[ CAS No. 1765-93-1 ] {[proInfo.proName]}

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2D 3D

Structure of 1765-93-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1765-93-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1765-93-1 ]

SDS Specification

Alternatived Products of [ 1765-93-1 ]

Product Details of [ 1765-93-1 ]

CAS No. :	1765-93-1	MDL No. :	MFCD00039136
Formula :	C₆H₆BFO₂	Boiling Point :	-
Linear Structure Formula :	B(OH)₂C₆H₄F	InChI Key :	LBUNNMJLXWQQBY-UHFFFAOYSA-N
M.W :	139.92	Pubchem ID :	285645
Synonyms :	P-Fluorophenylboronic acid	Chemical Name :	4-Fluorophenylboronic acid

Calculated chemistry of [ 1765-93-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	36.23
TPSA :	40.46 ?2

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) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.93
Log Po/w (WLOGP) :	-0.07
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.25

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	2.98 mg/ml ; 0.0213 mol/l
Class :	Very soluble
Log S (Ali) :	-1.37
Solubility :	6.03 mg/ml ; 0.0431 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.54
Solubility :	4.04 mg/ml ; 0.0288 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.82

Safety of [ 1765-93-1 ]

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 [ 1765-93-1 ]

* 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 [ 1765-93-1 ]
Downstream synthetic route of [ 1765-93-1 ]

[ 1765-93-1 ] Synthesis Path-Upstream 1~2

1
[ 1765-93-1 ]
[ 446-52-6 ]
[ 342-25-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium phosphate; palladium diacetate In water; methyl cyclohexane for 8 h; Reflux	Method of the present embodiment provides a 2,4 ′-difluorobenzophenone and preparation method thereof, as follows: in a 1000 ml round bottom flask The bottle was added sequentially o-fluoro benzaldehyde 124 g of 4-fluorophenylboronic acid and 140 g of potassium phosphate, 106 grams, 1.12 g of palladium acetate, then adding 500 ml of methyl cyclohexane and 100 ml of water and heated to reflux for 8 hours., sequentially passes through filtering, layering, washing with water, removing the solvent to obtain the product., 2,4 '-difluorobenzophenone 214 g, 98percent yield.

Reference： [1] Patent: CN104230691, 2016, B, . Location in patent: Paragraph 0028-0029

2
[ 30766-11-1 ]
[ 1765-93-1 ]
[ 845826-99-5 ]

Yield	Reaction Conditions	Operation in experiment
87.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,2-dimethoxyethane; water at 98℃; for 24 h; Inert atmosphere	Step A:5-bromopyridine-2-carboxylic acid (57, 1.0 g, 5.0 mmol)Dissolved in ethylene glycol dimethyl ether (12 mL) and water (4 mL),Add p-fluorophenylboronic acid (17, 1.0 g, 7.5 mmol)And anhydrous potassium carbonate (1.0 g, 7.5 mmol),Then tetrakis(triphenylphosphine)palladium (289 mg, 0.25 mmol) was added.The resulting mixture was stirred at 98 ° C for 24 hours under a nitrogen atmosphere.TLC analysis indicated that the reaction was over,The reaction solution was cooled to room temperature.Then add water (40 mL),The pH was adjusted to 2-3 with 6M hydrochloric acid.Filtered, the filter cake is dissolved in dichloromethane,The organic layer was washed with 20 mL of saturated sodium bicarbonate solution.Divide the water layer,The aqueous layer was adjusted to pH 2-3 with a 6M hydrochloric acid solution.Filter the solid,The filter cake is washed with water to neutrality.The filter cake was dried to give compound 61 (942 mg).Yield: 87.7percent.

Reference： [1] Patent: CN108623532, 2018, A, . Location in patent: Paragraph 0206; 0207; 0208
[2] Patent: EP1657242, 2006, A1, . Location in patent: Page/Page column 31
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 812 - 819
[4] Medicinal Chemistry, 2017, vol. 13, # 2, p. 176 - 185
[5] Medicinal Chemistry Research, 2018, vol. 27, # 2, p. 374 - 387

[ 1765-93-1 ] Synthesis Path-Downstream 1~16

1
[ 13195-50-1 ]
[ 1765-93-1 ]
[ 190966-91-7 ]

Reference： [1]Synlett,2008,p. 286 - 288
[2]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 779 - 786

2
[ 1765-93-1 ]
[ 4016-63-1 ]
8-(4-fluorophenyl)guanosine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 6767 - 6774

3
[ 1765-93-1 ]
[ 1005-38-5 ]
(6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-(4-fluoro-phenyl)-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 195 - 197

4
[ 13195-50-1 ]
tetrakis(triphenylphosphine)paJladium [ No CAS ]
[ 1765-93-1 ]
[ 190966-91-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In water; toluene;	Example 32 A specific procedure for the synthesis of: N-5-[(4-fluoro)phenyl-thien-2-yl]methanesulfonamide (32) STR20 <strong>[13195-50-1]2-Bromo-5-nitrothiophene</strong> (3.50 g, 16.8 mmol) was dissolved in toluene (50 mL). To this solution was added 4-fluorophenyl boronic acid (2.52 g, 18.0 mmol), tetrakis(triphenylphosphine)paJladium (0) (0.58 g, 3 molepercent), potassium carbonate (4.56 g, 33.0 mmol) and water (25 mL) and the resulting mixture refluxed for 18 hours after which time the layers were separated. The organic layer was evaporated to a crude solid which was recrystallized from ethanol-water to give 2-nitro-5-(4-fluoro)phenylthiophene (2.99 grams (80percent)1. Mp 129°-130° C.

Reference： [1]Patent: US5783597,1998,A

5
[ 78775-11-8 ]
[ 1765-93-1 ]
4-(4-fluorophenyl)-3-methylbenzaldehyde [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4276 - 4286

6
[ 1765-93-1 ]
[ 4983-28-2 ]
[ 1580440-61-4 ]

Yield	Reaction Conditions	Operation in experiment
17%	With copper diacetate; triethylamine; In dichloromethane;	To a stirred solution of <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (1.50 g, 1 1.6 mmol) in dichloromethane (20 mL) was added 4-fluorophenylboronic acid (3.30 g, 23.2 mmol), copper(II) acetate (2.49 g, 13.9 mmol) and triethylamine (8.0 mL, 57 mmol). The mixture was left open to the air and stirred overnight. The suspension was then filtered through a pad of Celite and concentrated. The residue was purified by flash chromatography over silica using a hexane/ethyl acetate eluant to afford 2-chloro-5-(4-fluorophenoxy)pyrimidine as a light yellow solid (0.400 g, 17percent). Exchanging 2-chloro-4-(4-fluorophenyl)pyrimidine for this intermediate, ethyl piperidine-4-carboxylate for ethyl 4-fluoropiperidine-4-carboxylate hydrochloride and Intermediate 5 for Intermediate 1 , the final three steps of Example 41 were used to prepare the title compound. 1H NMR (400 MHz, CD3OD) delta 8.20 (s, 2H), 7.09-6.99 (m, 4H), 4.70-4.66 (m, 2H), 3.33-3.16 (m, 3H), 2.90-2.83 (m, 5H), 2.30-2.01 (m, 3H), 1.92-1.89 (m, 4H), 1.70-1.50 (m, 5H) ppm. 13C NMR (100 MHz, CD3OD) delta 172.4, 172.2, 159.8, 158.5, 157.4, 154.4, 150.0, 143.3, 1 18.2, 1 18.1 , 1 16.1 , 1 15.8, 95.7, 93.8, 60.7, 52.8, 45.6, 45.5, 39.6, 31.5, 31.4, 31.3, 31.2, 29.3, 23.0, 21.8, 21.3 ppm. Purity: > 99percent LCMS (214 nm & 254 nm); retention time 1.39 min; (M+H+) 458.0.

Reference： [1]Patent: WO2014/43068,2014,A1 .Location in patent: Page/Page column 221

7
[ 1120-95-2 ]
[ 1765-93-1 ]
3-(4-fluorophenyl)pyridazine [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5878 - 5881

8
[ 1480-65-5 ]
[ 1765-93-1 ]
[ 1214342-02-5 ]

Reference： [1]Journal of the Iranian Chemical Society,2016,vol. 13,p. 637 - 644

9
[ 1765-93-1 ]
[ 1030825-20-7 ]

Reference： [1]Patent: WO2016/16852,2016,A1
[2]Patent: CN109336874,2019,A

10
C₁₆H₁₈BFN₂ [ No CAS ]
[ 1765-93-1 ]
[ 68176-57-8 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980

11
[ 1765-93-1 ]
[ 68176-57-8 ]
C₁₆H₁₈BFN₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980
[2]Journal of Organic Chemistry,2016,vol. 81,p. 969 - 980

12
[ 1765-93-1 ]
[ 42019-78-3 ]

Reference： [1]Organometallics,2016,vol. 35,p. 3378 - 3387

13
[ 363-52-0 ]
[ 1765-93-1 ]
C₁₂H₇BF₂O₂ [ No CAS ]

Reference： [1]New Journal of Chemistry,2018,vol. 42,p. 2815 - 2823

14
[ 1765-93-1 ]
[ 5350-41-4 ]
[ 587-79-1 ]

Reference： [1]RSC Advances,2019,vol. 9,p. 5738 - 5741

15
[ 1765-93-1 ]
[ 4983-28-2 ]
5-benzyloxy-2-(4-fluorophenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		4-Fluorophenylboronic acid (0.72 g, 5.1 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.26 g, 0.35 mmol) were dissolved in toluene (42 mL) and a mixed solvent of ethanol (21 mL),The resulting mixture isAn aqueous solution (7.5 mL) of sodium carbonate (1.7 g, 16 mmol) was added under nitrogen.After stirring for 10 minutes, 5-benzyloxy-2-chloro-pyrimidine 34b (0.76 g, 3.4 mmol) was added, and the mixture was reacted at 80 ° C for 2 hours.The reaction solution was cooled to room temperature and water (20 mL) was added.Extracted with ethyl acetate (30 mL).Dry over anhydrous sodium sulfate, concentrate by suction filtration, and the residue obtained was purified by silica gel column chromatography[ethyl acetate / petroleum ether (v / v) = 1/10] purified to give the title compound34c (0.75 g, yield 78percent) as a white solid.

Reference： [1]Patent: CN109251166,2019,A .Location in patent: Paragraph 0574; 0575; 0578; 0579

16
[ 1765-93-1 ]
[ 39549-79-6 ]
2-(4-fluorophenyl)-7-methyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5018 - 5024

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? Hydrogenolysis of Benzyl Ether ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Vilsmeier-Haack Reaction

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 1765-93-1 ] {[proInfo.proName]}

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[ 1765-93-1 ] Synthesis Path-Upstream 1~2

[ 1765-93-1 ] Synthesis Path-Downstream 1~16

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Fluorinated Building Blocks

Organoboron

Aryls

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[ 1765-93-1 ]