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441503

Sigma-Aldrich

1-Aminopyridinium iodide

97%

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About This Item

Empirical Formula (Hill Notation):
C5H7IN2
CAS Number:
6295-87-0
Molecular Weight:
222.03
Beilstein:
3713241
EC Number:
228-566-6
MDL number:
MFCD00051893
UNSPSC Code:
12352100
PubChem Substance ID:
24867664
NACRES:
NA.22

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.

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 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

441503-VAR:
441503-10G:4548173994079
441503-1G:
441503-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCG2194
MKBR0306V
MKBG7417V
03614TE
13103MD

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Supported room temperature ionic liquid membranes for CO2/CH4 separation.
Iarikov DD, et al.
Chemical Engineering Journal, 166(1), 401-406 (2011)
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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