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[ CAS No. 586-42-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 586-42-5
Chemical Structure| 586-42-5
Chemical Structure| 586-42-5
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Product Details of [ 586-42-5 ]

CAS No. :586-42-5 MDL No. :MFCD00045847
Formula : C9H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CHZPJUSFUDUEMZ-UHFFFAOYSA-N
M.W : 164.16 Pubchem ID :220324
Synonyms :

Calculated chemistry of [ 586-42-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.6
TPSA : 54.37 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) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 1.56
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 1.28
Log Po/w (SILICOS-IT) : 1.55
Consensus Log Po/w : 1.45

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.37 mg/ml ; 0.00834 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 0.801 mg/ml ; 0.00488 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.1
Solubility : 1.31 mg/ml ; 0.00798 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.14

Safety of [ 586-42-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 586-42-5 ]

* 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 [ 586-42-5 ]
  • Downstream synthetic route of [ 586-42-5 ]

[ 586-42-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 586-42-5 ]
  • [ 18107-18-1 ]
  • [ 21860-07-1 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 0.166667 h; 3.95 g (24.06 mmol) of 3-acetylbenzoic acid were initially charged in 100 ml of toluene and 75 ml of methanol. After dropwise addition of 4.12 g (36.09 mmol) of trimethylsilyldiazomethane 2M in diethyl ether at RT, an instant evolution of gas in the reaction solution was observed. Another 0.27 g (2.4 mmol) of trimethylsilyldiazomethane 2M in diethyl ether was added until the reaction solution remained yellow, and the mixture was stirred at RT for 10 min. The reaction solution was evaporated. Yield: 4.28 g (100percent of theory) LC-MS (Method 4): Rt=1.38 min; MS (ESIpos): m/z=179 [M+H]+.
Reference: [1] Patent: US2013/210795, 2013, A1, . Location in patent: Paragraph 0510-0513
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7719 - 7725
[3] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9467 - 9470
  • 2
  • [ 67-56-1 ]
  • [ 586-42-5 ]
  • [ 21860-07-1 ]
YieldReaction ConditionsOperation in experiment
97% for 26.5 h; Reflux concentrated sulfuric acid (4 mL) was added to methanol (60mL) solution of 3-acetyl-benzoic acid 20 (2.02 g, 12.3 mmol) and was refluxedwith stirring for 26.5 hours. After removing the solvent, the residue waspoured into water, and extracted with ethyl ether, and after washing theorganic layer with water and brine, it was dried over anhydrous sodium sulfate.Then, the filtrate was concentrated in vacuum to obtain compound 21 as a whitesolid 2.12 g (97percent yield).
87% Reflux 3-acetylbenzoic acid (200 g) was dissolved in 2 L methanol (or ethanol, propanol) and 128 ml concentrated sulfuric acid was slowly added at room temperature. The mixture was heated to reflux overnight. After the reaction was completed, the methanol was removed by concentration under reduced pressure. The remaining oil was dissolved in 2 L ethyl acetate and washed with 1 L water for once, 1 L saturated sodium bicarbonate for twice, and 0.5 L saturated brine for once. The organic phase was dried by using anhydrous sodium sulfate and the ethyl acetate was removed by concentration under reduced pressure to obtain a red oil, cooled at room temperature to obtain yellow solid (189 g), yield: 87percent, 1H NMR (400 MHz, Chloroform-d) 8.58 m, 1H), 8.30-8.18 (m, 2H), 7.60-7.54 (m, 1H), 3.96 (s, 3H), 2.66 (s, 3H).
83% for 24 h; Reflux The 3 - acetyl benzoic acid (compound 1) (5.00g, 30 . 7mmol) dissolved in 147 ml of methanol, slowly dropping 10 ml concentrated sulfuric acid, stirring reflux, the reaction 24h and reducing pressure to evaporate the methanol, add 80 ml water, extracted with ethyl acetate 3 times, the combined organic phase are water and saturated salt water washing, then drying with anhydrous sodium sulfate, filtered, concentrated to obtain yellow liquid 4.54g, yield is 83percent
83% for 24 h; Reflux To a solution of 3-acetylbenzoic acid (1) (5.00 g, 30.7 mmol) in MeOH (147 mL) added into 10 mL concentrated H2SO4. The reaction mixture was stirred at reflux for 24 h. After removal of the solvent, the residue was poured into H2O (80 mL) and extracted with EtOAc. The organic layer was washed with H2O and brine and dried over Na2SO4. Filtration and concentration in vacuo to give 2 as light yellow liquid (4.54 g, 83percent).
1H NMR (400 MHz, CDCl3) δ 8.60 (s, ArH, 1H), 8.24 (t, J = 7.5 Hz, ArH, 1H), 8.17 (d, J = 7.5 Hz, ArH, 1H), 7.57 (t, J = 7.7 Hz, ArH, 1H), 3.96 (s, OCH3, 3H), 2.66 (s, CH3, 3H). ESI-MS m/z: 179 [M+H]+.

Reference: [1] ChemMedChem, 2014, vol. 9, # 3, p. 657 - 664
[2] Patent: JP2016/17040, 2016, A, . Location in patent: Paragraph 0025; 0026
[3] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2091 - 2100
[4] Patent: US2018/79749, 2018, A1, . Location in patent: Paragraph 0144; 0145
[5] Patent: CN106866627, 2017, A, . Location in patent: Paragraph 0064; 0066-0068
[6] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 182 - 199
[7] Chemische Berichte, 1900, vol. 33, p. 3409
[8] Advanced Synthesis and Catalysis, 2009, vol. 351, # 10, p. 1677 - 1684
  • 3
  • [ 586-42-5 ]
  • [ 74-88-4 ]
  • [ 21860-07-1 ]
Reference: [1] Patent: US5521179, 1996, A,
  • 4
  • [ 586-42-5 ]
  • [ 21860-07-1 ]
Reference: [1] Patent: US4499299, 1985, A,
  • 5
  • [ 186581-53-3 ]
  • [ 586-42-5 ]
  • [ 21860-07-1 ]
Reference: [1] Journal of medicinal chemistry, 1970, vol. 13, # 4, p. 674 - 680
[2] Recueil des Travaux Chimiques des Pays-Bas, 1969, vol. 88, p. 52 - 61
[3] Magnetic Resonance in Chemistry, 1989, vol. 27, # 6, p. 585 - 591
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 23, p. 5033 - 5040
  • 6
  • [ 22071-15-4 ]
  • [ 56338-25-1 ]
  • [ 137474-24-9 ]
  • [ 586-42-5 ]
  • [ 579-18-0 ]
  • [ 28286-79-5 ]
  • [ 67173-18-6 ]
Reference: [1] Journal of Mass Spectrometry, 2011, vol. 46, # 4, p. 391 - 401
  • 7
  • [ 66067-43-4 ]
  • [ 56338-25-1 ]
  • [ 137474-24-9 ]
  • [ 586-42-5 ]
  • [ 579-18-0 ]
  • [ 28286-79-5 ]
  • [ 67173-18-6 ]
Reference: [1] Journal of Mass Spectrometry, 2011, vol. 46, # 4, p. 391 - 401
  • 8
  • [ 586-42-5 ]
  • [ 283608-37-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2628 - 2639
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