[ CAS No. 89466-07-9 ]

Name: 89466-07-9|4-Amino-3-nitrophenylboronicacid|98+%
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Quality Control of [ 89466-07-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 89466-07-9 ]

CAS No. :	89466-07-9	MDL No. :	MFCD07437851
Formula :	C₆H₇BN₂O₄	Boiling Point :	439.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	181.94 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 89466-07-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 89466-07-9 ]

Downstream synthetic route of [ 89466-07-9 ]

[ 89466-07-9 ] Synthesis Path-Downstream 1~20

1
[ 99768-11-3 ]
[ 89466-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid

Reference： [1]Torssell et al. [Arkiv foer Kemi, 1957, vol. 10, p. 497,503]

2
[ 80500-27-2 ]
[ 89466-07-9 ]

Reference： [1]Arkiv foer Kemi,1957,vol. 10,p. 497,503

3
[ 80500-28-3 ]
[ 89466-07-9 ]

Reference： [1]Arkiv foer Kemi,1957,vol. 10,p. 497,503

4
[ 175278-33-8 ]
[ 89466-07-9 ]
[ 1259026-50-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 18h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Parks, Daniel J.; Parsons, William H.; Colburn, Raymond W.; Meegalla, Sanath K.; Ballentine, Shelley K.; Illig, Carl R.; Qin, Ning; Liu, Yi; Hutchinson, Tasha L.; Lubin, Mary Lou; Stone, Dennis J.; Baker, Judith F.; Schneider, Craig R.; Ma, Jianya; Damiano, Bruce P.; Flores, Christopher M.; Player, Mark R. [Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 233 - 247]

5
[ 89466-07-9 ]
[ 1276122-65-6 ]
[ 1276122-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 90 °C / Inert atmosphere 2: hydrogenchloride; iron / ethanol; water / 4 h / 80 °C 3: triethylamine / dichloromethane / 2 h / 20 °C

Reference： [1]Parks, Daniel J.; Parsons, William H.; Colburn, Raymond W.; Meegalla, Sanath K.; Ballentine, Shelley K.; Illig, Carl R.; Qin, Ning; Liu, Yi; Hutchinson, Tasha L.; Lubin, Mary Lou; Stone, Dennis J.; Baker, Judith F.; Schneider, Craig R.; Ma, Jianya; Damiano, Bruce P.; Flores, Christopher M.; Player, Mark R. [Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 233 - 247]

6
[ 89466-07-9 ]
C₁₃H₁₂F₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 90 °C / Inert atmosphere 2: hydrogenchloride; iron / ethanol; water / 4 h / 80 °C

7
[ 89466-07-9 ]
[ 1221349-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 90 °C / Inert atmosphere 2.1: hydrogenchloride; iron / ethanol; water / 4 h / 80 °C 3.1: triethylamine / dichloromethane / 2 h / 20 °C 3.2: 3 h / 100 °C

8
[ 89466-07-9 ]
[ 1259026-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / 1,2-dimethoxyethane; water / 18 h / 90 °C / Inert atmosphere 2.1: hydrogenchloride; iron / ethanol; water / 4 h / 80 °C 3.1: triethylamine / dichloromethane / 2 h / 20 °C 3.2: 3 h / 100 °C 4.1: hydrogenchloride / diethyl ether; ethyl acetate

9
[ 64248-56-2 ]
[ 89466-07-9 ]
[ 1259026-54-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110℃; for 1h;Microwave irradiation;	To a mixture of 4-amino-2-nitrophenylboronic acid (606 mg, 3.30 mmol, 90%), 2-bromo-1,3-difluoro-benzene (579 mg, 3.00 mmol) and Pd(PPh3)4 (347 mg, 0.300 mmol) in 1,4-dioxane (9 mL) was added 2.0 M aqueous Na2CO3 (6.00 mL, 12.0 mmol). The resulting mixture was stirred at 110 C. under microwave irradiation for 1 h and then cooled to room temperature. The resulting mixture was treated with EtOAc (50 mL), then was washed with H2O and brine and was dried (Na2SO4). The solvent was removed under reduced pressure followed by flash chromatography of the residue on silica gel (5-40% EtOAc-hexanes) to yield a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 8.30 (s, 1H), 7.50 (dd, J=8.6, 1.8 Hz, 1H), 7.23-7.34 (m, 1H), 6.95-7.05 (m, 1H), 6.90 (d, J=8.6 Hz, 1H), 6.19 (br. s., 2H). Mass Spectrum (LCMS, ESI pos.) Calculated For C12H8F2N2O2: 251.1 (M+H), Measured: 251.0.

Reference： [1]Patent: US2012/202856,2012,A1 .Location in patent: Page/Page column 44

10
[ 89466-07-9 ]
[ 1392517-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / 110 °C / Microwave irradiation 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/202856, 2012, A1

11
[ 89466-07-9 ]
[ 1392517-56-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 1 h / 110 °C / Microwave irradiation 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: acetic acid; iron / ethanol / 1 h / 110 °C / Microwave irradiation

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/202856, 2012, A1

12
4-[(4-chloro-6-phenylpyrimidin-2-ylamino)methyl]cyclohexanecarboxylic acid ethyl ester [ No CAS ]
[ 89466-07-9 ]
C₂₆H₂₉N₅O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 100℃; for 1h; Microwave irradiation; Sealed tube;

Reference： [1]Cervi, Giovanni; Magnaghi, Paola; Asa, Daniela; Avanzi, Nilla; Badari, Alessandra; Borghi, Daniela; Caruso, Michele; Cirla, Alessandra; Cozzi, Liviana; Felder, Eduard; Galvani, Arturo; Gasparri, Fabio; Lomolino, Antonio; Magnuson, Steven; Malgesini, Beatrice; Motto, Ilaria; Pasi, Maurizio; Rizzi, Simona; Salom, Barbara; Sorrentino, Graziella; Troiani, Sonia; Valsasina, Barbara; O'Brien, Thomas; Isacchi, Antonella; Donati, Daniele; D'Alessio, Roberto [Journal of Medicinal Chemistry, 2014, vol. 57, # 24, p. 10443 - 10454]

13
[ 89466-07-9 ]
4-(1-methyl-1H-pyrazol-4-yl)benzene-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 1 h / 120 °C 2: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 72 h / 20 °C

Reference： [1]Lefranc, Julien; Schulze, Volker Klaus; Hillig, Roman Christian; Briem, Hans; Prinz, Florian; Mengel, Anne; Heinrich, Tobias; Balint, Jozsef; Rengachari, Srinivasan; Irlbacher, Horst; Stöckigt, Detlef; Bömer, Ulf; Bader, Benjamin; Gradl, Stefan Nikolaus; Nising, Carl Friedrich; Von Nussbaum, Franz; Mumberg, Dominik; Panne, Daniel; Wengner, Antje Margret [Journal of Medicinal Chemistry, 2020, vol. 63, # 2, p. 601 - 612]

14
[ 89466-07-9 ]
tert-butyl 4-[(2-[6-(1-methyl-1H-pyrazol-4-yl)-1H-benzimidazol-2-yl]amino}pyridin-4-yl)methyl]piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 1 h / 120 °C 2.1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 72 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 0 - 20 °C 3.2: 2 h / 20 °C 3.3: 20 °C

15
[ 89466-07-9 ]
4-(4-amino-3-nitrophenyl)pyrimidin-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 3 h / Reflux 2: sodium thiomethoxide / N,N-dimethyl-formamide / 3 h / 60 °C

16
[ 89466-07-9 ]
2-nitro-4-{5-[(propan-2-yl)oxy]pyrimidin-4-yl}aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 3 h / Reflux 2: sodium thiomethoxide / N,N-dimethyl-formamide / 3 h / 60 °C 3: potassium carbonate / N,N-dimethyl acetamide / 1 h / 70 °C

17
[ 89466-07-9 ]
4-{5-[(propan-2-yl)oxy]pyrimidin-4-yl}benzene-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 3 h / Reflux 2: sodium thiomethoxide / N,N-dimethyl-formamide / 3 h / 60 °C 3: potassium carbonate / N,N-dimethyl acetamide / 1 h / 70 °C 4: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 2 h / 20 °C

18
[ 89466-07-9 ]
tert-butyl 4-[(1R)-1-{2-[(6-{5-[(propan-2-yl)oxy]pyrimidin-4-yl}-1H-benzimidazol-2-yl)amino]pyridin-4-yl}ethyl]piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium carbonate / propan-1-ol / 3 h / Reflux 2.1: sodium thiomethoxide / N,N-dimethyl-formamide / 3 h / 60 °C 3.1: potassium carbonate / N,N-dimethyl acetamide / 1 h / 70 °C 4.1: palladium 10% on activated carbon; hydrogen / dichloromethane; ethanol / 2 h / 20 °C 5.1: 1H-imidazole / dichloromethane / 0 - 20 °C 5.2: 2 h / 20 °C 5.3: 20 °C

19
[ 15803-02-8 ]
[ 89466-07-9 ]
[ 959909-79-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; triphenylphosphine In propan-1-ol at 120℃; for 1h;

20
[ 89466-07-9 ]
[ 695-85-2 ]
4-(5-methoxypyrimidin-4-yl)-2-nitroaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; triphenylphosphine In propan-1-ol for 3h; Reflux;

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Ghs Precautionary Statements

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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

[ CAS No. 89466-07-9 ]

Quality Control of [ 89466-07-9 ]

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Product Details of [ 89466-07-9 ]

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[ 89466-07-9 ] Synthesis Path-Downstream 1~20

Related Functional Groups of [ 89466-07-9 ]

Nitroes

Organoboron

Amines

Aryls

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[ 89466-07-9 ]