[ CAS No. 1993-03-9 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 1993-03-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1993-03-9 ]

SDS Specification

Alternatived Products of [ 1993-03-9 ]

Product Details of [ 1993-03-9 ]

CAS No. :	1993-03-9	MDL No. :	MFCD00674013
Formula :	C₆H₆BFO₂	Boiling Point :	-
Linear Structure Formula :	FC₆H₄B(OH)₂	InChI Key :	QCSLIRFWJPOENV-UHFFFAOYSA-N
M.W :	139.92	Pubchem ID :	2734354
Synonyms :		Chemical Name :	(2-Fluorophenyl)boronic acid

Calculated chemistry of [ 1993-03-9 ] 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 :	1.89

Safety of [ 1993-03-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1993-03-9 ]

* 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.

Upstream synthesis route of [ 1993-03-9 ]
Downstream synthetic route of [ 1993-03-9 ]

[ 1993-03-9 ] Synthesis Path-Upstream 1~2

1
[ 76-09-5 ]
[ 1993-03-9 ]
[ 18107-18-1 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: at 60℃; for 4 h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; water at 60℃; for 4 h;	To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 ° C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 ° C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81percent and its NMR data was as follows:

Reference： [1] Patent: CN105884808, 2016, A, . Location in patent: Paragraph 0148; 0149; 0150; 0151; 0152; 0153

2
[ 14221-01-3 ]
[ 1993-03-9 ]
[ 886444-12-8 ]

Reference： [1] Patent: US2007/37974, 2007, A1, . Location in patent: Page/Page column 23

[ 1993-03-9 ] Synthesis Path-Downstream 1~10

1
[ 1993-03-9 ]
[ 120157-97-3 ]
[ 257299-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4354 - 4358

2
[ 1993-03-9 ]
[ 1006-33-3 ]
[ 705556-87-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; In dichloromethane; at 60℃; for 12h;	A stirred solution of <strong>[1006-33-3]2-bromo-5-fluoroacetophenone</strong> (11.72 g, 54 MMOL) and 2-FLUOROPHENYLBORONIC acid (7.55 g, 54 MMOL) in tetrahydrofuran (600 mL) was treated under nitrogen with [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (ICI) 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 repetitive, preparative, liquid chromatography on a BIOTAGEE 40 Mi column of pre- packed silica gel (90 g), eluting with a gradient of between 3percent and 10percent methyl TERT- butylether 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 (10.2 g, 43.9 mmol, 81percent)

Reference： [1]Patent: WO2004/50631,2004,A1 .Location in patent: Page 94-95

3
[ 479691-42-4 ]
[ 1993-03-9 ]
[ 1143578-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 20 - 95℃;	(1) 4-(2-fluorophenyl)-2-piperazin-1-ylpyrimidine Dihydrochloride To a solution of <strong>[479691-42-4]tert-butyl 4-(4-chloropyrimidin-2-yl)piperazine-1-carboxylate</strong> (10 g, 33.5 mmol), 2-fluorophenyl boronic acid (7.02 g, 50.2 mmol), and 2 N aqueous sodium carbonate solution (45 ml) in 1,2-dimethoxyethane (300 ml) was added tetrakistriphenylphosphine palladium (4.64 g, 40.2 mmol) under nitrogen atmosphere at room temperature, and the mixture was stirred at 95 C. overnight. The reaction was poured into the saturated saline, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain tert-butyl 4-[4-(2-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylate.

Reference： [1]Patent: US2009/163508,2009,A1 .Location in patent: Page/Page column 45

4
[ 1333240-17-7 ]
[ 1993-03-9 ]
2-(2-fluorophenyl)-4,5-dimethoxypyrimidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 8086 - 8098

5
[ 16932-45-9 ]
[ 1993-03-9 ]
2’-fluoro-1,3-dimethoxy-2,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		Into a 500-mL three-neck flask were put 10 g (46 mmol) of <strong>[16932-45-9]2-bromo-1,3-dimethoxybenzene</strong>, 7.2 g (51 mmol) of 2-fluorophenylboronic acid, 66 mL of toluene, 66 mL of diethylene glycol dimethyl ether (diglyme), and 76 mL of a sodium carbonate aqueous solution (2.0 mol/L). This mixture was degassed by being stirred while the pressure in the flask was reduced. After the degassing, the atmosphere in the flask was replaced with nitrogen, and the mixture was heated to 80 C. To this mixture was added 1.1 g (0.95 mmol) of tetrakis(trismethylphenylphosphine)palladium(0), and the mixture was stirred for 5 hours. After the stirring, the obtained mixture was cooled down to room temperature. Then, 3.2 g (23 mmol) of 2-fluorophenylboronic acid and 1.0 g (0.87 mmol) of tetrakis(trismethylphenylphosphine)palladium(0) were added to the mixture. The mixture was degassed by being stirred while the pressure in the flask was reduced. The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred at 80 C. for 8 hours. After the stirring, the mixture was cooled down to the room temperature. Then, 5.2 g (37 mmol) of 2-fluorophenylboronic acid, 0.19 g (0.46 mmol) of 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl, and 50 mg (0.22 mmol) of palladium(II) acetate were added to the mixture. The mixture was degassed by being stirred while the pressure in the flask was reduced. The atmosphere in the flask was replaced with nitrogen, and the mixture was stirred at 80 C. for 4 hours. After the stirring, this mixture was cooled down to the room temperature, and the mixture was separated into an organic layer and an aqueous layer. The obtained aqueous layer was subjected to extraction with toluene three times, the extracted solution and the organic layer were combined, and this mixture was washed with saturated saline and dried with anhydrous magnesium sulfate. The obtained mixture was gravity-filtered, and then the obtained filtrate was concentrated to give a brown oily substance. The obtained oily substance was purified by silica gel column chromatography (a developing solvent was subjected to a gradient to change from hexane to chloroform gradually) and was then recrystallized with toluene/hexane to give 8.4 g (36 mmol) of a target solid at a yield of 78%. A synthesis scheme of the above synthesis method is shown in (C-1) below.

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 6676 - 6685
[2]Patent: US9997725,2018,B2 .Location in patent: Page/Page column 132; 133

6
[ 1993-03-9 ]
[ 120157-97-3 ]
2-(2'-fluoro-[1,1'-biphenyl]-4-yl)ethan-1-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%		General procedure: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 2-fluorophenylboronic acid (0.56?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol) and Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14c as a white solid (0.36?g, 43%); Rf?=?0.00 (EtOAc 9: acetone 1); 1H NMR (DMSO-d6, 400?MHz) delta 2.89-3.09 (m, NH3CH2CH2), 7.24-7.52 (m, 8 ArH), 8.32 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.1 (NCH2CH2), 116.6 (d, JC-F?=?22.4?Hz), 120.3, 125.4 (d, JC-F?=?3.5?Hz), 129.4, 129.5, 129.9 (d, JC-F?=?8.2?Hz), 131.1 (d, JC-F?=?3.3?Hz), 131.5, 131.9, 137.5 (d, JC-F?=?21.9?Hz), 159.6 (d, JC-F?=?244.2?Hz) (12 ArC).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 232 - 244

7
[ 105404-89-5 ]
[ 1993-03-9 ]
3-bromo-6-(2-fluorophenyl)-2,7-dimethoxynaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine; In toluene; at 110℃; for 7h;Inert atmosphere;	Into a 200-mL three-neck flask were put 3.0 g (8.7 mmol) of<strong>[105404-89-5]3,6-dibromo-2,7-dimethoxynaphthalene</strong>, 1.2 g (8.7 mmol) of 2-fluorophenylboronic acid, 2.4 g(17 mmol) of potassium carbonate, and 0.13 g (0.43 mmol) of tris(2-methylphenyl)phosphine.5 To this mixture was added 90 mL of toluene. The resulting mixture was degassed by beingstirred while the pressure was reduced. To the mixture was added 19 mg (87 IJ.mol) ofpalladium(II) acetate, and stirring was performed under a nitrogen stream at 110 oc for 7 hours.After the stirring, toluene was added to the mixture, and the resulting mixture wassuction-filtered through Florisil (manufactured by Wako Pure Chemical Industries, Ltd., Catalog10 No. 540-00135), Celite (manufactured by Wako Pure Chemical Industries, Ltd., Catalog No.531-16855), and alumina to give a filtrate. The filtrate was concentrated to give a solid. Thissolid was purified by silica gel column chromatography (as the developing solvent, first, tolueneand hexane in a ratio of 1:2 were used, and then toluene and hexane in a ratio of 1:1 were used)to give 1.1 g of a white solid which was an objective substance in a yield of 34 %. A synthesis15 scheme of Step 1 is shown below

Reference： [1]Patent: WO2018/167612,2018,A1 .Location in patent: Paragraph 0469; 0471; 0472

8
[ 881676-32-0 ]
[ 1993-03-9 ]
[ 881674-56-2 ]

Yield	Reaction Conditions	Operation in experiment
82.8%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere;	Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, 19.0 g (0.136 mol) of 2-fluorophenylboronic acid, 15.0 g of potassium carbonate in a four-necked flask, and add 100 g of DMF and 40 g of water in a nitrogen atmosphere. A catalytic amount of tetrakis(triphenylphosphine)palladium was added thereto, and the temperature was raised to 105 C, and the reaction was carried out for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with water, and extracted with ethyl acetate. The extract was dried, suction filtered, concentrated and weighed. Crystallization gave 13.5 g of gray solid 1, yield 82.8%, purity 99.94%
82.8%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere;	Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, respectively.19.0 g (0.136 mol) of 2-fluorophenylboronic acid,15.0g of potassium carbonate in a four-necked bottle,Add 100g DMF and 40g water,A catalytic amount of tetrakis(triphenylphosphine)palladium is added under a nitrogen atmosphere.Warming up to 105 C,Reaction for 20h,After the reaction is over,Down to room temperature,Dilute with water,Extracted with ethyl acetate,The extract is dried,Filtering,concentrate,Recrystallization gave 13.5 g of a gray solid 1,The yield is 82.8%.Purity 99.94%,

Reference： [1]Patent: CN109006823,2018,A .Location in patent: Paragraph 0060; 0062; 0070; 0071
[2]Patent: CN109006824,2018,A .Location in patent: Paragraph 0068; 0070; 0078; 0079

9
[ 1993-03-9 ]
[ 21193-80-6 ]
4-amino-5-(2-fluorophenyl)-N7-(β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere;	General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 164,p. 689 - 705

10
[ 6311-35-9 ]
[ 1993-03-9 ]
[ 505082-91-7 ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 1032 - 1050

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Technical Information

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P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
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. 1993-03-9 ] {[proInfo.proName]}

Quality Control of [ 1993-03-9 ]

Related Doc. of [ 1993-03-9 ]

Product Details of [ 1993-03-9 ]

Calculated chemistry of [ 1993-03-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1993-03-9 ]

Application In Synthesis of [ 1993-03-9 ]

[ 1993-03-9 ] Synthesis Path-Upstream 1~2

[ 1993-03-9 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 1993-03-9 ]

Fluorinated Building Blocks

Organoboron

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1993-03-9 ]