyridine
• 4-Methylpyridine
• Chromium picolinate
• Sulfasalazine
• 1-Hexadecylpyridinium bromide
• 2-Carboxybenzaldehyde
• 2-Bromopyridine
• 6-Bromonicotinic acid
• 5,6-DIBROMOPYRIDINE-3-CARBOXYLIC ACID
• t-butyl 6-bromo-3-pyridinecarboxylate
• N-methyl 2-bromo-5-pyridinecarboxamide
• 2-Bromo-5-formyl-3-methylpyridine
• 1-(6-BROMO-PYRIDIN-3-YL)-ETHANONE
• Methyl 6-bromonicotinate
• 6-BROMONICOTINAMIDE 98
• 5-Bromo-3-formylpyridine
• 2-Bromopyridine-4-carbaldehyde ,97%,2-BROMOPYRIDINE-4-CARBALDEHYDE
• 1-(6-BROMO-PYRIDIN-3-YL)-2,2,2-TRIFLUORO-ETHANONE