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CAS No. : | 1426424-00-1 | MDL No. : | MFCD26406995 |
Formula : | C6H7IN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VDMYDFPQXAWWLE-UHFFFAOYSA-N |
M.W : | 234.04 | Pubchem ID : | 71279477 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.93 |
TPSA : | 28.68 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.6 cm/s |
Log Po/w (iLOGP) : | 1.25 |
Log Po/w (XLOGP3) : | 1.59 |
Log Po/w (WLOGP) : | 1.5 |
Log Po/w (MLOGP) : | 1.68 |
Log Po/w (SILICOS-IT) : | 3.17 |
Consensus Log Po/w : | 1.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.7 |
Solubility : | 0.463 mg/ml ; 0.00198 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.8 |
Solubility : | 3.68 mg/ml ; 0.0157 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.02 |
Solubility : | 0.222 mg/ml ; 0.000951 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.39 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; | Intermediate i-12a 3-iodo-1.4.5.6-tetrahvdrocvclopenta[clpyrazole Intermediate i-12a 3-iodo-1.4.5.6-tetrahvdrocvclopenta[clpyrazole [00181] A mixture of 1,4,5, 6-tetrahydrocyclopenta[c]pyrazole (200 mg, 1.85 mmol) and NIS (416 mg, 1.85 mmol) in DMF (2.3 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and EtOAc. The organic layer was separated and washed twice with aqueous NaHCC and once with brine. Aqueous layers were back extracted once with EtOAc, combined organic layers were dried with Na2SC>4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/Hexane 25-90%) to afford the title compound. MS: 235 (M+l). | |
With N-iodo-succinimide In acetonitrile for 16h; Reflux; | 3-iodo-1,4,5,6-tetrahydrocyclopentapyrazole. N-Iodosuccinimide (5.64 g, 25 mmol is added in portions to a solution of 4,5,6,7-tetrahydrocyclopentapyrazole (2.10 g 20 mmol) in acetonitrile (50 mL) and the solution was heated to reflux for 16 hrs. The slurry is cooled to )C, and the solids are collected by vacuum filtration, rinsed with cold acetonitrile (2x20 mL) and dried to give 3-iodo-1,4,5,6-tetrahydrocyclopentapyrazole. | |
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; | Intermediate i-1a 3-iodo-1,4,5,6-tetrahydrocyclopenta[c]pyrazole A mixture of 1,4,5,6-tetrahydrocyclopenta[c]pyrazole (200 mg, 1.85 mmol) and NIS (416 mg, 1.85 mmol) in DMF (2.3 ml) was stirred at room temperature overnight. The reaction mixture was diluted with water and EtOAc. The organic layer was separated and washed twice with aqueous NaHCO3 and once with brine. Aqueous layers were back extracted once with EtOAc, combined organic layers were dried with Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography for Intermediate i-1a which (EtOAc/Hexane 25-90%) to afford the title compound. LCMS (ESI) calc'd for C6H7IN2 [M+H]+: 235, found: 235. |
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; | 3-iodo-1,4,5,6-tetrahydrocyclopenta[c]pyrazole A mixture of 1,4,5,6-tetrahydrocyclopenta[c]pyrazole (200 mg, 1.85 mmol) and NIS (416 mg, 1.85 mmol) in DMF (2.3 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and EtOAc. The organic layer was separated and washed twice with aqueous NaHCO3 and once with brine. Aqueous layers were back extracted once with EtOAc, combined organic layers were dried with Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/Hexane 25-90%) to afford the title compound. MS: 235 (M+1). | |
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; | Intermediate i-12a A mixture of 1,4,5,6-tetrahydrocyclopenta [c] pyrazole (200 mg, 1.85 mmol) and NIS (416 mg, 1.85 mmol) in DMF (2.3 mL) was stirred overnight at room temperature. The reaction mixture was diluted with water and EtOAc. The organic layer was separated and washed twice with aqueous NaHCO 3 and once with brine. The aqueous layer was back-extracted once with EtOAc and the combined organic layers were dried over Na 2 SO 4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc / hexane 25-90%) to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; dmap / tetrahydrofuran / 2 h / 25 °C 2: tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; dmap / tetrahydrofuran / 2 h / 25 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 80 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 3.2: 3 h / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triethylamine; dmap / tetrahydrofuran / 2 h / 25 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 80 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 3.2: 3 h / 0 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; triethylamine In tetrahydrofuran at 25℃; for 2h; | 1,N-(t-butoxycarbonyl)-3-iodo-1,4,5,6-tetrahydrocyclopentapyrazole. 3-Iodo-1,4,5,6-tetrahydrocyclopentapyrazole (4.68 g, 20 mmol) in THF (100 ml) is placed in a foil-covered round-bottom flask. 4-dimethylaminopyridine (0.24 g, 1.9 mmol, 0.1equiv) is added, followed by di-tert-butyl dicarbonate (5.4 ml, 24 mmol, 1.2 equiv). Triethylamine (5.4 ml, 39 mmol, 2.0 equiv) is slowly added to the solution by syringe, and stirred at 25 C for a further 2 hours. The reaction mixture is diluted with water (75 ml) and extracted with EtOAc (3 x 50 ml). The combined organic layers are washed with water (2 x 50 mL), saturated brine (100 ml), dried (MgSO4), and concentrated under reduced pressure to give a red oil which is purified by chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 90/10) to give 1,N-(t-butoxycarbonyl)-3-iodo-1,4,5,6-tetrahydrocyclopentapyrazole. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | Intermediate i-2a (2-chloro-6-(trifluoromethyl)phenyl)(3-iodo-5,6-dihydrocyclopenta[c]pyrazol-1(4H)-yl)methanone To a mixture of i-1a (90 mg, 0.39 mmol), DIPEA (134 μl, 0.77 mmol) and DMAP (71 mg, 0.58 mmol) in DMF (1.9 ml) was added 2-chloro-6-(trifluoromethyl)benzoyl chloride (140 mg, 0.58 mmol) drop wise and the reaction was allowed to stir at room temperature overnight. The reaction mixture was diluted with EtOAc. The organic layer was separated and washed twice with aqueous NaHCO3 and once with brine. The combined organic layers were dried with Na2SO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/Hexane 0-65%) to afford the title compound. LCMS (ESI) calc'd for C1-4H9ClF3IN2O [M+H]+: 440, found: 440. |
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