[ CAS No. 942070-32-8 ] {[proInfo.proName]}

Name: 942070-32-8|1-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethanone|98+%
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SKU: A106507
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Quality Control of [ 942070-32-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 942070-32-8 ]

SDS Specification

Alternatived Products of [ 942070-32-8 ]

Product Details of [ 942070-32-8 ]

CAS No. :	942070-32-8	MDL No. :	MFCD08063138
Formula :	C₁₂H₁₇BO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NQCVKFAFBSIAPA-UHFFFAOYSA-N
M.W :	252.14	Pubchem ID :	53398602
Synonyms :

Calculated chemistry of [ 942070-32-8 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.58
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	70.99
TPSA :	63.77 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	2.25
Log Po/w (MLOGP) :	0.82
Log Po/w (SILICOS-IT) :	2.87
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.15
Solubility :	0.178 mg/ml ; 0.000705 mol/l
Class :	Soluble
Log S (Ali) :	-3.63
Solubility :	0.0591 mg/ml ; 0.000234 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.61
Solubility :	0.0623 mg/ml ; 0.000247 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.34

Safety of [ 942070-32-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:
Hazard Statements:	H302-H312-H332	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 942070-32-8 ]

* 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 [ 942070-32-8 ]

[ 942070-32-8 ] Synthesis Path-Downstream 1~15

1
[ 88-15-3 ]
[ 25015-63-8 ]
[ 942070-32-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 6103 - 6114

2
[ 942070-32-8 ]
[ 1266480-24-3 ]
[ 1266478-02-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere;	Step 2. The mixture of l-(5-(4-(5-cyclopropyl-lH-pyrazol-3-ylamino)-5-fluoropyrimidin-2- yl)thiophen-2-yl)ethanone , 2-bromo-N-(5-cyclopropyl-lH-pyrazol-3-yl)-5-fluoropyrimidiη-4- amine (825 mg, 2.77 mmol, 1.0 eq), Pd(dppf)2Cl2 (226 mg, 0.28 mmol, 0.1 eq) and saturated Na2CO3 aqueous (8 mL) in 1,4-dioxane (60 mL) was stirred at 1000C for 2 hours under N2. Then, the reaction mixture was cooled down to rt and partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified by column chromatography to give the compound l-(5-(4-(5-cyclopropyl-lH-pyrazol-3-ylamino)-5-fluoropyrimidin-2-yl)thiophen- 2-yl)ethanone (Compound 137) (450 mg, 45%). LC-MS (m/z) = 344.0 [M+H]+. 1H NMR (400 MHz, DMSO-40: δ 0.74-0.77 (m, 2H), 0.99-1.02 (m, 2H), 1.94-1.97 (m, IH), 2.57 (s, 3H), 6.52 (s, IH), 7.79 (d, J=3.2Hz, IH), 7.96 (d, J=3.6Hz, IH), 8.36 (d, J=3.2Hz, IH), , 10.23 (s, IH), 12.27 (s, H).

Reference： [1]Patent: WO2011/19405,2011,A1 .Location in patent: Page/Page column 160

3
[ 942070-32-8 ]
[ 1266478-09-4 ]
[ 1266478-12-9 ]

Reference： [1]Patent: WO2011/19405,2011,A1

4
[ 942070-32-8 ]
[ 1310543-66-8 ]

Reference： [1]Patent: WO2011/19405,2011,A1

5
[ 942070-32-8 ]
[ 1352878-18-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 4h;Cooling with ice;	Compound 1e (3 mmol, 756 mg) was added to a 50 mL, two-necked, round-bottomed flask containing anhydrous methanol (10 mL). The resulting solution was cooled to 0 C with an ice bath. Next, NaBH4 (3.6 mmol, 136 mg) was added, and the mixture was stirred for 0.5 h at 0 C and for an additional 3.5 h at room temperature. The mixture was cooled to 0 C and treated with 1 N HCl aqueous solution until pH 7. The mixture was then extracted with EtOAc (3 × 5 mL), dried over anhydrous MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography using hexanes/EtOAc (8:2) as eluent. Compound 2e was obtained as a colourless oil. Yield: 671 mg (88%). 1H NMR (200 MHz, CDCl3) δ = 1.33 (s, 12H), 1.59 (d, J = 6.6 Hz, 3H), 5.15 (m, 1H), 7.05 (dd, J = 3.6, 0.8 Hz, 1H), 7.50 (d, J = 3.6 Hz, 1H). 13C NMR (50 MHz, CDCl3): δ = 24.92, 25.59, 66.43, 84.27, 124.82, 137.36, 157.58. 11B NMR (96 MHz, CDCl3) δ = 29.00. HRMS (ESI): Calculated for C12H19BO3SNa [M+Na]+ = 277.1046; found: 277.1042.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1772 - 1777

6
[ 942070-32-8 ]
[ 1351956-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With isopropyl alcohol; NADH; at 30℃; for 24h;pH 7.5;aq. phosphate buffer; Enzymatic reaction;	General procedure: To a phosphate buffer solution (50 mM, pH 7.5, 1 mM NADPH in the case of ADH-LB or 1 mM NADH in the case of ADH-A), substrates (50 mM), 2-propanol (100 μL) and ADH-A (150 μL, thermic precipitated) or ADH-LB (300 μL, crude extract) were added leading to a final volume of 1 mL. Samples were incubated for 24 h at 30 C and 120 rpm.CommentThe reaction was stopped by the addition of diethyl ether (500 μL). The mixture was mixed thoroughly and centrifuged for 5 min at 13,000 rpm. Then the organic layer was separated from the aqueous phase and the procedure was repeated with diethyl ether (400 μL). The combined organic layers were dried (Na2SO4) and the supernatant was transferred into GC-glass-vials for analysis

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1772 - 1777

7
[ 76-09-5 ]
(5-acetylthiophen-2-yl)boronic acid [ No CAS ]
[ 942070-32-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	In tetrahydrofuran; at 40℃;Low pressure;	The (5-acetylthiophen-2-yl)boronic acid (5 mmol, 850 mg) and pinacol (5 mmol, 591 mg) were added to a 50 mL, two-necked, round-bottomed flask containing anhydrous THF (30 mL). The resulting solution was evaporated under reduced pressure at 40 C. This procedure was repeated (3 times) until TLC analysis indicated complete conversion. The crude product was purified by column chromatography using hexanes/EtOAc (8:2) as the eluent. Compound 1e was obtained as a white solid (mp = 67.9-68.8 C). Yield: 1.221 g (97%). 1H NMR (200 MHz, CDCl3) δ = 1.35 (s, 12H), 2.58 (s, 3H), 7.58 (d, J = 3.8 Hz, 1H), 7.73 (d, J = 3.8 Hz, 1H). 13C NMR (50 MHz, CDCl3): δ = 24.86, 27.56, 84.77, 132.81, 137.39, 149.62, 190.71. 11B NMR (96 MHz, CDCl3) δ = 28.90. HRMS [ESI (+)]: Calculated for C12H17BO3SNa [M+Na]+ = 275.0889; found: 275.0885.

Reference： [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1772 - 1777

8
[ 88-15-3 ]
[ 73183-34-3 ]
[ 942070-32-8 ]

Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 5022 - 5037
[2]Organic Letters,2021,vol. 23,p. 1561 - 1565
[3]Organic Letters,2012,vol. 14,p. 4266 - 4269

9
[ 942070-32-8 ]
[ 585-79-5 ]
1-(5-(3-nitrophenyl)thiophen-2-yl)ethan-1-one [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4266 - 4269

10
[ 942070-32-8 ]
[ 104-88-1 ]
[ 893735-36-9 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 4266 - 4269

11
[ 942070-32-8 ]
tert-butyl (Z)-(2-((4-(4-bromophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl)-3-fluoroallyl)carbamate [ No CAS ]
tert-butyl (Z)-(2-((4-(4-(5-acetylthiophen-2-yl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)methyl)-3-fluoroallyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.1%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 110℃;	30.0 mg of tert-butyl (Z)-(2-((4-(4-bromophenyl)-5-oxo-4,5-dihydro-lH-l,2,4- triazol-l-yl)methyl)-3-fluoroallyl)carbamate prepared in Reference Example 33, 35.4 mg of l-(5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)thiophen-2-yl)ethan-l-one, and 1.5 mg of palladiumdi[l, l'-bis(diphenylphosphino)ferrocene]dichloride (PdCh(dppf)) were dissolved in 0.81 mL of l,4-dioxane. To the resulting solution, 0.27 mL of 1M aqueous solution of potassium carbonate was added, and the solution was stirred overnight at 1 l0C. The resulting reaction mixture was concentrated, and then with addition of ethyl acetate, the reaction mixture was washed with distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain a yellow liquid residue. The residue was purified with silica gel column chromatography (developing solvent:dichloromethane/methanol = 20/1) to give 16.1 mg of the title compound as a yellow liquid (yield: 50.1 %). MS (ESI) m/z= 373.6 (M + H)+

Reference： [1]Patent: WO2019/180644,2019,A1 .Location in patent: Paragraph 0459-0461

12
[ 6310-09-4 ]
[ 73183-34-3 ]
[ 942070-32-8 ]

Reference： [1]Organic Letters,2021,vol. 23,p. 2320 - 2325
[2]Organic Letters,2020,vol. 22,p. 3273 - 3278

13
[ 6310-09-4 ]
[ 73183-34-3 ]
[ 88-15-3 ]
[ 942070-32-8 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 3273 - 3278

14
[ 5370-25-2 ]
[ 73183-34-3 ]
[ 88-15-3 ]
[ 942070-32-8 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 3273 - 3278

15
[ 30955-94-3 ]
[ 73183-34-3 ]
[ 88-15-3 ]
[ 942070-32-8 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 3273 - 3278

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 942070-32-8 ] {[proInfo.proName]}

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[ 942070-32-8 ] Synthesis Path-Downstream 1~15

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Organoboron

Esters

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[ 942070-32-8 ]