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[ CAS No. 917251-92-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Chemical Structure| 917251-92-4

Chemical Structure| 917251-92-4

Structure of 917251-92-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 917251-92-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 917251-92-4 ]

SDS Specification

Alternatived Products of [ 917251-92-4 ]

Product Details of [ 917251-92-4 ]

CAS No. :	917251-92-4	MDL No. :	MFCD11504935
Formula :	C₁₀H₅BrF₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SLRQZPDPELUOEM-UHFFFAOYSA-N
M.W :	276.05	Pubchem ID :	46739129
Synonyms :

Calculated chemistry of [ 917251-92-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.45
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.3
Log Po/w (XLOGP3) :	3.94
Log Po/w (WLOGP) :	5.17
Log Po/w (MLOGP) :	3.53
Log Po/w (SILICOS-IT) :	4.07
Consensus Log Po/w :	3.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.46
Solubility :	0.00955 mg/ml ; 0.0000346 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.91
Solubility :	0.0339 mg/ml ; 0.000123 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.44
Solubility :	0.00101 mg/ml ; 0.00000365 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 917251-92-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P280-P301+P310+P330-P305+P351+P338-P337+P313-P405-P501	UN#:	2811
Hazard Statements:	H301-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 917251-92-4 ]

* 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 [ 917251-92-4 ]
Downstream synthetic route of [ 917251-92-4 ]

[ 917251-92-4 ] Synthesis Path-Upstream 1~1

1
[ 917251-92-4 ]
[ 483-69-2 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14450 - 14453

[ 917251-92-4 ] Synthesis Path-Downstream 1~14

1
[ 454-79-5 ]
[ 56-81-5 ]
[ 917251-92-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of 2-bromo-4-(trifluoromethyl)aniline (commercially available, 5.0 g), glycerol (3.8 g) and m-nitrobenzene sulfonic acid sodium salt 7.0 g) was added 18 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 150 C. for 4 hours. The mixture then was cooled to room temperature, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and the resulting precipitate was collected by vacuum filtration to yield 3.00 g of the title compound as a brown solid that was used without further purification; MS (ES) m/z (relative intensity): 277 (M+H)+ (100).
	With sulfuric acid; sodium 3-nitrobenzenesulfonate; at 0 - 150℃; for 4h;Inert atmosphere;	70% Sulfuric acid (18 mL) was added drop-wise to the solution of 2-bromo-5- (trifluoromethyl)aniline (5.0 g, 21.0 mmol, 1.0 eq), propane- 1, 2,3 -triol (3.8 g, 42.0 mmol, 2.0 eq) and sodium m-Nitrobenzene sulfonate (7.3 g, 32.55 mmol, 1.55 eq) at 0 C and the mixture was stirred under nitrogen atmosphere, at 150 C for 4 h. After complete consumption of starting material, the mixture was cooled to ambient temperature, poured into chilled water and filtered through a celite bed. The filtrate was neutralized with 2N aqueous NaOH, which led to a precipitate, which was filtered and dried under vacuum to obtain 8-bromo-5- (trifluoromethyl)quinoline. LCMS: Purity 95.13%. MS calculated for [M] 274.96 and found [M+H] +276.04.

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453
[2]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000
[3]Patent: US2007/27160,2007,A1 .Location in patent: Page/Page column 58
[4]Patent: WO2017/147328,2017,A1 .Location in patent: Paragraph 0323

2
[ 917251-92-4 ]
[ 57260-71-6 ]
[ 917251-93-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; for 3h;Heating / reflux;	To a mixture of 5-bromo-8-trifluoromethylsulfonyloxy)quinoline (Step 1, 2.83 g) in anhydrous tetrahydrofuran (38 mL), was added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.04 g) sodium tert-butoxide (5.1 g), 2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.04 g), tetrakis(triphenylphosphine)-palladium (0) (0.04 g) and tert-butoxycarbonyl-piperazine (2.33 g). The mixture was refluxed for 3 hours under a nitrogen atmosphere. The reaction was then cooled to room temperature, diluted with ether, filtered through celite and concentrated on a rotary evaporator. The crude material was purified by flash chromatography on slilca gel using 100% CH2Cl2 to give 0.85 g of the desired product as an off-white solid; MP. 105-107 C.; MS (ES) m/z (relative intensity): 332 (M+H)+ (100).

Reference： [1]Patent: US2007/27160,2007,A1 .Location in patent: Page/Page column 59

3
[ 917251-92-4 ]
[ 159635-49-1 ]
tert-butyl 4-((5-(trifluoromethyl)quinolin-8-yl)methyl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.7%		Step 1: tert-butyl 4-(2-chlorobenzyl)piperidine-1-carboxylate[00269j A mixture of tert-butyl 4-methylenepiperidine- 1 -carboxylate (3.00 g, 15.21 mmol) and 9-borabicyclo [3,3,ljnonane (30.0 mL, 15.00 mmol, 0.5 mol/L in THF) was refluxed under N2 for 3 hours. Then the mixture was cooled to room temperature, and to the mixture was added 1-bromo-2-chlorobenzene (2.77 g, 14.45 mmol), Pd(dppf)C12 (330 mg, 0.45 mmol), 30 mL of DMF, 5 mL of H20 and potassium carbonate (2.50 g, 18.25 mmol). The resulted mixture was heated to 60C overnight. After the reaction was finished, the mixture was cooled to rt, and to the mixture was added H20 (100 mL). The mixture was adjusted to pH 11 with 10 % aquous NaOH solution and extracted with EtOAc (100 mL x 2). The combined organic phases were washed with water (100 mL x 2) and brine (100 mL) in turn, dried over anhydrous Na2SO4 (20 g), filtered and concentrated in vacuo. The crude was purified by silica column chromatography (PE/EtOAc (v/v) = 4/1) to give the title compound as a white solid (4.00 g, 84.9 %).Step 1: tert-butyl 4-((5-(trifluoromethyl)quinolin-8-yl)methyl)piperidine-1-carboxylate[004661 The title compound was prepared by the procedure described in step 1 of Example 15 using tert-butyl 4-methylenepiperidine-1-carboxylate (1.72 g, 8.69 mmol), 9-borabicyclo [3,3,ljnonane (17.4 mL, 8.70 mmol,0.5 mol/L in THF), <strong>[917251-92-4]8-bromo-5-(trifluoromethyl)quinoline</strong> (2.00 g, 7.24 mmol), Pd(dppf)C12 (265 mg, 0.36 mmol) and aqueous sodium hydroxide solution (3 mol/L, 7.3 mL, 21.90 mmol) to give the title compound as a white solid (820 mg, 28.7%). The compound was characterized by the following spectroscopic data:MS(ESI, pos.ion)m/z: 395.1 (M+1); exact mass of C2,H25F3N202: 394.19.

Reference： [1]Patent: WO2015/90232,2015,A1 .Location in patent: Paragraph 00269; 00466

4
[ 917251-92-4 ]
2,4,6-tribromo-3-(5-(trifluoromethyl)quinolin-8-yl)phenol [ No CAS ]
2,4,6-tribromo-3-(5-(trifluoromethyl)quinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

5
[ 917251-92-4 ]
2,4,6-tribromo-3-(5-(trifluoromethyl)quinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

6
[ 917251-92-4 ]
[ 87199-18-6 ]
3-(5-(trifluoromethyl)quinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

7
[ 917251-92-4 ]
C₂₂H₂₁F₃N₂O₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453

8
[ 917251-92-4 ]
[ 483-69-2 ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453

9
[ 917251-92-4 ]
N-(5-(trifluoromethyl)quinolin-8-yl)pivalamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453

10
[ 917251-92-4 ]
tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate [ No CAS ]
tert-butyl 4-(5-(trifluoromethyl)quinolin-8-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; at 85℃; for 16h;Inert atmosphere;	A mixture of <strong>[917251-92-4]8-bromo-5-(trifluoromethyl)quinoline</strong> (1.3 g, 4.71 mmol, 1.0 eq), tert- butyl 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-l(2H)-carboxylate (2.9 g, 9.42 mmol, 2.0 eq) and K3P04 (2.99 g, 14.13 mmol, 3.0 eq) in 1,4-Dioxane (15 mL) was purged with nitrogen for 15 min. Pd(PPh3)2Cl2 (0.33 g, 0.471 mmol, 0.1 eq) was added to the reaction mixture and was stirred under nitrogen atmosphere, at 85 C for 16 h. After complete consumption of starting material, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic extract was separated and the aqueous extract was again extracted with ethyl acetate. The combined organic extract was washed with brine, dried over anhydrous Na2S04, filtered and solvents evaporated from the filtrate under reduced pressure to obtain a crude product, which was purified by flash chromatography on silica gel, 230-400 mesh, using gradient of ethyl acetate in hexanes as eluent to obtain tert-butyl 4-(5- (trifluoromethyl)quinolin-8-yl)-3,6-dihydropyridine-l(2H)-carboxylate. LCMS: Purity 61.96%. MS calculated for [M] 378.40 and found [M+H] +379.31.

Reference： [1]Patent: WO2017/147328,2017,A1 .Location in patent: Paragraph 0324

11
[ 917251-92-4 ]
8-(piperidin-4-yl)-5-(trifluoromethyl)quinoline dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2017/147328,2017,A1

12
[ 917251-92-4 ]
tert-butyl 4-(5-(trifluoromethyl)quinolin-8-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/147328,2017,A1

13
[ 110-00-9 ]
[ 917251-92-4 ]
8-(furan-2-yl)-5-(trifluoromethyl)quinoline [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 432 - 441

14
[ 917251-92-4 ]
4-{2-[5-(trifluoromethyl)quinolin-8-yl]-furan-3-yl}benzonitrile [ No CAS ]
4,4'-{5-[5-(trifluoromethyl)quinolin-8-yl]furan-2,4-diyl}dibenzonitrile [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 432 - 441

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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Response
Code	Phrase
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P321
P322
P330	Rinse mouth.
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P378
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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P401
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Ghs Hazard Statements

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
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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
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H300	Fatal if swallowed
H301	Toxic if swallowed
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H310	Fatal in contact with skin
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H315	Causes skin irritation
H316	Causes mild skin irritation
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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