[ CAS No. 1432571-98-6 ] {[proInfo.proName]}

Name: 1432571-98-6|4,4,5,5-Tetramethyl-2-(4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl)-1,3,2-dioxaborolane|97%
Brand: Ambeed
SKU: A100922
Rating: 98 (27 reviews)

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2D 3D

Structure of 1432571-98-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 1432571-98-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1432571-98-6 ]

Product Details of [ 1432571-98-6 ]

CAS No. :	1432571-98-6	MDL No. :	MFCD28134483
Formula :	C₁₆H₂₂BF₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUUSYEYDUDIVNW-UHFFFAOYSA-N
M.W :	314.15	Pubchem ID :	86346259
Synonyms :

Calculated chemistry of [ 1432571-98-6 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.62
Num. rotatable bonds :	3
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	82.38
TPSA :	18.46 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) :	-4.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	5.16
Log Po/w (WLOGP) :	5.09
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	3.69
Consensus Log Po/w :	3.42

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.04
Solubility :	0.00285 mg/ml ; 0.00000907 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.29
Solubility :	0.0016 mg/ml ; 0.00000509 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.69
Solubility :	0.000644 mg/ml ; 0.00000205 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.98

Safety of [ 1432571-98-6 ]

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

Application In Synthesis of [ 1432571-98-6 ]

* 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 [ 1432571-98-6 ]

[ 1432571-98-6 ] Synthesis Path-Downstream 1~9

1
[ 1432571-98-6 ]
[ 188726-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 48.33 h / 3 - 20 °C 2: magnesium chloride; triethylamine / acetonitrile / 18 h / 80 °C 3: potassium carbonate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS NV - US2018/99931, 2018, A1

2
4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane [ No CAS ]
[ 886843-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 3 - 20℃; for 48.33h;	4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol 4,4,5,5-Tetramethyl-2-(4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl)-1,3,2-dioxaborolane (0.500 g, 1.592 mmol) in tetrahydrofuran (16 mL) was cooled in an ice bath to about 3° C. (internal temperature). Sodium hydroxide (1 M aqueous) (2.6 mL, 2.60 mmol) was added dropwise to keep the reaction temperature at 4° C. or lower. Hydrogen peroxide (30% aqueous) (0.2 mL, 1.958 mmol) was added dropwise, causing the reaction temperature to rise to 13° C. The mixture was stirred cold for 20 minutes, and was warmed to room temperature and stirred for 2 days. After this time, the mixture was treated with a 5 mL of saturated aqueous Na2S2O3 solution and was stirred vigorously for 30 minutes. HCl (1 N, aqueous) was then added to pH 4, and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with brine, and the combined aqueous washes were extracted once with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to provide the crude title compound, 4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenol, 698 mg, which was taken into the next reaction without additional purification. 1H NMR (501 MHz, CDCl3) δ ppm 7.38 (m, 2H), 6.85 (m, 2H), 5.53 (s, 1H), 1.57 (s, 6H).

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS - US2018/99931, 2018, A1 Location in patent: Paragraph 2027

3
[ 1432571-98-6 ]
[ 1123173-11-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 48.33 h / 3 - 20 °C 2: magnesium chloride; triethylamine / acetonitrile / 18 h / 80 °C

Reference： [1]Current Patent Assignee: ABBVIE INC; GALAPAGOS NV - US2018/99931, 2018, A1

4
[ 13061-96-6 ]
[ 1432571-98-6 ]
[ 1432571-68-0 ]
[ 1432570-58-5 ]

Yield	Reaction Conditions	Operation in experiment
28 mg	Stage #1: 4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane; 2,3-dibromo-6-butyl-5,6-dihydro-7H-imidazo[1,5-a]imidazole-7-one With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 100℃; for 2h; Inert atmosphere; Stage #2: dihydroxy-methyl-borane With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In ethanol; water; toluene at 100℃; for 4h; Inert atmosphere;	97 Example 97: 6-butyl-2-methyl-3-[4-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl]-5,6-dihydro-7H-imidazo[1,5-a]imidazol-7-one 2,3-dibromo-6-butyl-5,6-dihydro-7H-imidazo[1,5-a]imidazole-7-one obtained in the example 6 of manufacture (100 mg), The 4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane obtained in the example 10 of manufacture (102 mg), Tetrakis (triphenyl phosphine) palladium (0), (34 mg), The mixture of potassium carbonate (123 mg), ethanol (0.45 mL), toluene (0.45 mL), and water (0.30 mL) was agitated in 100 °C (oil bath temperature) under a nitrogen atmosphere for 2 hours. A methylboronic acid (36 mg), PEPPSI(registered trademark)-IPr (20 mg), potassium carbonate (123 mg), and water (0.30 mL) were added to reaction mixture, and it agitated in 100 °C (oil bath temperature) for 4 hours. Water was added to reaction mixture and chloroform extracted. After drying an organic layer with anhydrous sodium sulfate, it condensed under decompression. Residue was refined in the reverse phase column chromatography (SunFire, and 0.1% trifluoroacetic acid / water:0.1% trifluoroacetic acid / acetonitrile =90:10-0:100), and the title compound (28 mg) was obtained as a colorless solid.

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO LTD - JP2015/6993, 2015, A Location in patent: Paragraph 0180-0182

5
[ 886843-09-0 ]
[ 73183-34-3 ]
4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
726 mg	Stage #1: 4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenol With trifluoromethylsulfonic anhydride; triethylamine In chloroform at 20℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: bis(pinacol)diborane With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere;	10 Production Example 10 4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane Under a nitrogen atmosphere, a solution of 4- (1,1,1-trifluoro-2-methylpropan-2-yl) phenol (500 mg) and triethylamine (0.599 mL) in chloroform (6.1 mL) Trifluoromethanesulfonic anhydride (0.482 mL) was added dropwise under cooling. The reaction solution was gradually warmed to room temperature and stirred for 1 hour. Saturated sodium hydrogencarbonate aqueous solution was added dropwise to the reaction solution under ice bath cooling and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane: ethyl acetate = 95: 5 to 90: 10). The obtained pale yellow oil (714 mg), bis (pinacolato) diboron (933 mg), potassium acetate (721 mg), [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (100 mg) and 1,4-dioxane (6.1 mL) was stirred under a nitrogen atmosphere at 80 ° C. (oil bath temperature) for 2 hours. After diluting the reaction solution with ethyl acetate, the insoluble matter was filtered off through Celite (registered trademark) filtration. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane: ethyl acetate = 95: 5 to 90: 10) to give the title compound (726 mg) as a pale yellow solid.

Reference： [1]Current Patent Assignee: TAISHO PHARMACEUTICAL HOLDINGS CO., LTD. - JP2015/6993, 2015, A Location in patent: Paragraph 0089

6
[ 1225380-05-1 ]
[ 73183-34-3 ]
4,4,5,5-tetramethyl-2-[4-(1,1,1-trifluoro-2-methylpropane-2-yl)phenyl]-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; for 3h; Inert atmosphere;	15 Synthesis of Compound 15-2: Compound 15-1 (0.534 g, 2 mmol), boranoic acid pinacol ester (0.700 g, 2.8 mmol), KOAc (0.624 g, 6 mmol) was added to 15 mL of 1,4-dioxane, magnetically stirred, and replaced with nitrogen. Pd(dppf)Cl2 (0.166 g, 0.2 mmol) was added, and the mixture was subjected to a nitrogen atmosphere. The mixture was heated at 90 ° C for 3 h. TLC showed the reaction was complete and the reaction mixture was stood.

Reference： [1]Current Patent Assignee: SUZHOU YUANZHI MEDICINE TECH - CN109896991, 2019, A Location in patent: Paragraph 0272-0275

7
[ 1432571-98-6 ]
[ 2406339-73-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water / 3 h / 90 °C / Inert atmosphere 2.1: 1,2-dichloro-ethane / 0.5 h / Inert atmosphere 2.2: 20 °C

Reference： [1]Current Patent Assignee: SUZHOU YUANZHI MEDICINE TECH - CN109896991, 2019, A

8
[ 1432571-98-6 ]
[ 2406339-21-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water / 3 h / 90 °C / Inert atmosphere 2.1: 1,2-dichloro-ethane / 0.5 h / Inert atmosphere 2.2: 20 °C 3.1: methanol; sodium hydroxide / 1 h / 20 °C

Reference： [1]Current Patent Assignee: SUZHOU YUANZHI MEDICINE TECH - CN109896991, 2019, A

9
[ 1432571-98-6 ]
[ 2406339-30-6 ]
[ 2406339-72-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water at 90℃; for 3h; Inert atmosphere;	15 Synthesis of compound 15-4: To the reaction liquid of the compound 15-2, 15-3 (0.472 g, 1.8 mmol), potassium carbonate (0.824 g, 6 mmol) and water (1 ml) were replaced with nitrogen, and Pd(dppf)Cl2 (0.170 g, 0.2 mmol) was added. ), nitrogen protection, heating at 90 ° C for 3 h. TLC showed complete reaction, column chromatography yielded 0.730 g of product, yield: 98%.

Reference： [1]Current Patent Assignee: SUZHOU YUANZHI MEDICINE TECH - CN109896991, 2019, A Location in patent: Paragraph 0272; 0276-0278

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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. 1432571-98-6 ] {[proInfo.proName]}

Quality Control of [ 1432571-98-6 ]

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[ 1432571-98-6 ] Synthesis Path-Downstream 1~9

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Fluorinated Building Blocks

Organoboron

Aryls

Trifluoromethyls

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[ 1432571-98-6 ]