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[ CAS No. 80407-68-7 ] {[proInfo.proName]}

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Chemical Structure| 80407-68-7
Chemical Structure| 80407-68-7
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Product Details of [ 80407-68-7 ]

CAS No. :80407-68-7 MDL No. :MFCD24849701
Formula : C13H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KTOCATSUCSJPCT-UHFFFAOYSA-N
M.W : 251.28 Pubchem ID :16063392
Synonyms :

Calculated chemistry of [ 80407-68-7 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 65.54
TPSA : 60.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.93
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.61
Log Po/w (MLOGP) : 0.29
Log Po/w (SILICOS-IT) : 2.43
Consensus Log Po/w : 1.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 2.09 mg/ml ; 0.00831 mol/l
Class : Soluble
Log S (Ali) : -2.41
Solubility : 0.969 mg/ml ; 0.00386 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.84
Solubility : 0.036 mg/ml ; 0.000143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.37

Safety of [ 80407-68-7 ]

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 [ 80407-68-7 ]

* 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 [ 80407-68-7 ]
  • Downstream synthetic route of [ 80407-68-7 ]

[ 80407-68-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 80407-68-7 ]
  • [ 179688-29-0 ]
Reference: [1] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[2] Patent: CN107445907, 2017, A,
  • 2
  • [ 80407-68-7 ]
  • [ 236750-65-5 ]
YieldReaction ConditionsOperation in experiment
92.33% at 70℃; for 0.0166667 h; Example 17. Example 2 was repeated except that the nitration reaction temperature was 70 °C.
1) Nitrification reaction: 200 g of raw material is dissolved in 3 L of glacial acetic acid to dissolve as material I, concentrated sulfuric acid is used as material II, and concentrated nitric acid is used as material III.Adjust the flow rate of the flow pump so that the flow rate of the material I is 20 ml/min, and the flow rate of the material II is 10 ml/min.The flow rate of the material III is 6 ml/min, the molar ratio of the raw material to the HNO3 is 1:1.5, and the mass ratio of the concentrated nitric acid to the concentrated sulfuric acid is 1:4.The reaction temperature is 60 ° C, the residence time of the reaction is 60 seconds, and the temperature of the cooling module is 20 ° C.Collecting the reaction liquid flowing out from the outlet of the cooling module for post-treatment, which means that glacial acetic acid is recovered by distillation under reduced pressure.The residue was added to 1.2 L of water and extracted twice with 1 L of ethyl acetate.The organic phase is washed with a saturated sodium hydrogencarbonate solvent until neutral, dried over anhydrous sodium sulfate, and then evaporated.The nitrated product was obtained in 215.21 g, the yield was 90.58percent, and the purity was 98.95percent.
90% at 40℃; for 2 h; c) 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile:; To 70percent nitric acid (84ml) maintained at 4O0C was added 3,4-bis(2- methoxyethoxy) benzonitrile (42g) of the formula V slowly over a period of 2 hours under stirring. After complete addition of the compound, stirring continued for further an hour, quenched the reaction mass in ice-water, filtered, washed the precipitate with water and dried the material at 500C to get yellow solid i.e. 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile of the formula Vl (44.5g, 90percent); m.p. 139-143°C.NMR (CDCI3): δ 3.45 (s, 6H), 3.82(m, 4HO, 4.30(m, 4H), 7.28(s, 1H) and 7.85(s, 1 H).
90% at 40℃; for 3 h; c) 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile:; To 70percent nitric acid (84ml) maintained at 4O0C was added 3,4-bis(2- methoxyethoxy) benzonitrile (42g) of the formula V slowly over a period of 2 hours under stirring. After complete addition of the compound, stirring continued for further an hour, quenched the reaction mass in ice-water, filtered, washed the precipitate with water and dried the material at 500C to get yellow solid i.e. 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile of the formula Vl (44.5g, 90percent); m.p. 139-143°C.NMR (CDCI3): δ 3.45 (s, 6H), 3.82(m, 4HO, 4.30(m, 4H), 7.28(s, 1H) and 7.85(s, 1 H).
47% at 20 - 50℃; for 48 h; Nitric acid (65 percent, 16.2 g, 254.5 mmol) was dropwise added directly into flask containing 3,4-bis(2-methoxyethoxy)benzonitrile (12.8 g, 50.9 mmol). The mixture was then heated with stirring to 50 °C until starting material was completely dissolved. After stirring for two days at RT the reaction mixture was dissolved with water (50 ml) and formed precipitate was filtered off and washed with water (100 ml). After crystallization from chloroform the title compound was obtained in form of white crystals (7.1 g, 47 percent). Spectral data were in agreement with literature.Chandregowda, Venkateshappa; Rao, Gudapati Ventakeswara; Reddy, Goukanapalli Chandrasekara Heterocycles, 2007 , vol. 71, 1 p. 39 - 48.
47% at 20 - 50℃; Nitric acid (65 percent, 16.2 g, 254.5 mmol) was dropwise added directly into flask containing 3,4- bis(2-methoxyethoxy)benzonitrile (12.8 g, 50.9 mmol). The mixture was then heated with stirring to 50 °C until starting material was completely dissolved. After stirring for two days at RT the reaction mixture was dissolved with water (50 ml) and formed precipitate was filtered off and washed with water (100 ml). After crystallization from chloroform the title compound was obtained in form of white crystals (7.1 g, 47 percent). Spectral data were in agreement with literature. Chandregowda, Venkateshappa; Rao, Gudapati Ventakeswara; Reddy, Goukanapalli Chandrasekara Heterocycles, 2007 , vol. 71 , 1 p. 39 - 48.

Reference: [1] Patent: CN108358798, 2018, A, . Location in patent: Paragraph 0055; 0065; 0075; 0085; 0094-0099; 0102
[2] Patent: WO2007/138612, 2007, A2, . Location in patent: Page/Page column 10
[3] Patent: WO2007/138613, 2007, A2, . Location in patent: Page/Page column 11-12
[4] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
[5] Heterocycles, 2007, vol. 71, # 1, p. 39 - 48
[6] Patent: EP2769723, 2014, A1, . Location in patent: Paragraph 0150-0151
[7] Patent: WO2014/128206, 2014, A1, . Location in patent: Page/Page column 48-49
[8] Patent: CN106957274, 2017, A, . Location in patent: Paragraph 0051-0054
[9] Patent: CN107445907, 2017, A, . Location in patent: Paragraph 0062; 0063; 0064; 0065
  • 3
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  • [ 950596-58-4 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 3, p. 909 - 914
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