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About This Item
Empirical Formula (Hill Notation):
C5H7IN2
CAS Number:
Molecular Weight:
222.03
Beilstein/REAXYS Number:
3713241
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
97%
mp
159-161 °C (lit.)
storage temp.
2-8°C
SMILES string
[I-].N[n+]1ccccc1
InChI
1S/C5H7N2.HI/c6-7-4-2-1-3-5-7;/h1-5H,6H2;1H/q+1;/p-1
InChI key
NDRLPYIMWROJBG-UHFFFAOYSA-M
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General description
1-Aminopyridinium iodide, a pyridine derivative, is an important reagent for organic synthesis. It has various pharmaceutical applications. It participates in homogeneous transition metal-catalyzed reactions. Single-crystal X-ray diffraction studies suggest that the compound crystallizes in the monoclinic space group P21/c (phase II). Aza-ylide derived from 1-aminopyridinium iodide serves as a commercially available ammonia equivalent during the preparation of primary amines.
Application
1-Aminopyridinium iodide may be used in the preparation of room temperature ionic liquids (organic salts in liquid state at room temperature). It may also be used for the preparation of oligomycin A annelated with pyrazolo[1,5-a]pyridine.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Lyudmila N Lysenkova et al.
The Journal of antibiotics, 63(1), 17-22 (2009-11-17)
The first examples of chemical modification of antibiotic oligomycin A are described. The interaction of oligomycin A with hydroxylamine yielded six-membered nitrone annelated with the antibiotic at the positions 3,4,5,6,7. The reaction with 1-aminopyridinium iodide in pyridine led to pyrazolo[1,5-a]pyridine
P Andrew Evans et al.
Journal of the American Chemical Society, 131(25), 8722-8723 (2009-06-09)
The transition metal catalyzed allylic amination represents a powerful and versatile cross-coupling for the asymmetric construction of stereogenic C-N bonds that are present in secondary metabolites and medicinally important agents. We have developed a regio- and enantiospecific rhodium-catalyzed allylic amination
Crystal structure and characterization of a novel ferroelastic ionic crystal: 1-Aminopyridinium iodide (C 5 H 7 N 2)+ I-.
Owczarek M, et al.
Chemical Physics Letters, 537, 38-47 (2012)
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