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[ CAS No. 13330-65-9 ] {[proInfo.proName]}

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Chemical Structure| 13330-65-9
Chemical Structure| 13330-65-9
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Product Details of [ 13330-65-9 ]

CAS No. :13330-65-9 MDL No. :MFCD00060637
Formula : C8H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :MNVMYTVDDOXZLS-UHFFFAOYSA-N
M.W : 154.16 Pubchem ID :593006
Synonyms :

Calculated chemistry of [ 13330-65-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.45
TPSA : 38.69 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) : -6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 0.8
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 0.87
Log Po/w (SILICOS-IT) : 1.33
Consensus Log Po/w : 1.29

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.57
Solubility : 4.14 mg/ml ; 0.0268 mol/l
Class : Very soluble
Log S (Ali) : -1.19
Solubility : 9.87 mg/ml ; 0.064 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.06
Solubility : 1.34 mg/ml ; 0.00867 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 13330-65-9 ]

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 [ 13330-65-9 ]

* 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 [ 13330-65-9 ]
  • Downstream synthetic route of [ 13330-65-9 ]

[ 13330-65-9 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 613-45-6 ]
  • [ 13330-65-9 ]
YieldReaction ConditionsOperation in experiment
94% With sulfuric acid; dihydrogen peroxide In methanol at 20℃; for 20 h; To a solution of 2,4-dimethoxybenzaldehyde (54) (5.0g/30mmol) and 5mL of H2O2 30percent in 50mL of methanol, was added dropwise 0.5mL of sulfuric acid. The mixture was stirred for 20h at room temperature. Approximately 45mL of methanol were evaporated by rotary evaporator and the solution was partitioned between dichloromethane and distilled water. The aqueous phase was extracted 3×50mL of dichloromethane. The organic phase was washed with 3×50mL of distilled water, dried over sodium sulfate anhydrous, filtered and the organic solvent evaporated. The crude product was purified by column chromatography (chloroform). 2,4-Dimethoxyphenol (55) was obtained as light yellow oil (4.33g/94percent).2,4-Dimethoxyphenol (55). IR νmax (cm−1) (KBr): 3443, 2997, 2939, 2835, 1610, 1512, 1461, 1433, 1374, 1299, 1263, 1228, 1202, 1151, 1116, 1033, 918, 830, 792. 1H NMR (300.13MHz, CDCl3) δ (ppm): 6.75 (d, J=5.2), 6.42 (d, J=1.7), 6.31 (dd, J=5.2, 1.7), 3.79 (s, OCH3), 3.69 (s, OCH3). EIMS m/z (percent): 156 (4, [M+2]+.), 155 (40, [M+1]+.), 154 (100 [M]+.), 140 (4), 139 (58), 112 (4), 111 (90), 96 (22), 79 (10), 69 (10), 51 (20).
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 798 - 816
[2] Journal of Organic Chemistry, 1984, vol. 49, # 24, p. 4740 - 4741
[3] Organic Letters, 2012, vol. 14, # 11, p. 2806 - 2809
[4] Tetrahedron Letters, 1999, vol. 40, # 15, p. 3037 - 3040
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 5, p. 799 - 811
[6] Organic Letters, 2011, vol. 13, # 12, p. 3126 - 3129
[7] Journal of the American Chemical Society, 2012, vol. 134, # 7, p. 3571 - 3576
[8] Chemistry Letters, 1995, # 2, p. 127 - 128
[9] Organic and Biomolecular Chemistry, 2009, vol. 7, # 24, p. 5059 - 5062
[10] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 11, p. 1103 - 1104
[11] Chemistry - A European Journal, 2004, vol. 10, # 17, p. 4115 - 4125
[12] Organic Letters, 2003, vol. 5, # 21, p. 3859 - 3862
[13] Journal of Organic Chemistry, 2011, vol. 76, # 21, p. 9151 - 9156
[14] Chemische Berichte, 1940, vol. 73, p. 795,802
[15] Chemische Berichte, 1940, vol. 73, p. 935,937
[16] Tetrahedron, 1968, vol. 24, p. 2617 - 2622
[17] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 10, p. 1153 - 1160
[18] Synthesis, 1989, # 3, p. 167 - 172
[19] Journal of the American Chemical Society, 1950, vol. 72, p. 4986
[20] Heterocycles, 2013, vol. 87, # 8, p. 1727 - 1739
  • 2
  • [ 20469-63-0 ]
  • [ 13330-65-9 ]
YieldReaction ConditionsOperation in experiment
94% With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24 h; Inert atmosphere To a test tube containing a magnetic bar was added aryl halide (1.0 mmol), CuCl2 (13.4 mg, 0.1 mmol), KOH (336 mg, 6.0 mmol), ethylene glycol(12 μL, 0.2 mmol), and DMSO/H2O (1.0 mL/0.5 mL). After flushing with argon, the mixture was stirred in a preheated oil bath at 120 °C for 24 h. After cooled to ambient temperature, the reaction mixture was distributed in aqueous HCl (5 percent) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under vacuum. The crude product was further purified by column chromatography (EtOAc/n-Hexane) to provide the phenols.
Reference: [1] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 12, p. 2833 - 2840
  • 3
  • [ 151-10-0 ]
  • [ 13330-65-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3484 - 3486
[2] Synthesis, 1983, # 12, p. 1046 - 1048
[3] Letters in Organic Chemistry, 2009, vol. 6, # 7, p. 585 - 587
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 29, p. 7275 - 7278
  • 4
  • [ 613-45-6 ]
  • [ 13330-65-9 ]
YieldReaction ConditionsOperation in experiment
69% With sulfuric acid; dihydrogen peroxide In methanol (1)
Conc. sulfuric acid (0.4 ml) was added to a mixed solution comprising 3.3 g of 2,4-dimethoxybenzaldehyde and 30 ml of methanol, and under ice-cooling, 2.93 ml of 30percent hydrogen peroxide aqueous solution was added to the mixture.
After stirring at room temperature for 4 hours, a 5percent aqueous potassium hydrogen sulfite solution was added to the mixture and the solvent was removed under reduced pressure.
The residue was extracted with diethyl ether, the extract was washed and dried and the solvent was removed under reduced pressure.
The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 2.1 g of 2,4-dimethoxyphenol (yield: 69percent, state: colorless oily product).
Reference: [1] Patent: US5849732, 1998, A,
  • 5
  • [ 96826-27-6 ]
  • [ 13330-65-9 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 48, p. 7667 - 7668
  • 6
  • [ 613-45-6 ]
  • [ 13330-65-9 ]
  • [ 171737-44-3 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 20, p. 5924 - 5931
  • 7
  • [ 613-45-6 ]
  • [ 850836-62-3 ]
  • [ 13330-65-9 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9270 - 9282
  • 8
  • [ 1392229-41-2 ]
  • [ 77-76-9 ]
  • [ 13330-65-9 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 7, p. 3429 - 3439
  • 9
  • [ 171737-44-3 ]
  • [ 13330-65-9 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 4986
[2] Synthesis, 1989, # 3, p. 167 - 172
  • 10
  • [ 27257-07-4 ]
  • [ 13330-65-9 ]
Reference: [1] Journal of Applied Chemistry, 1959, vol. 8, p. 273,284
[2] Synthesis, 1989, # 3, p. 167 - 172
[3] Australian Journal of Chemistry, 1994, vol. 47, # 3, p. 461 - 470
  • 11
  • [ 109-72-8 ]
  • [ 2951-86-2 ]
  • [ 13330-65-9 ]
  • [ 100604-09-9 ]
Reference: [1] Liebigs Annalen der Chemie, 1986, # 6, p. 967 - 979
  • 12
  • [ 76335-79-0 ]
  • [ 13330-65-9 ]
Reference: [1] Magnetic Resonance in Chemistry, 1990, vol. 28, # 11, p. 973 - 978
  • 13
  • [ 2426-87-1 ]
  • [ 13330-65-9 ]
Reference: [1] Magnetic Resonance in Chemistry, 1990, vol. 28, # 11, p. 973 - 978
  • 14
  • [ 40232-88-0 ]
  • [ 13330-65-9 ]
Reference: [1] Magnetic Resonance in Chemistry, 1990, vol. 28, # 11, p. 973 - 978
  • 15
  • [ 829-20-9 ]
  • [ 13330-65-9 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1963, p. 1003 - 1007
[2] Journal of Medicinal Chemistry, 1971, vol. 14, p. 1199 - 1202
[3] Journal of Heterocyclic Chemistry, 1984, vol. 21, # 4, p. 1141 - 1144
  • 16
  • [ 79-21-0 ]
  • [ 829-20-9 ]
  • [ 13330-65-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1949, vol. 79, p. 924,927
  • 17
  • [ 66417-42-3 ]
  • [ 13330-65-9 ]
Reference: [1] Chemische Berichte, 1940, vol. 73, p. 795,802
  • 18
  • [ 60-29-7 ]
  • [ 7722-84-1 ]
  • [ 613-45-6 ]
  • [ 13330-65-9 ]
Reference: [1] Chemische Berichte, 1940, vol. 73, p. 935,937
  • 19
  • [ 79-21-0 ]
  • [ 104-15-4 ]
  • [ 64-19-7 ]
  • [ 829-20-9 ]
  • [ 13330-65-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1949, vol. 79, p. 924,927
  • 20
  • [ 67-66-3 ]
  • [ 10028-15-6 ]
  • [ 613-45-6 ]
  • [ 13330-65-9 ]
  • [ 91-52-1 ]
Reference: [1] Chemische Berichte, 1940, vol. 73, p. 795,802
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