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[ CAS No. 54884-55-8 ] {[proInfo.proName]}

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Chemical Structure| 54884-55-8
Chemical Structure| 54884-55-8
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Product Details of [ 54884-55-8 ]

CAS No. :54884-55-8 MDL No. :MFCD08235006
Formula : C9H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :QLUHWZADTAIBKK-UHFFFAOYSA-N
M.W : 150.17 Pubchem ID :640238
Synonyms :

Calculated chemistry of [ 54884-55-8 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 43.29
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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 1.82
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.13
Solubility : 1.12 mg/ml ; 0.00748 mol/l
Class : Soluble
Log S (Ali) : -1.89
Solubility : 1.94 mg/ml ; 0.0129 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.216 mg/ml ; 0.00144 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.06

Safety of [ 54884-55-8 ]

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 [ 54884-55-8 ]

* 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 [ 54884-55-8 ]
  • Downstream synthetic route of [ 54884-55-8 ]

[ 54884-55-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 54884-55-8 ]
  • [ 6161-64-4 ]
Reference: [1] Tetrahedron, 1996, vol. 52, # 6, p. 2199 - 2216
  • 2
  • [ 54884-55-8 ]
  • [ 74-88-4 ]
  • [ 6161-64-4 ]
Reference: [1] Synthesis, 1983, # 12, p. 1000 - 1002
  • 3
  • [ 18362-36-2 ]
  • [ 74-88-4 ]
  • [ 54884-55-8 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 20℃;
General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg,0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg,0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 μL, 68 mg,0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.
Reference: [1] Tetrahedron, 2008, vol. 64, # 49, p. 11050 - 11057
[2] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 734 - 746
[3] Journal of the American Chemical Society, 1979, vol. 101, p. 7114 - 7116
  • 4
  • [ 2944-49-2 ]
  • [ 54884-55-8 ]
YieldReaction ConditionsOperation in experiment
44.2% With dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate In water; acetonitrile for 0.25 h; Reflux 2-Methoxy-6-methylbenzaldehyde
Potassium peroxy disulphate (89.31g, 0.33mol) and copper (II) sulphate pentahydrate (27.22 g, 0.11 mol) was added to a solution of 2,3-dimethylanisole (15 g, 0.11 mol) in acetonitrile water mixture (750 ml, 1:1).
The reaction mixture was stirred for 15 min at reflux until no starting material remained as judged by TLC (Thin Layer Chromatography).
On cooling the reaction mixture to room temperature, the product was extracted into dichloromethane (2 x 225ml).
The organic layer was washed with water (2 x 100ml) and brine solution (100 ml).
The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give the crude product.
Column chromatography using 4/96 ethyl acetate/ hexane yielded 2-Methoxy-6-methylbenzaldehyde (7.32g, 44.2percent).
1H NMR (300 MHz, CDCl3), δ 2.60 (3H, s), 3.90 (3H, s), 6.80(2H, t), 7.40(1H, t), 10.65(1 H, s).
Reference: [1] Tetrahedron, 1996, vol. 52, # 6, p. 2199 - 2216
[2] Chemical Communications, 2013, vol. 49, # 77, p. 8626 - 8628
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 762 - 766[4] Angew. Chem., 2013, vol. 125, # 2, p. 791 - 796,6
[5] Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10322 - 10325
[6] Patent: EP2110374, 2009, A1, . Location in patent: Page/Page column 26-27
[7] Synthesis, 1983, # 12, p. 1000 - 1002
[8] Synthesis, 1987, # 8, p. 723 - 724
[9] Synthesis, 1984, # 6, p. 504 - 506
[10] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
[11] Angewandte Chemie - International Edition, 2012, vol. 51, # 4, p. 1071 - 1074
[12] Patent: WO2015/153410, 2015, A1, . Location in patent: Paragraph 00207-00211
[13] Chemical Communications, 2016, vol. 52, # 60, p. 9426 - 9429
[14] Patent: WO2018/17858, 2018, A1, . Location in patent: Paragraph 0157-0158
[15] Chemistry - A European Journal, 2018, vol. 24, # 14, p. 3413 - 3419
  • 5
  • [ 89244-39-3 ]
  • [ 54884-55-8 ]
Reference: [1] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 10, p. 1358 - 1361
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 1995, vol. 36, # 12, p. 1183 - 1191
[3] Patent: WO2015/66241, 2015, A1, . Location in patent: Page/Page column 48
  • 6
  • [ 35387-94-1 ]
  • [ 68-12-2 ]
  • [ 54884-55-8 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 8, p. 1732 - 1735
  • 7
  • [ 89244-40-6 ]
  • [ 54884-55-8 ]
Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
[2] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
  • 8
  • [ 2944-49-2 ]
  • [ 54884-55-8 ]
  • [ 137644-93-0 ]
Reference: [1] European Journal of Organic Chemistry, 2010, # 3, p. 555 - 564
  • 9
  • [ 6520-83-8 ]
  • [ 54884-55-8 ]
Reference: [1] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 10, p. 1358 - 1361
  • 10
  • [ 526-75-0 ]
  • [ 54884-55-8 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 29, p. 10322 - 10325
  • 11
  • [ 20383-28-2 ]
  • [ 54884-55-8 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1687 - 1700
  • 12
  • [ 3724-55-8 ]
  • [ 66947-61-3 ]
  • [ 54884-55-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 1383 - 1385
  • 13
  • [ 67-56-1 ]
  • [ 54884-55-8 ]
  • [ 79383-44-1 ]
Reference: [1] Synthesis, 1984, # 6, p. 504 - 506
  • 14
  • [ 54884-55-8 ]
  • [ 79383-44-1 ]
Reference: [1] Patent: WO2015/153410, 2015, A1,
[2] Patent: WO2018/17858, 2018, A1,
  • 15
  • [ 54884-55-8 ]
  • [ 53005-44-0 ]
Reference: [1] Patent: WO2012/151525, 2012, A1,
[2] Patent: US2012/289496, 2012, A1,
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