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Chemical Structure| 487-70-7
Chemical Structure| 487-70-7
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Product Details of [ 487-70-7 ]

CAS No. :487-70-7 MDL No. :
Formula : C7H6O4 Boiling Point : -
Linear Structure Formula :- InChI Key :BTQAJGSMXCDDAJ-UHFFFAOYSA-N
M.W :154.12 Pubchem ID :68099
Synonyms :
2,4,6-Trihydroxybenzaldehyde

Calculated chemistry of [ 487-70-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 37.9
TPSA : 77.76 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 : Yes
Log Kp (skin permeation) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.88
Log Po/w (XLOGP3) : 0.87
Log Po/w (WLOGP) : 0.62
Log Po/w (MLOGP) : -0.41
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 0.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.68
Solubility : 3.21 mg/ml ; 0.0208 mol/l
Class : Very soluble
Log S (Ali) : -2.09
Solubility : 1.26 mg/ml ; 0.00819 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.6
Solubility : 38.3 mg/ml ; 0.248 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 487-70-7 ]

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 [ 487-70-7 ]

* 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 [ 487-70-7 ]
  • Downstream synthetic route of [ 487-70-7 ]

[ 487-70-7 ] Synthesis Path-Upstream   1~18

  • 1
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Reference: [1] Justus Liebigs Annalen der Chemie, 1907, vol. 357, p. 373
[2] Tetrahedron Letters, 2009, vol. 50, # 33, p. 4769 - 4772
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  • [ 2632-13-5 ]
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YieldReaction ConditionsOperation in experiment
65%
Stage #1: With thiamine hydrochloride In ethanol at 20℃; for 0.25 h; Green chemistry
Stage #2: at 20℃; for 2 h; Green chemistry
General procedure: To prepare catalyst, 0.21 g of thiamine hydrochloride (0.6 mmol) was dissolved in 0.64 mL of water and added 2.4 mLof 95percent ethanol (water : 95percent ethanol = ~1:4). The solution was cooled in an ice bath, then added 0.40 mL of 3 M NaOH(1.2 mmol) dropwise with stirring in a manner such that thetemperature remained below 20 °C. Intense yellow coloured solution changed to pale yellow solution of thiamine (thiazolium ion)/N-heterocyclic carbene (Scheme 1).47 In a 25-mL round bottom flask, a mixture of phenacylbromide 1 (2.5 mmol, 0.5 g in case of 1a) and thiamine (0.6 mmol, 25 mol percent) in ethanol (4 mL) was stirred at room temperature for 15 min. Then, salicylaldehyde 2 (2.5 mmol, 0.26 mL in case of 2a) was added slowly and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC) (Table 3) . The reaction mixture was then poured into 20 mL of distilled water and extracted with ethyl acetate (3 × 10 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The resulting product isoflavone 3 was further purified either by recrystallizationor by column chromatography (Ethyl acetate:Hexane, 1:4v/v). All compounds were characterized by their mp and 1HNMR, 13CNMR and mass spectral data.
Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1070 - 1076
  • 3
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YieldReaction ConditionsOperation in experiment
92% With trichlorophosphate In ethyl acetate at 0 - 20℃; for 2 h; Inert atmosphere To a solution of 15 (1.9 g, 15 mmol) in EtOAc (20 ml) was added DMF (1.26 ml, 16.5 mmol) and POCl3 (1.5 ml, 16.5 mmol) at 0 °C in an ice bath. Remove ice bath and the solution was stirred for 2 h. Water was added and the reaction mixture was refluxed for 30 min. When the solution cooled down, ethyl acetate was added to extract. The organic layers were combined and washed with brine, and dried over anhydrous Na2SO4. And then filtration and concentration in vacuo gave a residue, which was purified by flash column chromatography on silica gel (petroleum ether-EtOAc, 4:1) to yield 16 (2.12 g, 92percent) as a white solid. 1H NMR (500 MHz, DMSO) δ 9.92 (s, 1H), 5.78 (s, 2H). 13CNMR (126 MHz, DMSO) δ 191.4, 167.6, 164.5, 105.0, 94.6.
83% With trichlorophosphate In water; ethyl acetate Example 1
- Synthesis of Phloroglucinaldehyde (III)
9 l (1.47 kg, 96.4 moles) of phosphorus oxychloride are added to a solution containing 11.2 kg (88.9 moles) of anhydrous phloroglucinol (II) and 7.5 l (7 kg, 96.4 moles) of N,N-dimethylformamide in 33 l of ethyl acetate.
The precipitated solid is filtered and the residue is dissolved in hot water.
After cooling to room temperature, the crystallizate is filtered. 11.4 kg of III are obtained (yield: 83percent) having a m.p. of 185°-186°C, E
80% at 20℃; for 4 h; Inert atmosphere; Cooling with ice A 100 mL round bottom flask was charged with phloroglucin (3 g, 24 mmol) and DMF (30 mL).
After the flask was flushed with Ar and covered with the rubber plug, POCl3 (2.2 mL, 24 mmol) was added dropwise under the condition of ice bath.
After completion of adding, the mixture was stirred at room temperature for 4 h. TLC analysis indicated that the reaction was completed.
After quenching the reaction mixture with ice cold water (50 mL), the slurry was extracted with CH2Cl2 (20 mL * 3).
The combined organic extracts were washed with 20percent LiCl aqueous solution (10 mL * 2), brine and then dried over anhydrous sodium sulfate.
The solvent was evaporated in vacuo.
The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 2:1) to provide 2,4,6-trihydroxybenzaldehyde (2.9 g, 80percent) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 11.46 (s, 2H), 10.65 (s, 1H), 9.93 (s, 1H), 5.79 (s, 2H).
13C NMR (75 MHz, DMSO-d6) δ 190.9, 167.2, 164.1, 104.6, 94.2. MS (ESI): m/z 153.0 [M-H]-.
70% With trichlorophosphate In ethyl acetate at 0 - 20℃; for 7 h; Inert atmosphere To a cooled (0 °C) solution of phloroglucinol (13) (20.0 g, 0.159 mol) and DMF (12.2 mL, 0.159 mol) in EtOAc (300 mL), POCl3 (14.83 mL, 0.159 mol) was added dropwise within 60 min.
After complete addition the resulting suspension was left to stir at room temperature for 6 h.
When full consumption was achieved, the yellow suspension was poured on ice-water (500 mL), and the two-phase mixture was stirred vigorously while adding satd.
NaOAc solution to it until a pH of 5-6 was reached.
During the addition the solution became dark-red, then it was extracted with EtOAc (4*600 mL).
The combined organic layers were washed with satd. NaCl solution (1*500 mL), dried over Na2SO4, filtered, and evaporated to dryness.
The residue was recrystallized from water (200 mL) to provide benzaldehyde 26 (17.18 g, 70percent) as red crystals. 1H NMR (400 MHz, DMSO-d6): δ=5.78 (s, 2H, 3-H), 9.92 (s, 1H, CHO), 10.64 (s, 1H, OH), 11.45 (s, 2H, OH); 13C NMR (100 MHz, DMSO-d6): δ=94.1 (C-3), 104.5 (C-1), 164.1 (C-2), 167.2 (C-4), 190.9 (CHO).

Reference: [1] Organic Letters, 2015, vol. 17, # 16, p. 4110 - 4113
[2] Tetrahedron Letters, 2016, vol. 57, # 17, p. 1856 - 1859
[3] Synthetic Communications, 1998, vol. 28, # 15, p. 2861 - 2869
[4] Organic Letters, 2010, vol. 12, # 8, p. 1676 - 1679
[5] Synlett, 2007, # 1, p. 129 - 130
[6] Patent: EP348121, 1989, A1,
[7] Molecules, 2018, vol. 23, # 12,
[8] Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 1, p. 116 - 124
[9] Australian Journal of Chemistry, 2005, vol. 58, # 7, p. 551 - 555
[10] Tetrahedron, 2015, vol. 71, # 52, p. 9662 - 9666
[11] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 19, p. 3151 - 3153
[12] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 6, p. 1750 - 1760
  • 4
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YieldReaction ConditionsOperation in experiment
98% With trichlorophosphate In ethyl acetate at 20℃; for 1 h; Cooling with ice In a 1 L single-necked flask, phloroglucinol dihydrate (38.6 g, 0.238 mol), DMF (55.03 mL, 0.714 mol), ethyl acetate (450 mL),Phosphorus oxychloride (66.32 mL, 0.714 mol) was slowly added dropwise under ice bath.After the addition, transfer to room temperature for 1 h, filter, wash with ethyl acetate, place the filter cake in a 500 mL single-necked flask, add water (150 mL), protect with nitrogen, warm to reflux and maintain for 10 min, then cool to room temperature and then refrigerate in the refrigerator. 1h,Filter, wash with water, collect the filter cake and dry in vacuo without further purification.A white solid was obtained in 36 g, yield 98percent.
Reference: [1] Patent: CN108947787, 2018, A, . Location in patent: Paragraph 0016
  • 5
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  • [ 506-68-3 ]
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Reference: [1] Journal of the American Chemical Society, 1929, vol. 51, p. 1269
[2] Helvetica Chimica Acta, 1919, vol. 2, p. 92
  • 6
  • [ 108-73-6 ]
  • [ 67-66-3 ]
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Reference: [1] Organic Mass Spectrometry, 1984, vol. 19, # 7, p. 330 - 333
  • 7
  • [ 108-73-6 ]
  • [ 74-90-8 ]
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Reference: [1] Journal of the Chemical Society, 1925, vol. 127, p. 1134
[2] Journal fuer Praktische Chemie (Leipzig), 1922, vol. <2> 104, p. 315,322
[3] Chemische Berichte, 1899, vol. 32, p. 279
  • 8
  • [ 18470-06-9 ]
  • [ 530-57-4 ]
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  • [ 109717-92-2 ]
Reference: [1] Food Chemistry, 2016, vol. 199, p. 902 - 910
  • 9
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Reference: [1] Chemische Berichte, 1901, vol. 34, p. 1443
  • 10
  • [ 528-58-5 ]
  • [ 99-50-3 ]
  • [ 83-30-7 ]
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Reference: [1] RSC Advances, 2014, vol. 4, # 36, p. 18939 - 18944
  • 11
  • [ 108-73-6 ]
  • [ 103-70-8 ]
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Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 195[2] Journal of the Chemical Society, 1925, vol. 127, p. 1132 Anm.
  • 12
  • [ 491-70-3 ]
  • [ 99-50-3 ]
  • [ 487-70-7 ]
  • [ 30048-34-1 ]
  • [ 18003-33-3 ]
Reference: [1] Monatshefte fur Chemie, 2016, vol. 147, # 8, p. 1375 - 1383
  • 13
  • [ 6906-38-3 ]
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Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 12, p. 5271 - 5278
  • 14
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Reference: [1] Journal of Agricultural and Food Chemistry, 2009, vol. 57, # 12, p. 5271 - 5278
  • 15
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Reference: [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314
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Reference: [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314
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Reference: [1] Tetrahedron, 1994, vol. 50, # 31, p. 9303 - 9314
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Reference: [1] Chemische Berichte, 1964, vol. 97, p. 2606 - 2613
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