[ CAS No. 855230-60-3 ] {[proInfo.proName]}

Name: 855230-60-3|(2-Fluoro-3-hydroxyphenyl)boronic acid|97%
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Quality Control of [ 855230-60-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 855230-60-3 ]

CAS No. :	855230-60-3	MDL No. :	MFCD06797222
Formula :	C₆H₆BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FUYFURLPSFAOGC-UHFFFAOYSA-N
M.W :	155.92	Pubchem ID :	17750950
Synonyms :

Safety of [ 855230-60-3 ]

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 [ 855230-60-3 ]

* 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 [ 855230-60-3 ]
Downstream synthetic route of [ 855230-60-3 ]

[ 855230-60-3 ] Synthesis Path-Upstream 1~1

1
[ 352303-67-4 ]
[ 855230-60-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: With boron tribromide In dichloromethane at 5 - 20℃; Inert atmosphere Stage #2: With sodium hydrogencarbonate In ethanol; dichloromethaneCooling	2-Fluoro-3-methoxyphenylboronic acid (1.1g, 6.5 mmol) was dissolved in 30 mL dichloromethane and cooled to 5 °C under nitrogen. 32 mL boron tribromide solution (1M in dichloromethane, 32 mmol) was added drop-wise with stirring. Upon addition, the mixture was stirred for 1 h at room temperature. The mixture was added drop-wise to 50 mL cold ethanol. The mixture was then neutralised with portion-wise addition of excess solid sodium bicarbonate with cooling. The mixture was stirred for 15 min, filtered and the filtrate evaporated. The residue was taken up in tetrahydrofuran, re-filtered and re-evaporated to give 0.96 g (96percent) of the title compound. ¹H NMR (200 MHz, DMSO-d₆) ppm 9.53 (1 H, s), 8.13 (2 H, m), 6.91 (3 H, m)

Reference： [1] Patent: EP2196465, 2010, A1, . Location in patent: Page/Page column 30; 31
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497
[3] Patent: WO2006/5918, 2006, A1, . Location in patent: Page/Page column 89

[ 855230-60-3 ] Synthesis Path-Downstream 1~11

1
[ 352304-10-0 ]
[ 855230-60-3 ]
{2-[3-(2,6-difluoro-benzyl)-5-(2-fluoro-3-hydroxy-phenyl)-2,6-dioxo-3,6-dihydro-2<i>H</i>-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2519 - 2522

2
[ 876621-30-6 ]
[ 855230-60-3 ]
[ 1062642-64-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2519 - 2522

3
[ 71381-75-4 ]
[ 855230-60-3 ]
[ 873566-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl acetamide; at 20℃; for 2h;	Diisopropylethylamine (1.07 g) was added to a stirred solution ofA^-(te?t-butoxycarbonyl)piperidine-3-carboxylic acid (1.23 g), 2-(7-azabenzotriazol-l-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (2.04 g) and DMA (20 ml) and the mixturewas stirred at ambient temperature for 5 minutes. 4-(3-Aminophenyl)-2-chloro-6-morpholinopyrimidine (1.2 g) was added and the reaction mixture was stirred at ambienttemperature for 2 hours. The solution was evaporated and the residue was adsorbed ontoreversed-phase silica using an 'Isolute SCX-3' column (50 g) and allowed to stand for5 minutes. The column was eluted initially with a 10:1 mixture of methylene chloride andmethanol. There was thus obtained 4-{3-[W-(te?t-butoxycarbonyl)piperidin-3-ylcarbonylamino]phenyl}-2-chloro-6-morpholinopyrimidine (0.52 g); NMR Spectrum:(CDC13) 1.41 (s, 9H),L43-1.51 (m, 2H), 1.81-1.9 (m, 1H), 1.99-2.06 (m, 1H), 2.41-2.49 (m,1H), 3.11-3.26 (m, 1H), 3.43-3.84 (m, 11H), 6.7 (s, 1H), 7.19 (s, 1H), 7.33 (t, 1H), 7.62-7.68(m, 2H), 8.11 (s, 1H). The column was subsequently eluted with a 7M methanolic ammoniasolution. There was thus obtained 2-chloro-6-morpholino-4-(3-piperidin-3-ylcarbonylaminophenyl)pyrimidine as a solid (0.52 g); NMR Spectrum: (CDCls) 1.69-1.82 (m,3H), 3.06-3.17 (m, 2H), 3.25-3.31 (m, 1H), 3.62-3.82 (m, 11H), 6.75 (s, 1H), 7.36 (t, 1H), 7.64(d, 1H), 7.74 (d, 1H), 8.15 (s, 1H), 10.04 (s, 1H).

Reference： [1]Patent: WO2006/5918,2006,A1 .Location in patent: Page/Page column 89-90

4
[ 352303-67-4 ]
[ 855230-60-3 ]

Yield	Reaction Conditions	Operation in experiment
96%		2-Fluoro-3-methoxyphenylboronic acid (1.1g, 6.5 mmol) was dissolved in 30 mL dichloromethane and cooled to 5 C under nitrogen. 32 mL boron tribromide solution (1M in dichloromethane, 32 mmol) was added drop-wise with stirring. Upon addition, the mixture was stirred for 1 h at room temperature. The mixture was added drop-wise to 50 mL cold ethanol. The mixture was then neutralised with portion-wise addition of excess solid sodium bicarbonate with cooling. The mixture was stirred for 15 min, filtered and the filtrate evaporated. The residue was taken up in tetrahydrofuran, re-filtered and re-evaporated to give 0.96 g (96%) of the title compound. 1H NMR (200 MHz, DMSO-d6) ppm 9.53 (1 H, s), 8.13 (2 H, m), 6.91 (3 H, m)
		A solution of boron tribromide (0.85 ml) in dry methylene chloride (2 ml) was added toa stirred solution of <strong>[352303-67-4]2-fluoro-3-methoxyphenylboronic acid</strong> (0.51 g) in dry methylene chloride(20 nil) that had been cooled to 0C. The reaction mixture was stirred at 0C for 1 hour.Methanol (7 ml) was added and the reaction stirred for a further hour at 0C. The resultantmixture was evaporated. Methanol (2 ml) was added to the residue and the solution wasevaporated. The residue was triturated under diethyl ether and the mixture was filtered. Thefiltrate was evaporated and the residue was triturated under acetonitrile. The resultant solidwas isolatedby filtration, washed with acetonitrile and dried. There was thus obtained2-fluoro-3-hydroxyphenylboronic acid (0.064 g); NMR Spectrum: (DMSOde) 6.86-6.98 (m,3H), 8.07 (s, 2H), 9.47 (s, 1H).

Reference： [1]Patent: EP2196465,2010,A1 .Location in patent: Page/Page column 30; 31
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 10479 - 10497
[3]Patent: WO2006/5918,2006,A1 .Location in patent: Page/Page column 89

5
2-chloro-6-morpholino-4-(3-piperidin-3-ylcarbonylaminophenyl)pyrimidine [ No CAS ]
[ 855230-60-3 ]
2-(2-fluoro-3-hydroxyphenyl)-6-morpholino-4-(3-piperidin-3-ylcarbonylaminophenyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 140℃; for 0.25h;Microwave irradiation;	Example 5; 2-(2-fluoro-3-hydroxyphenyl)-6-morpholino-4-(3-piperidin-3-ylcarbonylaminophenyl)pyrimidine; A mixture of <strong>[855230-60-3]2-fluoro-3-hydroxyphenylboronic acid</strong> (0.058 g), 2-chloro-6-morpholino-4-(3-piperidin-3-ylcarbonylaminophenyl)pyrimidine (0.151 g),tetrakis(triphenylphosphine)palladium(0) (0.014 g), a saturated aqueous solution containingsodium carbonate (0.106 g) and 1,4-dioxane (3 ml) was placed in a sealed glass tube under anatmosphere of nitrogen and heated to 140C using microwave radiation for 15 minutes. Theresultant reaction mixture was evaporated and the residue was partitioned between methylenechloride and water. The organic layer was washed with brine, dried over magnesium sulphateand evaporated. The residue was purified by HPLC using a Waters 'Xterra' preparativereversed-phase column (5 microns silica, 19 mm diameter, 100 mm length) using decreasinglypolar mixtures of water [containing 1% aqueous ammonium hydroxide (d=0.88)] andacetonitrile as eluent. The material so obtained was purified further by columnchromatography on silica using an increasingly polar gradient of 0% to 10% methanol inmethylene chloride as eluent. There was thus obtained the title compound as a colourless solid(0.013 g); NMR Spectrum: (DMSOde) 1.48 (m, 1H), 1.8 (m, 2H), 1.88 (m, 1H), 2.63 (m, 1H),2.84 (m, 1H), 3.02 (m, 1H), 3.71 (m, 8H), 7.05 (m, 2H), 7.18 (s, 1H), 7.4 (m, 2H), 7.84 (d,2H), 8.3 (s, 1H), 10.08 (s, 1H): Mass Spectrum: M+H^ 478.

Reference： [1]Patent: WO2006/5918,2006,A1 .Location in patent: Page/Page column 88-89

6
(Z)-methyl 3-cyclopropyl-2-methyl-3-(tosyloxy)acrylate [ No CAS ]
[ 855230-60-3 ]
(Z)-methyl3-cyclopropyl-3-(2-fluoro-3-hydroxyphenyl)-2-methyl acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 80℃; for 3h;Inert atmosphere;	Step 1: 1 ,4-Dioxane (2400 ml) and water (240 ml) was added to a large reaction flask followed by degassing with nitrogen for 30 minutes. (Z)-Methyl 3 -cyclopropyl-2-methyl-3 -(tosyloxy)acrylate (240 g, 766 mmol), <strong>[855230-60-3](2-fluoro-3-hydroxyphenyl)boronic acid</strong> (131 g, 843 mmol), Cs2CO3 (275 g, 843mmol) and dichloro [1,1 ?-bis(diphenylphosphino)ferrocene] -palladium (II) dichloromethane adduct (25.03 g, 30.7 mmol) were added. The mixture was stirred at 80 C for 3 h, then diluted with ethyl acetate (2 L) and water (1 L). The organic layer was separated and back extracted with ethyl acetate. The combined organic layers were washed with 10% NaC1 solution (1 L x2) and dried over MgSO4 (300 g), and concentrated. The resulting he crude residue was purified by columnchromatography (0-50% EtOAc in hexanes) to afford methyl (Z)-3-cyclopropyl-3-(2-fluoro-3- hydroxyphenyl)-2-methylacrylate.

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 824 - 830
[2]Patent: WO2016/22742,2016,A1 .Location in patent: Page/Page column 100

7
[ 1229442-29-8 ]
[ 855230-60-3 ]
[ 1229437-82-4 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10479 - 10497

8
ethyl 1-(3-bromophenyl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate [ No CAS ]
[ 855230-60-3 ]
ethyl 1-(2'-fluoro-3'-hydroxy-[1,1'-biphenyl]-3-yl)-5-(2-(1-methyl-1H-1,2,3-triazol-4-yl)cyclopropyl)-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; at 75℃; for 16h;Inert atmosphere;	234a) Ethyl 1 -(2'-fluoro-3'-hydroxy-[1 ,1 '-biphenyl]-3-yl)-5-(2-(1 -methyl-1 H-1 ,2,3- triazol-4-yl)cyclopropyl)-1 H-pyrazole-4-carboxylate To a solution of ethyl 1 -(3-bromophenyl)-5-(2-(1 -methyl-1 H-1 ,2,3-triazol-4-yl)cyclopropyl)- 1 H-pyrazole-4-carboxylate (400 mg, 0.961 mmol) in tetrahydrofuran (THF) (2 ml_) was added <strong>[855230-60-3](2-fluoro-3-hydroxyphenyl)boronic acid</strong> (180 mg, 1 .153 mmol), sodium carbonate (204 mg, 1 .922 mmol) and water (0.5 ml_). The reaction mixture was degassed with argon for 15 min, then tetrakis(triphenylphosphine)palladium(0) (1 1 1 mg, 0.096 mmol) was added under nitrogen atmosphere. It was heated at 75C for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate (2 x 30 ml_). The combined organic layer was washed with brine solution (20 ml_), dried over anhydrous Na2S04 and concentrated. The crude residue was purified by column chromatography eluting with 60 % ethyl acetate in n-hexane. Desired fractions were concentrated to give the title compound (450 mg, 0.961 mmol, 100 % yield). LC-MS m/z 448.35 (M+H)+, 3.26 min (ret. time).

Reference： [1]Patent: WO2017/60854,2017,A1 .Location in patent: Page/Page column 543; 544

9
[ 1422513-84-5 ]
[ 855230-60-3 ]
3-(2-fluoro-3-hydroxyphenyl)-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With 5%-palladium/activated carbon; sodium carbonate; In 1,2-dimethoxyethane; water; at 45℃; for 1h;	Intermediate 6 (17 mg, 0.5 mmol), Na2CO3 (159 mg, 1.5 mmol), <strong>[855230-60-3](2-fluoro-3-hydroxyphenyl)boronic acid</strong>(91.2 mg, 0.6 mmol), Pd/C (26.5 mg, 5 mol%)Place in a reaction flask and add 3 mL of ethylene glycol dimethyl ether and 3 mL of water.Then react at 45 C for 1 h, remove the solids through diatomaceous earth,The filter cake was washed with CH 2 Cl 2 , and the obtained filtrate was extracted three times with CH 2 Cl 2 .The organic phases were combined, dried over anhydrous sodium sulfate, filtered and dried.The compound 8c was isolated and purified by silica gel column chromatography.60%,
60%	With palladium 10% on activated carbon; sodium carbonate; In 1,2-dimethoxyethane; water; at 45℃; for 1h;	General procedure: Compound 7 (106mg, 0.3mmol) was dissolved in premixed solution of DME (1.8mL) and H2O (1.8mL). Then, Na2CO3 (95mg, 0.9mmol), aryl boronic acid (0.36mmol), and Pd/C (16mg, 5mol %) were added. After 1h stirring at 45C, the reaction mixture was filtered, and the cake was washed with H2O (4mL) and CH2Cl2 (6mL). The aqueous phase was then extracted twice with CH2Cl2, 8a-8u were obtained from the CH2Cl2 extracts by flash chromatography.

Reference： [1]Patent: CN109810115,2019,A .Location in patent: Paragraph 0110-0114
[2]Bioorganic Chemistry,2019,vol. 88

10
[ 1422513-84-5 ]
[ 855230-60-3 ]
3-(8,8-dimethyl-4-oxo-4H,8H-pyrano[2,3-f]chromen-3-yl)-2-fluorophenyl heptylcarbamate [ No CAS ]

Reference： [1]Bioorganic Chemistry,2019,vol. 88

11
3-chloro-6-(furan-3-yl)-[1,2,4]triazolo[4,3-a]pyridine [ No CAS ]
[ 855230-60-3 ]
2-fluoro-3-(6-(furan-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-phenol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 3935 - 3955

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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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

[ CAS No. 855230-60-3 ] {[proInfo.proName]}

Quality Control of [ 855230-60-3 ]

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Application In Synthesis of [ 855230-60-3 ]

[ 855230-60-3 ] Synthesis Path-Upstream 1~1

[ 855230-60-3 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 855230-60-3 ]

Fluorinated Building Blocks

Organoboron

Aryls

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Health hazards

Environmental hazards

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[ 855230-60-3 ]