6-Iodo-1H-indazole
Physical Form- Product Name
- 6-Iodo-1H-indazole
- CAS No.
- 261953-36-0
- Chemical Name
- 6-Iodo-1H-indazole
- Synonyms
- 6-IODOINDAZOLE;6-IodoindazoL;6-iodo-1h1indazole;6-IODO (1H)INDAZOLE;1H-Indazole, 6-iodo-;Axitinib Intermediate 3;6-Iodo-(1H)indazole, 96%;6-IODO (1H)INDAZOLE ISO 9001：2015 REACH
- CBNumber
- CB2178484
- Molecular Formula
- C7H5IN2
- Formula Weight
- 244.03
- MOL File
- 261953-36-0.mol
6-Iodo-1H-indazole Property
- 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)
- InChIKey
- RSGAXJZKQDNFEP-UHFFFAOYSA-N
- SMILES
- N1C2=C(C=CC(I)=C2)C=N1
Safety
- HS Code
- 29339980
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- I0933
- Product name
- 6-Iodoindazole
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $151
- Updated
- 2025/07/31
- Product number
- I0933
- Product name
- 6-Iodoindazole
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $526
- Updated
- 2025/07/31
- Product number
- I707370
- Product name
- 6-Iodo-1H-indazole
- Packaging
- 250mg
- Price
- $140
- Updated
- 2021/12/16
- Product number
- 3H32-H-07
- Product name
- 6-Iodo-1H-indazole
- Purity
- 98%
- Packaging
- 5G
- Price
- $125
- Updated
- 2021/12/16
- Product number
- 068734
- Product name
- 6-Iodoindazole
- Purity
- 95+%
- Packaging
- 1g
- Price
- $98
- Updated
- 2021/12/16
6-Iodo-1H-indazole Chemical Properties,Usage,Production
Physical Form
Light yellow to Brown powder to crystal
Uses
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].
References
[1] Patent: EP3127900, 2017, A1. Location in patent: Paragraph 0250; 0251
[2] Patent: US6531491, 2003, B1
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Patent: US6716837, 2004, B1. Location in patent: Page column 30
[5] Patent: WO2017/68064, 2017, A1. Location in patent: Page/Page column 183; 184
6-Iodo-1H-indazole Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-Iodo-1H-indazole manufacturers
- Product
- 6-Iodo-1H-indazole 261953-36-0
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 1
- Release date
- 2025-08-28
- Product
- 6-IODO (1H)INDAZOLE 261953-36-0
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-13
- Product
- 6-Iodo-1H-indazole 261953-36-0
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- ≥98% by HPLC
- Supply Ability
- 100kg/month
- Release date
- 2023-01-05