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[ CAS No. 698-26-0 ] {[proInfo.proName]}

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Chemical Structure| 698-26-0
Chemical Structure| 698-26-0
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Product Details of [ 698-26-0 ]

CAS No. :698-26-0 MDL No. :MFCD00022785
Formula : C7H5ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :FVNCILPDWNBPLK-UHFFFAOYSA-N
M.W :152.58 Pubchem ID :69681
Synonyms :

Calculated chemistry of [ 698-26-0 ]

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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.22
Log Po/w (XLOGP3) : 2.31
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.72
Log Po/w (SILICOS-IT) : 2.71
Consensus Log Po/w : 2.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.189 mg/ml ; 0.00124 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.429 mg/ml ; 0.00281 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 : 1.39

Safety of [ 698-26-0 ]

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 [ 698-26-0 ]

* 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 [ 698-26-0 ]
  • Downstream synthetic route of [ 698-26-0 ]

[ 698-26-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 95-69-2 ]
  • [ 698-26-0 ]
Reference: [1] Pharmazie, 1985, vol. 40, # 2, p. 105 - 108
[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
  • 2
  • [ 7758-89-6 ]
  • [ 19335-11-6 ]
  • [ 698-26-0 ]
Reference: [1] Patent: US2002/161022, 2002, A1,
  • 3
  • [ 86991-00-6 ]
  • [ 698-26-0 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 13, p. 1385 - 1386
  • 4
  • [ 41475-06-3 ]
  • [ 698-26-0 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 11, p. 3529 - 3536
  • 5
  • [ 98083-43-3 ]
  • [ 698-26-0 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
[2] Liebigs Annalen der Chemie, 1980, # 6, p. 908 - 927
  • 6
  • [ 61495-07-6 ]
  • [ 698-26-0 ]
Reference: [1] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227
  • 7
  • [ 13436-49-2 ]
  • [ 698-26-0 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
  • 8
  • [ 61495-07-6 ]
  • [ 64-19-7 ]
  • [ 698-26-0 ]
Reference: [1] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227
  • 9
  • [ 698-26-0 ]
  • [ 108-24-7 ]
  • [ 98083-43-3 ]
Reference: [1] Pharmazie, 1985, vol. 40, # 2, p. 105 - 108
[2] Chemische Berichte, 1920, vol. 53, p. 1213,1216, 1227
  • 10
  • [ 698-26-0 ]
  • [ 351456-45-6 ]
YieldReaction ConditionsOperation in experiment
90% With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 3 h; General procedure: 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole (3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol)in DMF (7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 × 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136–138 °C (lit.:[36] 134–136 °C); IR (KBr) ν (cm−1): 3086 (NH); 424 (C-I). 1H-NMR δ (ppm): 13.50 (1H, s, H-1); 7.55(1H, d, J = 8.6 Hz, H-7); 7.45–7.40 (2H, m, H-6 and H-4); 7.19 (1H, dd, J = 7.5 Hz, H-5). 13C-NMR δ(ppm): 140.41; 127.22; 126.79; 121.23; 120.39; 110.51; 93.49; HRMS calculated for C7H5IN2: 243.9497,Found: 243.9499.3-Iodo-1H-indazole (1a). 3-Iodoindazoles were obtained by direct iodination of commercial indazoles by the method previously described by Bocchi [28] with slight modifications. A solution of 1H-indazole(3 g, 25.4 mmol), iodine (12.7 g, 50.03 mmol) and potassium hydroxide (5.34 g, 95.25 mmol) in DMF(7 mL) was stirred for 3 h at room temperature. The reaction was quenched by dilution with saturated solution of sodium bisulfite (150 mL) and a precipitated was formed. The precipitated was filtered over vacuum and washed with water (3 30 mL). The solid was left to dry at 30 °C in a vacuum oven overnight obtaining 6.17 g of a pale yellow solid. Yield: 100percent; m.p.: 136–138 °C (lit.: [36] 134–136 °C)
85.3% With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; To a mixture of 5-chloro-1H-indazole(2.0 g, 13.1 mmol, 1.0 eq.), KOH (2.4 g,45.8 mmol) in DMF was added ‘2 (6.6 g, 26.1 mmol, 2.0 eq.). The mixture was stirred at rt overnight, then quenched by aqueous Na2S2O4 solution. The mixture was extracted with EtOAc (2 x 50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (PE/EA =10:1) to provide 5-chloro-3 -iodo- 1H-indazole (3.1 g, 85.3percent).
Reference: [1] Molecules, 2018, vol. 23, # 8,
[2] Patent: WO2017/98328, 2017, A2, . Location in patent: Paragraph 00208
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2793 - 2800
  • 11
  • [ 698-26-0 ]
  • [ 885521-43-7 ]
YieldReaction ConditionsOperation in experiment
94% With N-Bromosuccinimide In dichloromethane at 20℃; for 1 h; To a solution of 5-chloro- 1H-indazole (2.5 g, 16.1 mmol) in dichloromethane (150 mL) was added N-bromosuccinimide (2.9 g, 16.6 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (100 mL), washed with water (50 mL) and brine (50 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 3-bromo-5-chloro-1H-indazole (3.7 g, 94percent) as a brown solid. ‘H NMR (DMSO-d6, 400 MHz) 13.63 (s, 1H), 7.67 — 7.59 (m, 2H), 7.49 — 7.44 (m, 1H). TLC: 50percent ethyl acetate/heptane (R1: 0.43).
Reference: [1] Patent: WO2017/31325, 2017, A1, . Location in patent: Paragraph 0764
[2] Synthesis, 2011, # 16, p. 2651 - 2663
[3] Patent: US2013/281433, 2013, A1, . Location in patent: Paragraph 1088
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