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[ CAS No. 581-43-1 ] {[proInfo.proName]}

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Chemical Structure| 581-43-1
Chemical Structure| 581-43-1
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Product Details of [ 581-43-1 ]

CAS No. :581-43-1 MDL No. :MFCD00004082
Formula : C10H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MNZMMCVIXORAQL-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :93552
Synonyms :

Calculated chemistry of [ 581-43-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.99
TPSA : 40.46 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) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.9
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.88

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.65
Solubility : 0.361 mg/ml ; 0.00226 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.679 mg/ml ; 0.00424 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.91
Solubility : 0.197 mg/ml ; 0.00123 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 581-43-1 ]

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 [ 581-43-1 ]

* 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 [ 581-43-1 ]
  • Downstream synthetic route of [ 581-43-1 ]

[ 581-43-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 581-43-1 ]
  • [ 13720-06-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 8, p. 1055 - 1060
  • 2
  • [ 135-19-3 ]
  • [ 581-43-1 ]
  • [ 575-38-2 ]
  • [ 575-44-0 ]
  • [ 582-17-2 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3099 - 3102
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3099 - 3102
  • 3
  • [ 581-43-1 ]
  • [ 74-88-4 ]
  • [ 5486-55-5 ]
Reference: [1] Canadian Journal of Chemistry, 1987, vol. 65, p. 2397 - 2404
[2] CrystEngComm, 2017, vol. 19, # 11, p. 1464 - 1469
[3] Chinese Journal of Chemistry, 2017, vol. 35, # 8, p. 1289 - 1293
[4] Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 8744 - 8758
[5] Journal of Chemical Research, 2012, vol. 36, # 11, p. 675 - 677
  • 4
  • [ 581-43-1 ]
  • [ 77-78-1 ]
  • [ 5486-55-5 ]
Reference: [1] Israel Journal of Chemistry, 2014, vol. 54, # 5-6, p. 796 - 816
[2] Chemische Berichte, 1907, vol. 40, p. 1413
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 20, p. 2891 - 2898
[4] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 545 - 550
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 22, p. 5293 - 5300
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5720 - 5733
  • 5
  • [ 581-43-1 ]
  • [ 77-78-1 ]
  • [ 5486-55-5 ]
  • [ 5111-66-0 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 15, p. 2347 - 2354
[2] Patent: US6365775, 2002, B1, . Location in patent: Page column 11
  • 6
  • [ 581-43-1 ]
  • [ 80-48-8 ]
  • [ 5486-55-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1964, vol. 7, p. 519 - 524
  • 7
  • [ 74-83-9 ]
  • [ 581-43-1 ]
  • [ 5486-55-5 ]
Reference: [1] Journal of Fluorine Chemistry, 2014, vol. 168, p. 193 - 197
  • 8
  • [ 67-56-1 ]
  • [ 581-43-1 ]
  • [ 5486-55-5 ]
Reference: [1] Chemische Berichte, 1903, vol. 36, p. 570
  • 9
  • [ 581-43-1 ]
  • [ 77-78-1 ]
  • [ 5111-66-0 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 1738
[2] Journal of medicinal chemistry, 1971, vol. 14, # 11, p. 1023 - 1026
[3] Patent: US5238981, 1993, A,
[4] Patent: US5585042, 1996, A,
  • 10
  • [ 581-43-1 ]
  • [ 5111-66-0 ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate; dimethyl sulfate In N,N-dimethyl-formamide Example 1
(Reference Example)
6-Methoxy-2-naphthol
Potassium carbonate (1.244 g) was added to a solution of commercially available 2,6-dihydroxynaphthalene (961 mg) in N,N-dimethylformamide (100 ml), and the admixture was stirred at room temperature for 30 minutes.
Dimethyl sulfate (1.14 ml) was slowly added dropwise to the mixture and the resulting mixture was further stirred at room temperature overnight.
The reaction mixture thus prepared was neutralized with a 2N HCl solution and then partitioned between water and ethyl acetate, and the ethyl acetate layer was dried with anhydrous magnesium sulfate.
After removing the solvent by distillation under reduced pressure, the resulting residue was purified by column chromatography on silica gel (eluding with chloroform/ethyl acetate) to obtain 307 mg of the title compound (yield: 29percent).
1 H-NMR (CDCl3, 90 MHz): δ 3.89 (s, 3H), 7.00~7.18 (m, 4H), 7.53~7.70 (m, 2H)
Mass spectrometry data (FD-MS, m/z): 174 (M+)
Reference: [1] Patent: US6143764, 2000, A,
  • 11
  • [ 581-43-1 ]
  • [ 77-78-1 ]
  • [ 5486-55-5 ]
  • [ 5111-66-0 ]
Reference: [1] Tetrahedron, 1982, vol. 38, # 15, p. 2347 - 2354
[2] Patent: US6365775, 2002, B1, . Location in patent: Page column 11
  • 12
  • [ 581-43-1 ]
  • [ 52727-28-3 ]
Reference: [1] Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1474 - 1477
  • 13
  • [ 581-43-1 ]
  • [ 132178-78-0 ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide In tetrahydrofuranReflux Example 1 - l,5-dibromonaphthalene-2,6-diol [00123] To a solution of naphthalene -2, 6-diol (1) (5.1 g) in 50 mL of Tetrahydrofuran (THF), was added N-Bromosuccinimide (NBS, 1 1.4 g). The mixture was re fluxing and monitored by GCMS. The reaction was quenched with saturated sodium thiosulfate, and filtered. The solid was washed by water to afford 1 ,5- dibromonaphthalene-2,6-diol (90percent). LRMS (ESI): Calcd. for Ci0H6Br2O2: 317.8714, Found: 317.9.
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 36, p. 6487 - 6490
[2] Patent: WO2013/149001, 2013, A2, . Location in patent: Paragraph 00123
[3] Journal of the Chemical Society, 1937, p. 1859,1861
[4] Patent: US2011/224445, 2011, A1, . Location in patent: Page/Page column 8
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