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: 2024-08-14 18:30:21
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].
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) |
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 |
Abamectin manufacturer
TYNDAL LABS PVT LTD
JSK Chemicals
ALS INDIA LIFE SCIENCES
AATAMI Molecular Research Laboratories Pvt Ltd (AMRL)
BASR Fine Chemicals Pvt. Ltd.
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