154258-82-9|3-(4-Fluorophenyl)pyrazole| Ambeed

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

Quality Control of [ 154258-82-9 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 154258-82-9 ]

CAS No. :	154258-82-9
Formula :	C₉H₇FN₂
M.W :	162.16
SMILES Code :	FC1=CC=C(C2=NNC=C2)C=C1
MDL No. :	MFCD00665857
InChI Key :	STTNBHIFTZEPSH-UHFFFAOYSA-N
Pubchem ID :	688691

Safety of [ 154258-82-9 ]

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

Computational Chemistry of [ 154258-82-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	11
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	43.98
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	28.68 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.64
Log P_o/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.	1.88
Log P_o/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	3.0
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.71
Solubility	0.32 mg/ml ; 0.00197 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.	-2.21
Solubility	1.0 mg/ml ; 0.00619 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	-4.02
Solubility	0.0155 mg/ml ; 0.0000953 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	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.	-5.88 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)	1.66

Application In Synthesis of [ 154258-82-9 ]

* 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 [ 154258-82-9 ]

[ 154258-82-9 ] Synthesis Path-Downstream 1~35

1
[ 1192-62-7 ]
[ 403-42-9 ]
[ 154258-82-9 ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 4025 - 4035.

2
[ 154258-82-9 ]
C₂₇H₁₈BF₃N₆^(1-)*K⁽¹⁺⁾ [ No CAS ]

References: [1]Journal of the Chemical Society, Dalton Transactions,1997,p. 4025 - 4035.

3
[ 403-42-9 ]
[ 4637-24-5 ]
[ 154258-82-9 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 1 3-(4-Fluerophenyl)-1H-pyrazole 25 g 4'-fluoroacetophenone and 24 g N,N-dimethylformamide dimethyl acetal were heated for 6 hours under reflux, concentrated and evaporated into dryness to give 34.3 g of a reddish brown solid.. The product was dissolved in 150 ML ethanol, and 9.9 ML hydrazine monohydrate was added thereto and heated at 70C for 2 hours.. The reaction solution was poured into water, extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was evaporated.. The product was recrystallized from ethyl acetate and hexane to give 24.5 g pale yellow crystals.1H-NMR (CDCl3) delta: 6.57(d, J=2. 4Hz, 1H), 7.05-7.12(m, 2H), 7.60(d, J=2. 4Hz, 1H), 7.70-7.76(m, 2H)

References: [1]Patent: EP1382603,2004,A1 .Location in patent: Page 42; 43.
[2]Journal of Organometallic Chemistry,2010,vol. 695,p. 1753 - 1760.

4
[ 154258-82-9 ]
[ 474706-36-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 1h;	To a solution of 3-(4-fluorophenyl)-lH-pyrazole (10 g, 61.7 mmol) in DMF (50 ml) was added NBS (11 g, 61.7 mmol). The reaction mixture was stirred at rt for lh, quenched with water, extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product Intermediate 2A (14.47 g, 99%) as a white solid. MS(ES): m/z= 240.89/242.89 [M+H]+. HPLC Ret time (Method B): 3.56 min. NMR (400MHz, chloroform-d) delta 7.86 - 7.74 (m, 2H), 7.66 (s, 1H), 7.20 - 7.1 1 (m, 2H).
		Production Example 8 4-Bromo-<strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> 24 g <strong>[154258-82-9]3-(4-fluorophenyl)pyrazole</strong> was dissolved in 150 ML N,N-dimethylformamide, then 28 g N-bromosuccinimide was added thereto little by little, and the mixture was stirred for 2 hours.. An aqueous sodium thiosulfate solution and an aqueous sodium dicarbonate solution were added thereto and stirred for 1 hour, and the formed solid was collected by filtration.. The product was dissolved in ethyl acetate, dried over magnesium sulfate, and then purified by silica gel column chromatography (ethyl acetate).. The resulting solid was crystallized from diethyl ether/hexane, to give 33.6 g colorless crystals.1H-NMR (CDCl3) delta: 7.10-7.17(m, 2H), 7.62(d, J=2.4Hz, 1H), 7.73-7.79(m, 2H)

References: [1]Patent: WO2014/100540,2014,A1 .Location in patent: Page/Page column 55.
[2]Patent: EP1382603,2004,A1 .Location in patent: Page 44.

5
[ 922-67-8 ]
[ 154258-82-9 ]
C₁₃H₁₁FN₂O₂ [ No CAS ]
C₁₃H₁₁FN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 90℃; for 15h;	EXAMPLE 18; The parafluorophenyl pyrazole (200 g) and propargylate ( 1 g) were mixed and heated to 90 0C for 15 h, dried in vacuo to obtain a crude mixture of products, which were hydrogenated in MeOH/Pd/C at RT for 16 h to obtain the saturated ester intermediate after filtration and removal of solvent in vacuo. Then KHMDS (2 eq, 0.5 M7 8.54 mL) was added to this ester (530 mg ) in THF (20 mL) at -780C and stirred for 30 min. Trisylazide (2 eq, 1.32Ig) in THF (10 mL) was added. The mixture was allowed to stir at -78 0C for 10 min followed by addition of acetic acid (2 eq, 0.244 mL). The solution was warmed to RT overnight, and CH2CI2 was added, and then washed with NaHCtheta3, followed by water. The product was purified by Biotage (25S) hexane/AcOEt 10-20% to obtain the azidoester as a colorless oil. This oil was dissolved in MeOH and Pd/C was added under N2, followed by a balloon hydrogenation for 16 h to obtain the alpha-amino-methyl ester. This intermediate (260 mg) was dissolved in 7 N NHbeta/MeOH (8 mL) and heated to 52 0C for 5 h, and the solvent removed in vacuo to obtain the amino carboxamide. This intermediate was elaborated into Example 18 under similar reaction conditions described above. 1H NMR, CD3OD delta 8.44 (d, IH), 8.07 (dd, IH), 7.75(dd, 2H), 7.66 (dd, IH), 7.57 (t, IH), 7.21 (t, IH), 7.07 (t7 2H), 6.59 (d, IH), 4.80 (m, 2H), 4.69 (t, IH); LCMS m/z 369 (M+H).

References: [1]Patent: WO2007/75749,2007,A2 .Location in patent: Page/Page column 29; 48.

6
[ 105-36-2 ]
[ 154258-82-9 ]
[ 945906-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In toluene; for 6h;Heating / reflux;	Preparation of ethyl 3-f4-fluorophenyl>lH-pyrazole-l-acetateA mixture of 3-(4-fluorophenyl)-li?-pyrazole (1.0 g, 6.2 mmol), ethyl bromoacetate (1.38 mL, 12.4 mmol), and potassium carbonate (1.71 g, 12.4 mmol) in 6.5 mL toluene was heated to reflux for 6 hours under nitrogen. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic extracts were dried and concentrated. The residue was purified by chromatography on silica gel using hexanes/ethyl acetate as eluent to give 1.31 g of the title compound as a yellow oil. 1H NMR (CDCl3): delta 1.29 (t, 3H), 4.24 (q, 2H), 4.94 (s, 2H), 6.57 (d, IH), 7.07 (m, 2H), 7.49 (d, 2H), 7.77 (m, 2H).

References: [1]Patent: WO2007/89455,2007,A1 .Location in patent: Page/Page column 21.

7
[ 154258-82-9 ]
[ 74-88-4 ]
[ 863605-35-0 ]

Yield	Reaction Conditions	Operation in experiment
29%		3-(4-Fluorophenyl)-1-methyl-1H-pyrazole; Treat a solution of <strong>[154258-82-9]3-(4-fluorophenyl)pyrazole</strong> (7. 17 g, 44. 2 mmol) in dry DMF (60 mL) with NaH (2. 2 g, 92. 8 mmol) at 0 C for 15 min. Add iodomethane (3. 3 mL, 53. 04 mmol) and slowly warm to RT. Quench the reaction mixture with methanol (5 mL) and dilute with water (100 mL). Extract with EtOAc (3 x 70 mL), dry (MgS04) and concentrate and purify (Biotage system elueting with dichloromethane : methanol 50 : 1) to give desired compound as a white solid (2. 3 g, 29% yield). MS (ESi+) : 177 (M+H) +.

References: [1]Patent: WO2005/80380,2005,A1 .Location in patent: Page/Page column 40-41.

8
[ 2969-81-5 ]
[ 154258-82-9 ]
[ 1229953-22-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 100℃;	Step 1 / ethyl 4-[3-(4-fluorophenyl)pyrazol-1 -yl]butanoatePrepared from commercial <strong>[154258-82-9]3-(4-fluorophenyl)pyrazole</strong> [154258-82-9] and used without purification. MS (ESI+) : m/z = 277 [M+H]+ Step 1 : alkylationTo a solution of the starting material (1 eq) in N,N-dimethylformamide (1.7 ml_ / mmol) were added anhydrous potassium carbonate (1.5eq) and ethyl 4-bromobutyrate (1.2eq). The mixture was stirred at room temperature overnight, then 3 to 6 hours at 100<?. After cooling, water was added and the resulting mixture was extracted 3 times with ethyl acetate, the organic layers were combined, dried on anhydrous MgSO4, filtered and concentrated in vacuum to afford the title compound which was used without purification.

References: [1]Patent: WO2010/66847,2010,A1 .Location in patent: Page/Page column 109; 110.

9
[ 6959-47-3 ]
[ 154258-82-9 ]
[ 1240360-27-3 ]

References: [1]Journal of Organometallic Chemistry,2010,vol. 695,p. 1753 - 1760.

10
[ 154258-82-9 ]
[ 411235-57-9 ]
[ 1286230-88-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With pyridine; triethylamine; In tetrahydrofuran; for 18h;Reflux;	1-Cyclopropyl-<strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> [XX-1]; A mixture of 10 g of <strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> (62 mmol), 10.59 g of cyclopropylboronic acid (123 mmol), 44 mL triethylamine (308 mmol) and 40 mL pyridine (493 mmol) in dry THF is heated under reflux for 18 hrs. Next the reaction mixture is cooled, filtered over Celite and concentrated. The residue is taken up in ethyl acetate, washed with Na2CO3 solution, dried and evaporated under vacuum. The crude product is chromatographed over silica gel and 5 g (40%) of 1-cyclopropyl-<strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> are obtained.MS (ESI): 203.0 ([M+H]+)1H-NMR (400MHz, CDCl3) delta=7.76-7.73 (m, 2H) 7.435 (d, J=2.04 Hz, 1H), 7.05 (t, J=8.6 Hz, 2H), 6.44 (s, 1H), 3.64-3.58 (m, 1H), 1.24-1.14 (m, 2H), 1.06-1.01 (m, 2H) ppm
39.5%	With pyridine; dmap; copper diacetate; In 1,4-dioxane; at 100℃;	Intermediate 3 A was prepared according to the procedures described in Org. Lett., 1653-1655 (2008). To a solution of 3-(4-fluorophenyl)-lH-pyrazole (6.5 g, 40.1 mmol) in dioxane (80 mL) were added cyclopropylboronic acid (7.26 g, 85 mmol), DMAP (14.7 g, 120 mmol), diacetoxycopper (7.28 g, 40.1 mmol), and pyridine 3.24 mL, 40.1 mmol). The reaction mixture was heated at 100 C overnight. The reaction mixture was cooled to rt, quenched with water, and extracted with EtOAt. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by BIOTAGE (90g Thomson, 0-40% EtOAc/hex) to give Intermediate 3 A (3.2 g, 39.5%) as a tan oil. MS(ES): m/z= 203.13 [M+H]+. HPLC Ret time (Method B): 3.52 min. XH NMR (400MHz, chloroform-d) delta 7.84 - 7.72 (m, 2H), 7.13 - 7.01 (m, 2H), 6.46 (d, J=2.3 Hz, 1H), 3.63 (dt, J=7.2, 3.5 Hz, 1H), 1.21 - 1.11 (m, 2H), 1.11 - 0.90 (m, 2H).

References: [1]Patent: US2011/183978,2011,A1 .Location in patent: Page/Page column 58.
[2]Patent: WO2014/100540,2014,A1 .Location in patent: Page/Page column 56-57.

11
[ 74929-22-9 ]
[ 154258-82-9 ]

References: [1]Molecules,2011,vol. 16,p. 9340 - 9356.

12
[ 352-34-1 ]
[ 154258-82-9 ]

References: [1]Molecules,2011,vol. 16,p. 9340 - 9356.

13
[ 853058-46-5 ]
[ 154258-82-9 ]
1-(4-benzoylpiperazin-1-yl)-2-(4-(3-(4-fluorophenyl)-1H-pyrazol-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl)ethane-1,2-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 218 - 222.

14
nickel(II) perchlorate hexahydrate [ No CAS ]
[ 154258-82-9 ]
hexakis[μ²-3-(4-fluorophenyl)pyrazolato]trinickel(II) [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 6049 - 6059.

15
[ 75175-77-8 ]
[ 154258-82-9 ]

References: [1]European Journal of Inorganic Chemistry,2013,p. 6049 - 6059.

16
[ 25109-08-4 ]
[ 154258-82-9 ]
[ 1587712-74-0 ]

References: [1]Archiv der Pharmazie,2014,vol. 347,p. 174 - 184.

17
[ 141071-82-1 ]
[ 154258-82-9 ]
[ 1587712-75-1 ]

References: [1]Archiv der Pharmazie,2014,vol. 347,p. 174 - 184.

18
[ 154258-82-9 ]
[ 863605-34-9 ]