2-chloro-4-iodopyrimidine
- Product Name
- 2-chloro-4-iodopyrimidine
- CAS No.
- 395082-55-0
- Chemical Name
- 2-chloro-4-iodopyrimidine
- Synonyms
- 2-chloro-4-iodopyrimidine;Pyrimidine, 2-chloro-4-iodo-;2-chloro-4-iodo-pyrimidine - [C86655]
- CBNumber
- CB42617534
- Molecular Formula
- C4H2ClIN2
- Formula Weight
- 240.43
- MOL File
- 395082-55-0.mol
2-chloro-4-iodopyrimidine Property
- Melting point:
- 111.3-112.4 °C
- Boiling point:
- 317.8±15.0 °C(Predicted)
- Density
- 2.187±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- pka
- -2.88±0.20(Predicted)
- Appearance
- White to yellow Solid
- InChI
- InChI=1S/C4H2ClIN2/c5-4-7-2-1-3(6)8-4/h1-2H
- InChIKey
- LOPQDJJEZFCJMU-UHFFFAOYSA-N
- SMILES
- C1(Cl)=NC=CC(I)=N1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 1994AQ
- Product name
- 2-chloro-4-iodopyrimidine
- Packaging
- 100mg
- Price
- $179.6
- Updated
- 2021/12/16
- Product number
- CM252706
- Product name
- 2-Chloro-4-iodopyrimidine
- Purity
- 95%
- Packaging
- 1g
- Price
- $294
- Updated
- 2021/12/16
- Product number
- CD11130263
- Product name
- 2-Chloro-4-iodopyrimidine
- Purity
- 95+%
- Packaging
- 1g
- Price
- $311
- Updated
- 2021/12/16
- Product number
- 395082550
- Product name
- 2-Chloro-4-iodopyrimidine
- Packaging
- 250mg
- Price
- $898.6
- Updated
- 2021/12/16
- Product number
- CD11130263
- Product name
- 2-Chloro-4-iodopyrimidine
- Purity
- 95+%
- Packaging
- 5g
- Price
- $932
- Updated
- 2021/12/16
2-chloro-4-iodopyrimidine Chemical Properties,Usage,Production
Description
2-Chloro-4-iodopyrimidine is an inhibitor of protein kinases. It binds to the ATP site of a kinase and inhibits its activity by forming a covalent bond with the serine or threonine residue of the active site. 2-Chloro-4-iodopyrimidine has been shown to inhibit tumor cell proliferation and induce apoptosis in vitro and in vivo. This compound has been shown to inhibit the activity of family kinases, including those involved in tumor growth and angiogenesis.
Preparation
The raw material and cuprous iodide are homogeneously mixed in acetonitrile. Add tert-butyl nitroso ester at -2 °C and stir for 5 min to heat the reaction to 73 °C. After 3h of the reaction, the raw material reaction was completed by TLC detection, cooled to room temperature, and water and saturated sodium carbonate solution were added to the reaction. Finally, the product is purified to obtain the product
Synthesis
1722-12-9
395082-55-0
General procedure for the synthesis of 2-chloro-4-iodopyrimidine from 2-chloropyrimidine: n-butyllithium (ca. 1.6 M hexane solution, 3.0 mmol) was sequentially added to a stirred solution of 2,2,6,6-tetramethylpiperidine (0.50 mL, 3.0 mmol) in tetrahydrofuran (THF, 6 mL) at 0 °C. After 5 min, ZnCl2-TMEDA ( 0.26 g, 1.0 mmol). The reaction mixture was continued to be stirred at 0 °C for 15 min, followed by the addition of 2-chloropyrimidine (0.11 g, 1.0 mmol). After 2 h of reaction at this temperature, a THF (10 mL) solution of iodine (I2, 0.76 g, 3.0 mmol) was added. The mixture was stirred overnight and upon completion of the reaction, the reaction was quenched by the addition of saturated sodium thiosulfate (Na2S2O3, 10 mL) solution and extracted with ethyl acetate (AcOEt, 3 x 20 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. Purification by silica gel column chromatography (eluent: heptane/ethyl acetate, 95/5) afforded the target product 2-chloro-4-iodopyrimidine (4a) in 18% yield as a beige powder.
References
[1] Chemistry - A European Journal, 2009, vol. 15, # 6, p. 1468 - 1477
[2] Synlett, 2015, vol. 26, # 20, p. 2811 - 2816
2-chloro-4-iodopyrimidine Preparation Products And Raw materials
Raw materials
Preparation Products
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