2-Amino-5-iodopyridine 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 

Yes

HS Code 

29333990

MSDS

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

2-Amino-5-iodopyridine Usage And Synthesis

Uses

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

Uses

2-Amino-5-iodopyridine can be used as a chemical and pharmaceutical intermediate in laboratory research and development and chemical and pharmaceutical synthesis processes.

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

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

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