Home Cart Sign in  
Chemical Structure| 1108724-32-8 Chemical Structure| 1108724-32-8

Structure of 1108724-32-8

Chemical Structure| 1108724-32-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 1108724-32-8 ]

CAS No. :1108724-32-8
Formula : C7H6BrF2N
M.W : 222.03
SMILES Code : CC(C1=CN=CC(Br)=C1)(F)F
MDL No. :MFCD18254770
InChI Key :WHDYQJPECGZSLP-UHFFFAOYSA-N
Pubchem ID :68669965

Safety of [ 1108724-32-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 1108724-32-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.29
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 41.7
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.

2.01
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

2.35
Log Po/w (WLOGP)?

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

3.69
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.

2.49
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

3.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.72

Water Solubility

Log S (ESOL):?

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

-3.03
Solubility 0.205 mg/ml ; 0.000923 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.

-2.26
Solubility 1.22 mg/ml ; 0.00549 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

-3.88
Solubility 0.0293 mg/ml ; 0.000132 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.

-5.99 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

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

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)

1.81

Application In Synthesis of [ 1108724-32-8 ]

* 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 [ 1108724-32-8 ]

[ 1108724-32-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1013-88-3 ]
  • [ 1108724-32-8 ]
  • [ 1529769-48-9 ]
YieldReaction ConditionsOperation in experiment
92% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; at 100.0℃; for 16.0h;Inert atmosphere; Add benzophenone imine (215 mg, 1.19 mmol), cesium carbonate (640 mg, 1.96 mmol), (±)-2,2'-bis(diphenylphosphino)-l, -binaphthalene (BINAP, 98 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 90 mg, 0.098 mmol] to the solution of 3-bromo-5-(l, 1 -difluoroethyl)pyridine (200 mg, 0.9 mmol) in dioxane (10 mL), stir the resulting mixture under nitrogen atmosphere at 100C for 16 hrs. Cool the reaction mixture to room temperature, filter off the solid, concentrate the filtrate under reduced pressure, purify by flash chromatography (silica gel, EtOAc:PE=2:l) to yield the title compound (296 mg, 92%). MS: (M+l): 323.
92% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100.0℃; for 16.0h;Inert atmosphere; Add benzophenone imine (215 mg, 1.19 mmol), cesium carbonate (640 mg, 1.96 mmol), (+-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (BINAP, 98 mg, 0.16 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 90 mg, 0.098 mmol] to the solution of <strong>[1108724-32-8]3-bromo-5-(1,1-difluoroethyl)pyridine</strong> (200 mg, 0.9 mmol) in dioxane (10 mL), stir the resulting mixture under nitrogen atmosphere at 100 C. for 16 hrs. Cool the reaction mixture to room temperature, filter off the solid, concentrate the filtrate under reduced pressure, purify by flash chromatography (silica gel, EtOAc:PE=2:1) to yield the title compound (296 mg, 92%). MS: (M+1): 323.
  • 2
  • [ 38940-62-4 ]
  • [ 1108724-32-8 ]
YieldReaction ConditionsOperation in experiment
36% With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 60.0℃;Sealed tube; Heat the mixture of l-(5-bromopyridin-3-yl)ethanone (500 mg, 2.5 mmol), bis-(2-methoxyethyl)aminosulfur trifluoride (BAST, 2.2 g, 10 mmol) in dichloromethane (8 mL) in a sealed tube at 60C overnight. TLC (PE:EtOAc=l :l) shows the reaction is complete. Concentrate the mixture, purify the residue by flash chromatography (silica gel, PE:EtOAc=l :1) to afford the title compound (200 mg, 36%). MS: (M+1): 222/224.
36% With (bis-(2-methoxyethyl)amino)sulfur trufluoride; In dichloromethane; at 60.0℃;Sealed tube; Heat the mixture of 1-(5-bromopyridin-3-yl)ethanone (500 mg, 2.5 mmol), bis-(2-methoxyethyl)aminosulfur trifluoride (BAST, 2.2 g, 10 mmol) in dichloromethane (8 mL) in a sealed tube at 60 C. overnight. TLC (PE:EtOAc=1:1) shows the reaction is complete. Concentrate the mixture, purify the residue by flash chromatography (silica gel, PE:EtOAc=1:1) to afford the title compound (200 mg, 36%). MS: (M+1): 222/224.
With diethylamino-sulfur trifluoride; In dichloromethane; at 50.0℃; for 18.0h; Step 1. 3-Bromo-5-(l,l-difluoroethyl)pyridine To a stirred solution of l-(5-bromopyridin-3-yl)ethanone (2.4 g, 12 mmol) in 24 mL of CH2CI2 was added DAST (15.5 mL, 96 mmol) dropwise over a period of 10 min. The mixture was heated to 50 C for 18 h. The mixture was cooled to RT and carefully poured into ice-cold 2N NaOH. The layers were separated and the aqueous phase was extracted with CH2CI2. The organic phases were combined, dried over a2S04, and the solvent was removed in vacuo. The crude product was chromatographed on an 80g S1O2 column using 0-30% EtOAc:hexane over 30 min at 60 mL/min. Fractions containing product were combined and the solvents were removed in vacuo to give the title compound. LCMS m/z (M+H)+ = 223.9.
  • 3
  • [ 1108724-32-8 ]
  • [ 1211540-26-9 ]
  • 4
  • [ 1108724-32-8 ]
  • [ 7486-35-3 ]
  • 3-(1,1-difluoroethyl)-5-vinylpyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 100.0℃; for 1.5h;Inert atmosphere; To a stirred solution of 3-bromo-5-(l, l-difluoroethyl)pyridine (1.86 g, 8.38 mmol) in 40 mL toluene was added vinyl tri-n-butylstannane (3.2 mL, 11 mmol) and the solution was sparged with nitrogen gas. Bis(triphenylphosphine)palladium(II) chloride (0.6 g, 0.8 mmol) was added and the mixture was heated to 100 C for 1.5 h. The mixture was cooled to RT, diluted with EtOAc, and washed with water and brine, then dried (MgS04), filtered and the solvent was removed in vacuo. The crude product was chromatographed on a 40 g S1O2 column using 0-40% EtOAc:hexane over 20 min at 40 mL/min. Fractions containing product were combined and the solvents were removed in vacuo to give the title compound. LCMS m/z = 170.1 (M+H)+.
  • 5
  • [ 1108724-32-8 ]
  • 5-(1,1-difluoroethyl)nicotinaldehyde [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 1108724-32-8 ]

Fluorinated Building Blocks

Chemical Structure| 436799-33-6

A230656 [436799-33-6]

3-Bromo-5-(trifluoromethyl)pyridine

Similarity: 0.90

Chemical Structure| 71701-92-3

A822485 [71701-92-3]

3-Bromo-2-chloro-5-(trifluoromethyl)pyridine

Similarity: 0.75

Chemical Structure| 79456-30-7

A166451 [79456-30-7]

3-Bromo-5-(trifluoromethyl)pyridin-2-amine

Similarity: 0.74

Chemical Structure| 1227563-37-2

A136183 [1227563-37-2]

(3-Bromo-5-(trifluoromethyl)pyridin-2-yl)methanol

Similarity: 0.73

Chemical Structure| 76041-73-1

A219972 [76041-73-1]

3-Bromo-5-(trifluoromethyl)pyridin-2-ol

Similarity: 0.73

Bromides

Chemical Structure| 436799-33-6

A230656 [436799-33-6]

3-Bromo-5-(trifluoromethyl)pyridine

Similarity: 0.90

Chemical Structure| 142337-95-9

A285693 [142337-95-9]

3-Bromo-5-ethylpyridine

Similarity: 0.79

Chemical Structure| 118775-69-2

A267858 [118775-69-2]

3-Bromo-5-(prop-1-en-2-yl)pyridine

Similarity: 0.77

Chemical Structure| 142137-17-5

A204358 [142137-17-5]

3-Bromo-5-phenylpyridine

Similarity: 0.76

Chemical Structure| 38749-76-7

A327545 [38749-76-7]

3-Bromo-4-ethylpyridine

Similarity: 0.75

Related Parent Nucleus of
[ 1108724-32-8 ]

Pyridines

Chemical Structure| 436799-33-6

A230656 [436799-33-6]

3-Bromo-5-(trifluoromethyl)pyridine

Similarity: 0.90

Chemical Structure| 142337-95-9

A285693 [142337-95-9]

3-Bromo-5-ethylpyridine

Similarity: 0.79

Chemical Structure| 118775-69-2

A267858 [118775-69-2]

3-Bromo-5-(prop-1-en-2-yl)pyridine

Similarity: 0.77

Chemical Structure| 142137-17-5

A204358 [142137-17-5]

3-Bromo-5-phenylpyridine

Similarity: 0.76

Chemical Structure| 38749-76-7

A327545 [38749-76-7]

3-Bromo-4-ethylpyridine

Similarity: 0.75