2,5-DIBROMO-3-AMINOPYRIDINE Chemical Properties

Melting point:

152.0 to 156.0 °C

Boiling point:

325.0±37.0 °C(Predicted)

Density 

2.147±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

-0.56±0.10(Predicted)

form 

powder to crystal

color 

White to Brown

InChI

InChI=1S/C5H4Br2N2/c6-3-1-4(8)5(7)9-2-3/h1-2H,8H2

InChIKey

VHGBUYMPBFPXQM-UHFFFAOYSA-N

SMILES

C1(Br)=NC=C(Br)C=C1N

CAS DataBase Reference

90902-84-4

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-41

Safety Statements 

26-39-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

2,5-DIBROMO-3-AMINOPYRIDINE Usage And Synthesis

Chemical Properties

Brown solid

Uses

3-Amino-2,5-dibromopyridine is used as a pharmaceutical synthesis intermediate.

Synthesis

(b) Synthesis of 2,5-dibromo-3-aminopyridine: 2,5-dibromo-3-nitropyridine (2.5 g, 8.87 mmol) was dissolved in acetic acid (10 mL) and stirred until completely dissolved. Powdered iron (2.476 g, 44.3 mmol) was then added and the reaction mixture was heated to 80 °C under vigorous stirring and maintained for 15 min. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove solid impurities and the filter cake was washed with ether and ethyl acetate (EtOAc). The organic layers were combined and washed sequentially with water and saturated brine to remove water-soluble impurities. The organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography using 0-30% ethyl acetate/hexane gradient elution to collect the target components, and concentrated under reduced pressure to give 2,5-dibromopyridin-3-amine (1.7 g, 6.75 mmol, 76% yield) as a white solid. The mass spectrum (electrospray positive ion mode) showed m/z 252 ([M+H]+).

References

[1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 1, p. 51 - 54
[2] Patent: WO2008/128961, 2008, A1. Location in patent: Page/Page column 37; 73
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3927 - 3936
[4] Patent: WO2007/107758, 2007, A1. Location in patent: Page/Page column 125
[5] Journal of the Chemical Society, 1952, p. 2042,2044

2,5-DIBROMO-3-AMINOPYRIDINE(90902-84-4)Related Product Information

• PYRAZOLO[1,5-A]PYRIMIDINE-2-CARBOXYLIC ACID
• (S)-1-(4-FLUOROPHENYL)ETHANOL
• 1-Methyl-1H-pyrazol-4-aMine dihydrochloride
• 6-BROMO-[1,2,4]TRIAZOLO[1,5-A]PYRIDINE
• 1,3-Bis(4,5-dihydro-2-oxazolyl)benzene
• (R)-1-(4-FLUOROPHENYL)ETHANOL
• 4-bromo-1-methylpyrazole-3-carboxy acid
• 5-HYDROXY-1-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID METHYL ESTER
• 4,5-Dihydrooxazole, 2-vinyl-
• 1-methyl-1H-pyrazol-4-amine
• 2,4-DIBROMO-3-AMINOPYRIDINE
• 2,5-Dibromo-3-nitropyridine
• 2,3,6-TRIBROMO-4-METHOXY-5-NITROPYRIDINE
• 2,5-DIBROMO-3-AMINOPYRIDINE
• 3-BROMO-2,6-DIMETHYL-5-NITROPYRIDIN-4-OL
• 2,5-Dibromo-4-methyl-3-nitropyridine
• 2,5,6-TRIBROMOPYRIDIN-3-YLAMINE
• 2,6-DIBROMO-3-AMINOPYRIDINE