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[ CAS No. 13395-85-2 ] {[proInfo.proName]}

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Chemical Structure| 13395-85-2
Chemical Structure| 13395-85-2
Structure of 13395-85-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 13395-85-2 ]

CAS No. :13395-85-2 MDL No. :MFCD16657845
Formula : C10H13ClO Boiling Point : -
Linear Structure Formula :- InChI Key :YLSXYZWJAZVUBD-UHFFFAOYSA-N
M.W :184.66 Pubchem ID :518765
Synonyms :

Calculated chemistry of [ 13395-85-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.74
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 3.81
Log Po/w (WLOGP) : 3.34
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 3.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.69
Solubility : 0.0378 mg/ml ; 0.000205 mol/l
Class : Soluble
Log S (Ali) : -3.93
Solubility : 0.0217 mg/ml ; 0.000118 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.65
Solubility : 0.0414 mg/ml ; 0.000224 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.24

Safety of [ 13395-85-2 ]

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 [ 13395-85-2 ]

* 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 [ 13395-85-2 ]
  • Downstream synthetic route of [ 13395-85-2 ]

[ 13395-85-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 106-48-9 ]
  • [ 75-65-0 ]
  • [ 13395-85-2 ]
YieldReaction ConditionsOperation in experiment
71% for 48 h; Inert atmosphere The ligand precursor 3-ter -butyl-5-chlorosalicylaldehyde has been previously reported, and FontWeight="Bold" FontSize="10" H NMR assignments are included that match well with those in the literature. The yield represents average isolated yields. The precursor to the salicylaldehyde, 2-tert- butyl-4-chlorophenol, was synthesized according to literature procedure. 4-Chlorophenol (Combi-B locks, 8.00 g, 62.2 mmol) was dissolved in tert-butyl alcohol (Aldrich, 1 1.9 mL, 124 mmol), and 7.50 mL of concentrated H2S04 was added dropwise over 5 minutes, turning the solution from a pale yellow to a light orange. The solution was stirred for 2 days, neutralized with Na2C03 (aq), and then extracted into diethyl ether and dried over Na2S04. The product was concentrated and purified by column chromatography (95:5, hex:EtOAc) resulting in a yellow oil (71percent isolated yield). Using a modified Duff reaction, 2-/ert-butyl-4- chlorophenol was formylated as reported by Jacobsen et al. The product was purified by column chromatography (90: 10, hex:EtOAc) to yield a crystalline yellow solid (24percent isolated yield). NMR spectrum in ppm (CDC13, 400 MHz): δ 1 1.72 (s, I H); 9.82 (s, IH); 7.46 (d, J = 2.6 Hz, IH); 7.38 (d, J = 2.6 Hz, IH); 1.41 (s, 12H).
68% at 20℃; for 48 h; Step 1 : 2-(teff-Butyl)-4-chlorophenol (P19a) To a mixture of 4-chlorophenol (50 g, 0.39 mol) and M3uOH (57.6 g, 0.78 mol) was added cone. H2S04 (40 mL) and the solution was stirred at rt for 48 h, poured into ice-water and extracted with EA twice. The combined organic layers were washed with water (3x) and brine consecutively, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 40/1) to give compound P19a (48.5 g, 68percent) as a colorless solid
54% at 20℃; for 48 h; To a mixture of p-chlorophenol (19.0 g, 147.8 mmol) and tert-butanol (21.9 g, 295.6 mmol) was added concentrated sulfuric acid (15 mL), and the mixture was stirred at room temperature for 2 days.
The reaction mixture was poured into ice water (300 mL), and the mixture was extracted with ethyl acetate.
The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered.
The filtrate was concentrated under reduced pressure.
The residue was purified by silica gel column chromatography (hexane:ethyl acetate 95:5) to give the title compound (14.3 g, yield 54percent) as a brown oil.
1H NMR (300 MHz, CDCl3) δ 7.21 (d, J=2.7Hz, 1H), 7.02 (dd, J=8.3, 2.7Hz, 1H), 6.60 (d, J=8.7Hz, 1H), 4.95 (br s, 1H), 1.39 (s, 9H).
Reference: [1] Patent: WO2016/25675, 2016, A1, . Location in patent: Paragraph 0100
[2] Journal of the American Chemical Society, 2014, vol. 136, # 45, p. 15897 - 15900
[3] Journal of the American Chemical Society, 2016, vol. 138, # 22, p. 7107 - 7113
[4] Patent: WO2013/79223, 2013, A1, . Location in patent: Page/Page column 77
[5] European Journal of Inorganic Chemistry, 2013, # 14, p. 2538 - 2548
[6] Patent: EP2202223, 2010, A1, . Location in patent: Page/Page column 58-59
[7] Journal of the American Chemical Society, 1956, vol. 78, p. 4604,4608
  • 2
  • [ 88-18-6 ]
  • [ 13395-85-2 ]
  • [ 4237-37-0 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[3] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[4] Dalton Transactions, 2008, # 48, p. 6883 - 6885
  • 3
  • [ 88-18-6 ]
  • [ 13395-85-2 ]
Reference: [1] Synlett, 2018, vol. 29, # 16, p. 2155 - 2160
  • 4
  • [ 88-18-6 ]
  • [ 13395-85-2 ]
  • [ 4237-37-0 ]
  • [ 13395-86-3 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 2, p. 809 - 813
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