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[ CAS No. 56525-63-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 56525-63-4
Chemical Structure| 56525-63-4
Chemical Structure| 56525-63-4
Structure of 56525-63-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 56525-63-4 ]

CAS No. :56525-63-4 MDL No. :MFCD00205141
Formula : C9H9ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KTFQDZCNPGFKAH-UHFFFAOYSA-N
M.W : 184.62 Pubchem ID :2801405
Synonyms :

Calculated chemistry of [ 56525-63-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.7
TPSA : 26.3 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) : -4.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.44
Log Po/w (XLOGP3) : 3.46
Log Po/w (WLOGP) : 2.44
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 2.8
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.4
Solubility : 0.0731 mg/ml ; 0.000396 mol/l
Class : Soluble
Log S (Ali) : -3.69
Solubility : 0.0374 mg/ml ; 0.000202 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.0616 mg/ml ; 0.000333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 56525-63-4 ]

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 [ 56525-63-4 ]

* 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 [ 56525-63-4 ]
  • Downstream synthetic route of [ 56525-63-4 ]

[ 56525-63-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 99-75-2 ]
  • [ 34040-64-7 ]
  • [ 56525-63-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, p. 24 - 32[2] Zhurnal Organicheskoi Khimii, 1986, vol. 22, # 1, p. 30 - 39
  • 2
  • [ 56525-63-4 ]
  • [ 74733-30-5 ]
YieldReaction ConditionsOperation in experiment
92% With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; potassium bromide In water at 120℃; Microwave irradiation General procedure: The reaction mixture was treated in a controlled microwavesynthesizer (Biotage Initiator+SP Wave model, 0–200 W at2.45 GHz, capped at 60 W during steady state) for severalminutes (the reaction attained 120 °C at 1 bar pressure). Thefinal products were isolated by column chromatographyusing an EtOAc–hexane gradient
84% With 2,2'-azobis(2-methylpropionitrile); N-Bromosuccinimide In tetrachloromethane for 18 h; Heating / reflux To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added N-bromosuccinimide (5.8 g, 32.0 mmol) and 2,2'-azo-bis(2-methylpropionitrile) (0.442 g, 2.70 mmol). The mixture was heated at reflux for 18 h, then allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether --> 5percent ethyl acetate/95percent pet. ether) to give an oil identified as methyl 4-bromomethyl-3-chlorobenzoate (5.96 g, 84percent).
84% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 18 h; Heating / reflux To a solution of methyl 3-chloro-4-methylbenzoate (5.0g, 27.1mmol) in carbon tetrachloride (50ml) were added NBS (5.8g, 32.0mmol) and AIBN (0.442g, 2.70mmol). The mixture was stirred at reflux for 18h. The mixture was al;lowed to cool to room temperature and then concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96g (84percent).
84% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 18 h; Heating / reflux To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added NBS (5.8 g, 32.0 mmol) and AIBN (0.442 g, 2.70 mmol)..
The mixture was stirred at reflux for 18 h..
The mixture was allowed to cool to room temperature and then concentrated in vacuo..
The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96 g (84percent).
75% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4 h; Heating / reflux step 1-A mixture of 184a (2 mmol), NBS (2.2 mmol) and AIBN (100 mg) in CCl4 (20 mL) was heated at reflux for 4 h.
The mixture was cooled, filtered and the filtrate was concentrated in vacuo.
The residue was purified by SiO2 chromatography to afford 0.395 g (75percent) of 184b.
84% With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane A1.
Methyl 4bromomethyl-3-chlorobenzoate
To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added NBS (5.8 g, 32.0 mmol) and AIBN (0.442 g, 2.70 mmol).
The mixture was stirred at reflux for 18 h.
The mixture was allowed to cool to room temperature and then concentrated in vacuo.
The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96 g (84percent).
84% With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane A1.
Methyl 4-bromomethyl-3-chlorobenzoate
To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added NBS (5.8 g, 32.0 mmol) and AIBN (0.442 g, 2.70 mmol).
The mixture was stirred at reflux for 18 h.
The mixture was allowed to cool to room temperature and then concentrated in vacuo.
The residue was purified by flash chromatography on silica (eluant EtOAc:pet. ether 0:100 to 5:95); yield 5.96 g (84percent).

Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 23, p. 7774 - 7789
[2] Synlett, 2014, vol. 25, # 17, p. 2485 - 2487
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 17, p. 4585 - 4589
[4] Patent: EP1449844, 2004, A1, . Location in patent: Page 20
[5] Patent: WO2006/18443, 2006, A1, . Location in patent: Page/Page column 19
[6] Patent: US6664249, 2003, B1, . Location in patent: Page column 10
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7703 - 7724
[8] Patent: US2008/146595, 2008, A1, . Location in patent: Page/Page column 39; 40
[9] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 345 - 348
[10] Patent: US2003/87892, 2003, A1,
[11] Patent: US5409928, 1995, A,
[12] Patent: US2004/38962, 2004, A1,
[13] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4481 - 4487
[14] Patent: WO2012/118782, 2012, A1, . Location in patent: Page/Page column 97-98
[15] Patent: US2013/317003, 2013, A1, . Location in patent: Paragraph 0468
[16] Patent: US2015/284375, 2015, A1, . Location in patent: Paragraph 0309
[17] Patent: WO2017/156165, 2017, A1, . Location in patent: Paragraph 00525; 00528; 00529
  • 3
  • [ 56525-63-4 ]
  • [ 1134777-59-5 ]
  • [ 74733-30-5 ]
Reference: [1] Patent: WO2009/36996, 2009, A2, . Location in patent: Page/Page column 97-98
  • 4
  • [ 56525-63-4 ]
  • [ 74733-26-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
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