Home Cart Sign in  
Chemical Structure| 174603-55-5 Chemical Structure| 174603-55-5

Structure of 174603-55-5

Chemical Structure| 174603-55-5

3-(2-Bromo-4-fluorophenyl)propionic acid

CAS No.: 174603-55-5

4.5 *For Research Use Only !

Cat. No.: A162701 Purity: 97%

Change View

Size Price

US Stock

Global Stock

In Stock
100mg łËǶÊÊ Inquiry Inquiry
250mg łËò¶ÊÊ Inquiry Inquiry
1g łîǶÊÊ Inquiry Inquiry

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

  • 100mg

    łËǶÊÊ

  • 250mg

    łËò¶ÊÊ

  • 1g

    łîǶÊÊ

In Stock

- +

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 [ 174603-55-5 ]

CAS No. :174603-55-5
Formula : C9H8BrFO2
M.W : 247.06
SMILES Code : O=C(O)CCC1=CC=C(F)C=C1Br
MDL No. :MFCD06656907
InChI Key :VHFQIJJCQTZKFK-UHFFFAOYSA-N
Pubchem ID :10922852

Safety of [ 174603-55-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 174603-55-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 50.45
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.84
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

2.47
Log Po/w (WLOGP)?

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

3.03
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.

3.11
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

2.99
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.69

Water Solubility

Log S (ESOL):?

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

-3.07
Solubility 0.21 mg/ml ; 0.000848 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.

-2.9
Solubility 0.313 mg/ml ; 0.00127 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

-3.72
Solubility 0.0473 mg/ml ; 0.000191 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.

-6.05 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

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

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)

1.69

Application In Synthesis of [ 174603-55-5 ]

* 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.

  • Downstream synthetic route of [ 174603-55-5 ]

[ 174603-55-5 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 174603-55-5 ]
  • 3-(2-bromo-4-fluorophenyl)propionyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 18h; To a solution of <strong>[174603-55-5]3-(2-bromo-4-fluoro-phenyl)-propionic acid</strong> (5.6 g, 22.67 mmol) in 0H2012 (56 mL) was added oxalyl chloride (4.13 mL, 48.18 mmol) at 0 00 and allowed to stir atRT for 1 8h. Excess oxalyl chloride was removed in vacuo to give the acid chloride as a semi-solid. The acid chloride was dissolved in 0H2012 (30 mL) and added to a suspension of anhydrous AId3 (3.77 g, 28.340 mmol) in 0H2012 (60 mL) at 0 00 and the reaction mixture was heated under reflux for 2h. The reaction mixture was cooled to RT, poured into ice-water and extracted with 0H2012 (1 x 150 mL). The combined organiclayers were washed with 0.1 M sodium hydroxide solution and water. The organic layer was dried (Na2SO4) and concentrated in vacuo to afford 4-bromo-6-fluoro-indan-1-one as an off-white solid (4.1 g, 78%).Rt:0.5 (10% EtOAc/pet-ether).1H NMR (400MHz, 0D013): O 7.55-7.52 (m, 1H), 7.39-7.37 (m, 1H), 3.06-3.03 (m, 2H),2.79-2.76 (m, 2H).
  • 2
  • [ 174603-54-4 ]
  • [ 174603-55-5 ]
YieldReaction ConditionsOperation in experiment
33% With water; potassium hydroxide; for 4.5h;Reflux; To a mixture of 2-(2-bromo-4-fluoro-benzyl)-malonic acid diethyl ester (2.1 g, 6.07 mmol)and water (14 mL) was added potassium hydroxide (0.68 g, 12.14 mmol) and the reactionmixture was heated under reflux for 4.5h. The reaction mixture was cooled to RT and theethanol removed in vacuo. The aqueous residue was cooled to 0 00, acidified with conc.H2S04, and heated at 120 00 for 16h. The reaction mixture was cooled to 0 00 theprecipitated solid was collected by filtration, washed with water and dried to obtain 3-(2-bromo-4-fluoro-phenyl)-propionic acid as an off-white solid (0.5 g, 33%).R: 0.2 (30% EtOAc/pet-ether).1H NMR (400MHz, DMSO-d6): O 12.26 (5, 1H), 7.55-7.52 (m, 1H), 7.42-7.38 (m, 1H),7.23-7.18 (m, 1H), 2.90 (t, J= 7.8 Hz, 2H), 2.52 (t, J= 7.8 Hz, 2H).
  • 3
  • [ 1422-53-3 ]
  • [ 174603-55-5 ]
  • 5
  • [ 174603-55-5 ]
  • [ 174603-56-6 ]
YieldReaction ConditionsOperation in experiment
970 mg In trifluorormethanesulfonic acid; at 60 - 80℃; for 18h;Inert atmosphere; Under argon <strong>[174603-55-5]3-(2-bromo-4-fluorophenyl)propanoic acid</strong> (1 .2 g) is added in small portions to trifluoromethanesulfonic acid (15 mL) at room temperature. The mixture is stirred for 2 hours at 60C and for 16 hours at 80C. After cooling to room temperature the mixture is poured slowly in ice-water. The aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated aqueous Na2CO3 solution and brine. After drying (MgSO4) the solvent is evaporated. The residue is stirred with dichloromethane (40 ml_), filtered and washed with dichloromethane. The combined dichloromethane phases are concentrated to give the title compound. Yield: 970 mg; LC (method 3): tR = 0.60 min; Mass spectrum (ESI+): m/z = 229 [M+H]+.
  • 6
  • [ 174603-55-5 ]
  • [ 174603-60-2 ]
  • 7
  • [ 174603-55-5 ]
  • (E)-2-(4-bromo-6-fluoro-1-indanylidene)acetamide [ No CAS ]
  • 8
  • [ 174603-55-5 ]
  • [ 174603-59-9 ]
  • 9
  • [ 174603-55-5 ]
  • [ 174603-58-8 ]
  • 10
  • [ 174603-55-5 ]
  • [ 174603-57-7 ]
YieldReaction ConditionsOperation in experiment
20.6 g (91%) c) Preparation of 3-(2-Bromo-4-Fluorophenyl) Propionic Acid A mixture of diethyl 2-(2-bromo-4-fluorobenzyl) malonate (31.8 g, 0.09 mol) and potassium hydroxide (10.3 g, 0.18 mol) in water (200 ml) was refluxed for 4.5 h. The mixture was concentrated in vacuo to remove the ethanol. To the resulting solution was added concentrated sulphuric acid (15.7 ml, 0.29 mol) and the mixture was refluxed for 18 h. The reaction mixture was chilled in an ice bath and the resulting solid was filtered, washed with water, and air dried to give 20.6 g (91%) of crude 3-(2-bromo-4-fluorophenyl) propionic acid. This material was used without further purification.
  • 12
  • 2-bromo-4-fluoro-1-iodobenzene [ No CAS ]
  • [ 174603-55-5 ]
  • 13
  • methyl 3-(2-bromo-4-fluorophenyl)propanoate [ No CAS ]
  • [ 174603-55-5 ]
YieldReaction ConditionsOperation in experiment
1.2 g To a solution of methyl 3-(2-bromo-4-fluorophenyl)propanoate (1 .4 g) in tetrahydrofuran (10 mL) and methanol (10 mL) is added 4 M aqueous NaOH solution (10 mL) and the mixture is heated to 50C for 3 hours. The organic solvents are evaporated in vacuo the residue is diluted with water and washed with tert. -butyl- methyl-ether. The aqueous phase is neutralized by addition of 4 M hydrochloric acid (10 mL) and the mixture is stirred for 1 hour. The precipitate formed is filtered off, washed with water and dried to give the title compound. Yield: 1 .2 g; LC (method 3): tR = 0.71 min; Mass spectrum (ESI"): m/z = 245 [M-H]
  • 14
  • [ 174603-55-5 ]
  • 6-fluoro-1-oxo-indan-4-carbonitrile [ No CAS ]
  • 15
  • [ 174603-55-5 ]
  • ethyl 5-bromo-7-fluoro-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]
  • 16
  • [ 174603-55-5 ]
  • 5-bromo-7-fluoro-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
  • 17
  • [ 64-17-5 ]
  • [ 174603-55-5 ]
  • ethyl 2-bromo-4-fluorophenethylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; at 80℃; for 18h; A mixture of <strong>[174603-55-5]3-(2-bromo-4-fluorophenyl)propanoic acid</strong> (2.00 g, 8.10 mmol), EtOH (0.945 mL, 16.2 mmol), TEA (3.38 mL, 24.3 mmol) and diphenylphosphoryl azide (2.45 g, 8.90 mmol) in anhydrous THF (20 mL) was heated at 80 C. for 18 h. The mixture was concentrated and the residue was subjected to column chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-100%) to provide ethyl 2-bromo-4-fluorophenethylcarbamate as a colorless gum (2.03 g, 82% yield). Mass spectrum m/z 290, 292 (M+H)+. 1H NMR (400 MHz, CDCl3) delta 7.31 (dd, J=8.3, 2.5 Hz, 1H), 7.24-7.16 (m, 1H), 6.99 (td, J=8.3, 2.6 Hz, 1H), 4.68 (br. s., 1H), 4.19-4.06 (m, 2H), 3.43 (q, J=6.6 Hz, 2H), 2.95 (t, J=6.9 Hz, 2H), 1.30-1.19 (m, 3H).
  • 19
  • [ 174603-55-5 ]
  • (E)-3-(2-(3-(dibenzylamino)propyl)-5-fluorophenyl)acrylaldehyde [ No CAS ]
  • 20
  • [ 174603-55-5 ]
  • (E)-dimethyl 2-(3-(2-(3-(dibenzylamino)propyl)-5-fluorophenyl)allylidene)malonate [ No CAS ]
  • 21
  • [ 174603-55-5 ]
  • C10H9BrFN [ No CAS ]
  • 22
  • [ 174603-55-5 ]
  • C10H10BrFO2 [ No CAS ]
  • 23
  • [ 174603-55-5 ]
  • C11H12BrFO2 [ No CAS ]
  • 24
  • [ 174603-55-5 ]
  • C10H12BrFO [ No CAS ]
  • 25
  • [ 174603-55-5 ]
  • C10H11Br2F [ No CAS ]
  • 26
  • [ 174603-55-5 ]
  • dimethyl 4-benzyl-10-fluoro-3-phenyl-3,4,4a,5,6,7,12,12a-octahydrobenzo[4,5]cycloocta[1,2-b]pyridine-2,2(1H)-dicarboxylate [ No CAS ]
  • dimethyl 4-benzyl-10-fluoro-3-phenyl-3,4,4a,5,6,7,12,12a-octahydrobenzo[4,5]cycloocta[1,2-b]pyridine-2,2(1H)-dicarboxylate [ No CAS ]
  • 27
  • [ 174603-55-5 ]
  • N,N-dibenzyl-4-(2-bromo-4-fluorophenyl)butan-1-amine [ No CAS ]
  • 28
  • [ 174603-55-5 ]
  • (E)-3-(2-(4-(dibenzylamino)butyl)-5-fluorophenyl)acrylaldehyde [ No CAS ]
  • 29
  • [ 174603-55-5 ]
  • (E)-dimethyl 2-(3-(2-(4-(dibenzylamino)butyl)-5-fluorophenyl)allylidene)malonate [ No CAS ]
  • 30
  • [ 174603-55-5 ]
  • dimethyl 1-benzyl-7-fluoro-2-phenyl-4,4a,5,10,11,11a-hexahydro-1H-benzo[4,5] cyclohepta[1,2-b]pyridine-3,3(2H)-dicarboxylate [ No CAS ]
  • 31
  • [ 174603-55-5 ]
  • N,N-dibenzyl-3-(2-bromo-4-fluorophenyl)propan-1-amine [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 174603-55-5 ]

Fluorinated Building Blocks

Chemical Structure| 739336-26-6

A158539 [739336-26-6]

2-Bromo-5-fluorophenylacetic acid

Similarity: 0.93

Chemical Structure| 958454-33-6

A512850 [958454-33-6]

2-(2-Bromo-3-fluorophenyl)acetic acid

Similarity: 0.87

Chemical Structure| 866862-24-0

A120134 [866862-24-0]

3-(3-Bromo-4-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 127425-80-3

A159947 [127425-80-3]

3-(4-Bromo-3-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 202000-99-5

A296990 [202000-99-5]

2-(3-Bromo-5-fluorophenyl)acetic acid

Similarity: 0.86

Aryls

Chemical Structure| 739336-26-6

A158539 [739336-26-6]

2-Bromo-5-fluorophenylacetic acid

Similarity: 0.93

Chemical Structure| 958454-33-6

A512850 [958454-33-6]

2-(2-Bromo-3-fluorophenyl)acetic acid

Similarity: 0.87

Chemical Structure| 866862-24-0

A120134 [866862-24-0]

3-(3-Bromo-4-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 127425-80-3

A159947 [127425-80-3]

3-(4-Bromo-3-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 202000-99-5

A296990 [202000-99-5]

2-(3-Bromo-5-fluorophenyl)acetic acid

Similarity: 0.86

Bromides

Chemical Structure| 739336-26-6

A158539 [739336-26-6]

2-Bromo-5-fluorophenylacetic acid

Similarity: 0.93

Chemical Structure| 958454-33-6

A512850 [958454-33-6]

2-(2-Bromo-3-fluorophenyl)acetic acid

Similarity: 0.87

Chemical Structure| 866862-24-0

A120134 [866862-24-0]

3-(3-Bromo-4-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 127425-80-3

A159947 [127425-80-3]

3-(4-Bromo-3-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 202000-99-5

A296990 [202000-99-5]

2-(3-Bromo-5-fluorophenyl)acetic acid

Similarity: 0.86

Carboxylic Acids

Chemical Structure| 739336-26-6

A158539 [739336-26-6]

2-Bromo-5-fluorophenylacetic acid

Similarity: 0.93

Chemical Structure| 958454-33-6

A512850 [958454-33-6]

2-(2-Bromo-3-fluorophenyl)acetic acid

Similarity: 0.87

Chemical Structure| 866862-24-0

A120134 [866862-24-0]

3-(3-Bromo-4-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 127425-80-3

A159947 [127425-80-3]

3-(4-Bromo-3-fluorophenyl)propanoic acid

Similarity: 0.86

Chemical Structure| 202000-99-5

A296990 [202000-99-5]

2-(3-Bromo-5-fluorophenyl)acetic acid

Similarity: 0.86