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[ CAS No. 22479-95-4 ] {[proInfo.proName]}

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Chemical Structure| 22479-95-4
Chemical Structure| 22479-95-4
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Product Details of [ 22479-95-4 ]

CAS No. :22479-95-4 MDL No. :MFCD00060092
Formula : C10H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :JJXVDRYFBGDXOU-UHFFFAOYSA-N
M.W : 210.18 Pubchem ID :89726
Synonyms :

Calculated chemistry of [ 22479-95-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.02
TPSA : 72.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.21
Log Po/w (XLOGP3) : 1.24
Log Po/w (WLOGP) : 0.97
Log Po/w (MLOGP) : 1.26
Log Po/w (SILICOS-IT) : 1.16
Consensus Log Po/w : 1.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 2.32 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (Ali) : -2.37
Solubility : 0.902 mg/ml ; 0.00429 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.98
Solubility : 2.19 mg/ml ; 0.0104 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 22479-95-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22479-95-4 ]

* 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 [ 22479-95-4 ]
  • Downstream synthetic route of [ 22479-95-4 ]

[ 22479-95-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 22479-95-4 ]
  • [ 50727-04-3 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2981 - 2989
[2] Journal of the American Chemical Society, 2014, vol. 136, # 17, p. 6239 - 6242
[3] Chemistry - A European Journal, 2016, vol. 22, # 34, p. 11997 - 12001
  • 2
  • [ 22479-95-4 ]
  • [ 28281-76-7 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 17, p. 6239 - 6242
[2] Chemistry - A European Journal, 2016, vol. 22, # 34, p. 11997 - 12001
  • 3
  • [ 67-56-1 ]
  • [ 610-35-5 ]
  • [ 22479-95-4 ]
YieldReaction ConditionsOperation in experiment
99% at 80℃; for 4 h; [00176] Preparation of dimethyl 4-hydroxyphthalate (‘1-2. To a solution of 4- hydroxyphthalic acid (20 g, 110 mmol) in CH3OH (100 mL) was added SOC12 (20 mL), The resulting solution was stirred at 80 °C for 4 hrs, The volatile was removed in vacuo to yield compound C1-2 as a white solid (23 g, yield: 99percent), which was used directly in the next step without further purification. ‘H NMR (CDCI3, 400 MHz) : 7.77(d, J = 8.8 Hz, lH), 7.03 (d, J 2 Hz, lH), 6.95 (dd, J 8.4 and 2.0 Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H); MS (ESI): ,n/z 21 l(M÷l).
92% at 0℃; for 20 h; A solution of 4-hydroxyphthalic acid 1 (25.0 g, 137 mmol) in MeOH (700 mL) was charged with SOCl2 (30.0 mL, 412 mmol) at 0° C. and stirred at room temperature for 20 h.
The solvent was removed and the residue was partitioned between saturated aqueous NaHCO3 solution (100 mL) and CH2Cl2 (250 mL).
The CH2Cl2 layer was separated and the aqueous layer was extracted with CH2Cl2 (2*250 mL).
The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated to afford compound 2 (26.5 g, 92percent) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.72 (d, J=8.5 Hz, 1H), 7.00 (d, J=2.6 Hz, 1H), 6.91 (dd, J=8.5, 2.6 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H).
90% Heating / reflux A solution of 5 g (27.6 mmol) of 4-aminophthalic acid in 50 ml of 1M sulphuric acid is cooled to 0° C. and a solution of 2.27 g of sodium nitrite in 6 ml of water is then slowly added. After 15 minutes at 0° C., 15 ml of concentrated sulphuric acid are added and the mixture is heated at 100° C., with vigorous stirring, for 1 hour. At room temperature, the reaction medium is extracted with ethyl acetate and washed with water. After decantation, the organic phase is dried over magnesium sulphate and concentrated. The residue is purified on a silica column (dichloromethane 80-methanol 20). It is then dissolved in 100 ml of methanol and refluxed with 2 ml of acetic acid. After the disappearance of the diacid, the methanol is evaporated and the product is taken up in ethyl acetate and washed with water. [00350] M=5.2 g. Y=90percent. 1H NMR (DMSO): 3.64 (3H, s), 3.67 (3H, s), 6.79-6.86 (2H, m), 7.56-7.60 (1H, d, J=8.4 Hz), 10.51 (1H, OH, s).
87% With hydrogenchloride In isopropyl alcohol at 0℃; for 24 h; Reflux A solution of 4-hydroxyphthalic acid 16 (25.0 g, 137 mmol) in MeOH (500 mL) was charged with 6 N HCl in z'-PrOH (46.0 mL, 274 mmol) at 0 °C and refluxed for 24 h. The solvent was removed and the residue was partitioned between saturated aqueous NaHCC solution (100 mL) and EtOAc (250 mL). The EtOAc layer was separated and the aqueous layer was extracted with EtOAc (2 χ 250 mL). The combined organic extracts were washed with brine, dried over Na2S04, and concentrated to afford compound 17 (25.0 g, 87percent) as a brown color solid: NMR (400 MHz, (Χ,) δ 7.72 id, ./ 8.5 Hz, 1 H), 7.00 (d, J = 2.6 Hz, H I ), 6.91 (dd, J = 8.5, 2.6 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H).
55% at 10 - 70℃; 4-hydroxyphthalic acid (50g, 274.5mmol) was dissolved in methanol (800mL) and cooled to 10°C. Sulfuric acid (134g, 1.37mol) was slowly added dropwise with stirring. After the addition was complete the reaction temperature was raised to 70°C overnight. Cooling to room temperature, it was concentrated in vacuo. It was extracted with ethyl acetate (700mL) and washed with water (500mL × 3). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to give the product (32g, 55percent yield).

Reference: [1] Patent: WO2014/18866, 2014, A1, . Location in patent: Paragraph 00175; 00176
[2] ChemMedChem, 2010, vol. 5, # 2, p. 213 - 231
[3] Chemistry of Materials, 2014, vol. 26, # 14, p. 4151 - 4162
[4] Patent: US2015/56305, 2015, A1, . Location in patent: Paragraph 0270; 0271; 0387; 0388
[5] Chemical Science, 2018, vol. 9, # 24, p. 5312 - 5321
[6] Patent: US6689922, 2004, B1, . Location in patent: Page column 20
[7] Patent: WO2016/176423, 2016, A1, . Location in patent: Page/Page column 74
[8] Toxicology Letters, 2000, vol. 118, # 1-2, p. 1 - 8
[9] Journal of Fluorine Chemistry, 2003, vol. 119, # 2, p. 141 - 149
[10] Patent: CN105524045, 2016, A, . Location in patent: Paragraph 0221; 0222; 0223
[11] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[12] Journal of the Chemical Society, 1886, vol. 49, p. 518
[13] Monatshefte fuer Chemie, 1902, vol. 23, p. 401
[14] Journal of the Chemical Society, 1907, vol. 91, p. 103
[15] Journal of Organic Chemistry, 1983, vol. 48, # 18, p. 2981 - 2989
[16] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 22, p. 4125 - 4128
[17] Patent: WO2007/20046, 2007, A1, . Location in patent: Page/Page column 97-98
[18] Patent: US6706725, 2004, B1, . Location in patent: Page column 11
[19] Journal of the American Chemical Society, 2014, vol. 136, # 17, p. 6239 - 6242
[20] Chemistry - A European Journal, 2016, vol. 22, # 34, p. 11997 - 12001
[21] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 76 - 87
  • 4
  • [ 610-35-5 ]
  • [ 18107-18-1 ]
  • [ 22479-95-4 ]
YieldReaction ConditionsOperation in experiment
13% at 20℃; for 15 h; To a solution of 4-hydroxyphthalic acid (1.04 g, 5.71 mmol) in MeOH (11.4 mL) was slowly added TMSCHN2 (6.28 mL, 12.56 mmol). The reaction mixture was stirred at RT for 15 h, then was concentrated in vacuo. The residue was partitioned between EtOAc and H2O. The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo. The crude residue was chromatographed (SiO2; continuous gradient from 0percent EtOAc/Hexane to 100percent EtOAc/Hexane) to provide Part A compound (150 mg, 13percent) as a solid.
Reference: [1] Patent: US2008/21052, 2008, A1, . Location in patent: Page/Page column 31
  • 5
  • [ 610-35-5 ]
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YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In methanol Example 9
4-Hydroxyphthalic acid dimethyl ester
Thionyl chloride (30 ml, 0.413 mmol) is added dropvise at -10° C. to a solution of 4-hydroxyphthalic acid (15 g, 82.4 mmol) in methanol (150 ml).
The resulting mixture is heated at reflux temperature for 3 hours, cooled to room temperature and evaporated to dryness in vacuo to give 4-hydroxyphthalic acid dimethyl ester (yield: 17.1 g(99percent)) as white crystals. 1H-NMR (CDCl3) in ppm: δ 3.86 (3H,s), 3.92 (3H,s), 6.92 (1H,d,d.), 7.0 (1H,d), 7.76 (1H,d).
In a similar way the following compounds were prepared:
3-Hydroxyphthalic acid dimethyl ester from 3-hydroxyphthalic acid. 1H-NMR (CDCl3) in ppm: δ 3.88 (3H,s); 3.92 (3H,s); 6.97 (1H,d.d.); 7.08 (1H,d.d.); 7.47 (1H,d.d.).
Reference: [1] Patent: US6590118, 2003, B1,
  • 6
  • [ 54125-02-9 ]
  • [ 762-42-5 ]
  • [ 22479-95-4 ]
Reference: [1] Synthetic Communications, 1991, vol. 21, # 21, p. 2231 - 2256
[2] Journal of the American Chemical Society, 1974, vol. 96, p. 7807 - 7808
[3] Journal of the American Chemical Society, 1979, vol. 101, p. 6996 - 7000
[4] Synthetic Communications, 1991, vol. 21, # 8-9, p. 1055 - 1069
  • 7
  • [ 762-42-5 ]
  • [ 22479-95-4 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 4, p. 1487 - 1489
  • 8
  • [ 89-08-7 ]
  • [ 22479-95-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[2] Journal of the Chemical Society, 1886, vol. 49, p. 518
[3] Chemical Science, 2018, vol. 9, # 24, p. 5312 - 5321
  • 9
  • [ 483-84-1 ]
  • [ 22479-95-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[2] Journal of the Chemical Society, 1886, vol. 49, p. 518
  • 10
  • [ 88-99-3 ]
  • [ 22479-95-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1886, vol. 233, p. 226[2] Journal of the Chemical Society, 1886, vol. 49, p. 518
  • 11
  • [ 59414-23-2 ]
  • [ 762-42-5 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 7, p. 1832 - 1835
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 7, p. 1832 - 1835
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