2-AMINO-5-IODOPYRIMIDINE Chemical Properties

Melting point:

219 °C

Boiling point:

364.9±34.0 °C(Predicted)

Density 

2.204±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder

pka

2.08±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Sensitive 

Light Sensitive

InChI

InChI=1S/C4H4IN3/c5-3-1-7-4(6)8-2-3/h1-2H,(H2,6,7,8)

InChIKey

HAFKCGZQRIIADX-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(I)C=N1

CAS DataBase Reference

1445-39-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

37/39-26-39

WGK Germany 

3

HS Code 

2933599590

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-AMINO-5-IODOPYRIMIDINE Usage And Synthesis

Chemical Properties

cream to brown crystalline powder

Uses

2-Amino-5-iodopyrimidine is used as a reactant in the synthesis of aminopyrimidine and cyclic guanidine amino acids.

Synthesis

General procedure for the synthesis of 2-amino-5-iodopyrimidine from 2-aminopyrimidine: a mixture of 2-aminopyrimidine (2.4 g, 25 mmol, 1.0 eq.) and elemental iodine (2.7 g, 10.7 mmol, 0.43 eq.) was dissolved in 60 mL of glacial acetic acid, followed by the addition of periodate (0.86 g, 3.76 mmol, 0.15 eq.) and 0.5 mL of concentrated sulfuric acid dissolved in 3 mL of water. The reaction mixture was heated to 80 °C and maintained for 24 h under nitrogen protection. Upon completion of the reaction, the reaction mixture was poured into saturated aqueous sodium thiosulfate solution until the solution was clarified (200 mL each time for 3 times) and then extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel column chromatography afforded 2-amino-5-iodopyrimidine (1.4 g, 22.2% yield) as a white solid.

References

[1] Heterocycles, 1984, vol. 22, # 5, p. 1195 - 1210
[2] Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7468 - 7474
[3] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[4] Synthesis, 1984, # 3, p. 252 - 254
[5] Patent: CN105622638, 2016, A. Location in patent: Paragraph 0362

2-AMINO-5-IODOPYRIMIDINE(1445-39-2)Related Product Information

• 5-IODOPYRIMIDINE
• 4-Amino-5-iodopyrimidine
• 5-AMINO-2-IODOPYRIMIDINE
• 4-Iodopyrimidin-2-amine
• 4-AMINO-6-IODOPYRIMIDINE
• 2-AMINO-4-HYDROXY-5-IODO-6-PHENYLPYRIMIDINE
• 2-AMINO-4-HYDROXY-5-IODO-6-PHENOXYPYRIMIDINE
• 5-Iodo-2-(piperazin-1-yl)pyrimidine
• 2-AMINO-4,6-DIMETHYL-5-IODOPYRIMIDINE
• 2-AMINO-5-IODOPYRIMIDINE