[ CAS No. 107818-55-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 107818-55-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 107818-55-3 ]

SDS Specification

Alternatived Products of [ 107818-55-3 ]

Product Details of [ 107818-55-3 ]

CAS No. :	107818-55-3	MDL No. :	MFCD12031265
Formula :	C₆H₆BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RZYLOBBUEWSONL-UHFFFAOYSA-N
M.W :	236.09	Pubchem ID :	20158931
Synonyms :

Calculated chemistry of [ 107818-55-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.7
TPSA :	80.56 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	2.68
Log Po/w (WLOGP) :	1.89
Log Po/w (MLOGP) :	1.08
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	1.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.2
Solubility :	0.15 mg/ml ; 0.000636 mol/l
Class :	Soluble
Log S (Ali) :	-4.02
Solubility :	0.0223 mg/ml ; 0.0000946 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.24
Solubility :	1.35 mg/ml ; 0.00571 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.49

Safety of [ 107818-55-3 ]

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 [ 107818-55-3 ]

* 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 [ 107818-55-3 ]

[ 107818-55-3 ] Synthesis Path-Downstream 1~1

1
[ 79128-68-0 ]
[ 107818-55-3 ]

Yield	Reaction Conditions	Operation in experiment
18%		To stirred tetrahydrofuran (100 inL) at -78C were added dropwise diisopropylamine (9.00 mL, 63.9 mmol) and n-butyl lithium (37.1 mL, 59.4 mmol, 1.6 M solution in n-hexane) successively. The reaction mixture was allowed to warm to 00C and stirred for additional 10 min. The mixture was cooled to -78C again and methyl 3- (2,2, 2- trifluoroacetamido) thiophene-2-carboxylate (4.56 g, 18.0 mmol) was added to the mixture. After 1 h, bromine (2.78 mL, 54.0 mmol) was added to the mixture, and stirring was continued at -78C for 2 h and at room temperature for 30 min. The mixture was then poured into sat. aqueous sodium hydrogen carbonate (180 mL) . Extraction with ethyl acetate (150 mL) , washing with brine, drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. The oil was purified by column chromatography (Combiflash, 12 g silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford a mixture of the title compound and methyl 3-aminothiophene-2-carboxylate (1.86 g) as a white solid. The ratio was about 2:1 estimated by 1H NMR analysis:1H NMR (300 MHz, DMSO-d6) delta 3.84 (3H, s) , 7.79 (IH, s) , 11.22 (IH, br s) .A mixture of methyl 5-bromo-3- (2, 2, 2- trifluoroacetamido) thiophene-2-carboxylate (1.86 g) , potassium carbonate (3.72 g, 26.9 mmol), methanol (40 mL) and water (10 mL) was stirred at room temperature for 1.5 h. The mixture was concentrated in vacuo and then ethyl acetate and water were added to the residue for extraction. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (Combiflash, silica gel, hexanes to 90:10 hexanes/ethyl acetate) to afford the title compound (0.781 g, 18% from methyl 3- (2, 2, 2-trifluoroacetamido) thiophene-2- carboxylate) as a white solid:1H NMR (300 MHz, DMSO-d6) delta 3.70 (3H, s), 6.69 (2H,br s) , 6.75 (IH, s).

Reference： [1]Patent: WO2010/101302,2010,A1 .Location in patent: Page/Page column 130-131
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2535 - 2539
[3]Patent: EP2540728,2013,A1

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Bouveault-Blanc Reduction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Ester Cleavage ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Reactions with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

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