ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Bromopyridine 5-Bromo-2-hydrazinopyridine

5-Bromo-2-hydrazinopyridine

Product Name5-Bromo-2-hydrazinopyridine
CAS77992-44-0
MFC5H6BrN3
MW188.03
EINECS
MOL File77992-44-0.mol

Chemical Properties

Melting point	132.0 to 136.0 °C
Boiling point	238.2±50.0 °C(Predicted)
Density	1.82±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
form	powder to crystal
pka	8.97±0.70(Predicted)
color	White to Light yellow to Light orange
InChI	1S/C5H6BrN3/c6-4-1-2-5(9-7)8-3-4/h1-3H,7H2,(H,8,9)
InChIKey	QYQLEYTXFMOLEI-UHFFFAOYSA-N
SMILES	NNc1ccc(Br)cn1
CAS DataBase Reference	77992-44-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,T
Risk Statements	25-37/38-41
Safety Statements	26-36-45
RIDADR	2811
WGK Germany	3
Hazard Note	Irritant
HazardClass	6.1
PackingGroup	Ⅲ
HS Code	2933399990
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Uses

5-Bromo-2-hydrazinopyridine serves as a derivatization reagent for the simultaneous LC-MS analysis of carboxyl and carbonyl-containing metabolites in biofluids[3]. The compound acts as a precursor for synthesizing L1 from 9,10-phenanthrene quinone, hydrazone intermediates from carbonyl compounds, and 5-bromo-7-azaindole derivatives via Fischer cyclization[1][2].

Synthesis

2-Chloro-5-bromopyridine (64 g, 333 mmol) was suspended in hydrazine monohydrate (250 mL), and the mixture was heated at 70° C. for 72 hours. The reaction mixture was then diluted with water (750 mL), and the resulting precipitate was filtered off and azeotrope, firstly with toluene (*2) and then dichloromethane (*2), to afford 5-Bromo-2-hydrazinopyridine as a pale brown solid in 83percent yield, 52 g.

References

[1] Patent: US2006/35922, 2006, A1. Location in patent: Page/Page column 31
[2] Patent: WO2007/91152, 2007, A1. Location in patent: Page/Page column 48
[3] Patent: WO2012/65546, 2012, A1. Location in patent: Page/Page column 19
[4] Patent: WO2012/65297, 2012, A1. Location in patent: Page/Page column 19
[5] Patent: US2010/305085, 2010, A1. Location in patent: Page/Page column 17

References

[1]Vu, T. N. A., Polyanskaya, N., Bozhenkova, S., Khrustalev, V., Utenyshev, A., Shetnev, A., Filenko, I., Huynh, M. C., Nguyen, A. V., & Kovalchukova, O. (2026). Synthesis, structure, and antimicrobial activity of a series of novel heterocyclic azo-colorants derived from α-dicarbonyl compounds. RSC Advances, 16(26), 24128–24140. https://doi.org/10.1039/d5ra10033j
[2]Alekseyev, R., Amirova, S., & Terenin, V. (2015). Preparation of 2,3-Disubstituted 5-Bromo-1H-pyrrolo[2,3-b]pyridine Framework by Fischer Cyclization. Synthesis, 47(20), 3169–3178. https://doi.org/10.1055/s-0034-1381040
[3]Han, J., Yang, Q., Zhi, Z., Li, N., & Wu, J.-L. (2025). Bromine signature coded derivatization LC-MS for specific profiling of carboxyl or carbonyl-containing metabolites in Mycoplasma pneumoniae infection. Talanta, 285, 127345. https://doi.org/10.1016/j.talanta.2024.127345

5-Bromo-2-hydrazinopyridine

Chemical Properties

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Usage And Synthesis

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