[ CAS No. 174603-55-5 ] {[proInfo.proName]}

Name: 174603-55-5|3-(2-Bromo-4-fluorophenyl)propionic acid|97%
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SKU: A162701
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Quality Control of [ 174603-55-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 174603-55-5 ]

CAS No. :	174603-55-5	MDL No. :	MFCD06656907
Formula :	C₉H₈BrFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHFQIJJCQTZKFK-UHFFFAOYSA-N
M.W :	247.06	Pubchem ID :	10922852
Synonyms :

Calculated chemistry of [ 174603-55-5 ]

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 :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	3.03
Log Po/w (MLOGP) :	3.11
Log Po/w (SILICOS-IT) :	2.99
Consensus Log Po/w :	2.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.21 mg/ml ; 0.000848 mol/l
Class :	Soluble
Log S (Ali) :	-2.9
Solubility :	0.313 mg/ml ; 0.00127 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.72
Solubility :	0.0473 mg/ml ; 0.000191 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 174603-55-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 174603-55-5 ]
Downstream synthetic route of [ 174603-55-5 ]

[ 174603-55-5 ] Synthesis Path-Upstream 1~4

1
[ 174603-55-5 ]
[ 174603-56-6 ]

Yield	Reaction Conditions	Operation in experiment
970 mg	at 60 - 80℃; for 18 h; Inert atmosphere	Under argon 3-(2-bromo-4-fluorophenyl)propanoic acid (1 .2 g) is added in small portions to trifluoromethanesulfonic acid (15 mL) at room temperature. The mixture is stirred for 2 hours at 60°C and for 16 hours at 80°C. 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): t_R = 0.60 min; Mass spectrum (ESI⁺): m/z = 229 [M+H]⁺.

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2013/144098, 2013, A1, . Location in patent: Page/Page column 114; 115
[3] Patent: WO2015/36759, 2015, A1,

2
[ 174603-54-4 ]
[ 174603-55-5 ]

Yield	Reaction Conditions	Operation in experiment
33%	for 4.5 h; 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, 33percent).R: 0.2 (30percent 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).

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1, . Location in patent: Page/Page column 171

3
[ 61150-57-0 ]
[ 174603-55-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416
[2] Patent: WO2015/36759, 2015, A1,

4
[ 1422-53-3 ]
[ 174603-55-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416

[ 174603-55-5 ] Synthesis Path-Downstream 1~37

1
[ 174603-55-5 ]
3-(2-bromo-4-fluorophenyl)propionyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416
[2]Patent: WO2015/36759,2015,A1 .Location in patent: Page/Page column 171

2
[ 174603-54-4 ]
[ 174603-55-5 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416
[2]Patent: WO2015/36759,2015,A1 .Location in patent: Page/Page column 171

3
[ 1422-53-3 ]
[ 174603-55-5 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

4
[ 61150-57-0 ]
[ 174603-55-5 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416
[2]Patent: WO2015/36759,2015,A1

5
[ 174603-55-5 ]
[ 174603-56-6 ]

Yield	Reaction Conditions	Operation 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]+.

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416
[2]Patent: WO2013/144098,2013,A1 .Location in patent: Page/Page column 114; 115
[3]Patent: WO2015/36759,2015,A1

6
[ 174603-55-5 ]
[ 174603-60-2 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

7
[ 174603-55-5 ]
(E)-2-(4-bromo-6-fluoro-1-indanylidene)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

8
[ 174603-55-5 ]
[ 174603-59-9 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

9
[ 174603-55-5 ]
[ 174603-58-8 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

10
[ 174603-55-5 ]
[ 174603-57-7 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416

Yield	Reaction Conditions	Operation 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 ]

Reference： [1]Patent: WO2013/144098,2013,A1

13
methyl 3-(2-bromo-4-fluorophenyl)propanoate [ No CAS ]
[ 174603-55-5 ]

Yield	Reaction Conditions	Operation 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]

Reference： [1]Patent: WO2013/144098,2013,A1 .Location in patent: Page/Page column 114

14
[ 174603-55-5 ]
6-fluoro-1-oxo-indan-4-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2015/36759,2015,A1

15
[ 174603-55-5 ]
ethyl 5-bromo-7-fluoro-3,4-dihydroisoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Patent: US2016/115126,2016,A1

16
[ 174603-55-5 ]
5-bromo-7-fluoro-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Reference： [1]Patent: US2016/115126,2016,A1

17
[ 64-17-5 ]
[ 174603-55-5 ]
ethyl 2-bromo-4-fluorophenethylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Patent: US2016/115126,2016,A1 .Location in patent: Paragraph 0575-0576

18
[ 2033-24-1 ]
[ 59142-68-6 ]
[ 174603-55-5 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 9334 - 9338
[2]Chemical Communications,2019,vol. 55,p. 13856 - 13859

19
[ 174603-55-5 ]
(E)-3-(2-(3-(dibenzylamino)propyl)-5-fluorophenyl)acrylaldehyde [ No CAS ]