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4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

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CAS:5399-92-8
Purity:97% Package:10G 100G 1KG 25KG

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  • 2025-09-25
  • CAS:5399-92-8
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  • Purity: 99%, 99.5% Sublimated
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4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Basic information
Product Name:4-Chloro-1H-pyrazolo[3,4-d]pyrimidine
Synonyms:IFLAB-BB F0909-0060;4-CHLORO-1H-PYRAZOLO3,4-DPYRIMIDINE;AKOS BBS-00002106;1H-Pyrazolo[3,4-d]pyrimidine, 4-chloro-;4-Chloropyrazolo[3,4-d]pyrimidine;NSC 4937;4-chloro-1H-pyrazolo[3;4-Chlor-1(2)Hpyrazolo[3,4-d]pyriMidine
CAS:5399-92-8
MF:C5H3ClN4
MW:154.56
EINECS:640-617-8
Product Categories:Heterocycle-Pyrimidine series;Halides;Bases & Related Reagents;Heterocycles;Inhibitors;Nucleotides;Fused Ring Systems
Mol File:5399-92-8.mol
4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Structure
4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Chemical Properties
Melting point >350?C
Boiling point 224.6±50.0 °C(Predicted)
density 1.84±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility DMSO (Slightly), Methanol (Slightly, Sonicated)
pka10.16±0.20(Predicted)
form Solid
color Yellow to Orange
CAS DataBase Reference5399-92-8(CAS DataBase Reference)
Safety Information
Hazard Note Harmful
HazardClass IRRITANT
HS Code 29335990
MSDS Information
4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Usage And Synthesis
Chemical PropertiesPale Yellow Solid
UsesHas a SK channel blocker effect.
Synthesis
4,6-Dichloro-5-pyrimidinecarbaldehyde

5305-40-8

4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

5399-92-8

Synthesis of compound 4.1. Hydrazine hydrate (11.5 mL, 23.7 mmol) was slowly added dropwise to a 1,4-dioxane solution (600 mL) containing 4,6-dichloro-5-pyrimidinecarboxaldehyde (40.0 g, 22.6 mmol) and triethylamine (30 mL, 22 mmol) under the cooling of an ice bath, and the temperature of the reaction was controlled to be no more than 20°C. The reaction temperature was controlled to be no higher than 20°C. After dropwise addition, the reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the precipitate was collected by filtration. The filtrate was concentrated under reduced pressure to give compound 4.1 (29 g, 83% yield) in the form of a light yellow solid. The product was characterized by 1H NMR (400.13 MHz, DMSO-d6) and mass spectrometry: 1H NMR δ 14.52 (br.s, 1H), 8.83 (s, 1H), 8.45 (s, 1H); MS m/z 155 [M + 1]+.

References[1] Patent: US2009/5359, 2009, A1. Location in patent: Page/Page column 18
[2] Patent: WO2008/153947, 2008, A2. Location in patent: Page/Page column 42; 63-64
[3] Molecules, 2017, vol. 22, # 4,
[4] Patent: CN106496232, 2017, A. Location in patent: Paragraph 0049; 0050; 0051; 0052
[5] Patent: CN107383014, 2017, A. Location in patent: Paragraph 0075; 0076; 0077; 0078
Tag:4-Chloro-1H-pyrazolo[3,4-d]pyrimidine(5399-92-8) Related Product Information
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