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Sigma-Aldrich

2-Amino-5-bromopyridine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H5BrN2
CAS Number:
Molecular Weight:
173.01
Beilstein:
108737
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

133-138 °C (lit.)

SMILES string

Nc1ccc(Br)cn1

InChI

1S/C5H5BrN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)

InChI key

WGOLHUGPTDEKCF-UHFFFAOYSA-N

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General description

2-Amino-5-bromopyridine is a brominated aromatic amine reagent and is used for labeling of model reducing-end oligosaccharides via reductive amination.

Application

2-Amino-5-bromopyridine has been used to study the hydrogen-bonding patterns in the 2-amino-5-bromopyridine benzoic acid (1/1) cocrystal. It has been used in the synthesis of 2-amino-5-bromo­pyridinium 3-amino­benzoate salt and polycyclic azaarenes.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Slide 1 of 3

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Madhukar Hemamalini et al.
Acta crystallographica. Section E, Structure reports online, 66(Pt 3), o663-o663 (2010-01-01)
In the title adduct, C(5)H(5)BrN(2)·C(7)H(6)O(2), the carboxyl group of the benzoic acid mol-ecule is twisted away from the attached ring by 12.97 (11)°. The 2-amino-5-bromo-pyridine mol-ecules inter-act with the carboxylic group of neighbouring benzoic acid mol-ecules through N-H⋯O and O-H⋯N hydrogen
Madhukar Hemamalini et al.
Acta crystallographica. Section E, Structure reports online, 66(Pt 3), o664-o664 (2010-01-01)
In the title salt, C(5)H(6)BrN(2) (+)·C(7)H(6)NO(2) (-), the pyridine N atom of the 2-amino-5-bromo-pyridine mol-ecule is protonated. In the crystal, the protonated N atom and the 2-amino group are hydrogen-bonded to the carboxyl-ate O atoms via a pair of N-H⋯O
Min Li et al.
Rapid communications in mass spectrometry : RCM, 17(13), 1462-1466 (2003-06-24)
Model reducing-end oligosaccharides were successfully labeled by a brominated aromatic amine reagent, 2-amino-5-bromopyridine (ABP), through reductive amination. Using either a combination of liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) with in-source fragmentation or liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS), sequence
Tetrahedron Letters, 48, 5039-5039 (2007)

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