Home Cart Sign in  
Chemical Structure| 161957-61-5 Chemical Structure| 161957-61-5

Structure of 161957-61-5

Chemical Structure| 161957-61-5

*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 [ 161957-61-5 ]

CAS No. :161957-61-5
Formula : C8H6BrFO
M.W : 217.04
SMILES Code : BrC1=CC=CC(=C1F)C(C)=O
MDL No. :MFCD09264507
Boiling Point : No data available
InChI Key :GSLFYQYBXIVNLS-UHFFFAOYSA-N
Pubchem ID :14937359

Safety of [ 161957-61-5 ]

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

Computational Chemistry of [ 161957-61-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 44.29
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.81
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

2.4
Log Po/w (WLOGP)?

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

3.21
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.

2.94
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

3.25
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.

-3.04
Solubility 0.2 mg/ml ; 0.000922 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.

-2.4
Solubility 0.864 mg/ml ; 0.00398 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

-3.87
Solubility 0.0291 mg/ml ; 0.000134 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.

-5.92 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)

1.54

Application In Synthesis of [ 161957-61-5 ]

* 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.

  • Upstream synthesis route of [ 161957-61-5 ]

[ 161957-61-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 680610-73-5 ]
  • [ 75-16-1 ]
  • [ 161957-61-5 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: at -78 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 0℃;
1-(3-Bromo-2-fluorophenyl)-ethanone [161957-61-5]
Methylmagnesium bromide (3 M in diethyl ether, 21 mL) was added to 3-bromo-2-fluoro-N-methoxy-N-methylbenzamide (10.89 g) in tetrahydrofuran (100 mL) at -78° C.
This was allowed to warm to room temperature and stir for 16 h.
The reaction was then cooled to 0° C. and carefully quenched with 2 M HCl until pH=1.
The solvent was removed by evaporation and the product extracted with ethyl acetate (3*100 mL).
The organic layers were combined, dried over sodium sulfate and the solvent removed by evaporation to yield the product as a light brown solid.
This was dissolved in dichloromethane (200 mL) and washed with sat. NaHCO3 (200mL).
The dichloromethane layer was dried over sodium sulfate and the solvent removed by evaporation to yield 1-(3-bromo-2-fluorophenyl)-ethanone as a yellow oil (8.8 g, 97percent).
1H NMR (CDCl3): 2.67 (3H, d, ArCOCH3), 7.11 (1H, t, Ar), 7.69-7.81 (2H, m, Ar).
64% at 0℃; for 2 h; Methylmagnesium bromide (0.8 mL of a 1.4 M solution in THF/toluene), was added to a solution of 3-Bromo-2-fluoro-N-methoxy-N-methyl-benzamide (190 g, 0.73 mmol) in THF (1 mL) at 0° C. and the reaction was stirred at 0° C. for 2 h. The reaction was quenched with dilute aqueous HCl and extracted with EtOAc. The organics were dried over MgSO4, concentrated and chromatographed to provide 100 mg (64percent yield) of the title compound as colorless oil.
References: [1] Patent: US2009/209529, 2009, A1, . Location in patent: Page/Page column 34.
[2] Patent: US2008/76771, 2008, A1, . Location in patent: Page/Page column 18.
  • 2
  • [ 75-36-5 ]
  • [ 161957-53-5 ]
  • [ 161957-61-5 ]
References: [1] Tetrahedron Letters, 1995, vol. 36, # 6, p. 881 - 884.
[2] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 2, p. 133 - 141.
[3] Patent: US2005/239795, 2005, A1, . Location in patent: Page/Page column 35.
  • 3
  • [ 161957-53-5 ]
  • [ 161957-61-5 ]
References: [1] Patent: US2004/220194, 2004, A1, . Location in patent: Page 43.
[2] Patent: WO2005/121087, 2005, A1, . Location in patent: Page/Page column 65.
  • 4
  • [ 1072-85-1 ]
  • [ 161957-61-5 ]
References: [1] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 2, p. 133 - 141.
[2] Tetrahedron Letters, 1995, vol. 36, # 6, p. 881 - 884.
  • 5
  • [ 161957-56-8 ]
  • [ 161957-61-5 ]
References: [1] Patent: US2008/76771, 2008, A1, .
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 161957-61-5 ]

Fluorinated Building Blocks

Chemical Structure| 864773-64-8

A203164 [864773-64-8]

1-(5-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.96

Chemical Structure| 1210824-63-7

A121272 [1210824-63-7]

1-(3-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.93

Chemical Structure| 1007-15-4

A147307 [1007-15-4]

3'-Bromo-4'-fluoroacetophenone

Similarity: 0.93

Chemical Structure| 1273595-81-5

A140917 [1273595-81-5]

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Chemical Structure| 1242157-14-7

A651351 [1242157-14-7]

5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Aryls

Chemical Structure| 864773-64-8

A203164 [864773-64-8]

1-(5-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.96

Chemical Structure| 1210824-63-7

A121272 [1210824-63-7]

1-(3-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.93

Chemical Structure| 1007-15-4

A147307 [1007-15-4]

3'-Bromo-4'-fluoroacetophenone

Similarity: 0.93

Chemical Structure| 1273595-81-5

A140917 [1273595-81-5]

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Chemical Structure| 1242157-14-7

A651351 [1242157-14-7]

5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Bromides

Chemical Structure| 864773-64-8

A203164 [864773-64-8]

1-(5-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.96

Chemical Structure| 1210824-63-7

A121272 [1210824-63-7]

1-(3-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.93

Chemical Structure| 1007-15-4

A147307 [1007-15-4]

3'-Bromo-4'-fluoroacetophenone

Similarity: 0.93

Chemical Structure| 1273595-81-5

A140917 [1273595-81-5]

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Chemical Structure| 1242157-14-7

A651351 [1242157-14-7]

5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Ketones

Chemical Structure| 864773-64-8

A203164 [864773-64-8]

1-(5-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.96

Chemical Structure| 1210824-63-7

A121272 [1210824-63-7]

1-(3-Bromo-2,4-difluorophenyl)ethanone

Similarity: 0.93

Chemical Structure| 1007-15-4

A147307 [1007-15-4]

3'-Bromo-4'-fluoroacetophenone

Similarity: 0.93

Chemical Structure| 1273595-81-5

A140917 [1273595-81-5]

6-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89

Chemical Structure| 1242157-14-7

A651351 [1242157-14-7]

5-Bromo-7-fluoro-2,3-dihydro-1H-inden-1-one

Similarity: 0.89