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[ CAS No. 578-39-2 ] {[proInfo.proName]}

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Chemical Structure| 578-39-2
Chemical Structure| 578-39-2
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Product Details of [ 578-39-2 ]

CAS No. :578-39-2 MDL No. :MFCD02182261
Formula : C8H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BBMFSGOFUHEVNP-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :68475
Synonyms :

Calculated chemistry of [ 578-39-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.39
TPSA : 57.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.29

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.05
Solubility : 1.37 mg/ml ; 0.00897 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 0.79 mg/ml ; 0.00519 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 4.13 mg/ml ; 0.0272 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 578-39-2 ]

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

Application In Synthesis of [ 578-39-2 ]

* 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 [ 578-39-2 ]
  • Downstream synthetic route of [ 578-39-2 ]

[ 578-39-2 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 578-39-2 ]
  • [ 14143-26-1 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 667 - 672
  • 2
  • [ 578-39-2 ]
  • [ 74-88-4 ]
  • [ 35598-05-1 ]
Reference: [1] Patent: WO2011/156518, 2011, A2, . Location in patent: Page/Page column 115
  • 3
  • [ 578-39-2 ]
  • [ 77-78-1 ]
  • [ 35598-05-1 ]
Reference: [1] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
  • 4
  • [ 578-39-2 ]
  • [ 57556-31-7 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride In methanol; water; ethyl acetate Example 12
Synthesis of 4-(2',3'-dihydrophytyloxy)-2-methylbenzyl alcohol
To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0° C., 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60° C. overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1N hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
1H-NMR (300 MHz): δ 2.57 (3H, s, C2-Me), 3.86 (3H, s, -COOMe), 5.68 (1H, s, br, -OH), 6.66-6.72 (2H, m, C3, 5-H), 7.89 (1H, dd, J=2.4, 6.9 Hz, C6-H).
Reference: [1] Patent: US2012/59149, 2012, A1,
[2] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
  • 5
  • [ 67-56-1 ]
  • [ 578-39-2 ]
  • [ 57556-31-7 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0°C, 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60°C overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1N hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
1H-NMR(300MHz):δ2.57(3H,s,C2-Me),3.86(3H,s,-COOMe), 5.68(1H,s,br,-OH), 6.66-6.72(2H,m,C3,5-H), 7.89(1H,dd,J=2.4,6.9Hz,C6-H).
100% at 0 - 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0°C, 4-hydroxy-2-methylbenzoicacid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60°C overnight. After completion of thereaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml). The mixture was washedtwice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml), andonce with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
100% at 60℃; To methanol (10 ml) was added dropwise thionyl chloride (1.92 ml, 26.3 mmol) at 0° C., 4-hydroxy-2-methylbenzoic acid (2.00 g, 13.1 mmol) was added, and the mixture was stirred at 60° C. overnight.
After completion of the reaction, the solvent was evaporated, and the residue was dissolved in ethyl acetate (20 ml).
The mixture was washed twice with 5percent aqueous sodium hydrogen carbonate solution (10 ml), once with 1 mol/l hydrochloric acid (10 ml), and once with water (10 ml), and the solvent was evaporated to give methyl 4-hydroxy-2-methylbenzoate (2.24 g, yield 100percent).
95% Heating / reflux a) 4-Hydroxy-2-methyl-benzoic acid methyl ester4-Hydroxy-2-methyl-benzoic acid (4.8 g, 32.0 mmol) was dissolved in MeOH <n="52"/>(40 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated NaHCO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (5.0 g, yield 95?/o) was used without further purification.C9H10O31H-NMR (dmso-d6): 2.43 (3H, s); 3.72 (3H, s); 6.62-6.64 (2H, m); 7.71-7.73 (IH, m); 10.10 (IH, s).
95% Reflux a) 4 -Hydroxy- 2 -methyl- benzoic acid methyl ester; [0182] 4-Hydroxy-2-methyl-benzoic acid (4.8 g, 32.0 mmol) was dissolved in MeOH (40 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated NaHCO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (5.0 g, yield 95percent) was used without further purification.C9H10O3 1H-NMR (dmso-de): 2.43 (3H, s); 3.72 (3H, s); 6.62-6.64 (2H, m); 7.71-7.73 (1H, m); 10.10 (1H, s).
95% Heating / reflux 4-Hydroxy-2-methyl-benzoic acid methyl ester (1.0 g, 6.0 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.45 g, 3.0 mmol, 0.5 eq) and K2CO3 (1.66 g, 12.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (0.53 mL, 5.4 mmol, 0.9 eq) was added, and the mixture was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10percent was added, and the crude was extracted with DCM and dried. 0.42 g of title product (yield 32percent) were recovered and used without further purification. C13H16O31H-NMR (CDCl3): 0.23-0.34 (2H, m); 0.52-0.64 (2H, m); 1.15-1.24 (IH, m); 2.52 (3H, s); 3.75 (2H, d, J=7.2 Hz); 3.77 (3H, s); 6.64-6.66 (IH, m); 7.83-7.85 (2H, m).

Reference: [1] Patent: EP2612845, 2013, A1, . Location in patent: Paragraph 0269; 0270
[2] Patent: EP2816053, 2014, A1, . Location in patent: Paragraph 0341
[3] Patent: US9371353, 2016, B2, . Location in patent: Page/Page column 71
[4] Patent: WO2008/87529, 2008, A1, . Location in patent: Page/Page column 51
[5] Patent: WO2010/9290, 2010, A1, . Location in patent: Page/Page column 67
[6] Patent: WO2009/91832, 2009, A1, . Location in patent: Page/Page column 43; 50
  • 6
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  • [ 74-88-4 ]
  • [ 57556-31-7 ]
Reference: [1] Patent: WO2008/157330, 2008, A1, . Location in patent: Page/Page column 83
  • 7
  • [ 186581-53-3 ]
  • [ 578-39-2 ]
  • [ 57556-31-7 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 644 - 647
  • 8
  • [ 6245-57-4 ]
  • [ 578-39-2 ]
YieldReaction ConditionsOperation in experiment
80% With boron tribromide In dichloromethane 4-Hvdroxy-2-methyl-benzoic acid: BBr3 (20 mmol, 5g, 10 eq.) was added to a solution of 4-methoxy-2-methyl benzoic acid (2 mmol, 0.332g) in DCM (20 ml) and the mixture was stirred under argon until HPLC indicated no starting material remained. HCI (0.1 M, 20 ml) was added and the mixture was filtered. The aqueous layer was evaporated then dissolved in methanol. The solvent was evaporated. The EPO <DP n="95"/>dissolution/evaporation protocol was repeated a further 3 times and gave the pure product as a yellow solid (0.24g, 80percent).
80%
Stage #1: With boron tribromide In dichloromethane
Stage #2: With hydrogenchloride; water In dichloromethane
4.4 4-Hvdroxy-2-methyl-benzoic acid; BBr3 (20 mmol, 5 g, 10 eq.) was added to a solution of 4-methoxy-2-methyl benzoic acid (2 mmol, 0.332 g) in DCM (20 ml) and the mixture was stirred under argon until HPLC indicated no starting material remained. HCI (0.1 M, 20 ml) was added and the mixture was filtered. The aqueous layer was evaporated then dissolved in methanol. The solvent was evaporated. The dissolution/evaporation protocol was repeated a further 3 times and gave the pure product as a yellow solid (0.24 g, 80percent).
Reference: [1] European Journal of Organic Chemistry, 2008, # 5, p. 816 - 825
[2] Patent: WO2006/64286, 2006, A1, . Location in patent: Page/Page column 93-94
[3] Patent: WO2007/144379, 2007, A1, . Location in patent: Page/Page column 39
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 679 - 682
[5] Patent: WO2006/79099, 2006, A2, . Location in patent: Page/Page column 68; 69
  • 9
  • [ 41877-16-1 ]
  • [ 578-39-2 ]
YieldReaction ConditionsOperation in experiment
82.2%
Stage #1: With pyridine In ethyl acetate at 20 - 70℃; for 1 h;
Stage #2: With sodium hydroxide In water for 1 h; Heating / reflux
B. 2-Methyl-4-hydroxybenzoic Acid 76.8 g of the compound obtained in the preceding stage are introduced into 310 ml of ethyl acetate and then 70.8 ml of pyridine are added. The temperature gradually rises from 20° C. to 50° C. The reaction medium is then heated at 70° C. for 1 hour and is then allowed to return to ambient temperature. The reaction mixture is filtered and then the isolated solid is taken up in 710 ml of 10percent aqueous sodium hydroxide. The mixture is brought to reflux for 1 hour and is then allowed to return to ambient temperature. The aqueous phase is washed with diethyl ether, acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The extracts are subsequently washed with water and a saturated sodium chloride solution. [lacuna] Purification is then carried out by recrystallization from water. In this way, 41.94 g of the desired compound are obtained. Yield: 82.2percent M.p.: 178-182° C.
Reference: [1] Patent: US2003/225100, 2003, A1, . Location in patent: Page 16
  • 10
  • [ 56-23-5 ]
  • [ 108-39-4 ]
  • [ 567-61-3 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 1, p. 174 - 178
  • 11
  • [ 875-59-2 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 2089,2090
[2] Patent: US5229381, 1993, A,
  • 12
  • [ 56-23-5 ]
  • [ 108-39-4 ]
  • [ 578-39-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 8, p. 800 - 801
  • 13
  • [ 111220-35-0 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 859 - 866
  • 14
  • [ 52289-54-0 ]
  • [ 578-39-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 679 - 682
  • 15
  • [ 100-84-5 ]
  • [ 578-39-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 679 - 682
  • 16
  • [ 19177-04-9 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 859 - 866
  • 17
  • [ 111220-31-6 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 859 - 866
  • 18
  • [ 108-39-4 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 859 - 866
  • 19
  • [ 86-66-8 ]
  • [ 578-39-2 ]
  • [ 108-39-4 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 93
  • 20
  • [ 56-23-5 ]
  • [ 108-39-4 ]
  • [ 50-85-1 ]
  • [ 578-39-2 ]
Reference: [1] Chemische Berichte, 1879, vol. 12, p. 818,821
[2] Chemische Berichte, 1879, vol. 12, p. 818,821
  • 21
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 679 - 682
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  • [ 10425-07-7 ]
  • [ 578-39-2 ]
Reference: [1] Journal of the American Chemical Society, 1927, vol. 49, p. 1029
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  • [ 2486-75-1 ]
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Reference: [1] Chemische Berichte, 1884, vol. 17, p. 161
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Reference: [1] Chemische Berichte, 1884, vol. 17, p. 161
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  • [ 56-23-5 ]
  • [ 108-39-4 ]
  • [ 50-85-1 ]
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Reference: [1] Chemische Berichte, 1879, vol. 12, p. 818,821
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  • [ 2486-75-1 ]
  • [ 7782-77-6 ]
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Reference: [1] Chemische Berichte, 1884, vol. 17, p. 161
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