[ CAS No. 1310384-98-5 ] {[proInfo.proName]}

Name: 1310384-98-5|2-(3-Methoxythiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|98%
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SKU: A328903
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Quality Control of [ 1310384-98-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1310384-98-5 ]

Product Details of [ 1310384-98-5 ]

CAS No. :	1310384-98-5	MDL No. :	MFCD09837621
Formula :	C₁₁H₁₇BO₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FXKKXDGOIQJEJS-UHFFFAOYSA-N
M.W :	240.13	Pubchem ID :	45588124
Synonyms :

Safety of [ 1310384-98-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1310384-98-5 ]

* 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 [ 1310384-98-5 ]

[ 1310384-98-5 ] Synthesis Path-Downstream 1~9

1
1,4-dibromotriptycenediol [ No CAS ]
[ 1310384-98-5 ]
C₃₀H₂₂O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate; C₃₉H₅₅ClNPPd In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

Reference： [1]Vanveller, Brett; Schipper, Derek J.; Swager, Timothy M. [Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7282 - 7285]

2
[ 15155-41-6 ]
[ 1310384-98-5 ]
4-bromo-7-(3-methoxythiophen-2-yl)-2,1,3-benzothiadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With C₄₅H₅₉ClNPPd; caesium carbonate In tetrahydrofuran at 30℃; for 1.16667h; Sealed tube; Inert atmosphere;

Reference： [1]Heiskanen, Juha P.; Vivo, Paola; Saari, Niko M.; Hukka, Terttu I.; Kastinen, Tuuva; Kaunisto, Kimmo; Lemmetyinen, Helge J.; Hormi, Osmo E. O. [Journal of Organic Chemistry, 2016, vol. 81, # 4, p. 1535 - 1546]

3
[ 1310384-98-5 ]
C₃₈H₂₀Br₂N₄ [ No CAS ]
C₄₈H₃₀N₄O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine In 1,4-dioxane; water; toluene at 60℃; for 14h; Schlenk technique; Inert atmosphere;	Preparation of Compounds 8 - 13 General procedure: Preparation of compounds 8 - 13 (GP1): A Schlenk flask was filled with 7 (10 mg, 14.4 μmol),arylboronic acid (2.2 equiv., 31.7 μmol) and K3PO4 (12.3 mg, 57.8 μmol), evacuated and purged withargon. A mixture of water/toluene/1,4-dioxane (1:1.8:5.5, 0.5 mL) was added and the resultingsuspension degassed with argon for 15 min. Subsequently, Pd2(dba)3 (0.4 mg, 0.437 μmol) and P(otol)3 (1.1 mg, 3.61 μmol) were added, and the reaction was heated to 60 °C for 14 h. Upon fullconversion of the starting material, the reaction was diluted with CH2Cl2 (10 mL) and washed withwater (15 mL) three times. The organic phase was dried over MgSO4, the solvent evaporated underreduced pressure and the crude purified by column chromatography (SiO2, gradient of hexane/CH2Cl2).

Reference： [1]Schleper, A. Lennart; Voll, Constantin-Christian A.; Engelhart, Jens U.; Swager, Timothy M. [Synlett, 2017, vol. 28, # 20, p. 2783 - 2789]

4
[ 17573-92-1 ]
[ 61676-62-8 ]
[ 1310384-98-5 ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 3-methoxy-thiophene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	1 Synthesis of Compound A1 3-methoxythiophene (100 mmol) and tetrahydrofuran (500 mL) was added to a flask, and the reaction system was cooled to -78° C. under a nitrogen atmosphere. Then, n-butyllithium (100 mmol) was slowly added dropwise, and after stirring for one hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 mmol) was added. The reaction system was cooled to a room temperature, and stirred for another three hours. Water was added to the reaction system followed by separation, and the obtained crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate) to obtain a compound A1 as a white fine crystal (42.7 mmol, yield: 43%).1H NMR (400 MHz, CDCl3) δ(ppm)=7.47 (d, 1H), 6.89 (d, 1H), 3.91 (s, 3H), 1.34 (s, 12H).
	Stage #1: 3-methoxy-thiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃;	1 Synthesis example 1 In a three-necked flask, 3-methoxythiophene (5.7 g, 50 mmol) of the following formula (5), 250 ml of THF were added, and the atmosphere was purged with nitrogen, and cooled to -78° A 1.6 M normal butyl lithium hexane solution was added dropwise thereto, and after completion of the addition, the mixture was stirred at -78 ° C for 1 hour.To thereIsopropoxyboronic acid pinacol(16.2 ml, 80 mmol) was added, and the mixture was gradually returned to room temperature and stirred overnight. After water was added, it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and the solvent was evaporated. The obtained crude product was purified by silica gel chromatography (mobile phase: ethyl acetate / hexane) to obtain a thiophene derivative of the following formula (6) as a target product.

Reference： [1]Current Patent Assignee: NIPPON KAYAKU CO LTD - US2019/270758, 2019, A1 Location in patent: Paragraph 0107; 0109-0111
[2]Current Patent Assignee: NIPPON SHOKUBAI CO LTD - JP2019/19083, 2019, A Location in patent: Paragraph 0034; 0035

5
[ 58372-55-7 ]
[ 1310384-98-5 ]
C₁₅H₁₅N₃O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 70℃; Inert atmosphere;	2 Synthesis example 2 In a 200 ml two-necked reaction vessel, 2,6-diamino-3,5-diiodopyridine (1.3 g, 3.7 mmol) of the following formula (7), thiophene derivative of the following formula (6) (1.9 g, 7. 7 mmol), potassium carbonate (3.0 g, 22 mmol), tetrakistriphenylphosFin palladium (0.25 g, 0.22 mmol), 33 ml of THF and 5 ml of water were added and purged with nitrogen. The mixture was heated to 70 ° C. and stirred overnight. Water was added after cooling to room temperature. After extraction with chloroform, the organic layer was dried over magnesium sulfate, filtered and evaporated. The obtained crude product was purified by silica gel chromatography (mobile phase: ethyl acetate / hexane) to obtain the desired product of the following formula (8).

Reference： [1]Current Patent Assignee: NIPPON SHOKUBAI CO LTD - JP2019/19083, 2019, A Location in patent: Paragraph 0036; 0037

6
[ 850349-02-9 ]
[ 1310384-98-5 ]
C₁₂H₁₀N₂OS [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 2143 - 2146

7
[ 1310384-98-5 ]
[ 22813-65-6 ]
C₁₄H₁₁NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium hydroxide In 1,4-dioxane; water at 90℃; for 3h;	1 Synthesis of Compound A2 1-(3-bromo-1H-isoindol-1-ylidene)-N,N-dimethylmethanamine (40 mmol, synthesized with reference to Tetrahedron, 2011, 67, 2072-2080), a compound A1 (42 mmol), dioxane (700 mL), an aqueous solution of potassium hydroxide (2M, 700 mL) were added to a flask followed by nitrogen bubbling, and the contents of the flask were stirred at 90° C. for 3 hours with heating. After cooling the reaction system to a room temperature, water was added followed by separation with chloroform, and the obtained crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain a compound A2 as a greenish yellow powder (17.8 mmol, yield: 45%).1H NMR (400 MHz, CD2Cl2) δ(ppm)=9.87 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.43-7.37 (m, 2H), 7.25 (t, 1H), 7.06 (d, 1H), 4.15 (s, 3H).

Reference： [1]Current Patent Assignee: NIPPON KAYAKU CO LTD - US2019/270758, 2019, A1 Location in patent: Paragraph 0107; 0112-0114

8
[ 1310384-98-5 ]
C₂₇H₁₉BF₂N₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium hydroxide / 1,4-dioxane; water / 3 h / 90 °C 2.1: trichlorophosphate / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 0.17 h / Inert atmosphere 2.3: 2 h / Inert atmosphere

Reference： [1]Current Patent Assignee: NIPPON KAYAKU CO LTD - US2019/270758, 2019, A1

9
[ 17573-92-1 ]
[ 73183-34-3 ]
[ 1310384-98-5 ]
C₁₇H₂₈B₂O₅S [ No CAS ]
C₁₁H₁₇BO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: 3-methoxy-thiophene In tetrahydrofuran at 65℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction;

Reference： [1]Hartwig, John F.; Karmel, Caleb; Kharitonova, Elena V.; Rubel, Camille Z. [Angewandte Chemie - International Edition, 2020, vol. 59, # 15, p. 6074 - 6081][Angew. Chem., 2020, vol. 132, p. 6130 - 6137,8]

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[ 1310384-98-5 ]

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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. 1310384-98-5 ] {[proInfo.proName]}

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[ 1310384-98-5 ] Synthesis Path-Downstream 1~9

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Organoboron

Ethers

Esters

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[ 1310384-98-5 ]