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Structure of 2923-18-4

Chemical Structure| 2923-18-4

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Product Citations

Product Citations

Mukherjee, Kallol ; Hall, Sarah ; Krummel, Amber ;

Abstract: We have investigated the H-bonding structure of the ionic liquid (IL) 1-ethyl-3-methylimidazolium trifluoroacetate ([Emim:TFA]) via linear and two-dimensional infrared (2DIR) spectroscopy. We directly probed the asymmetric carbonyl stretching mode of the trifluoroacetate anion rather than using an extrinsic solute molecule as a vibrational probe, the more common approach in 2DIR studies of ILs. The C=O asymmetric stretching mode exhibits multimodal character in both linear IR and 2DIR measurements, indicating structural inhomogeneity in the H-bonding of TFA. Solvent-dependent linear IR spectra of dilute Emim:TFA in two protic (D2O and MeOH-d4) and two aprotic (DMSO-d6 and acetonitrile) solvents, comparisons with NaTFA spectra in these same solvents, and DFT calculations of Emim:TFA and small, solvated ion clusters were used to characterize the H-bonding structures present in the neat ionic liquid. The most prominent IR feature near 1690 cm-1 originates from hydrogen bonding between TFA and the C2H and C4/5H imidazolium ring protons. Calculations of the two different types of H-bonding interactions, C2H (and C6H, C7H)-TFA and C4H (and/or C5H)-TFA, indicate that their frequencies are different by several wavenumbers. Higher frequency features (>1695 cm-1) are associated with thosetriple ion structures and higher aggregates where the TFA makes a weak hydrogen bond to Emim+. The appearance of cross-peak features in the time-zero 2DIR spectra indicates the presence of intermolecular coupling between the C=O stretching modes of TFA anions, which can be expected for such pure IL systems. When diluted in polar aprotic solvents, Emim:TFA exists predominantly in ion pairs, while in polar protic solvents solvent-separated ions are the dominant species. The existence of significant ionic aggregation is only visible in the neat ionic liquid

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Product Details of [ 2923-18-4 ]

CAS No. :2923-18-4
Formula : C2F3NaO2
M.W : 136.01
SMILES Code : O=C([O-])C(F)(F)F.[Na+]
MDL No. :MFCD00013217
InChI Key :UYCAUPASBSROMS-UHFFFAOYSA-M
Pubchem ID :517019

Safety of [ 2923-18-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 2923-18-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 1
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 11.75
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

40.13 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-7.91
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.91
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.56
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.27
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.93
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.05

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.19
Solubility 8.77 mg/ml ; 0.0645 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.34
Solubility 6.24 mg/ml ; 0.0459 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.08
Solubility 112.0 mg/ml ; 0.826 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.48 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.0

Application In Synthesis of [ 2923-18-4 ]

* 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.

  • Downstream synthetic route of [ 2923-18-4 ]

[ 2923-18-4 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 32024-15-0 ]
  • [ 2923-18-4 ]
  • 3,4-dimethoxy-5-(trifluoromethyl)benzaldehyde [ No CAS ]
  • 3
  • [ 112220-68-5 ]
  • [ 2923-18-4 ]
  • [ 75-05-8 ]
  • [ 72287-26-4 ]
  • [ 494829-03-7 ]
  • [ 494828-93-2 ]
  • 4
  • [ 51934-41-9 ]
  • [ 2923-18-4 ]
  • [ 898787-14-9 ]
  • ethyl 4-(2,2,2-trifluoro-1,1-dihydroxyethyl)benzoate [ No CAS ]
  • 5
  • [ 19063-55-9 ]
  • [ 2923-18-4 ]
  • 6-bromo-3-((trifluoromethyl)thio)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With iron(III) chloride; sulfur; In ethanol; at 50℃; for 3h;Sealed tube; 6 mmol of <strong>[19063-55-9]6-bromocoumarin</strong> was added to the reaction vessel,Sodium trifluoroacetate 1 mmol,Elemental sulfur 1mmol,0.01 mmol of ferric chloride and 2 ml of ethanol,Sealing reaction at 50 C for 3 hours,The reaction column is subjected to column chromatography,The following target compounds were obtained:After identification,Performing a nuclear magnetic spectrum analysis on the above white solid powder,It was proved that the synthesis was 3-trifluoromethylthio-<strong>[19063-55-9]6-bromocoumarin</strong>.The yield was 99%.
  • 6
  • [ 120-72-9 ]
  • [ 2923-18-4 ]
  • [ 51310-54-4 ]
 

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