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Chemical Structure| 175018-77-6 Chemical Structure| 175018-77-6

Structure of 175018-77-6

Chemical Structure| 175018-77-6

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Product Details of [ 175018-77-6 ]

CAS No. :175018-77-6
Formula : C8H7BrF2
M.W : 221.04
SMILES Code : FC1=CC(CCBr)=CC=C1F
MDL No. :MFCD12025017
InChI Key :XCKJCCCKEWTUIV-UHFFFAOYSA-N
Pubchem ID :15020053

Safety of [ 175018-77-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:1760
Packing Group:

Computational Chemistry of [ 175018-77-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 44.0
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.44
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

3.14
Log Po/w (WLOGP)?

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

3.74
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.

4.25
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

3.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.51

Water Solubility

Log S (ESOL):?

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

-3.46
Solubility 0.0766 mg/ml ; 0.000347 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.

-2.81
Solubility 0.343 mg/ml ; 0.00155 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

-4.62
Solubility 0.00524 mg/ml ; 0.0000237 mol/l
Class?

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

Moderately soluble

Pharmacokinetics

GI absorption?

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

Low
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

Yes
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.

-5.42 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

1.0
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)

1.96

Application In Synthesis of [ 175018-77-6 ]

* 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 [ 175018-77-6 ]

[ 175018-77-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 174609-58-6 ]
  • [ 175018-77-6 ]
  • 1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]-4-[2-(3,4-difluorophenyl)-ethyl]piperazine [ No CAS ]
  • 3
  • [ 603-35-0 ]
  • [ 175018-77-6 ]
  • (3,4-difluorophenyl)ethyltriphenylphosphonium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; Preparation of (3,4-difluorophenyl)ethyltriphenylphosphonium bromide A mixture of 19.67 g (89 mmol) of 3,4-difluoro-phenethyl bromide, 28.07 g (107 mmol) of triphenyl phosphine and 134 ml of toluene was heated under reflux for 36 hrs. After cooling, the crystal was washed by decantation with toluene and dried in vacuo, while ice-cooling.
  • 4
  • [ 286440-92-4 ]
  • [ 175018-77-6 ]
YieldReaction ConditionsOperation in experiment
With sodium bicarbonate; sulfuric acid; hydrogen bromide; Preparation of 3,4-difluorophenethylbromide 17.59 g (111 mmol) of 2-(3,4-difluorophenyl)ethanol, 16 ml (137 mmol) of hydrogen bromide, 6.8 ml (234 mmol) of conc. sulfuric acid were added in the order, and the mixture was heated under reflux for 3 hrs. The reaction mixture was poured onto an ice-bath, an organic layer and an aqueous layer were separated, the aqueous layer was extracted with ether, the extract combined with the organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was distilled off, the solution condensed and purified by vacuum distillation to obtain 21.96 g (bp 68-70 C./2-4 Torr.) of oily product. The oily product was purified by column chromatography (elution solvent: hexane:ethyl acetate=3:1), the elude was further purified by vacuum distillation to obtain 19.79 g of the title compound (81%, bp 73-75 C./4 Torr.) as oily product.
With sulfuric acid; hydrogen bromide; In acetic acid; at 100.0℃; for 4.0h; A mixture of 2-(3,4-difluorophenyl)ethanol (5 g, 0.032 mol; see step (iii) above), HBr in acetic acid (51.84 mL of 49%, 0.64 mol) and 5 mL of sulfuric acid was stirred at 1000C for 4 h. The reaction mixture was poured onto ice and extracted with diethylether. The organic layer was washed with NaHCO3 and water and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed <n="90"/>by purification (three times) over silica gel (using petroleum ether as eluent), afforded 1.8 g of the title compound as a liquid.
  • 5
  • [ 658-93-5 ]
  • [ 175018-77-6 ]
YieldReaction ConditionsOperation in experiment
a 3,4-(Difluoro)phenethyl bromide Prepared from 3,4-(difluoro)phenylacetic acid using the procedures described for Intermediate 3. delta (250 MHz, CDCl3) 3.12 (2H, t, J=7.3 Hz, CH2), 3.54 (2H, t, J=7.3 Hz, CH2), 6.90-7.16 (3H, m, Ar--H).
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Arndt-Eistert Homologation • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hunsdiecker-Borodin Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Carboxylic Acids • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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