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Chemical Structure| 2420-26-0
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Product Details of [ 2420-26-0 ]

CAS No. :2420-26-0 MDL No. :MFCD06252499
Formula : C7H5ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QNZWAJZEJAOVPN-UHFFFAOYSA-N
M.W : 156.57 Pubchem ID :520101
Synonyms :

Calculated chemistry of [ 2420-26-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.86
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 2.14
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.12 mg/ml ; 0.00714 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 1.92 mg/ml ; 0.0123 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.37
Solubility : 0.663 mg/ml ; 0.00424 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.03

Safety of [ 2420-26-0 ]

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

Application In Synthesis of [ 2420-26-0 ]

* 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 [ 2420-26-0 ]
  • Downstream synthetic route of [ 2420-26-0 ]

[ 2420-26-0 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 2420-26-0 ]
  • [ 698-25-9 ]
Reference: [1] Heterocycles, 2018, vol. 96, # 1, p. 74 - 85
  • 2
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  • [ 108-43-0 ]
  • [ 2420-26-0 ]
YieldReaction ConditionsOperation in experiment
61.7%
Stage #1: With triethylamine; magnesium chloride In acetone at 25℃; for 0.5 h;
Stage #2: for 5 h; Inert atmosphere; Reflux
General procedure: Into a 1 L 3-necked round-bottomflask was added 3-fluorophenol (33.6 g, 0.3 mol), anhydrous MgCl2 (85.7 g, 0.9mmol), triethylamine (75.9 g, 0.75 mol) and anhydrous acetone (340 mL). Theresulting solution was stirred at 25 °C for 30 min, followed by the addition ofparaformaldehyde (45 g, 1.5 mol). Then the reaction mixture was heated to refluxfor 5 h under a nitrogen atmosphere. Once TLC showed the consumption of startingmaterial, acetone was evaporated under vacuum. The residue was acidified to pH 3with 10percent hydrochloride and extracted with ethyl acetate (3 × 150 mL). Thecombined organic layer was washed with water, dried over anhydrous sodium sulfate,and evaporated in vacuum to afford an oily brownish red oil (18.1 g, 43.1percent in yield)which was used directly in the next reaction (Byun et al. 2008; Uini and Lars 1999).
Reference: [1] Applied Organometallic Chemistry, 2018, vol. 32, # 2,
[2] Drug Metabolism and Disposition, 2017, vol. 45, # 12, p. 1354 - 1363
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1530 - 1536
[4] Organic Letters, 2015, vol. 17, # 23, p. 5824 - 5827
[5] Organic and Biomolecular Chemistry, 2016, vol. 14, # 30, p. 7268 - 7274
[6] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5591 - 5593
[7] Organic Letters, 2017, vol. 19, # 23, p. 6340 - 6343
[8] Organic Letters, 2018, vol. 20, # 10, p. 2880 - 2883
  • 3
  • [ 64917-81-3 ]
  • [ 2420-26-0 ]
YieldReaction ConditionsOperation in experiment
72% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dichloromethane at 20℃; for 4 h; 2,3-Dichloro-5,6-dicyano-1-4-benzoquinone (DDQ, 9.92 g, 43.7 mmol) was added to a solution of 5-chloro-2-hydroxymethylphenol in dichloromethane (65 mL) and tetrahydrofuran (15 mL),. The reaction mixture was stirred at room temperature for 4 h. Then, the solvent was evaporated under vacuum and the crude was purified by chromatography on silica to afford the title compound (72percent): 1H NMR (400 MHz, CDCl3) δ 11.17 (s, 1H), 9.86 (s, 1H), 7.49 (d, J= 7.3 Hz, 1H), 7.00 (m, 2H).
72% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; dichloromethane at 20℃; for 4 h; 2,3-Dichloro-5,6-dicyano-1-4-benzoquinone (DDQ, 9.92 g, 43.7 mmol) was added to a solution of 5-chloro-2-hydroxymethylphenol in dichloromethane (65 mL) and tetrahydrofuran (15 mL).
The reaction mixture was stirred at room temperature for 4 h.
Then, the solvent was evaporated under vacuum and the crude was purified by chromatography on silica to afford the title compound (72percent):
1H NMR (400 MHz, CDCl3) δ 11.17 (s, 1H), 9.86 (s, 1H), 7.49 (d, J=7.3 Hz, 1H), 7.00 (m, 2H).
Reference: [1] Patent: EP1712235, 2006, A2, . Location in patent: Page/Page column 51
[2] Patent: US2004/220179, 2004, A1, . Location in patent: Page 32-33
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
[4] Patent: WO2006/5909, 2006, A1, . Location in patent: Page/Page column 58
  • 4
  • [ 82944-19-2 ]
  • [ 2420-26-0 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 9, p. 3646 - 3649
  • 5
  • [ 108-43-0 ]
  • [ 925-90-6 ]
  • [ 2420-26-0 ]
Reference: [1] Patent: US5861359, 1999, A,
[2] Patent: US5262390, 1993, A,
  • 6
  • [ 53581-86-5 ]
  • [ 2420-26-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 24, p. 8206 - 8220
[2] ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78
  • 7
  • [ 50-00-0 ]
  • [ 108-43-0 ]
  • [ 68-12-2 ]
  • [ 2420-26-0 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 10, p. 3964 - 3970
  • 8
  • [ 50-00-0 ]
  • [ 108-43-0 ]
  • [ 2420-26-0 ]
  • [ 18362-30-6 ]
Reference: [1] Acta Chemica Scandinavica, 1999, vol. 53, # 4, p. 258 - 262
[2] Journal of Chemical Sciences, 2011, vol. 123, # 4, p. 459 - 466
  • 9
  • [ 5106-98-9 ]
  • [ 2420-26-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 13, p. 3463 - 3468
[2] Journal of Organic Chemistry, 2006, vol. 71, # 9, p. 3646 - 3649
  • 10
  • [ 108-43-0 ]
  • [ 67-66-3 ]
  • [ 2420-26-0 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
  • 11
  • [ 88-33-5 ]
  • [ 2420-26-0 ]
Reference: [1] Patent: DE942808, 1953, ,
[2] Patent: DE942808, 1953, ,
  • 12
  • [ 874-42-0 ]
  • [ 2420-26-0 ]
Reference: [1] Patent: DE942808, 1953, ,
[2] Patent: DE942808, 1953, ,
  • 13
  • [ 104-88-1 ]
  • [ 2420-26-0 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11735 - 11744
  • 14
  • [ 5306-98-9 ]
  • [ 2420-26-0 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
  • 15
  • [ 108-43-0 ]
  • [ 76-03-9 ]
  • [ 2420-26-0 ]
  • [ 56962-11-9 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 496,498
  • 16
  • [ 106-43-4 ]
  • [ 2420-26-0 ]
  • [ 5306-98-9 ]
  • [ 615-74-7 ]
  • [ 104-88-1 ]
  • [ 873-76-7 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 4, p. 551 - 556
  • 17
  • [ 108-43-0 ]
  • [ 76-03-9 ]
  • [ 2420-26-0 ]
  • [ 56962-11-9 ]
Reference: [1] Journal of the Chemical Society, 1933, p. 496,498
  • 18
  • [ 50-00-0 ]
  • [ 108-43-0 ]
  • [ 2420-26-0 ]
  • [ 18362-30-6 ]
Reference: [1] Acta Chemica Scandinavica, 1999, vol. 53, # 4, p. 258 - 262
[2] Journal of Chemical Sciences, 2011, vol. 123, # 4, p. 459 - 466
  • 19
  • [ 2420-26-0 ]
  • [ 30818-28-1 ]
Reference: [1] Bollettino delle Sedute della Accademia Gioenia di Scienze Naturali in Catania, 1957, vol. <4> 4, p. 205,213
  • 20
  • [ 2420-26-0 ]
  • [ 30818-28-1 ]
  • [ 52112-68-2 ]
Reference: [1] Bollettino delle Sedute della Accademia Gioenia di Scienze Naturali in Catania, 1957, vol. <4> 4, p. 205,213
  • 21
  • [ 2420-26-0 ]
  • [ 77-78-1 ]
  • [ 53581-86-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 1, p. 260 - 266
[2] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
[3] Journal of Organic Chemistry, 1964, vol. 29, p. 2693 - 2698
  • 22
  • [ 2420-26-0 ]
  • [ 78443-72-8 ]
Reference: [1] Patent: US6921763, 2005, B2,
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