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Chemical Structure| 72537-17-8 Chemical Structure| 72537-17-8

Structure of 72537-17-8

Chemical Structure| 72537-17-8

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Product Details of [ 72537-17-8 ]

CAS No. :72537-17-8
Formula : C6H2ClF4N
M.W : 199.53
SMILES Code : FC1=NC=C(C=C1Cl)C(F)(F)F
MDL No. :MFCD00191918
InChI Key :GDSROTVTTLUHCO-UHFFFAOYSA-N
Pubchem ID :1268075

Safety of [ 72537-17-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 72537-17-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 1
Num. H-bond acceptors 5.0
Num. H-bond donors 0.0
Molar Refractivity 34.21
TPSA ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.82
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

2.8
Log Po/w (WLOGP)?

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

4.47
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.

2.6
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

3.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.03

Water Solubility

Log S (ESOL):?

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

-3.15
Solubility 0.143 mg/ml ; 0.000716 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-2.73
Solubility 0.374 mg/ml ; 0.00187 mol/l
Class?

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

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

-3.81
Solubility 0.0308 mg/ml ; 0.000155 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

No
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.

-5.53 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

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<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)

2.09

Application In Synthesis of [ 72537-17-8 ]

* 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 [ 72537-17-8 ]

[ 72537-17-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 22300-52-3 ]
  • [ 72537-17-8 ]
  • [ 1192847-40-7 ]
  • 2
  • [ 67-56-1 ]
  • [ 72537-17-8 ]
  • [ 94050-90-5 ]
  • [ 72619-32-0 ]
  • 3
  • [ 110-80-5 ]
  • [ 72537-17-8 ]
  • [ 94050-90-5 ]
  • haloxyfop-etotyl [ No CAS ]
  • 4
  • [ 72537-17-8 ]
  • [ 94050-90-5 ]
  • [ 71-36-3 ]
  • [ 99320-80-6 ]
  • 5
  • [ 69045-83-6 ]
  • [ 72537-17-8 ]
YieldReaction ConditionsOperation in experiment
97.56% 1. In a 200 mL autoclave, add 23.0 g (0.1 mol) of 2,3,-dichloro-5-trichloromethylpyridine, place a lid on the kettle, and fill it with nitrogen for 1 hour at a pressure of 10.0 MPa for 5 hours to leak the reaction kettle. After confirming that the reactor is leak-free, the pressure in the kettle is vented.The reactor was then placed in an ice-salt bath and cooled when the temperature in the kettle fell below -5C.The kettle was charged with anhydrous HF 40.0 g (~2.0 mol), and the reaction system was heated to 180C with stirring, and the reaction was incubated for 12 hours.2. After the reaction is completed, cool down to 25C, exchange nitrogen in the reactor for half an hour (exchanged gas is passed into 10% aqueous sodium hydroxide for neutralization absorption), and hydraulically introduce the reaction into a 250 mL round bottom flask. ,70 g (~1.0 mol) of a 25% aqueous ammonia solution was added and reacted at 35C for 12 hours under normal pressure.3. After the reaction is complete, collect the oil layer and wash three times until neutral. Add 10g of anhydrous sodium sulfate to the oily liquid and dry it for 6h. Filter the solids out and then conduct vacuum distillation to collect the fraction with a boiling point of 50-55C/11mmHg.Obtained 16.0 g of 2-fluoro-3-chloro-5-trifluoromethylpyridine product.The content of 2-fluoro-3-chloro-5-trifluoromethylpyridine in the product was determined to be 99.95% (GC) and the yield was 97.56%.
With hydrogen fluoride; antimony pentafluoride; at 180℃; under 45004.5 Torr; for 24h;Large scale; The chlorinated <strong>[69045-83-6]2,3-dichloro-5-trichloromethylpyridine</strong> was put into a fluorination kettle (about 2300 kg).Injecting catalyst into the reaction fluorineAntimony pentafluoride 200kg,Add 1700kg of anhydrous hydrogen fluoride,The molar ratio of <strong>[69045-83-6]2,3-dichloro-5-trichloromethylpyridine</strong> to hydrogen fluoride is 1:10.Excessive hydrogen fluoride facilitates the reaction.Turn on the reactor and stir, heat up and keep at 180 C.The reaction was carried out at a pressure of 6 MPa for 24 hours, and the temperature was lowered to 60 C.Transfer the material to 3000L in advanceWater in the washing kettle,The material is washed twice and then neutralized to a pH of 7,The material is then layered into a rectification tank.The mixture was subjected to vacuum distillation to obtain 2-fluoro-3-chloro-5-trifluoromethylpyridine having a content of ?99%.
 

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