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[ CAS No. 55289-04-8 ] {[proInfo.proName]}

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Chemical Structure| 55289-04-8
Chemical Structure| 55289-04-8
Structure of 55289-04-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 55289-04-8 ]

CAS No. :55289-04-8 MDL No. :MFCD02683035
Formula : C8H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :BQAMEYNBQIHQPO-UHFFFAOYSA-N
M.W : 133.15 Pubchem ID :22616094
Synonyms :

Calculated chemistry of [ 55289-04-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.15
TPSA : 44.02 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 : Yes
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.42
Log Po/w (XLOGP3) : 1.65
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 1.12
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 0.945 mg/ml ; 0.0071 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 0.864 mg/ml ; 0.00649 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.26
Solubility : 0.73 mg/ml ; 0.00548 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 55289-04-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55289-04-8 ]

* 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 [ 55289-04-8 ]
  • Downstream synthetic route of [ 55289-04-8 ]

[ 55289-04-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 77533-17-6 ]
  • [ 55289-04-8 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 20℃; for 3.25 h;
Stage #2: With water In dichloromethane for 0.5 h;
Preparation 74: 3-Hydroxy-2-methylbenzonitrile A solution of 3-methoxy-2-methylbenzonitrile [(1 g, 6.79 mmol) U.S. Pat. No. 5,965,766, p6] and tetra nbutyl ammonium iodide (4.12 g, 17 mmol) in dichloromethane (15 mL) was cooled to -78° C. and purged with nitrogen. Boron trichloride (1M in dichloromethane, 17 mL, 17 mmol) was added dropwise and the mixture was stirred for 15 minutes at -78° C. and at room temperature for 3 hours. The reaction mixture was quenched with water, stirred for 30 minutes and concentrated in vacuo. The aqueous residue was extracted with diethyl ether and the organic solution was washed with water (.x.5), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a brown solid in 91percent yield, 826 mg. 1H NMR(400 MHz, CDCl3) δ: 2.20 (s, 3H), 7.10 (m, 1H), 7.20 (d, 1H), 10.10 (s, 1H); LRMS APCI m/z 132 [M-H]-
Reference: [1] Patent: US2006/160786, 2006, A1, . Location in patent: Page/Page column 36-37
  • 2
  • [ 7766-23-6 ]
  • [ 55289-04-8 ]
YieldReaction ConditionsOperation in experiment
7 g With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 120℃; for 16 h; Inert atmosphere A) 3-hydroxy-2-methylbenzonitrile To a solution of 3-bromo-2-methylphenol (20.0 g) in DMF (250 mL) were added copper (I) cyanide (19.0 g) and tetrakis (triphenylphosphine) palladium(O) (3.70 g) , and the mixture was heated with stirring at 120°C for 16 hr under nitrogen atmosphere. The reaction mixture was poured into water, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with tert- butyl methyl ether to give the title compound (7.00 g) . 1H NMR (400 MHz, CDC13) δ 2.28 (3H, s) , 7.00-7.15 (1H, m) , 7.14-7.24 (2H, m) , 10.11 (1H, brs) .
Reference: [1] Patent: WO2015/163485, 2015, A1, . Location in patent: Paragraph 0398
  • 3
  • [ 71516-35-3 ]
  • [ 55289-04-8 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1021
  • 4
  • [ 3260-87-5 ]
  • [ 544-92-3 ]
  • [ 55289-04-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 2435 - 2447
  • 5
  • [ 69022-35-1 ]
  • [ 55289-04-8 ]
Reference: [1] Chemische Berichte, 1904, vol. 37, p. 1021
  • 6
  • [ 55289-04-8 ]
  • [ 55289-05-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 2435 - 2447
  • 7
  • [ 55289-04-8 ]
  • [ 55289-16-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 2435 - 2447
  • 8
  • [ 55289-04-8 ]
  • [ 603-80-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1974, p. 2435 - 2447
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