ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Iodopyridine 2-Amino-5-iodopyridine

2-Amino-5-iodopyridine

Product Name2-Amino-5-iodopyridine
CAS20511-12-0
MFC5H5IN2
MW220.01
EINECS626-319-0
MOL File20511-12-0.mol

Chemical Properties

Melting point	128-131 °C (lit.)
Boiling point	293.8±25.0 °C(Predicted)
Density	2.055±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Chloroform (Slightly), DMSO (Slightly)
pka	4.91±0.13(Predicted)
form	Solid
color	Pale Yellow to Light Beige
Water Solubility	Insoluble
Sensitive	Light Sensitive
BRN	108738
InChI	InChI=1S/C5H5IN2/c6-4-1-2-5(7)8-3-4/h1-3H,(H2,7,8)
InChIKey	IVILGUFRMDBUEQ-UHFFFAOYSA-N
SMILES	C1(N)=NC=C(I)C=C1
CAS DataBase Reference	20511-12-0(CAS DataBase Reference)
EPA Substance Registry System	2-Pyridinamine, 5-iodo- (20511-12-0)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-20/21/22
Safety Statements	26-36-37/39
WGK Germany	3
Hazard Note	Irritant
TSCA	TSCA listed
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
2-Amino-5-iodopyridine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Uses

2-Amino-5-iodopyridine is a compound that can be used in organic synthesis.

Application

2-Amino-5-iodopyridine, also known as 2-amino-5-iodopyridine or 5-iodo-2-aminopyridine, is an important intermediate in organic synthesis. It is mainly used as a pharmaceutical intermediate, and also in the production of dyes, pesticides, and fragrances.

Chemical Properties

Light yellow needles

Synthesis

504-29-0

20511-12-0

Example 20: Scheme C10 2-Aminopyridine (II) (1.0 eq, 318 mmol, 30.0 g), periodate dihydrate (0.15 eq, 48 mmol, 10.7 g), and iodine (0.42 eq, 134 mmol, 32.4 g) were dissolved in a mixture of acetic acid (800 mL), water (36 mL), and sulfuric acid (6.2 mL), and heated to react at 80°C for 4 for 4 hours. Upon completion of the reaction, the reaction mixture was poured into 10% Na2S2O3 aqueous solution to quench unreacted iodine and subsequently extracted with ether. The organic phases were combined, washed with 10% NaOH aqueous solution, dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (elution gradient: heptane/ethyl acetate 25:75 → pure ethyl acetate) to afford the target compound 2-amino-5-iodopyridine (116) (52.0 g, 74% yield). 1H NMR (δ, CDCl3): 4.51 (2H, s), 6.35 (1H, d, J = 8 Hz), 7.62 (1H, d, J = 8 Hz), 8.21 (1H, s).

References

[1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2656 - 2663
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 3, p. 1211 - 1219
[3] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[4] Synthetic Communications, 2013, vol. 43, # 21, p. 2913 - 2925
[5] Journal of the American Chemical Society, 2003, vol. 125, # 3, p. 616 - 617

2-Amino-5-iodopyridine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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