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[ CAS No. 886497-81-0 ] {[proInfo.proName]}

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2D 3D

Chemical Structure| 886497-81-0

Chemical Structure| 886497-81-0

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Quality Control of [ 886497-81-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 886497-81-0 ]

SDS Specification

Alternatived Products of [ 886497-81-0 ]

Product Details of [ 886497-81-0 ]

CAS No. :	886497-81-0	MDL No. :	MFCD04115886
Formula :	C₈H₄F₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FMDGCHMPSCBYFX-UHFFFAOYSA-N
M.W :	208.11	Pubchem ID :	2783324
Synonyms :

Calculated chemistry of [ 886497-81-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	38.47
TPSA :	26.3 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) :	-5.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	4.22
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	2.99
Consensus Log Po/w :	2.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.3
Solubility :	0.105 mg/ml ; 0.000505 mol/l
Class :	Soluble
Log S (Ali) :	-3.48
Solubility :	0.0695 mg/ml ; 0.000334 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.26
Solubility :	0.115 mg/ml ; 0.000552 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 886497-81-0 ]

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 [ 886497-81-0 ]

* 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 [ 886497-81-0 ]
Downstream synthetic route of [ 886497-81-0 ]

[ 886497-81-0 ] Synthesis Path-Upstream 1~1

1
[ 352-67-0 ]
[ 68-12-2 ]
[ 886497-81-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: With tert.-butyl lithium In tetrahydrofuran; pentane at -70℃; for 0.25 h; dry ice bath Stage #2: at -70 - 20℃; for 0.5 h; Stage #3: With water; ammonium chloride In tetrahydrofuran; pentane at 20℃;	EXAMPLE 49 3-Trifluoromethoxy-10-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine; a) 2-Fluoro-5-trifluoromethoxy-benzaldehyde; A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 ml) was cooled to <-70° C. Tert.-butyllithium (86 ml of a 1.5 molar solution in pentane, 129 mmol) was added at such a rate that temperature was kept <-70° C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 ml, 150 mmol) was added dropwise keeping temperature <-70° C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH₄Cl solution and extracted with ether. The organic phase was washed with brine, concentrated and chromatographed (SiO₂, heptane:ethyl acetate=100:0 to 80:2). The title compound (11.0 g, 53percent) was obtained as a light yellow oil. ¹H-NMR (300 MHz, DMSO): δ=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).

Reference： [1] Patent: US2006/128691, 2006, A1, . Location in patent: Page/Page column 23-24

[ 886497-81-0 ] Synthesis Path-Downstream 1~13

1
[ 886497-81-0 ]
[ 890132-95-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydroxylamine hydrochloride; sodium acetate; In ethanol; for 2h;Heating / reflux;	b) E-2-Fluoro-5-trifluoromethoxy-benzaldehyde oxime A solution of <strong>[886497-81-0]2-fluoro-5-trifluoromethoxy-benzaldehyde</strong> (9.78 g, 47 mmol) in ethanol (50 ml) was treated with hydroxylamine HCl (3.59 g, 52 mmol) and sodium acetate (4.27 g, 52 mmol). The mixture was refluxed for 2 h, the solvent was evaporated and the residue stirred with water (50 ml). The precipitate was filtered, dried and chromatographed (SiO2, heptanes:Ethyl acetate=100:0 to 80:2) and afforded the title compound (9.21 g, 88%) as a white solid. MS: m/e=223.0 [M]+.

Reference： [1]Patent: US2006/128691,2006,A1 .Location in patent: Page/Page column 24

2
[ 352-67-0 ]
[ 68-12-2 ]
[ 886497-81-0 ]

Yield	Reaction Conditions	Operation in experiment
53%		EXAMPLE 49 3-Trifluoromethoxy-10-methyl-9H-imidazo[1,5-a][1,2,4]triazolo[1,5-d][1,4]benzodiazepine; a) 2-Fluoro-5-trifluoromethoxy-benzaldehyde; A solution of 1-fluoro-4-trifluoromethoxy-benzene (21.0 g, 117 mmol) in THF (233 ml) was cooled to <-70 C. Tert.-butyllithium (86 ml of a 1.5 molar solution in pentane, 129 mmol) was added at such a rate that temperature was kept <-70 C. Stirring in the dry ice bath was continued for 15 min, then DMF (11.6 ml, 150 mmol) was added dropwise keeping temperature <-70 C. After 30 min the reaction mixture was allowed to reach rt, quenched with saturated NH4Cl solution and extracted with ether. The organic phase was washed with brine, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 80:2). The title compound (11.0 g, 53%) was obtained as a light yellow oil. 1H-NMR (300 MHz, DMSO): delta=7.60 (t, J=9.2 Hz, 1H), 7.75-7.85 (m, 2H), 10.20 (s, 1H).

Reference： [1]Patent: US2006/128691,2006,A1 .Location in patent: Page/Page column 23-24

3
[ 109-04-6 ]
[ 886497-81-0 ]
2-[(2-fluoro-5-trifluoromethoxyphenyl)(1-methylpiperidin-4-yloxy)methyl]pyridine [ No CAS ]

Reference： [1]Patent: US2013/324507,2013,A1

4
[ 109-04-6 ]
[ 886497-81-0 ]
(2-fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1B [0232] To a solution of 2-bromopyridine (380 mg) in anhydrous tetrahydrofuran (3 mL) is slowly added a 1M solution of isopropylmagnesium bromide in tetrahydrofuran (2.64 mL) at room temperature. After stirring for 2 hours, <strong>[886497-81-0]2-fluoro-5-(trifluoromethoxy)benzaldehyde</strong> (0.50 mL) is added and the reaction mixture stirred for 2 hours. After hydrolysis with water and 3N hydrochloric acid, the mixture is washed with diethyl ether, basified with concentrated sodium hydroxide and extracted with ethyl acetate twice. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography over silica gel (heptane/ethyl acetate 2/1) to afford (2-fluoro-5-trifluoromethoxyphenyl)pyridin-2-ylmethanol as an orange oil.

Reference： [1]Patent: US2013/324507,2013,A1 .Location in patent: Paragraph 0232

5
[ 886497-81-0 ]
[ 2365-48-2 ]
methyl 5-trifluoromethoxybenzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.38 g	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;	12279] A mixture of 3.00 g of 2-fluoro-3-trifluoromethoxy- benzaldehyde, 1.33 g of methyl thioglycolate, 2.66 g ofpotassium carbonate, and 10 ml of N,N-dimethylformamide was stirred for 2 hours at 80 C. After the reaction mixture was cooled to room temperature, water was added thereto, and extraction was performed three times by using ethyl acetate. The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure, thereby obtaining 1.38 g of methyl 5-trifluoromethoxybenzo[b]thiophene-2-carboxylate (hereinafier, described as a ?compound 98 of the present invention?).12280] Compound 98 of the Present Invention 12281] ?H-NMR(CDC13) oe: 8.05 (s, 1H), 7.87 (d, 1H, J=8.8Hz), 7.73 (d, 1H, J=1 .0Hz), 7.34 (dq, 1H, J=8.8, 1.0Hz), 3.96(s, 3H).
1.38 g	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 2h;	A mixture of 3.00 g of <strong>[886497-81-0]2-fluoro-5-trifluoromethoxybenzaldehyde</strong>, 1.33 g of methyl thioglycolate, 2.66 g of potassiumcarbonate, and 10 ml of N,N-dimethylformamide was stirred for 2 hours at 80C. After the reaction mixture wascooled to room temperature, water was added thereto, and extraction was performed three times by using ethyl acetate.The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and thenconcentrated under reduced pressure, thereby obtaining 1.38 g of methyl 5-trifluoromethoxybenzo[b]thiophene-2-carboxylate.

Reference： [1]Patent: US2015/282482,2015,A1 .Location in patent: Paragraph 2279; 2280; 2281
[2]Patent: EP2926660,2015,A1 .Location in patent: Paragraph 0434

6
[ 886497-81-0 ]
[ 885279-13-0 ]

Reference： [1]Patent: EP2926660,2015,A1

7
[ 886497-81-0 ]
[ 716-06-3 ]
N-(2-fluoro-5-(trifluoromethoxy)benzyl)-2-(5-methoxy-1-methyl-1H-indol-3-yl)ethan-1-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1118 - 1129

8
[ 886497-81-0 ]
[ 716-06-3 ]
C₂₀H₁₈F₄N₂O₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1118 - 1129

9
[ 886497-81-0 ]
(R)-5-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)-2,6-dimethylnicotinamide [ No CAS ]

Reference： [1]Patent: WO2018/148626,2018,A1

10
[ 886497-81-0 ]
(S)-N-((R)-1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)-2-methylpropane-2-sulfinamide [ No CAS ]

Reference： [1]Patent: WO2018/148626,2018,A1
[2]Patent: WO2020/56072,2020,A1

11
[ 886497-81-0 ]
(R)-1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethan-2,2,2-d3-1-amine hydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/148626,2018,A1

12
[ 886497-81-0 ]
(S)-N-((R)-1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl)-2-methylpropane-2-sulfinamide [ No CAS ]

Reference： [1]Patent: WO2018/148626,2018,A1

13
[ 886497-81-0 ]
[ 343338-28-3 ]
(S,E)-N-(2-fluoro-5-(trifluoromethoxy)benzylidene)-2-methylpropane-2-sulfinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With titanium(IV)isopropoxide; In tetrahydrofuran; at 20℃; for 72h;	Titanium(IV) isopropoxide (5.69 mL, 19.22 mmol) was added to a THF (20 mL) solution of <strong>[886497-81-0]2-fluoro-5-(trifluoromethoxy)benzaldehyde</strong> (2.0 g, 9.61 mmol) and (S)-(10 )-2-methyl-2-propanesulfinamide (1.165 g, 9.61 mmol) at ft and stirred for 72 h. Thereaction mixture was quenched by adding brine (10 mL) and hexanes (10 mL) at 0 C.The mixture was filtered through a pad of celite, and the pad was rinsed with ethyl acetate(2 x 10 mL). The combined organic solutions were dried over sodium sulfate, filtered andconcentrated under reduced pressure to give crude product which was purified on a silicagel column with Hexanes/EtOAc (100/0 to 50/50) to give (S,E)-N-(2-fluoro-5-(trifluoromethoxy)benzylidene)-2-methylpropane-2-sulfinamide (2.827 g, 8.73 mmol, 91%yield).MS ESI m/z 312.0 (M+H)

Reference： [1]Patent: WO2018/148626,2018,A1 .Location in patent: Page/Page column 290; 322; 323
[2]Patent: WO2020/56072,2020,A1 .Location in patent: Page/Page column 48; 49

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
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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.
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Code	Phrase
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P322
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
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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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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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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.
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Ghs Hazard Statements

Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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H205	May mass explode in fire
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H240	Heating may cause an explosion
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H242	Heating may cause a fire
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H316	Causes mild skin irritation
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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