[ CAS No. 510771-54-7 ] {[proInfo.proName]}

Name: 510771-54-7|3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline|98%
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SKU: A828827
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Quality Control of [ 510771-54-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 510771-54-7 ]

Product Details of [ 510771-54-7 ]

CAS No. :	510771-54-7	MDL No. :	MFCD16996234
Formula :	C₁₃H₁₇BF₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MBZAVZRGXBFAPQ-UHFFFAOYSA-N
M.W :	287.09	Pubchem ID :	53217135
Synonyms :

Calculated chemistry of [ 510771-54-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.54
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	72.32
TPSA :	44.48 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.11
Log Po/w (WLOGP) :	3.75
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	2.16
Consensus Log Po/w :	2.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.0615 mg/ml ; 0.000214 mol/l
Class :	Soluble
Log S (Ali) :	-3.71
Solubility :	0.0557 mg/ml ; 0.000194 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.52
Solubility :	0.00869 mg/ml ; 0.0000303 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.96

Safety of [ 510771-54-7 ]

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 [ 510771-54-7 ]

* 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 [ 510771-54-7 ]

[ 510771-54-7 ] Synthesis Path-Downstream 1~13

1
[ 510771-54-7 ]
[ 374671-03-1 ]
[ 1224100-66-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; water for 18h; Inert atmosphere; Reflux;

Reference： [1]Location in patent: experimental part Jones, Darin E.; South, Michael S. [Tetrahedron, 2010, vol. 66, # 14, p. 2570 - 2581]

2
[ 508178-08-3 ]
[ 510771-54-7 ]
[ 510771-55-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; water for 18h; Inert atmosphere; Reflux;

Reference： [1]Location in patent: experimental part Jones, Darin E.; South, Michael S. [Tetrahedron, 2010, vol. 66, # 14, p. 2570 - 2581]

3
[ 73183-34-3 ]
[ 54962-75-3 ]
[ 510771-54-7 ]

Yield	Reaction Conditions	Operation in experiment
56.9%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere;	To a mixture of <strong>[54962-75-3]3-bromo-5-(trifluoromethyl)aniline</strong> (1 g, 4.17 mmol) in 1,4-dioxane (12 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.164 g, 4.58 mmol), PdCl2(dppf) (0.305 g, 0.417 mmol) and CS2CO3 (2.71 g, 8.33 mmol). The mixture was stirred at 100 °C for 2 h under N2. The mixture was filtered and concentrated, which was purified by silica column chromatography (PE/EA = 5: 1). All fractions found to contain product by TLC (PE/EA = 2: 1, Rf = 0.8) were combined and concentrated to yield a light yellow solid of 3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline (800 mg, 2.369 mmol, 56.9percent yield): NMR (400 MHz, CD3OD) delta 7.27 (s, 1H), 7.23 (s, 1H), 7.03 (s, 1H), 1.37 (s, 12H). ES-LCMS m/z 287.9 (M+H).

Reference： [1]Tetrahedron,2010,vol. 66,p. 2570 - 2581
[2]Patent: WO2014/141187,2014,A1 .Location in patent: Page/Page column 141; 142

4
4,4,5,5-tetramethyl-N-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-amine [ No CAS ]
[ 25015-63-8 ]
5-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine [ No CAS ]
[ 510771-54-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 153 mg 2: 62 mg	Stage #1: 4,4,5,5-tetramethyl-N-(3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-amine; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Glovebox; Stage #2: With methanol In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;

Reference： [1]Preshlock, Sean M.; Plattner, Donald L.; Maligres, Peter E.; Krska, Shane W.; Maleczka Jr., Robert E.; Smith III, Milton R. [Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12915 - 12919][Angew. Chem., 2013, vol. 125, # 49, p. 13153 - 13157,5]

5
[ 98-16-8 ]
[ 73183-34-3 ]
5-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine [ No CAS ]
[ 510771-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Overall yield = 86 %;

6
[ 98-16-8 ]
5-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine [ No CAS ]
[ 510771-54-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Glovebox 2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere; Glovebox 2.2: 20 °C / Inert atmosphere; Glovebox

7
[ 510771-54-7 ]
N-(3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere 2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 1 h / 25 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/141187, 2014, A1

8
[ 510771-54-7 ]
N-(3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)acetamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere 2: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / 1 h / 25 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 25 °C

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2014/141187, 2014, A1

9
[ 510771-54-7 ]
[ 1150271-23-0 ]
3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.7%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; for 16.0h;Inert atmosphere;	To a mixture of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)aniline (500 mg, 1.742 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was added fert-butyl 4-bromo-lH- pyrazole-l-carboxylate (473 mg, 1.916 mmol), PdCl2(dppf) (127 mg, 0.174 mmol) and Cs2C03 (1135 mg, 3.48 mmol). The mixture was stirred at 100 C for 16 h under N2. The mixture was filtered and concentrated, which was purified by silica column chromatography (PE/EA = 1 : 1). All fractions found to contain product by TLC (PE/EA = 1: 1, Rf = 0.2) were combined and concentrated. Then the residue was purified by preparative TLC (DCM/MeOH = 15: 1, Rf = 0.6) to yield a yellow solid of 3-(lH-pyrazol-4-yl)-5-(trifluoromethyl)aniline (8 mg, 0.030 mmol, 1.7% yield): 1H NMR (400 MHz, CD3OD) delta 7.93 (s., 2H), 7.08 (s, 1H), 7.06 (s, 1H), 6.78 (s, 1H). ES- LCMS ra/z 228.1 (M +H).

Reference： [1]Patent: WO2014/141187,2014,A1 .Location in patent: Page/Page column 142; 143

10
[ 510771-54-7 ]
3-[2-(2-aminopyrimidin-5-yl)ethynyl]-4-methyl-N-[3-(1-methylimidazol-2-yl)-5-(trifluoromethyl)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 2.5 h / 90 °C / Inert atmosphere; Microwave irradiation 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 25 °C

Reference： [1]Current Patent Assignee: QILU REGOR THERAPEUTICS - WO2020/206583, 2020, A1

11
[ 510771-54-7 ]
3-[2-[2-(cyclopropanecarbonylamino)pyrimidin-5-yl]ethynyl]-4-methyl-N-[3-(1-methylimidazol-2-yl)-5-(trifluoromethyl)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 2.5 h / 90 °C / Inert atmosphere; Microwave irradiation 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 16 h / 25 °C 3: pyridine / dichloromethane / 2 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: QILU REGOR THERAPEUTICS - WO2020/206583, 2020, A1

12
[ 510771-54-7 ]
[ 16681-59-7 ]
3-(1-methylimidazol-2-yl)-5-(trifluoromethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24.04%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane at 90℃; for 2.5h; Inert atmosphere; Microwave irradiation;	57.12.2 Step 12-2: 3- (1-Methylimidazol-2-yl)-5-(trifluoromethyl) aniline. The mixture of 3- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl)-5-(trifluoromethyl) aniline (891 mg, 3.10 mmol), 2-bromo-1-methyl-1H-imidazole (499.68 mg, 3.10 mmol), cesium carbonate (2.02 g, 6.21 mmol), and Pd (dppf) Cl 2*CH 2Cl 2 (227.09 mg, 310.36 μmol) in dioxane (6 mL) was stirred for 2.5 hours at 90 °C under N 2. The reaction mixture was filtered through a pad of Celite. The cake was washed with EA (100 mL), and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (100% EA) to provide 3- (1-methylimidazol-2-yl)-5-(trifluoromethyl) aniline (180 mg, 24.04% yield) as pale yellow solid. LCMS: (M+H) + = 242.0.

Reference： [1]Current Patent Assignee: QILU REGOR THERAPEUTICS - WO2020/206583, 2020, A1 Location in patent: Page/Page column 78-79

Yield	Reaction Conditions	Operation in experiment
99%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 16h; Inert atmosphere;	Aniline A1 : 3-Fluoro-5-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline General procedure: A mixture of 3-bromo-5-fluoroaniline (21.2 g, 111.61 mmol), bis(pinacolato)diboron (28.34 g, 111.61 mmol), potassium acetate (32.86 g, 334.83mmol) and [1 ,T-bis(diphenylphosphino) ferrocene]dichloropalladium(ll) (2.45 g, 3.90mmol) in 1 ,4-Dioxane (120mL) was purged with argon and then heated at 90°C for 16h. The hot reaction mixture was filtered through a Whatmann paper filter. The filtrate was diluted in ethyl acetate and washed with water and Brine. The organic layer was dried over anhydrous sodium sulfate then filtered and evaporated under reduced pressure. The residue was purified by silica gel chromatography (eluting gradient 0-20% pentane/ethyl acetate). The residue was triturated in n-Heptane, then filtered and dried to afford the expected compound (11 .73 g, 44% yield) as a beige solid. LCMS (MA) RT = 2.53 min, m/z = 238.2 (M+H)+.

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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. 510771-54-7 ] {[proInfo.proName]}

Quality Control of [ 510771-54-7 ]

Related Doc. of [ 510771-54-7 ]

Product Details of [ 510771-54-7 ]

Calculated chemistry of [ 510771-54-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 510771-54-7 ]

Application In Synthesis of [ 510771-54-7 ]

[ 510771-54-7 ] Synthesis Path-Downstream 1~13

Related Functional Groups of [ 510771-54-7 ]

Fluorinated Building Blocks

Organoboron

Aryls

Esters

Amines

Trifluoromethyls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 510771-54-7 ]