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3-Iodopyridin-2-amine

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CAS:104830-06-0
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3-Iodopyridin-2-amine Basic information
Product Name:3-Iodopyridin-2-amine
Synonyms:3-IODOPYRIDIN-2-AMINE;3-IODO-PYRIDIN-2-YLAMINE;2-Amino-3-iodopyridine 97%;3-IODO-PYRIDIN-2-YLAMINE,98%;3-Iodopyrid-2-ylaMine;2-Amino-3-iodopyridine,98%;2-AMINO-3-IODOPYRIDINE;2-Amino-3-iodopyridine >
CAS:104830-06-0
MF:C5H5IN2
MW:220.01
EINECS:624-002-1
Product Categories:Boronic Acid;Amines;Pyridines;Pyridine;Amines and Anilines;Heterocycles
Mol File:104830-06-0.mol
3-Iodopyridin-2-amine Structure
3-Iodopyridin-2-amine 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
pka4.50±0.36(Predicted)
color White to pale brown
Sensitive Air & Light Sensitive
InChIInChI=1S/C5H5IN2/c6-4-2-1-3-8-5(4)7/h1-3H,(H2,7,8)
InChIKeyUUDNBWSHTUFGDQ-UHFFFAOYSA-N
SMILESC1(N)=NC=CC=C1I
CAS DataBase Reference104830-06-0(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
MSDS Information
ProviderLanguage
ALFA English
3-Iodopyridin-2-amine Usage And Synthesis
Chemical PropertiesLight yellow Needles
Uses2-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

3-Iodopyridin-2-amine

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
Tag:3-Iodopyridin-2-amine(104830-06-0) Related Product Information
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