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[ CAS No. 1013-04-3 ] {[proInfo.proName]}

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Chemical Structure| 1013-04-3
Chemical Structure| 1013-04-3
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Product Details of [ 1013-04-3 ]

CAS No. :1013-04-3 MDL No. :MFCD18252916
Formula : C11H7ClO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SHCCGXNIGGRSMX-UHFFFAOYSA-N
M.W : 206.63 Pubchem ID :12749143
Synonyms :

Calculated chemistry of [ 1013-04-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.92
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) : -4.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 3.73
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 3.19
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.93
Solubility : 0.0241 mg/ml ; 0.000117 mol/l
Class : Soluble
Log S (Ali) : -4.21
Solubility : 0.0129 mg/ml ; 0.0000624 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.07
Solubility : 0.0176 mg/ml ; 0.0000853 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.13

Safety of [ 1013-04-3 ]

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 [ 1013-04-3 ]

* 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 [ 1013-04-3 ]
  • Downstream synthetic route of [ 1013-04-3 ]

[ 1013-04-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 16726-68-4 ]
  • [ 1013-04-3 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With potassium hydroxide In water for 12 h; Inert atmosphere; Reflux
Stage #2: With hydrogenchloride In water
To a solution of 2.44 g (11.9 mmol) of 1-acetyl-4-chloronaphthalene in 5 mL of freshly distilled pyridine under N2 was added 3.33 g (13.1 mmol) of I2 dissolved in 15 mL of freshly distilled pyridine. The mixture was heated at reflux for 40 min, cooled to ambient temperature and diluted with ether until a brown precipitate formed. The precipitate was filtered off, suspended in 12 mL of 6 M aqueous NaOH and heated at reflux for 2 h. After cooling the solution was acidified with 10percent HCl, the crude 4-chloro-1-naphthoic acid was extracted into ether and the ethereal extract was washed with brine. After drying (MgSO4) the solution was concentrated in vacuo. The product was dissolved in 25 mL of MeOH to which 5 mL of concentrated H2SO4 was cautiously added. The solution was heated at reflux for 3 h. After cooling to ambient temperature the crude ester was extracted into ether, the ethereal solution was washed with brine and dried (MgSO4). The solution was concentrated in vacuo to give 1.66 g (63percent) of methyl 4-chloro-1-naphthoate as a brown oil, which was used without further purification: 1H NMR (300 MHz, CDCl3) δ 3.90 (s, 3H), 7.38 (d, J = 7.8, 1H), 7.45-7.56 (m, 2H), 7.87 (d, J = 8.1, 1H), 8.18 (d, J = 8.4, 1H), 8.93 (d, J = 8.1, 1H); 13C NMR (75.5 MHz, CDCl3) δ 52.1, 124.6, 124.9, 125.8. 126.2, 127.1, 128.3, 129.9, 130.7, 132.3, 137.2, 166.9; GC/MS (EI) m/z (rel intensity) 220 (61), 189 (100), 161 (48), 126 (42).A mixture of 0.25 g (1.1 mmol) of methyl 4-chloro-1-naphthoate and 2.10 g (37.4 mmol) of KOH in 20 mL of H2O was heated at reflux for 12 h under N2. The reaction mixture was cooled to ambient temperature, acidified with concentrated HCl and the product was extracted into ether and dried (MgSO4). The organic phase was concentrated in vacuo to give 0.27 g (88percent) of 4-chloro-1-naphthoic acid as an off-white solid: mp 223-224 °C (lit mp 220-221 °C44); 1H NMR (300 MHz, DMSO-d6) δ 7.74-7.81 (m, 3H), 8.11 (d, J = 6 Hz, 1H), 8.28-8.31 (m, 1H), 8.93-8.97 (m, 1H), 13.8 (br s, 1H); 13C NMR (75.5 MHz, DMSO-d6) δ 124.7, 126.1, 126.7, 127.9, 128.3, 129.0, 130.4, 130.6, 132.3, 135.7, 168.5.
84%
Stage #1: With methanol; sodium hydroxide; water In tetrahydrofuran at 20℃;
Stage #2: With hydrogenchloride In water
To a solution of methyl 4-chloro-1-naphthoate (0.299 g, 1.355 mmol) in methanol (10 ml)-tetrahydrofuran (5 ml) was added 1N aqueous sodium hydroxide solution (2.71 ml, 2.71 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was concentrated, diluted with water, acidified with 1N hydrochloric acid and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was crystallized from diethyl ether-hexane to give the objective substance. pale-brown crystal yield 0.234 g, 84percent mp 215-217°C; 1H-NMR (DMSO-d6, 200MHz) δ 7.74-7.85 (3H, m) , 8.12 (1H, d, J = 7.6 Hz), 8.27 8.35 (1H, m), 8.91-9.00 (1H, m); IR (KBr) 3100-2500, 1690, 1510, 1283, 1252, 785, 762 cm-1; Anal. Calcd for C11H7ClO2*0.2H2O: C, 62.85; H, 3.55. Found: C, 62.99; H, 3.31.
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
[2] Patent: EP1362846, 2003, A1, . Location in patent: Page/Page column 50-51
  • 2
  • [ 22531-53-9 ]
  • [ 1013-04-3 ]
Reference: [1] Canadian Journal of Chemistry, 1997, vol. 75, # 10, p. 1346 - 1353
[2] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[3] Journal of Organic Chemistry, 1946, vol. 11, p. 27,30
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
  • 3
  • [ 90-13-1 ]
  • [ 1013-04-3 ]
Reference: [1] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
[2] Journal of Organic Chemistry, 1946, vol. 11, p. 27,30
[3] Journal of the Chemical Society, 1946, p. 144
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
  • 4
  • [ 4053-08-1 ]
  • [ 16650-52-5 ]
  • [ 1013-04-3 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 19, p. 4690 - 4697
  • 5
  • [ 16243-44-0 ]
  • [ 1013-04-3 ]
Reference: [1] Chemische Berichte, 1895, vol. 28, p. 1839
[2] Collection of Czechoslovak Chemical Communications, 1997, vol. 62, # 11, p. 1737 - 1746
  • 6
  • [ 32018-87-4 ]
  • [ 1013-04-3 ]
Reference: [1] Journal of the American Chemical Society, 1962, vol. 84, p. 3541 - 3546
  • 7
  • [ 58728-64-6 ]
  • [ 1013-04-3 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1997, vol. 62, # 11, p. 1737 - 1746
  • 8
  • [ 129667-52-3 ]
  • [ 1013-04-3 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1997, vol. 62, # 11, p. 1737 - 1746
  • 9
  • [ 53220-82-9 ]
  • [ 1013-04-3 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 1426
  • 10
  • [ 50265-01-5 ]
  • [ 1013-04-3 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 144
  • 11
  • [ 22531-53-9 ]
  • [ 1013-04-3 ]
  • [ 32405-50-8 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 7, p. 646 - 649
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