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HomeProduct name list6-Iodo-1H-indazole

6-Iodo-1H-indazole

  • CAS NO.:261953-36-0
  • Empirical Formula: C7H5IN2
  • Molecular Weight: 244.03
  • MDL number: MFCD04114695
  • EINECS: 607-884-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-13 18:13:23
6-Iodo-1H-indazole Structural

What is 6-Iodo-1H-indazole?

The Uses of 6-Iodo-1H-indazole

6-Iodo-1H-indazole is an intermediate used to synthesize inhibitors of Chk1.

Synthesis Reference(s)

[1] NOOLVI M N, PATEL H M. Small Molecule Tyrosine Kinase Inhibitors: The New Dawn for Cancer Therapy[J]. Letters in Drug Design & Discovery, 1900, 9(1): 84-125. DOI:10.2174/157018012798192892.

Synthesis

Revill P. and co-worker synthesized Axitinib by iodination of 6-iodo-1H-indazole (100) to give 3,6-di iodo- 1H-indazole (101) ,which on further reaction with 2- mercapto-N-methylbenzenesulfinamide gives 2-(3-iodo-1Hindazol-6-ylthio)-N-methylbenzamide (101), the same can be obtained via 2-(1H-indazol-6-ylthion)-N-methylbenzamide (102) starting from 6-iodo-1H-indazole (100) through alternative route. N-protection of 2-(3-iodo-1H-indazol-6- ylthio)-N-methylbenzamide (101) by Boc2, DMAP or DHP, TsOH gives respective N-protected intermediates 103, 104. Further treatment of 103, 104 with 2-vinyl pyridine give rise to N-protected-2-(1-methyl-3-(2-(pyridine-2-yl) vinyl)-1Hindazole-6-ylthio) benzothioamide 105 and 106. Deprotection of 105 and 106 gives destination compound axitinib (107), the same can be obtained without protection from 2-(3-iodo-1H-indazol-6-ylthio)-N-methylbenzamide (101) by simple reaction with 2-vinyl pyridine[1].
6-IODO (1H)INDAZOLE

Properties of 6-Iodo-1H-indazole

Melting point: 207.0 to 211.0 °C
Boiling point: 358.2±15.0 °C(Predicted)
Density  2.082±0.06 g/cm3(Predicted)
storage temp.  under inert gas (nitrogen or Argon) at 2–8 °C
solubility  DMSO (Slightly), Methanol (Slightly)
pka 12.96±0.40(Predicted)
form  Liquid
color  Clear colorless to light yellow
InChI InChI=1S/C7H5IN2/c8-6-2-1-5-4-9-10-7(5)3-6/h1-4H,(H,9,10)

Safety information for 6-Iodo-1H-indazole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 6-Iodo-1H-indazole

InChIKey RSGAXJZKQDNFEP-UHFFFAOYSA-N
SMILES N1C2=C(C=CC(I)=C2)C=N1

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