[ CAS No. 913835-74-2 ] {[proInfo.proName]}

Name: 913835-74-2|(4-Fluoro-3-hydroxyphenyl)boronic acid|97%
Brand: Ambeed
SKU: A167403
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Quality Control of [ 913835-74-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 913835-74-2 ]

SDS Specification

Alternatived Products of [ 913835-74-2 ]

Product Details of [ 913835-74-2 ]

CAS No. :	913835-74-2	MDL No. :	MFCD08689483
Formula :	C₆H₆BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GNCXNRGBOBWFSO-UHFFFAOYSA-N
M.W :	155.92	Pubchem ID :	44717470
Synonyms :

Calculated chemistry of [ 913835-74-2 ]

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 :	3.0
Molar Refractivity :	38.25
TPSA :	60.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.57
Log Po/w (WLOGP) :	-0.37
Log Po/w (MLOGP) :	0.09
Log Po/w (SILICOS-IT) :	-0.77
Consensus Log Po/w :	-0.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.5
Solubility :	4.89 mg/ml ; 0.0314 mol/l
Class :	Very soluble
Log S (Ali) :	-1.42
Solubility :	5.97 mg/ml ; 0.0383 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.98
Solubility :	16.4 mg/ml ; 0.105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 913835-74-2 ]

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

Application In Synthesis of [ 913835-74-2 ]

* 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 [ 913835-74-2 ]

[ 913835-74-2 ] Synthesis Path-Downstream 1~23

1
[ 942189-39-1 ]
[ 913835-74-2 ]
[ 1093064-44-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 75.0℃;	A suspension of 3-bromo-5-nitro-1-trityl-1 H-indazole 1AJ (10.0 g, 20.68 mmol), 4-fluoiO-3-hydroxyphenylboronic acid 6AU (3.55 g, 22.78 mmol), Pd(dppf)CI2 (1.6 mg, 1.96 mmol) and K3PO4 (10.6 g, 4.99 mmol) in 200 ml_ of dioxane/H2O (4/1 ) was heated to 75C for overnight. After removal of most of the solvent, the black residue was diluted with EtOAc (250 ml_) and H2O (60 ml_). The resulting mixture was filtered through a pad of Celite. Additional 150 mL of EtOAc was used to wash the Celite cake. The filtrates were combined. The aqueous layer was separated and the organic layer was washed with brine, dried (MgSO4) and concentrated to give a green solid, which was recrystallized from Ch^CVhexane to give 3-(4-fluoro-3-hydroxyphenyl)-5- nitro-1-trityl-1 H-indazole 7AU (8.1 g).

Reference： [1]Patent: WO2008/153858,2008,A1 .Location in patent: Page/Page column 283

2
[ 913835-74-2 ]
[ 1285505-86-3 ]
[ 1285505-39-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90.0℃; for 2.0h;	Example 76Synthesis of N-[(E)-3-(2,4-di(3-hydroxy-4-fluorophenyl)-phenyl)-2-methyl-acryloyl]-guanidine<Step 1>Intermediate 4 (50 mg, 0.105 mmol) and <strong>[913835-74-2]4-fluoro-3-hydroxyphenyl boronic acid</strong> (39.4 mg, 0.253 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 2.0 mL). Pd(PPh3)4 (12.2 mg, 0.0105 mmol) and Na2CO3 (133.8 mg, 1.262 mmol) were added to the solution and then stirred at 90 C. for 2 hours. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the compound of Example 76 (26.4 mg, 47%).MS: 424

Reference： [1]Patent: US2011/82109,2011,A1 .Location in patent: Page/Page column 36-37

3
[ 913835-74-2 ]
[ 1285505-81-8 ]
[ 1285505-15-8 ]

Yield	Reaction Conditions	Operation in experiment
15%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90.0℃; for 2.0h;	Example 63Synthesis of N-[(E)-3-(4'-fluoro-3'-hydroxy-5-methyl-biphenyl-2-yl)-2-methyl-acryloyl]-guanidine<Step 1>Intermediate 2 (50 mg, 0.122 mmol) and <strong>[913835-74-2]4-fluoro-3-hydroxyphenyl boronic acid</strong> (22.8 mg, 0.146 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 2.0 mL). Pd(PPh3)4 (7.0 mg, 6.10 mumol) and Na2CO3 (38.8 mg, 0.366 mmol) were added to the solution and then stirred at 90 C. for 2 hours. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the compound of Example 63 (7.9 mg, 15%).MS: 328

Reference： [1]Patent: US2011/82109,2011,A1 .Location in patent: Page/Page column 32

4
[ 913835-74-2 ]
[ 1285505-93-2 ]
[ 1285505-63-6 ]

Yield	Reaction Conditions	Operation in experiment
18.9%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90.0℃; for 2.0h;	Example 89Synthesis of N-[(E)-3-(4'-fluoro-3'-hydroxy-biphenyl-4-yl)-2-methyl-acryloyl]-guanidine<Step 1>Intermediate 5 (50 mg, 0.126 mmol) and <strong>[913835-74-2]4-fluoro-3-hydroxyphenyl boronic acid</strong> (21.7 mg, 0.139 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 2.0 mL). Pd(PPh3)4 (7.23 mg, 6.3 mumol) and Na2CO3 (40.1 mg, 0.378 mmol) were added to the solution and then stirred at 90 C. for 2 hours. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the compound of Example 89 (10.2 mg, 18.9%).MS: 314

Reference： [1]Patent: US2011/82109,2011,A1 .Location in patent: Page/Page column 40

5
[ 76-09-5 ]
[ 913835-74-2 ]
[ 1392234-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; at 20.0℃; for 17.0h;	<strong>[913835-74-2](4-fluoro-3-hydroxyphenyl)boronic acid</strong> (850 mg, 5.452 mmol) and pinacol (612 mg, 5.179 mmol) were dissolved in Et20 (1 1 ml_). The reaction was stirred at room temperature for 17 hours. The reaction mixture was directly applied to a silica gel column. Purification with silica gel chromatography (3:1 hexanes/EtOAc) obtained the title compound as a clear oil which solidified to a waxy white solid upon standing under vacume. TLC Rf = 0.55 (3:1 hexanes/EtOAc). MS m/z 239.1 (M + H+) (Method M).

Reference： [1]Patent: WO2012/120469,2012,A1 .Location in patent: Page/Page column 53

6
[ 913835-74-2 ]
[ 1398923-87-9 ]

Reference： [1]Patent: WO2012/120469,2012,A1

7
[ 913835-74-2 ]
[ 1398923-91-5 ]

Reference： [1]Patent: WO2012/120469,2012,A1

8
[ 913835-74-2 ]
1-(2,3-dihydro-1H-inden-1-yl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine [ No CAS ]
5-(4-amino-1-indan-1-ylpyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73 mg	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 100.0℃;	To a solution of 1-indan-1-yl-3-iodo-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.530 mmol) and (4-fluoro-3-hydroxy-phenyl)boronic acid (124 mg, 0.795 mmol) in DMF (3 mL) was added a solution of sodium carbonate (112 mg, 1.060 mmol) in water (3 mL) followed by the addition of tetrakis(triphenylphosphine)palladium(0) (61 mg, 0.0530 mmol). The reaction mixture was heated in a reagent bottle at 100 C overnight. The reaction was monitored by TLC. After completion of reaction, water (20 mL) was added to the reaction mixture and the product was extracted with EtOAc (2x20 mL). The combined organic layer was again washed with water (2x15 mL) and finally with brine solution (15 mL). The organic layer was separated, dried over anhydrous sodium sulfate. Removal of EtOAc under reduced pressure afforded a crude product that was purified by reverse phase preparative HPLC to afford 5- (4-amino-i -indan- 1 -yl-pyrazolo [3 ,4-d]pyrimidin-3-yl)-2-fluoro-phenol (73 mg) as an off-white solid. LCMS: 361.9 (M+i). ?H NMR (400 MHz, DMSO-d6) oe (ppm): 8.25 (s, 1H), 7.32 (d, J = 7.5 Hz, 1H), 7.23 (dd, J = 12.0, 7.9 Hz, 2H), 7.09 (t, J = 8.0 Hz, 2H), 6.96 (dt, J= 7.2, 3.1 Hz, 1H), 6.87 (d, J= 7.5 Hz, 1H), 6.37 (t, J= 7.4 Hz, 1H), 3.24-3.09 (m, 1H), 2.98 (dt, J = 15.8, 7.8 Hz, 1H), 2.62 - 2.50 (m, 2H). Separation by chiral HPLC provides Compound Nos. lOa and lOb.

Reference： [1]Patent: WO2015/58084,2015,A1 .Location in patent: Paragraph 0220

9
[ 913835-74-2 ]
[ 2927-71-1 ]
5-(2-chloro-5-fluoropyrimidin-4-yl)-2-fluorophenol [ No CAS ]