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[ CAS No. 99-50-3 ] {[proInfo.proName]}

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Chemical Structure| 99-50-3
Chemical Structure| 99-50-3
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Product Details of [ 99-50-3 ]

CAS No. :99-50-3 MDL No. :MFCD00002509
Formula : C7H6O4 Boiling Point : -
Linear Structure Formula :- InChI Key :YQUVCSBJEUQKSH-UHFFFAOYSA-N
M.W : 154.12 Pubchem ID :72
Synonyms :
3,4-Dihydroxybenzoic acid;NSC 16631;PCA
Chemical Name :3,4-Dihydroxybenzoic acid

Calculated chemistry of [ 99-50-3 ]      Expand+

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 : 37.45
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) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.66
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 0.8
Log Po/w (MLOGP) : 0.4
Log Po/w (SILICOS-IT) : 0.26
Consensus Log Po/w : 0.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 2.14 mg/ml ; 0.0139 mol/l
Class : Very soluble
Log S (Ali) : -2.38
Solubility : 0.646 mg/ml ; 0.00419 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.6
Solubility : 38.3 mg/ml ; 0.248 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 99-50-3 ]

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 [ 99-50-3 ]

* 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 [ 99-50-3 ]
  • Downstream synthetic route of [ 99-50-3 ]

[ 99-50-3 ] Synthesis Path-Upstream   1~20

  • 1
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  • [ 4442-54-0 ]
Reference: [1] Journal of Coordination Chemistry, 2014, vol. 67, # 7, p. 1265 - 1278
  • 2
  • [ 99-50-3 ]
  • [ 106-93-4 ]
  • [ 4442-54-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 112
  • 3
  • [ 99-50-3 ]
  • [ 21852-32-4 ]
Reference: [1] Asian Journal of Chemistry, 2014, vol. 26, # 7, p. 2092 - 2098
  • 4
  • [ 99-50-3 ]
  • [ 64-17-5 ]
  • [ 3943-89-3 ]
YieldReaction ConditionsOperation in experiment
89% at 40 - 80℃; for 10 h; 3,4-dihydroxybenzoic acid (5.0 g, 32.0 mmol) was placed in a reaction flask, 40 mL of ethanol was added, and the temperature was raised to 40 ° C, and 5 mL of concentrated sulfuric acid was added dropwise. After the dropwise addition, the temperature was raised to 80 ° C and refluxed for 10 h. Cooled to room temperature, add 10M potassium hydroxide solution to adjust the pH to neutral. The solvent was evaporated under reduced pressure to precipitate a solid which was washed with a small amount of water to give ethyl 3,4-dihydroxybenzoate. Ethyl 3,4-dihydroxybenzoate: white solid; 89percent yield;
86.8% Reflux 15.4 g (0.1 mol) of 3,4-dihydroxybenzoic acid and 200 mL of absolute ethanol were added to a 500 mL flask,In the constant stirring slowly dropping 5mL 98percent concentration of concentrated sulfuric acid.The mixture was heated to reflux, the TLC was followed by the reaction, 80percent by volume of solvent was distilled off under reduced pressure,Diluted with 30 mL of ethyl acetate and 25 mL of water, and the aqueous layer was extracted with 300 mL of ethyl acetate,The organic layers were combined, washed with saturated aqueous NaHCO3, saturated brine,Anhydrous Na2SO4 dry, filtered, decompression,To obtain 15.8 g of ethyl 3,4-dihydroxybenzoate in 86.8percent yield.
70% at 0℃; Reflux; Inert atmosphere General procedure: Thionyl chloride (1.16 g, 1.5 equiv) was added drop-wise to a solution of acid (1.0 g, 1.0 equiv) in the corresponding alcohol (15 ml) at 0&d eg;C. The solution was refluxed under a nitrogen atmosphere until all starting material was consumed (TLC monitoring). Then the solvent was removed under vacuo and the residue was purified by silica gel column chromatography eluting with ethyl acetate/n-hexane to afford the corresponding carboxylic esters.#10;
15.8 g for 4 h; Reflux To a solution of 3,4-dihydroxybenzoic acid (15.4g, 0.1mol) in absolute ethanol (200mL) was added 5mL concentrated sulfuric acid. This mixture was heated at reflux for 4h. After cooling to ambient temperature, water (100mL) was slowly introduced over a period of 10min. The mixture was extracted with EtOAc, washed with diluted HCl followed by water, dried with Na2SO4. Then solvent was removed under reduced pressure, the yellow powder as ethyl 3,4-dihydroxybenzoate was used without further disposal. Yield 15.8g, 86.8percent.

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  • 7
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  • 12
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  • 17
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  • 18
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  • 19
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  • 20
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  • [ 950596-58-4 ]
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