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[ CAS No. 345226-19-9 ]

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3d Animation Molecule Structure of 345226-19-9

Chemical Structure| 345226-19-9

Chemical Structure| 345226-19-9

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Quality Control of [ 345226-19-9 ]

COA NMR CNMR HPLC LC-MS

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SDS

Alternatived Products of [ 345226-19-9 ]

Product Details of [ 345226-19-9 ]

CAS No. :	345226-19-9	MDL No. :	MFCD08458089
Formula :	C₇H₃ClF₃IO	Boiling Point :	233.5°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	322.45 g/mol	Pubchem ID :	26985436
Synonyms :

Calculated chemistry of of [ 345226-19-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.85
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.52
Log Po/w (XLOGP3) :	4.38
Log Po/w (WLOGP) :	5.1
Log Po/w (MLOGP) :	3.73
Log Po/w (SILICOS-IT) :	4.02
Consensus Log Po/w :	3.95

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.81
Solubility :	0.00502 mg/ml ; 0.0000156 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.29
Solubility :	0.0165 mg/ml ; 0.0000513 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.57
Solubility :	0.00872 mg/ml ; 0.000027 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.39

Safety of [ 345226-19-9 ]

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 [ 345226-19-9 ]

* 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 [ 345226-19-9 ]
Downstream synthetic route of [ 345226-19-9 ]

[ 345226-19-9 ] Synthesis Path-Upstream 1~1

1
[ 345226-19-9 ]
[ 68-12-2 ]
[ 1079351-20-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5639 - 5659

[ 345226-19-9 ] Synthesis Path-Downstream 1~9

1
[ 345226-19-9 ]
[ 59016-93-2 ]
[ 1198422-70-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate; In ethanol; water; toluene; at 88℃; for 1h;	A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-l-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 0C for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5x 100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2'-chloro-4'-(trifluoromethoxy)[l,r-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C; 1H NMR (CDCl3) delta 7.46 (br d, J = 8.2 Hz, 2 H), 7.42 (dt, J = 8.3, 2.0 Hz, 2 H), 7.37 (br s, 1 H), 7.36 (d, J = 8.5 Hz, 1 H), 7.19 (m,I H), 4.77 (d, J = 5.9 Hz, 2 H), 1.70 (t, J = 5.9 Hz, 1 H); HREIMS calcd for C14H10ClF3O2 mlz (M+) 304.0292, 302.0321 , found 304.0294, 302.0317.
98%	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In ethanol; toluene; at 88℃; for 1h;Inert atmosphere;	EXAMPLE 2Methods of PreparationA. Synthesis of (6S)-6-[{2'-chloro-4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]methoxy}-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (1) by the method of Scheme 1 A stirred mixture of 4-(hydroxymethyl)phenylboronic acid (34) (308 mg, 2.03 mmol) and Pd(dppf)Cl2 (191 mg, 0.261 mmol) in toluene (22 mL) and EtOH (11 mL) was degassed for 8 min (vacuum pump) and then N2 was added. An aqueous solution of 2M Na2CO3 (4.4 mL, 8.8 mmol) was added by syringe and the stirred mixture was again degassed for 8 min, and then N2 was added. 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene (35) (585 mg, 1.81 mmol) was added by syringe and the resulting mixture was stirred at 88 C. for 60 min. The cooled mixture was then diluted with aqueous NaHCO3 (100 mL) and extracted with CH2Cl2 (5×100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-50% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 50% CH2Cl2/petroleum ether gave 2'-chloro-4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]methanol (37) (537 mg, 98%) as a white solid: mp (pentane) 38-39 C.; 1H NMR (CDCl3) delta 7.46 (br d, J=8.2 Hz, 2H), 7.42 (dt, J=8.3, 2.0 Hz, 2H), 7.37 (br s, 1H), 7.36 (d, J=8.5 Hz, 1H), 7.19 (m, 1H), 4.77 (d, J=5.9 Hz, 2H), 1.70 (t, J=5.9 Hz, 1H); HREIMS calcd for C14H10ClF3O2 m/z (M+) 304.0292, 302.0321, found 304.0294, 302.0317.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 282 - 294
[2]Patent: WO2011/14774,2011,A1 .Location in patent: Page/Page column 20
[3]Patent: US2012/28973,2012,A1 .Location in patent: Page/Page column 8

2
[ 345226-19-9 ]
(2-chloro-4-(trifluoromethoxy)phenyl)boronic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8421 - 8439

3
[ 345226-19-9 ]
[ 1198422-41-1 ]

Reference： [1]Patent: WO2011/14774,2011,A1
[2]Patent: US2012/28973,2012,A1

4
[ 345226-19-9 ]
[ 1198422-75-1 ]

Reference： [1]Patent: WO2011/14774,2011,A1
[2]Patent: US2012/28973,2012,A1

5
[ 345226-19-9 ]
[ 1321963-68-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5639 - 5659

6
[ 345226-19-9 ]
[ 68-12-2 ]
[ 1079351-20-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5639 - 5659

7
[ 345226-19-9 ]
8-[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1-one [ No CAS ]
8-[tert-butyl(dimethyl)silyl]oxy}-2-[2-chloro-4-(trifluoromethoxy)phenyl]-2-azaspiro[4.5]decan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1 g	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In o-xylene; at 140℃; for 48h;Inert atmosphere; Microwave irradiation;	To a mixture of 8-[tert-butyl(dimethyl)silyl]oxy}-2-azaspiro[4.5]decan-1 -one (500 mg, 1 .76mmol) (isomer 1) and <strong>[345226-19-9]3-chloro-4-iodophenyl trifluoromethyl ether</strong> (696 mg, 98% purity, 2.12mmol) in o-xylol (38 ml) was added under an argon atmosphere copper(l) iodide (67.2 mg, 353 pmol), N,N?-dimethylethylenediamine (77 pI, 710 pmol) and potassium phosphate (749 mg, 3.53 mmol) and the reaction was heated to 1400 for 48 h in a microwave reactor. Upon cooling, the reaction mixture was filtrated through a pad of celite the residue was washedwith ethyl acetate and the filtrate was concentrated under reduced pressure. Another batch was prepared accordingly, the batches were combined and the crude product was purified by flash chromatography (hexanes/ethyl acetate-gradient, 50% -> 100% ethyl acetate) to give the title compound as single isomer (1.0 g). [C-MS (Method 2): R = 1.78 mm; MS (ESipos): m/z = 478 [M+H]1H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 7.71 (d, 1H), 7.62-7.36 (m, 2H), 3.94 (br 5, 1H),3.62 (t, 2H), 2.07 (t, 2H), 2.01-1.83 (m, 2H), 1.71-1.54 (m, 4H), 1.33 (brd, 2H), 0.88 (s, 9H),0.05 (s, 6H).

Reference： [1]Patent: WO2016/177658,2016,A1 .Location in patent: Page/Page column 316; 317

8
[ 4363-93-3 ]
[ 345226-19-9 ]
(2-chloro-4-(trifluoromethoxy)phenyl)(quinolin-4-yl)methanol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 1828 - 1832

9
[ 345226-19-9 ]
[ 5006-22-4 ]
C₁₂H₁₀ClF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.7%	Stage #1: 2-chloro-1-iodo-4-(trifluoromethoxy)benzene With isopropylmagnesium chloride In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; Large scale; Stage #2: Cyclobutanecarbonyl chloride With copper(l) chloride; lithium chloride In tetrahydrofuran at -20 - 20℃; for 1.5h; Inert atmosphere; Large scale;	28.c.c1; 28.c.c2 Step c. Synthesis of compound 8 Step d . Preparation of a Grignard solution i-PrMgCI (2 M, 4.03 L) was added dropwise to the solution of compound 7 (2.00 kg, 6.20 mol) in THF (10.0 L) under nitrogen at -40°C. The resulting mixture was stirred for 1h. Step c2. Grignard reaction. To the solution of compound r-2 (1.10 kg, 9.30 mol, 1.06 L) in THF (5.50 L) under nitrogen were added CuCI (92.1 g, 930 mmol, 22.3 ml_) and LiCI (78.9 g, 1.86 mol, 38.1 ml_) and the mixture was stirred for 30 min. The Grignard solution from Step d was then added quickly under nitrogen at -20 °C. Then the reaction was warmed up to 20°C and stirred for 1h. The reaction mixture was quenched with aq. NH4CI (5.00 L) and extracted with methyl-tert-butyl ether (5.00 L x 2), the organic layer was washed with aq. NaHCOs (5.00 L) and brine (5.00 L), dried over Na2S04 and concentrated. The residue was purified by column chromatography (S1O2, petroleum ether/ethyl acetate = 1/0) to give compound 8 (2.20 kg, 79.7% yield) as a yellow oil. 1H NMR (400 MHz CDCIs): 6 7.51 (d, J = 8.4 Hz, 1H), 7.29-7.28 (m, 1 H), 7.19-7.17 (m, 1H), 3.98-3.90 (m, 1H), 2.39-2.34 (m, 2H), 2.27-2.24 (m, 2H), 2.05-1.92 (m, 2H).

Reference： [1]Current Patent Assignee: BASF SE - WO2021/249800, 2021, A1 Location in patent: Page/Page column 103-105

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Code	Phrase
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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