2-Iodopyrimidine Chemical Properties

Melting point:

30-32 °C

Boiling point:

277.4±23.0 °C(Predicted)

Density 

2.102±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder to crystal

pka

-1.18±0.13(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C4H3IN2/c5-4-6-2-1-3-7-4/h1-3H

InChIKey

AXDGIPMYJALRKV-UHFFFAOYSA-N

SMILES

C1(I)=NC=CC=N1

Safety Information

HS Code 

2933599590

2-Iodopyrimidine Usage And Synthesis

Chemical Properties

Light yellow powder

Synthesis

Under nitrogen protection, 2-chloropyrimidine (200 g, 1.75 mol) was slowly added in five portions to an aqueous solution of hydriodic acid (850 ml, 57%) pre-cooled to -10 to -5 °C. The reaction temperature was maintained in the range of -10 to -5°C and the progress of the reaction was monitored by high performance liquid chromatography (HPLC). After completion of the reaction (60 to 120 min), the pH was adjusted to 7.25 ± 0.25 with 30% sodium hydroxide solution and the temperature of the reaction mixture was raised to 18-23°C. Subsequently, sodium sulfite (16 g) was added for decolorization and the pH was adjusted to 3 ± 1. Tert-butyl methyl ether (TBME, 600 ml) was added to the mixture and saturated with sodium chloride (300 g). The organic and aqueous phases were separated and the aqueous phase was extracted with tert-butyl methyl ether (4 x 400 ml). The organic layers were combined and washed sequentially with 1% aqueous sodium sulfite (50 ml) and water (100 ml). The organic layers were concentrated to dryness and co-evaporated with tert-butyl methyl ether (100 ml) at 45 to 50 °C to remove residual water. The final product 2-iodopyrimidine 330 g was obtained in 90% yield and 98% purity as determined by HPLC, which was consistent with the standard.

References

[1] Patent: US2006/58343, 2006, A1. Location in patent: Page/Page column 7
[2] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6550 - 6552
[3] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1990, # 7, p. 1269 - 1274
[4] Patent: EP2395055, 2011, A1. Location in patent: Page/Page column 8
[5] Journal of the American Chemical Society, 2012, vol. 134, # 12, p. 5528 - 5531

2-Iodopyrimidine(31462-54-1)Related Product Information

• Uracil
• Sulfadimethoxine sodium salt
• 2-Iodopyrimidine
• 5-Bromo-2-iodopyrimidine
• 2-Chloro-5-iodopyrimidine
• 6-Bromo-2-iodoquinazoline
• 2-Iodoadenine
• 2-Iodo-6-chloropurine
• Pyrimidine, 2-iodo-4-methoxy- (9CI)
• 4,6-Dimethyl-2-iodopyrimidine
• ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(6-CHLORO-2-IODO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER
• 2-IODO-5'-ETHYLCARBOXAMIDOADENOSINE
• 2-IODOADENOSINE
• 2,4-DIIODOPYRIMIDINE
• (1R,2S,4S,5S)-4-[2-IODO-6-(METHYLAMINO)-9H-PURIN-9-YL]-2-(PHOSPHONOOXY)BICYCLO[3.1.0]HEXANE-1-METHANOL DIHYDROGEN PHOSPHATE ESTER TETRAAMMONIUM SALT
• 5-AMINO-2-IODOPYRIMIDINE
• 2-IODO-9H-PURINE
• 2-IODO-5-NITROPYRIMIDINE