ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Iodopyridine 3-Iodopyridin-2-amine

3-Iodopyridin-2-amine

Product Name3-Iodopyridin-2-amine
CAS104830-06-0
MFC5H5IN2
MW220.01
EINECS624-002-1
MOL File104830-06-0.mol

Chemical Properties

Melting point	87-91 °C
Boiling point	289.6±25.0 °C(Predicted)
Density	2.055±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	soluble in Methanol
form	Powder, Crystalline Powder or Needles
pka	4.50±0.36(Predicted)
color	White to pale brown
Sensitive	Air & Light Sensitive
InChI	InChI=1S/C5H5IN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)
InChIKey	UUDNBWSHTUFGDQ-UHFFFAOYSA-N
SMILES	C1(N)=NC=CC=C1I
CAS DataBase Reference	104830-06-0(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	22-37/38-41
Safety Statements	26-39
WGK Germany	2
HazardClass	IRRITANT
HS Code	29333990
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ALFA	English

Usage And Synthesis

Chemical Properties

Light yellow Needles

Uses

2-Amino-3-iodopyridine (3-Iodopyridin-2-amine) can be coupled with formyl derivatives under a copper-catalyzed indole synthesis method, and then constructed azide analogs through copper-mediated conjugated adducts things. The nucleophilicity of 2-Amino-3-iodopyridine is lower than that of the corresponding aniline used in the synthesis of indole, a potential obstacle for future synthesis[1].

Synthesis

N-(3-IODO-PYRIDIN-2-YL)-2,2-DIMETHYL-PROPIONAMIDE

113975-31-8

104830-06-0

General procedure for the synthesis of 2-amino-3-iodopyridine from N-(3-iodopyridin-2-yl)palmitamide: N-(3-iodopyridin-2-yl)neopentanamide (13.80 g, 45.36 mmol) was dissolved in 24 wt% sulfuric acid solution (394 mL), and the reaction mixture was stirred for 60 min under reflux conditions. After completion of the reaction, it was cooled to room temperature and neutralized with 4N sodium hydroxide solution and solid sodium bicarbonate. The aqueous phase was extracted with dichloromethane (3 x 200 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporator to give 3-iodopyridin-2-amine (9.70 g, 97% yield) as a cream colored solid.

References

[1] Patent: US2009/156593, 2009, A1. Location in patent: Page/Page column 17
[2] Patent: US2006/183758, 2006, A1. Location in patent: Page/Page column 8
[3] Patent: US2009/82403, 2009, A1. Location in patent: Page/Page column 51
[4] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 53
[5] Patent: US2010/331282, 2010, A1. Location in patent: Page/Page column 10

3-Iodopyridin-2-amine

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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