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122858

Sigma-Aldrich

2-Amino-5-bromopyridine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H5BrN2
CAS Number:
1072-97-5
Molecular Weight:
173.01
Beilstein:
108737
EC Number:
214-019-9
MDL number:
MFCD00006323
UNSPSC Code:
12352100
PubChem Substance ID:
24847511
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

mp

133-138 °C (lit.)

functional group

bromo

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL2263
STBJ9955
STBB9850V
MKBG2173V
S50844V

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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)
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

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