2,4-Dichloro-5-(iodomethyl)pyrimidine

2,4-Dichloro-5-(iodomethyl)pyrimidine Property

Melting point:

78-79°

Boiling point:

327.4±32.0 °C(Predicted)

Density 

2.141±0.06 g/cm3(Predicted)

storage temp. 

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

form 

Solid

pka

-3.39±0.29(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C5H3Cl2IN2/c6-4-3(1-8)2-9-5(7)10-4/h2H,1H2

InChIKey

NEIMQFSSWKAYTR-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=C(CI)C(Cl)=N1

Safety

HazardClass 

IRRITANT

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H272May intensify fire; oxidizer

H314Causes severe skin burns and eye damage

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P221Take any precaution to avoid mixing with combustibles/…

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P331Do NOT induce vomiting.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

2,4-Dichloro-5-(iodomethyl)pyrimidine Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2,4-dichloro-5-(chloromethyl)pyrimidine from 2,4-dichloro-5-(iodomethyl)pyrimidine: A mixture of 2,4-dichloro-5-(chloromethyl)pyrimidine (15.0 g, 76.0 mmol) and sodium iodide (13.7 g, 91.4 mmol) in acetone was stirred for 45 min at 60 °C. After completion of the reaction, the resulting sodium chloride precipitate was removed by filtration and the precipitate was washed with acetone. The filtrates were combined and concentrated under reduced pressure to give a light yellow solid crude product. The crude product was purified by silica gel column chromatography using dichloromethane as eluent to afford 2,4-dichloro-5-(iodomethyl)pyrimidine as a light yellow solid (30.8 g, 96% yield).LC-MS (m/z): 289.3 [M + H]+.

References

[1] Patent: WO2007/136465, 2007, A2. Location in patent: Page/Page column 43-44
[2] Patent: WO2018/53373, 2018, A1. Location in patent: Paragraph 00485; 00486
[3] Patent: WO2018/160774, 2018, A1. Location in patent: Paragraph 00377; 00378
[4] Patent: WO2018/25043, 2018, A1. Location in patent: Page/Page column 24
[5] Patent: US2016/75720, 2016, A1. Location in patent: Paragraph 0323