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4-Bromo-1H-indazole

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CAS:186407-74-9
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  • 2023-08-15
  • CAS:186407-74-9
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4-Bromo-1H-indazole Basic information
Product Name:4-Bromo-1H-indazole
Synonyms:4-BROMO (1H)INDAZOLE;4-BROMOINDAZOLE;1H-Indazole, 4-bromo-;4-bromo-1H-indazole£4-Bromoindazole;broMo-1H-indazole;4-BroMo-1H-indazole, 97+%;4-Bromoindazole >;186407-74-9
CAS:186407-74-9
MF:C7H5BrN2
MW:197.03
EINECS:803-241-7
Product Categories:Building Blocks;Indazoles;CHIRAL CHEMICALS;pharmacetical;Heterocycles series;Indazole
Mol File:186407-74-9.mol
4-Bromo-1H-indazole Structure
4-Bromo-1H-indazole Chemical Properties
Melting point 165-167°
Boiling point 333.8±15.0 °C(Predicted)
density 1.770±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility soluble in Ethanol
form Solid
pka12.78±0.40(Predicted)
color Off-white
InChIInChI=1S/C7H5BrN2/c8-6-2-1-3-7-5(6)4-9-10-7/h1-4H,(H,9,10)
InChIKeyKJIODOACRIRBPB-UHFFFAOYSA-N
SMILESN1C2=C(C(Br)=CC=C2)C=N1
CAS DataBase Reference186407-74-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,T
Risk Statements 25-36/37/38
Safety Statements 26-45
RIDADR 2811
WGK Germany 3
HazardClass 6.1
HazardClass IRRITANT
PackingGroup 
HS Code 2933998090
MSDS Information
4-Bromo-1H-indazole Usage And Synthesis
Description4-Bromo-1H-indazole is a derivative indazole which has a heterocyclic structure made up of benzene and pyrazole rings. Indazoles are an important class of heterocyclic compounds with a wide range of application as biologic and pharmaceutic agents. Indazole derivatives have a wide range of biological activities. For instance, indazole derivatives show vasorelaxant and anti-aggregator activities by stimulating NO release and increasing cGMP levels. Recent medical research and development studies resulted in the production of indazole derivatives for the treatment of osteoporosis, inflammatory diseases and neurodegenerative disorders. 4-bromo-1H indazole molecule is a much stronger inhibitor of 6-bromo-1H indazole and 7-bromo-1H indazole. 4-Bromo-1H-indazole may be strong inhibitor candidate for LPO and that caution should be exercised when using medicines containing indazole derivatives[1].
Chemical Propertiesbrown powder
SynthesisTo N-Acetyl-4-bromo-1H-indazole (1.6 g, 6.69 mmol) was added methanol (25.9 mL) and then 6 N HCl (15.6 mL). The resulting solution was stirred at room temperature until the reaction was completed after 7 h (monitored by TLC, petroleum ether/ethyl acetate 2:1). After evaporation of methanol in vacuo, the residue was extracted with ethyl acetate (50 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude was purified by flash chromatography (petroleum ether/ethyl acetate, 5:1) to yield 4-bromo-1H-indazole (0.8 g) as milky white solid, mp 164–166°C, yield 67.1%[2].
4-Bromo-1H-indazole
References[1] Koksal Z, et al. Lactoperoxidase, an antimicrobial enzyme, is inhibited by some indazoles. Drug and Chemical Toxicology, 2018; 43: 22-26.
[2] Wang Y, et al. Synthesis and Antibacterial Activity of Novel 4-Bromo-1H-Indazole Derivatives as FtsZ Inhibitors. Archiv der Pharmazie, 2015; 348: 266-274.
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