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[ CAS No. 94-08-6 ] {[proInfo.proName]}

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Chemical Structure| 94-08-6
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Product Details of [ 94-08-6 ]

CAS No. :94-08-6 MDL No. :MFCD00009117
Formula : C10H12O2 Boiling Point : -
Linear Structure Formula :CH3C6H4COOC2H5 InChI Key :NWPWRAWAUYIELB-UHFFFAOYSA-N
M.W : 164.20 Pubchem ID :66743
Synonyms :

Calculated chemistry of [ 94-08-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.49
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) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 2.86
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 2.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.242 mg/ml ; 0.00147 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.139 mg/ml ; 0.000849 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0911 mg/ml ; 0.000555 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.34

Safety of [ 94-08-6 ]

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 [ 94-08-6 ]

* 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 [ 94-08-6 ]
  • Downstream synthetic route of [ 94-08-6 ]

[ 94-08-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 94-08-6 ]
  • [ 7153-22-2 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4115 - 4122
  • 2
  • [ 94-08-6 ]
  • [ 6232-88-8 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 95, p. 11155 - 11157
  • 3
  • [ 94-08-6 ]
  • [ 26496-94-6 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4 h; Reflux To a stirred solution of 4-Methyl-benzoic acid ethyl ester (5 g, 30.49 mmol)) in carbon tetrachloride (35 ml) was added N-bromosuccinimide (5.90 g, 33.53 mmol) and benzoyl peroxide (720 mg, 1.52 mmol). The feaction mixture was heated under reflux for 4 h. It was monitored by thin layer chromatography. The reaction mixture was cooled to room temperature and then filtered. The filtrate was evaporated under vacuo to afford color less oil (7.25 g, 98 percent).
89% With Oxone; water; potassium bromide In dichloromethane at 20℃; for 26 h; Irradiation; Sealed tube General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 × 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93percent).
Reference: [1] Chinese Journal of Chemistry, 2012, vol. 30, # 8, p. 1906 - 1908
[2] Patent: WO2009/109999, 2009, A1, . Location in patent: Page/Page column 68
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[4] Synthesis (Germany), 2018, vol. 50, # 24, p. 4933 - 4939
[5] Tetrahedron, 2007, vol. 63, # 36, p. 8891 - 8901
[6] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 18, p. 5270 - 5273
[7] Synlett, 2003, # 5, p. 702 - 704
[8] European Journal of Organic Chemistry, 2006, # 2, p. 483 - 488
[9] New Journal of Chemistry, 2000, vol. 24, # 12, p. 977 - 985
[10] European Journal of Medicinal Chemistry, 2003, vol. 38, # 6, p. 581 - 586
[11] Journal of the American Chemical Society, 1958, vol. 80, p. 4622,4624
[12] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[13] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1981 - 1984
[14] European Journal of Medicinal Chemistry, 2009, vol. 44, # 5, p. 1913 - 1920
[15] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 12, p. 3283 - 3287
[16] Chemical Communications, 2013, vol. 49, # 95, p. 11155 - 11157
[17] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 4
  • [ 94-08-6 ]
  • [ 34241-39-9 ]
  • [ 26496-94-6 ]
YieldReaction ConditionsOperation in experiment
63% With N-Bromosuccinimide In tetrachloromethane (a)
Ethyl 4-bromomethylbenzoate
To a solution of ethyl p-toluate (40.0 g, 0.24 mol) and NBS (43.44 g, 0.24 mol) in carbon tetrachloride (200 ml) heated at reflux was added 2,2'-azobis-(2-methylpropionitrile) (180 mg).
The mixture was heated at reflux for 4 h, cooled to room temperature and stirred overnight.
The white precipitate of succinimide that formed on the surface of the solution was separated and discarded.
The filtrate was concentrated and crystallisation from hexane gave ethyl 4-bromomethylbenzoate (37.23 g, 63percent) as an off white crystalline solid.
m.p. 34°-35° C.
i.r. (KBr) 3020, 2980, 1710 cm-1
deltaH (250 MHz, CDCl3) 8.00 (2H, d, J 8.4 Hz), 7.43 (2H, d, J 8.4 Hz), 4.47 (2H, s), 4.35 (2H, q, J 7.1 Hz), 1.37 (3H, t, J 7.1 Hz).
Reference: [1] Patent: US5428168, 1995, A,
  • 5
  • [ 94-08-6 ]
  • [ 26496-94-6 ]
  • [ 26496-95-7 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[2] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1097 - 1099
[3] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[4] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 16, p. 2745 - 2752
  • 6
  • [ 109-72-8 ]
  • [ 94-08-6 ]
  • [ 1671-77-8 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667 h; Inert atmosphere
Stage #2: at 0℃; for 0.166667 h; Inert atmosphere
General procedure: The following experimental procedure for the synthesis of 1-phenylpentanone is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with morpholine (0.18mL, 2.1mmol) and 10mL THF. After cooling to 0°C, DIBALH (2.0mL, 1.0M in hexane, 2.0mmol) was added dropwise and stirred for 3h at same temperature. To a reaction mixture was slowly added ethyl benzoate (0.14g, 1.0mmol) and stirred for 10min. Then, n-BuLi (1.25mL, 1.6M in hexane, 2.0mmol) was added and the mixture was stirred for 10min again. The reaction was stopped by the aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel yielded 1-phenylpentanone (150mg, 92percent).
Reference: [1] Tetrahedron, 2014, vol. 70, # 29, p. 4420 - 4424
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