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[ CAS No. 698-25-9 ] {[proInfo.proName]}

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Chemical Structure| 698-25-9
Chemical Structure| 698-25-9
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Product Details of [ 698-25-9 ]

CAS No. :698-25-9 MDL No. :MFCD07774234
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :VUZQHUVRBPILAX-UHFFFAOYSA-N
M.W :152.58 Pubchem ID :417524
Synonyms :

Calculated chemistry of [ 698-25-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.1
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.25
Solubility : 0.0851 mg/ml ; 0.000557 mol/l
Class : Soluble
Log S (Ali) : -3.12
Solubility : 0.115 mg/ml ; 0.000756 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.51
Solubility : 0.0472 mg/ml ; 0.000309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 698-25-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 698-25-9 ]

* 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.

  • Upstream synthesis route of [ 698-25-9 ]
  • Downstream synthetic route of [ 698-25-9 ]

[ 698-25-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 95-79-4 ]
  • [ 698-25-9 ]
YieldReaction ConditionsOperation in experiment
65%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With sodium tetrafluoroborate In water at 0℃; for 0.666667 h;
Stage #3: With potassium acetate In chloroform at 20℃; for 4 h;
General procedure: NaNO2 aqueous solution (13.80g, 0.2mol, 32.20mL) was added dropwise to a mixture of 3a (21.40g, 0.2mol), H2O (190mL), and 12N HCl aqueous solution (50mL, 0.6mol) at 0°C. The mixture was stirred at 0°C for 30min and then was filtered. The precooled NaBF4 (24.20g, 0.22mol) dissolved in H2O (90mL) was added to the filtrate and kept stirring at 0°C for an additional 40min. The precipitate was collected by filtration, washed with cold ethanol (50mL×3), cold ethylether (50mL×3), and concentrated in vacuo to deliver diazonium salt (19.19g) as a yellow solid. To a solution of diazonium salt (19.19g, 0.093mol) in CHCl3 (231mL), KOAc (15.15g, 0.155mol) was added. The mixture was stirred at room temperature for 4h. Afterwards, the reaction was quenched with water (200mL) and extracted with CH2Cl2 (70mL×3). The organic phase was washed with brine (50mL×3), dried over anhydrous Na2SO4, and concentrated under reduced pressure. The obtained crude residue was purified by recrystallization to give the title compound 7.51g.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1858 - 1868
[2] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 1, p. 309 - 315
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
[5] Patent: US2017/174693, 2017, A1, . Location in patent: Paragraph 0864
  • 2
  • [ 2420-26-0 ]
  • [ 698-25-9 ]
Reference: [1] Heterocycles, 2018, vol. 96, # 1, p. 74 - 85
  • 3
  • [ 61072-56-8 ]
  • [ 698-25-9 ]
YieldReaction ConditionsOperation in experiment
3.86 g at 100℃; 6-Chloroindazole. A solution of 4-chloro-2-fluorobenzaldehyde (5.0 g, 31.6 mmol) in 12 mL of pyridine was treated with hydrazine hydrate (10 eq., 10 mL) and DMAP (3.85 g, 31.6 mmol) and the mixture heated to 100 °C for several hours. The mixture was allowed to cool to RT and was diluted with EtOAc and washed several times with dilute acid. The EtOAc solution was dried over MgS04 and concentrated in vacuo to give 6-chloroindazole as an off white solid (3.86 g).
Reference: [1] Patent: WO2011/149921, 2011, A1, . Location in patent: Page/Page column 78
[2] Patent: WO2013/169907, 2013, A1, . Location in patent: Paragraph 00114
[3] Patent: US2017/174693, 2017, A1, . Location in patent: Paragraph 0864
  • 4
  • [ 108-24-7 ]
  • [ 95-79-4 ]
  • [ 698-25-9 ]
Reference: [1] Patent: WO2011/149921, 2011, A1, . Location in patent: Page/Page column 77; 78
  • 5
  • [ 708-40-7 ]
  • [ 698-25-9 ]
Reference: [1] Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
  • 6
  • [ 698-25-9 ]
  • [ 717134-47-9 ]
Reference: [1] Synthesis, 2011, # 19, p. 3089 - 3098
  • 7
  • [ 698-25-9 ]
  • [ 885521-34-6 ]
YieldReaction ConditionsOperation in experiment
44% With bromine; sodium hydroxide In water at 20℃; for 1.5 h; Step la. To a suspension of 6-chloro-lH-indazole (3.0 g, 19.66 mmol) in 2M NaOH (70 mL) was added a solution of Bn (2.32 g, 14.52 mmol) in 2M NaOH (30 mL) drop wise. The mixture was stirred for 1.5 hours at rt. The pH value of the solution was adjusted to 8 with 3M HCl and partitioned (EtO Ac-brine). The organic was dried (Na2S04), filtered and concentrated. The residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a yellow solid (3.4 g, 44percent). ESI-MS m/z = 231.00, 233.00 [M+H]+
44% at 20℃; for 1.5 h; To a suspension of 6-chloro-1H-indazole (3.0 g, 19.66 mmol) in 2M NaOH (70 mL) was added a solution of Bra (2.32 g, 14.52 mmol) in 2M NaOH (30 mL) drop wise. The mixture was stirred for 1.5 hours at rt. The pH value of the solution was adjusted to 8 with 3M HCl, and partitioned (EtOAc-brine). The organic was dried (Na2SO4), filtered and concentrated. The residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a yellow solid (3.4 g, 44percent). ESIMS m/z=233.00 [M+H]+.
4.2 g With bromine; sodium hydroxide In water at 20℃; (6-Chloro-lH-indazol-3-yl)(2-chloropyridine-3-yl)methanone. 6-Chloro- indazole (3.86 g, 25.4 mmol) was added to 45 mL of 20percent aq. NaOH solution, and reacted with neat Br2 (0.85 mL, 16.3 mmol) for several hours at RT. The reaction was neutralized with the product, 3-bromo-6-chloroindazole, precipitating as a white solid (4.2 g). A solution of 3-bromo-6-chloroindazole (0.46 g, 2 mmol) in diethyl ether (6 mL) was cooled to -78 °C and n-BuLi (1.6 M in hexanes; 1.25 mL, 2 mmol) was added dropwise. After the addition was complete, i-BuLi (1.7 M in hexanes; 2.36 mL, 4 mmol) was added dropwise. The solution was allowed to stir 15 minutes at -78 °C, after which 2-chloronicotinoyl chloride (0.35 g, 2.0 mmol) was added as a solid. The solution was allowed to warm to RT, and was then quenched with IN HC1 and extracted with EtOAc. The EtOAc extract was concentrated in vacuo, and the residue purified by RPHPLC to give 100 mg of (6-chloro-lH-indazol-3-yl)(2-chloropyridine- 3-yl)methanone as an off white solid.
Reference: [1] Synthesis, 2011, # 16, p. 2651 - 2663
[2] Patent: WO2016/183266, 2016, A1, . Location in patent: Page/Page column 44-45
[3] Patent: US2016/289212, 2016, A1, . Location in patent: Paragraph 0191
[4] Patent: WO2013/169907, 2013, A1, . Location in patent: Paragraph 00115
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