2,3-Diamino-5-bromopyridine Chemical Properties

Melting point:

155 °C (dec.) (lit.)

Boiling point:

180 °C(Press: 0.005-0.01 Torr)

Density 

1.6770 (rough estimate)

refractive index 

1.6400 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

4.53±0.49(Predicted)

form 

Powder or Needles

color 

Light yellow to purple or light brown

Water Solubility 

soluble in hot water

BRN 

119436

InChI

InChI=1S/C5H6BrN3/c6-3-1-4(7)5(8)9-2-3/h1-2H,7H2,(H2,8,9)

InChIKey

YRGMYJUKFJPNPD-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

38875-53-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34

Safety Statements 

26-36-37/39-45-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT-HARMFUL

HazardClass 

6.1

PackingGroup 

III

HS Code 

29333990

MSDS

• Language:English Provider:2,3-Diamino-5-bromopyridine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,3-Diamino-5-bromopyridine Usage And Synthesis

Chemical Properties

light yellow to purple or light brown powder or

Uses

2,3-Diamino-5-bromopyridine may be used in the preparation of the following heterocyclic compounds:

• 6-bromoimidazo-[b]pyridine
• 11-bromopyrido[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline
• 6-bromo-3-(tetrahydro-2H-pyran-2-yl)-3H-imidazo[4,5-b]pyridine

General Description

2,3-Diamino-5-bromopyridine can be prepared from 2-amino-3-nitro-5-bromopyridine via reduction using stannous chloride.

Synthesis

The general procedure for the synthesis of 2,3-diamino-5-bromopyridine from 2-amino-3-nitro-5-bromopyridine is as follows: Part I: Synthesis of imidazo[4,5-b]pyridin-2(3H)-one boronic acid Step 1: Preparation of 5-bromopyridine-2,3-diamine 5-Bromo-3-nitropyridin-2-amine (3 g) was dissolved in a solvent mixture of isopropanol (56 mL) and water (28 mL). Ammonium chloride (1.47 g, 2 eq.) and iron powder (2.31 g, 3 eq.) were subsequently added. The reaction mixture was heated to 90°C and kept at this temperature for 45 minutes. Upon completion of the reaction, the mixture was cooled, diluted with ethyl acetate (EtOAc), filtered to remove insoluble matter, and the organic and aqueous layers were separated. The organic layer was subsequently washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 2,3-diamino-5-bromopyridine as a solid (2.45 g, 95% yield). Product characterization data: 1H-NMR (300 MHz, DMSO-d6) δ 7.25 (d, 1H), 6.77 (d, 1H), 5.70-5.40 (bs, 2H), 5.20-4.80 (bs, 2H).

References

[1] Journal of Medicinal Chemistry, 1995, vol. 38, # 18, p. 3524 - 3535
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[3] Patent: WO2010/121164, 2010, A2. Location in patent: Page/Page column 60
[4] Patent: EP1460067, 2004, A1. Location in patent: Page 29
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 1160 - 1170

2,3-Diamino-5-bromopyridine(38875-53-5)Related Product Information

• 2-Aminopyridine
• 3-Aminopyridine
• 1,3-Diaminoguanidine monohydrochloride
• 2,3-Diaminopyridine
• 2-Amino-5-bromopyridine
• 1-Hexadecylpyridinium bromide
• 3-Amino-5-bromopyridine
• 2,3-Dibromopyridine
• 4-Dimethylaminopyridine
• Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate
• 6-BROMO-1H-IMIDAZO[4,5-B]PYRIDIN-2(3H)-ONE
• 2-Amino-5-bromo-4-methyl-3-nitropyridine
• 7-BROMOPYRIDO[2,3-B]PYRAZINE-2,3(1H,4H)-DIONE
• 5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE
• 2-Amino-5-bromo-3-nitropyridine
• 3,4-diamino-5-bromopyridine
• 2,5-DIAMINO-3-BROMOPYRIDINE
• 5-BROMO-6-METHOXYPYRIDINE-2,3-DIAMINE