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Chemical Structure| 2751-90-8 Chemical Structure| 2751-90-8

Structure of 2751-90-8

Chemical Structure| 2751-90-8

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Product Details of [ 2751-90-8 ]

CAS No. :2751-90-8
Formula : C24H20BrP
M.W : 419.29
SMILES Code : C1([P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)=CC=CC=C1.[Br-]
MDL No. :MFCD00011915
InChI Key :BRKFQVAOMSWFDU-UHFFFAOYSA-M
Pubchem ID :2724163

Safety of [ 2751-90-8 ]

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

Computational Chemistry of [ 2751-90-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 24
Fraction Csp3 0.0
Num. rotatable bonds 4
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 120.15
TPSA ?

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

13.59 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-0.99
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

5.93
Log Po/w (WLOGP)?

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

1.31
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.

6.58
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

5.79
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.72

Water Solubility

Log S (ESOL):?

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

-6.59
Solubility 0.000107 mg/ml ; 0.000000254 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-5.99
Solubility 0.000429 mg/ml ; 0.00000102 mol/l
Class?

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

Moderately 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

-10.03
Solubility 0.0000000392 mg/ml ; 0.0000000001 mol/l
Class?

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

Insoluble

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

Yes
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.

-4.65 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

1.0
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

1.0 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<2.0
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)

4.75

Application In Synthesis of [ 2751-90-8 ]

* 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 [ 2751-90-8 ]

[ 2751-90-8 ] Synthesis Path-Downstream   1~6

  • 2
  • [ 126-33-0 ]
  • [ 115812-33-4 ]
  • 2H-tetrachlorobenzotrifluoride [ No CAS ]
  • [ 2751-90-8 ]
  • 2H-tetrafluorobenzotrifluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.5% With potassium fluoride; d) 812 g (14 mol) of potassium fluoride and 1400 ml of tetramethylene sulphone are subjected to incipient distillation at 20 mbar (quantity of distillate: 100 ml) in a stirred V4A steel apparatus. Then 40 g of tetraphenylphosphonium bromide and a mixture of 795 g (2.8 mm) of 2H-tetrachlorobenzotrifluoride and 170 g (0.78 mm) of 5-chloro-2,3,4-trifluorobenzotrifluoride are added and the mixture is stirred for 18 hours at 210 C. under the autogenous pressure (max. pressure 3.4 bar). Distillation yields 747 g of a crude distillate which is redistilled in a rotating strip column. 396 g of 2H-tetrafluorobenzotrifluoride and 318 g of 5-chloro-2,3,4-trifluorobenzotrifluoride are obtained. The recovery rate of the isolated yield is 90.5%.
  • 3
  • [ 22280-56-4 ]
  • [ 2751-90-8 ]
  • [ 19346-46-4 ]
YieldReaction ConditionsOperation in experiment
60% With KF; In hexane; acetonitrile; 18a. 2-fluoro-3-methyl-5-nitropyridine 2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.), KF (12 g, 258 mmol) and tetraphenylphosphonium bromide (20 g, 47.7 mmol; Aldrich) were combined in 200 mL of acetonitrile and heated at reflux for 4 days. The mixture was diluted with Et2 O (500 mL) and filtered, and the filtrate was concentrated. The residue was triturated with hot hexane (4*200 mL), and the hexane solutions were combined and concentrated to afford the title compound as a solid (8.4 g, 60%): 1 H NMR (DMSO-d6, 300 MHz) delta2.42 (s, 3H), 8.43 (m, 1H), 8.95 (dd, J=1.6 Hz, 1H); MS (CI/NH3) m/z: 157 (M+H)+.
  • 4
  • [ 126-33-0 ]
  • [ 611-06-3 ]
  • [ 2751-90-8 ]
  • [ 446-35-5 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; Comparison Example 6 Preparing 2,4-difluoronitrobenzene by Reacting 2,4-dichloronitrobenzene Using tetraphenylphosphonium bromide as Catalyst 192 g (1 mol) of 2,4-dichloronitrobenzene, 550 ml of tetramethylene sulfone, 136.8 g (2.4 mol) of potassium fluoride and 6.29 g (0.015 mol) of tetraphenylphosphonium bromide are employed and the procedure described in Example 7 and 8 is followed.
  • 5
  • [ 126-33-0 ]
  • [ 2751-90-8 ]
  • [ 100-00-5 ]
  • [ 350-46-9 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; Comparison Example 1 Preparing 4-nitrofluorobenzene by Reacting 4-nitrobenzene Using tetraphenylphosphonium bromide as Catalyst 157 g (1mol) of 4-nitrochlorobenzene, 400 ml of tetramethylene sulfone, and 62.7 g (1.1 mol) of potassium fluoride, but 4.19 g (0.01 mol) of tetraphenylphosphonium bromide, are employed and the procedure described in Example 1 is followed.
  • 6
  • uranyl nirate hexahydrate [ No CAS ]
  • [ 610-09-3 ]
  • [ 2751-90-8 ]
  • [ 75-05-8 ]
  • [NH4][PPh4][(UO2)8(cis-1,2-cyclohexanedicarboxylate)9(H2O)6]*3H2O [ No CAS ]
 

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