Home Cart Sign in  
Chemical Structure| 144025-03-6 Chemical Structure| 144025-03-6

Structure of 2,4-Difluorophenylboronic acid
CAS No.: 144025-03-6

Chemical Structure| 144025-03-6

*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 [ 144025-03-6 ]

CAS No. :144025-03-6
Formula : C6H5BF2O2
M.W : 157.91
SMILES Code : C1=C(F)C=CC(=C1F)B(O)O
MDL No. :MFCD01318998
InChI Key :QQLRSCZSKQTFGY-UHFFFAOYSA-N
Pubchem ID :2734334

Safety of [ 144025-03-6 ]

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

Computational Chemistry of [ 144025-03-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 36.18
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

1.03
Log Po/w (WLOGP)?

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

0.48
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.

1.15
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

0.13
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.56

Water Solubility

Log S (ESOL):?

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

-1.81
Solubility 2.47 mg/ml ; 0.0156 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.47
Solubility 5.35 mg/ml ; 0.0339 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very 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

-1.83
Solubility 2.31 mg/ml ; 0.0147 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

No
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.

-6.53 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

1.0 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)

2.16

Application In Synthesis of [ 144025-03-6 ]

* 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 [ 144025-03-6 ]

[ 144025-03-6 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 621-38-5 ]
  • [ 144025-03-6 ]
  • N-(2',4'-difluorobiphenyl-3-yl)acetamide [ No CAS ]
  • 2
  • [ 1006-33-3 ]
  • [ 144025-03-6 ]
  • [ 705563-34-4 ]
YieldReaction ConditionsOperation in experiment
52% With sodium hydroxide;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 60℃; for 12h; A stirred solution of <strong>[1006-33-3]2-bromo-5-fluoroacetophenone</strong> (11.72 g, 54 MMOL) and 2, 4-DIFLUOROPHENYLBORONIC acid (8.53 g, 54 MMOL) in tetrahydrofuran (600 mL) was treated under nitrogen with [1, 1APOS;-BIS (DIPHENYLPHOSPHINO) ferrocene] DICHLOROPALLADIUM (II) complex with DICHLOROMETHANE (2.20 g, 2.69 mmol, 5 molepercent) and a 5 N sodium hydroxide solution (21.6 mL, 108 MMOL). The reaction was heated at 60 °C for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent EVAPORATED IN VACUO to a crude brown oil (11.72 g). The crude oil was purified by preparative liquid chromatography on a BIOTAGE 40 Mi column of pre-packed silica gel (90 g), ELUTING with a gradient of between 3percent and 10percent methyl tert-butyl ether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (7.11 g, 28.4 mmol, 52percent); HRMS [ (+ESI), M/Z] : 251.06705 [M+H] +. Calcd for C14HGF3O : 251.06783 ; IR (FILM), VMAX : 2918,1695, 1604,1481, 1424,1267, 1186,1139, 1100,962, 850,814 CM-1 ; 1H NMR (400 MHz, DMSO-D6) B : 2.44 (s, 3H), 7.16 (tdd, J = 8. 5,2. 5,0. 9 Hz, 1 H), 7.28 (ddd, J = 10. 5,9. 4,2. 6 Hz, 1 H), 7.37-7. 45 (m, 2H), 7.50 (td, J = 8. 5,2. 7 Hz, 1 H), 7.75 (dd, J = 9. 4,2. 7 Hz, 1 H) ; Anal. calcd for C14HGF3O : C, 67.20 ; H, 3.63 ; N, 0.00. Found: C, 67.37 ; H, 3.46 ; N, 0.00.
  • 3
  • [ 363-52-0 ]
  • [ 144025-03-6 ]
  • [ 365458-32-8 ]
  • 4
  • [ 38557-72-1 ]
  • [ 144025-03-6 ]
  • [ 1092372-30-9 ]
YieldReaction ConditionsOperation in experiment
39% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; for 0.166667h;Microwave irradiation; Next, a synthesis method of a ligand of the present invention, 2-(2,4-difuluorophenyl)-3,5-dimethylpyrazine is described. 2.14 g of<strong>[38557-72-1]2-chloro-3,5-dimethylpyrazine</strong> which was obtained as the intermediate described above, 2.37 g of 2,4-difluorophenyl boronic acid, 1.59 g of sodium carbonate, 0.069 g of bis(triphenylphosphine)palladium(II)dichloride (abbreviation : Pd(PPh3)2Cl2), 15 mL of water, and 15 mL of acetonitrile were put in an eggplant flask equipped with a reflux pipe, and the inside thereof was substituted by argon. This reaction container was subjected to irradiation with microwave (2.45 GHz, 100W) for 10 minutes to be heated. Then, water was added to this solution, and extraction using dichloromethane was conducted to separate an organic layer. The organic layer obtained was washed with water and dried with magnesium sulfate. After the drying, the solution was filtrated. A solvent of this solution was distilled off, and then the residue obtained by the distillation was purified by silica gel column chromatography which uses dichloromethane as a developing solvent; thereby obtaining an objective pyrazine derivative, HdmF2ppr (white powder, yield of 39 %). A synthetic scheme of Step 1 is shown by the following (a-2).
  • 5
  • [ 479691-42-4 ]
  • [ 144025-03-6 ]
  • [ 1143577-33-6 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 20 - 100℃; (3) Tert-butyl 4-[4-(2,4-difluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylate To a mixture of <strong>[479691-42-4]tert-butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate</strong> (1.0 g, 3.35 mmol), 2,4-difluorophenylboric acid (793 mg, 5.02 mmol), 2N aqueous sodium carbonate solution (13.4 ml) and toluene (33 ml) was added tetrakistriphenylphosphine palladium (464 mg, 0.402 mmol) at room temperature under nitrogen atmosphere, and the mixture was stirred at 100 C. overnight. The reaction was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain the title compound (894 mg, 71%) as an oily material. 1H NMR (CDCl3) delta: 1.50 (9H, s), 3.46-3.58 (4H, m), 3.85-3.93 (4H, m), 6.83-7.08 (3H, m), 8.08-8.22 (1H, m), 8.39 (1H, d, J=5.3 Hz).
71% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 100℃;Inert atmosphere; General procedure: A mixture of tert-butyl 4-(2-chloropyrimidin-4-yl)piperazine-1-carboxylate (1.80g, 6.02mmol), (2,4-difluorophenyl)boronic acid (1.43g, 9.04mmol), 1M aq Na2CO3 (24 mL, 48.2 mmol), tetrakis(triphenylphosphine)palladium (0) (835mg, 0.723mmol), and toluene (60mL) was stirred at 100C overnight under N2 atmosphere. The mixture was diluted with water, and extracted with EtOAc. The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 8 (907mg, 40%) as a colorless viscous oil.
  • 6
  • [ 39856-56-9 ]
  • [ 144025-03-6 ]
  • [ 934477-86-8 ]
YieldReaction ConditionsOperation in experiment
3 g (80%) With potassium carbonate;Pd(PPh3)4; In 1,2-dimethoxyethane; dichloromethane; water; (2) Synthesis of 2-(2,4-difluorophenyl)-5-dimethylamino-pyridine <strong>[39856-56-9]2-bromo-5-dimethylaminopyridine</strong> (3.2 g, 16 mmol), 2,4-difluorophenylboronic acid (4.8 g, 30 mmol), K2CO3 (13 g, 94 mmol) and Pd(PPh3)4 (400 mg, 0.35 mmol) in a degassed mixture of DME/H2O (60/50 ml) were refluxed 24 hours under nitrogen. After being cooled to room temperature, the organic layer was separated and the aqueous phase extracted with EtOAc (100 ml). The combined organic fractions were washed with brine, dried over MgSO4 and evaporated to dryness. The crude compound was purified by column chromatography (SiO2, CH2Cl2 then CH2Cl2/MeOH: 97/3). The resulting brown solid was dissolved in CH2Cl2 and decolorized with charcoal. Filtration and evaporation of the solvent afford 3 g (80%) of the desired compound as a slightly yellow crystalline solid. 1H-NMR (CDCl3, 298K, 200 MHz, delta ppm) delta 3.03 (s, 6H), 6.9-7.1 (m, 3H), 7.60 (dd, J=2.5*9 Hz, 1H), 7.95 (m, 1H), 8.24 (d, J=2.5 Hz, 1H).
  • 7
  • [ 51376-06-8 ]
  • [ 144025-03-6 ]
  • [ 1395071-76-7 ]
  • 8
  • [ 63927-22-0 ]
  • [ 144025-03-6 ]
  • 8-(2,4-difluorophenyl)isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
312 mg With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; ethanol; water; at 100℃; for 18h;Inert atmosphere; General procedure: In an argon gas atmosphere, tetrakis(triphenylphosphine)palladium (83 mg) and a 2 M aqueous sodium carbonate solution (2.2 mL) were added to a mixture of <strong>[63927-22-0]8-bromoisoquinoline</strong> (300 mg), 2,4-difluorophenylboronic acid (342 mg), 1,2-dimethoxyethane (10 mL), and ethanol (1 mL), followed by stirring for 18 hours at an oil temperature of 100° C. The reaction liquid was cooled to room temperature, and then water and ethyl acetate were added thereto to perform liquid separation. The organic layer was washed with saturated brine and then dried, followed by concentration under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), thereby obtaining 8-(2,4-difluorophenyl)isoquinoline (312 mg).
  • 9
  • [ 307353-32-8 ]
  • [ 144025-03-6 ]
  • C15H12F2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium dihydrogenphosphate; In toluene; at 140℃; for 0.5h;Inert atmosphere; Microwave irradiation; Step 1 (0579) Compound iii-51 (300mg, 1.22mmol), (2,4-difluorophenyl)boronic acid (290mg, 1.84mmol), PdCl2 (dppf) (90mg, 0.12mmol) and potassium phosphate (780mg, 3.67mmol) were dissolved into toluene (12mL) under nitrogen atmosphere under microwave irradiation, and the mixture was stirred at 140C for 30 minutes. After the reaction mixture was filtrated by Celite, the solvent was removed in vacuo. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound iii-52 (304mg, 89%). 1H-NMR (CDCl3) delta: 8.09-8.05 (m, 2H), 7.72 (d, J = 1.5 Hz, 1H), 7.46-7.40 (m, 1H), 7.00-6.91 (m, 2H), 4.82 (d, J = 5.8 Hz, 2H), 3.94 (s, 3H), 1.83 (t, J = 5.9 Hz, 1H).
  • 10
  • [ 307353-32-8 ]
  • [ 144025-03-6 ]
  • C16H14F2O5S [ No CAS ]
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 144025-03-6 ]

Fluorinated Building Blocks

Chemical Structure| 193353-34-3

A169453 [193353-34-3]

(2,5-Difluorophenyl)boronic acid

Similarity: 0.96

Chemical Structure| 162101-25-9

A308353 [162101-25-9]

2,6-Difluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 182482-25-3

A500473 [182482-25-3]

2,4,6-Trifluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 1765-93-1

A107392 [1765-93-1]

4-Fluorophenylboronic acid

Similarity: 0.91

Chemical Structure| 768-35-4

A180833 [768-35-4]

(3-Fluorophenyl)boronic acid

Similarity: 0.89

Organoborons

Chemical Structure| 193353-34-3

A169453 [193353-34-3]

(2,5-Difluorophenyl)boronic acid

Similarity: 0.96

Chemical Structure| 162101-25-9

A308353 [162101-25-9]

2,6-Difluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 182482-25-3

A500473 [182482-25-3]

2,4,6-Trifluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 1765-93-1

A107392 [1765-93-1]

4-Fluorophenylboronic acid

Similarity: 0.91

Chemical Structure| 768-35-4

A180833 [768-35-4]

(3-Fluorophenyl)boronic acid

Similarity: 0.89

Aryls

Chemical Structure| 193353-34-3

A169453 [193353-34-3]

(2,5-Difluorophenyl)boronic acid

Similarity: 0.96

Chemical Structure| 162101-25-9

A308353 [162101-25-9]

2,6-Difluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 182482-25-3

A500473 [182482-25-3]

2,4,6-Trifluorophenylboronic acid

Similarity: 0.94

Chemical Structure| 1765-93-1

A107392 [1765-93-1]

4-Fluorophenylboronic acid

Similarity: 0.91

Chemical Structure| 768-35-4

A180833 [768-35-4]

(3-Fluorophenyl)boronic acid

Similarity: 0.89