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[ CAS No. 140-39-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 140-39-6
Chemical Structure| 140-39-6
Chemical Structure| 140-39-6
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Product Details of [ 140-39-6 ]

CAS No. :140-39-6 MDL No. :MFCD00008703
Formula : C9H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CDJJKTLOZJAGIZ-UHFFFAOYSA-N
M.W : 150.17 Pubchem ID :8797
Synonyms :

Calculated chemistry of [ 140-39-6 ]

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 : 42.91
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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.12
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 2.25
Log Po/w (SILICOS-IT) : 2.16
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.37
Solubility : 0.638 mg/ml ; 0.00425 mol/l
Class : Soluble
Log S (Ali) : -2.29
Solubility : 0.765 mg/ml ; 0.00509 mol/l
Class : 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 : 1.09

Safety of [ 140-39-6 ]

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 [ 140-39-6 ]

* 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 [ 140-39-6 ]
  • Downstream synthetic route of [ 140-39-6 ]

[ 140-39-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 140-39-6 ]
  • [ 1450-72-2 ]
YieldReaction ConditionsOperation in experiment
92% With aluminum (III) chloride In neat (no solvent) at 140 - 150℃; p-Tolyl acetate 2b (10 gm, 0.067 mol) was in 500 mL round bottom flask containing aluminium chloride (10.7 gm, 0.08 mol). It was heated on an oil bath at 140-150 °C for 5-6 hr. The progress of the reaction was monitored by TLC using ethyl acetate:hexane as a solvent system. The reaction mixture was quenched with crushed ice and obtained solid product was extracted with ethyl acetate (2×50 mL). The organic extracts were washed with brine solution (2×15 mL) and dried over anhydrous sodium sulphate. The solvent was evaporated under reduced pressure to afford the corresponding crude compounds. The obtained compound 3b was recrystallized using aq. ethanol. Yield 92percent. M.p. 45-48 °C.
80% at 130℃; for 1 h; To a solution of p-cresol (15 g, 139 mmol) in acetic anhydride (37.5 mL) was added pyridine (1.13 mL).After 12 h of stirring at 25 °C, the volatiles were evaporated. The resulting oil was taken up in diethylether, washed with 10percent aqueous sodium bicarbonate twice and brine once, and dried and evaporated togive the acetate (20.85 g, quant. yield) which was used without further purification; 1H NMR δ 7.15 (d, = 9 Hz, 2H, H-3 and 5), 6.95 (d, = 9 Hz, 2H, H-2 and 6), 2.32 (s, 3H, OMe), 2.25 (s, 3H, Me).To the crude ester (20.85 g, 0.14 mmol) was added anhydrous aluminium chloride (18.75 g, 0.14 mmol)and the mixture was heated for 1 h at 130 °C. It was then cooled to 25 °C, treated with ice (7.5 g),allowed to stand for 1 h, diluted with CH2Cl2, and stirred overnight. The organic phase phase wasseparated, dried, and evaporated to give the product (16.63 g, 80percent) as green crystals; mp 48–50 °C, (lit.,3550 °C); 1H NMR δ 12.10 (s, 1H, OH), 7.48 (d, = 1.8 Hz, 2H, H-6), 7.26 (dd, J = 8.4, 1.8 Hz, 1H, H-4),6.86 (d, J = 8.4 Hz, 1H, H-3), 2.32 (s, 3H, OMe), 2.25 (s, 2H,Me).
35.85 g
Stage #1: at 110 - 165℃; for 1 h;
Stage #2: With hydrogenchloride In water at 80 - 90℃; for 1 h;
36g of acetoxytoluene was added to a four-necked flask, heated to 110 ° C with anhydrous aluminum trichloride (36.77 g, 0.28 mol). After the addition, the temperature was raised to 165 ° C. After 1 hour of stirring at the same temperature, 1 19mL of 4mol / L hydrochloric acid solution was stirred at 80-90 ° C for 1 hour, then cooled to room temperature and stirred for 3 hours. Toluene (12.5mL * 6) extraction six times the solvent was evaporated and dried in vacuo to give the product 2-acetyl-p-cresol 35.85g
Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, p. 4971 - 4975
[2] Journal of Chemical Research, Miniprint, 2003, # 12, p. 1258 - 1270
[3] Journal of Chemical Research, Synopses, 1999, # 9, p. 574 - 575
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 7, p. 734 - 736
[5] Journal of Chemical Research, Miniprint, 1998, # 10, p. 2678 - 2695
[6] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[7] Bulletin de la Societe Chimique de France, 1987, # 1, p. 123 - 124
[8] Synthesis, 1985, # 9, p. 901 - 902
[9] Synthesis, 1982, # 11, p. 940 - 942
[10] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185
[11] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185
[12] European Journal of Pharmacology, 2005, vol. 512, # 2-3, p. 97 - 104
[13] Tetrahedron Letters, 1996, vol. 37, # 42, p. 7659 - 7660
[14] Synthetic Communications, 2004, vol. 34, # 8, p. 1433 - 1440
[15] Heterocycles, 2016, vol. 93, # 1, p. 164 - 184
[16] Synthesis, 2004, # 11, p. 1789 - 1792
[17] Tetrahedron Letters, 1996, vol. 37, # 12, p. 2053 - 2056
[18] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 5, p. 323 - 329
[19] Organic Letters, 2016, vol. 18, # 15, p. 3766 - 3769
[20] Chemische Berichte, 1924, vol. 57, p. 92[21] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
[22] Chemische Berichte, 1921, vol. 54, p. 1533
[23] Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 89
[24] Journal of the Chemical Society, 1958, p. 2926,2929
[25] Journal of the Chemical Society, 1958, p. 2926,2929
[26] Journal of the Chemical Society, 1958, p. 2926,2929
[27] Journal of the Chemical Society, 1958, p. 2926,2929
[28] Journal of the Chemical Society, 1957, p. 3016,3018
[29] Justus Liebigs Annalen der Chemie, 1954, vol. 587, p. 1,15
[30] Chemische Berichte, 1939, vol. 72, p. 1414,1424
[31] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1990, p. 1893 - 1898
[32] Chemical research in toxicology, 2002, vol. 15, # 8, p. 1106 - 1112
[33] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 21, p. 5996 - 6001
[34] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4188 - 4201
[35] Patent: US2011/98425, 2011, A1,
[36] Russian Journal of Physical Chemistry A, 2010, vol. 84, # 12, p. 2182 - 2186
[37] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 10, p. 2855 - 2859
[38] Asian Journal of Chemistry, 2011, vol. 23, # 10, p. 4616 - 4620
[39] Oriental Journal of Chemistry, 2011, vol. 27, # 3, p. 1053 - 1062
[40] Oriental Journal of Chemistry, 2012, vol. 28, # 2, p. 921 - 925,5
[41] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1971 - 1983
[42] Medicinal Chemistry Research, 2012, vol. 21, # 8, p. 1833 - 1849,17
[43] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 2826 - 2831
[44] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 389 - 402
[45] European Journal of Medicinal Chemistry, 2015, vol. 93, p. 64 - 73
[46] MedChemComm, 2013, vol. 4, # 9, p. 1257 - 1266
[47] Journal of Fluorine Chemistry, 2014, vol. 160, p. 77 - 81
[48] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 329, p. 238 - 245
[49] Asian Journal of Chemistry, 2017, vol. 29, # 1, p. 119 - 123
[50] Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 459 - 461[51] Zh. Org. Khim.,
[52] Heterocyclic Communications, 2017, vol. 23, # 4, p. 325 - 330
[53] Heterocyclic Communications, 2018, vol. 24, # 1, p. 59 - 65
[54] Patent: CN104803924, 2017, B, . Location in patent: Paragraph 0049; 0054; 0058
  • 2
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  • [ 64-19-7 ]
  • [ 1450-72-2 ]
  • [ 140-39-6 ]
Reference: [1] Journal of Catalysis, 2012, vol. 290, p. 101 - 107
  • 3
  • [ 7446-70-0 ]
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  • [ 1450-72-2 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 92[2] Justus Liebigs Annalen der Chemie, 1926, vol. 446, p. 157 Anm. 2, 177
[3] Chemische Berichte, 1921, vol. 54, p. 1553
[4] Justus Liebigs Annalen der Chemie, 1928, vol. 460, p. 89
  • 4
  • [ 140-39-6 ]
  • [ 7550-45-0 ]
  • [ 98-95-3 ]
  • [ 1450-72-2 ]
Reference: [1] Journal of the Chemical Society, 1957, p. 3016,3018
  • 5
  • [ 7446-70-0 ]
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  • [ 106-44-5 ]
  • [ 1450-72-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 2926,2929
  • 6
  • [ 140-39-6 ]
  • [ 7550-45-0 ]
  • [ 106-44-5 ]
  • [ 1450-72-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 2926,2929
  • 7
  • [ 7446-70-0 ]
  • [ 140-39-6 ]
  • [ 98-95-3 ]
  • [ 106-44-5 ]
  • [ 1450-72-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 2926,2929
  • 8
  • [ 140-39-6 ]
  • [ 7550-45-0 ]
  • [ 98-95-3 ]
  • [ 106-44-5 ]
  • [ 1450-72-2 ]
Reference: [1] Journal of the Chemical Society, 1958, p. 2926,2929
  • 9
  • [ 140-39-6 ]
  • [ 20628-07-3 ]
Reference: [1] Heterocycles, 2016, vol. 93, # 1, p. 164 - 184
[2] Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 459 - 461[3] Zh. Org. Khim.,
[4] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1971 - 1983
  • 10
  • [ 140-39-6 ]
  • [ 52727-95-4 ]
YieldReaction ConditionsOperation in experiment
89.2% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 50℃; for 3 h; Acetic acid(4-methyl) phenolate 50.0gSoluble in 500ml of carbon tetrachloride, add 4.0g BPO,Stirring at 50 ° C,Add 71.5g NBS ((4-methyl) phenolate (II) acetate and NBS in 3 batches,The molar ratio of BPO was 1:1.2:0.05), and the reaction was kept for 3 hours. Filtering,The filtrate was concentrated under reduced pressure.The orange-red oil was added dropwise to petroleum ether and stirred to disperse, and a solid precipitated. After suction filtration, the filtrate was washed with water.After drying, it was concentrated under reduced pressure to give (4-bromomethylene) phenyl ester (III), 68.3 g.Yield 89.2percent,
41% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform for 4 h; Inert atmosphere; Reflux NBS (13.91 g, 0.12 mol, 0.9 eq) and AIBN (2.17 g, 0.01 mol,0.1 eq) were placed in a Schlenk flask and put under an argonatmosphere. CHCI3was added followed by p-to\y\ acetate (19.67 g, 0.13 mol). The mixture was refluxed for 4 h. After cooling down the volume of the mixture was reduced on rotavap to approximately a third and the suspension was filtered. 200 mL of CHCI3was added to the filtrate and it was 3x washed with 80 mL of water, the combined organic layers were dried with MgSC>4, filtered and volatiles were removed on rotavap. 5 mL of AcOEt was added, the mixture was shortly sonicated and while stirring, 40 mL of hexane was added causing precipitation. The mixture was put to a freezer overnight and then filtered washing the white solid with 25 mL of hexane giving 12.05 g (41 percent, 0.05 mol) of the product. It was stored in the freezer. The NMR spectrum was in accordance with the literature (J. Org. Chem. 1981, 46 (15), 3029-3035)
Reference: [1] Patent: CN108640834, 2018, A, . Location in patent: Paragraph 0020; 0023; 0025
[2] Chemical Communications, 2010, vol. 46, # 20, p. 3526 - 3528
[3] Journal of Organic Chemistry, 1981, vol. 46, # 15, p. 3029 - 3035
[4] Chemical Communications, 2016, vol. 52, # 32, p. 5609 - 5612
[5] ChemMedChem, 2013, vol. 8, # 10, p. 1662 - 1667
[6] Patent: WO2018/94334, 2018, A1, . Location in patent: Page/Page column 49; 63; 64
[7] Journal of the Chemical Society, 1953, p. 764,771
[8] Inorganic Chemistry, 2010, vol. 49, # 5, p. 2541 - 2549
  • 11
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  • [ 34241-39-9 ]
  • [ 52727-95-4 ]
Reference: [1] Patent: US4645771, 1987, A,
  • 12
  • [ 77-48-5 ]
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  • [ 52727-95-4 ]
Reference: [1] Rev. Fac. Cienc. quim. Univ. La Plata, 1955, vol. 29, p. 53,56
  • 13
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  • [ 29976-82-7 ]
Reference: [1] Medicinal Chemistry Research, 2012, vol. 21, # 8, p. 1833 - 1849,17
  • 14
  • [ 140-39-6 ]
  • [ 5597-50-2 ]
Reference: [1] Patent: CN108640834, 2018, A,
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