[ CAS No. 146137-78-2 ] {[proInfo.proName]}

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

2D 3D

Structure of 146137-78-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 146137-78-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 146137-78-2 ]

SDS Specification

Alternatived Products of [ 146137-78-2 ]

Product Details of [ 146137-78-2 ]

CAS No. :	146137-78-2	MDL No. :	MFCD00061311
Formula :	C₈H₄F₄O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	-
M.W :	192.11	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 146137-78-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.79
TPSA :	17.07 ?2

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) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	4.23
Log Po/w (MLOGP) :	2.94
Log Po/w (SILICOS-IT) :	3.43
Consensus Log Po/w :	2.93

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.73
Solubility :	0.355 mg/ml ; 0.00185 mol/l
Class :	Soluble
Log S (Ali) :	-2.37
Solubility :	0.821 mg/ml ; 0.00428 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0588 mg/ml ; 0.000306 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 146137-78-2 ]

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

Application In Synthesis of [ 146137-78-2 ]

* 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 [ 146137-78-2 ]

[ 146137-78-2 ] Synthesis Path-Downstream 1~10

1
[ 2365-48-2 ]
[ 146137-78-2 ]
[ 146137-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;	Production Example 1; A mixture of 5.0 g of 2-fluoro-5- ( trifluoromethyl ) benzaldehyde, 3.3 g of methyl thioglycolate , 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60C for 2 hours, and then the reaction mixture was cooled . to room temperature. To the reaction mixture was added water, and extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from methanol to obtain 6.3 g of methyl 5- ( trifluoromethyl ) benzo[ b] thiophene-2- carboxylate (the present compound 1) .[ The present compound 1]1 H-N R ( CDCI3 ) δ: 8.16(s, ' 1H) , 8.13(s, 1H) , 7.99(d, J=8.7Hz, 1H) , 7.67(d, J=8.7Hz, 1H) , 3.98(s, 3H)
	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;	Production Example 1; A mixture of 5.0 g of 2-fluoro-5- ( trifluoromethyl ) benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60C for 2 hours, and then the reaction mixture was cooled to room temperature. To the reaction mixture was added water, and extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from methanol to obtain 6.3 g of methyl 5- (trifluoromethyl ) benzo[ b] thiophene-2- carboxylate.
6.3 g	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;	Production Example 1 A mixture of 5.0 g of 2-fluoro-5-(trifluoromethyl)benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60 C. for 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the mixture was extracted with tert-butyl methyl ether three times. The combined organic layers were washed with water and saturated saline, and dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was recrystallized from methanol, to obtain 6.3 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (present condensed ring compound 1). [Present Condensed Ring Compound 1] [0100] 1H-NMR (CDCl3) δ: 8.16 (s, 1H), 8.13 (s, 1H), 7.99 (d, J=8.7 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 3.98 (s, 3H)

6.3 g	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 2h;	A mixture of 5.0 g of 2-fluoro-5-(trifluoromethyl)benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60 C. for 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the mixture was extracted with tert-butyl methyl ether three times. The combined organic layers were washed with water and saturated saline, and dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was recrystallized from methanol, to obtain 6.3 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (present condensed ring compound 1). [Present Condensed Ring Compound 1]. 1H-NMR (CDCl3) δ: 8.16 (s, 1H), 8.13 (s, 1H), 7.99 (d, J=8.7 Hz, 1H), 7.67 (d, J=8.7 Hz, 1H), 3.98 (s, 3H)
		General procedure: To a solution of 15a-m in DMF, K2CO3 (25 mmol, 3.45 g) wasadded and the mixturewas stirred at room temperature for 30 min.Then 16 was added dropwise. The reactionwas allowed to warm to60 C and monitored by TLC. The reaction was poured into waterand the mixture was extracted with ethyl acetate three times. Thecombined extracts were dried, concentrated and purified to affordthe intermediate 17a-m. Intermediate AM4a-mwas prepared in a similar manner as thatfor intermediate AM1, using 17a-m instead of 9.

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 7499 - 7502
[2]Patent: WO2012/153860,2012,A1 .Location in patent: Page/Page column 20-21
[3]Patent: WO2012/153861,2012,A1 .Location in patent: Page/Page column 20-21
[4]Patent: US2014/135214,2014,A1 .Location in patent: Paragraph 0099-0100
[5]Patent: US2014/135213,2014,A1 .Location in patent: Paragraph 0102; 0103
[6]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 4684 - 4686
[7]Organic Letters,2020,vol. 22,p. 9199 - 9202
[8]European Journal of Medicinal Chemistry,2022,vol. 228

2
[ 146137-78-2 ]
[ 263266-18-8 ]
[ 548486-70-0 ]