475250-52-3|2-(4-Methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane| Ambeed

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Quality Control of [ 475250-52-3 ] Purity: 97% SDS Specification

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Product Details of [ 475250-52-3 ]

CAS No. :	475250-52-3
Formula :	C₁₄H₂₁BO₃
M.W :	248.13
SMILES Code :	CC1(C)C(C)(C)OB(CC2=CC=C(OC)C=C2)O1
MDL No. :	MFCD10698526
InChI Key :	HPNLRRQVSZVKHY-UHFFFAOYSA-N
Pubchem ID :	12012759

Safety of [ 475250-52-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 475250-52-3 ]

* 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 [ 475250-52-3 ]

[ 475250-52-3 ] Synthesis Path-Downstream 1~35

1
[ 70744-47-7 ]
[ 166330-03-6 ]
[ 475250-52-3 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 5647 - 5650.

2
[ 824-94-2 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris(2,4-pentanedionato)iron(III); magnesium; In tetrahydrofuran; at -10℃; for 8h;Inert atmosphere;	Example 3: Under the conditions of adding magnesium turnings in situ,The boron esterification of p-methoxybenzyl chloride with pinacol diboron catalyzed by Fe(acac)3 was carried out by adding the catalyst (3.5 mg, 0.010 mmol, 2 mol%) in order under argon protection.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol),Tetrahydrofuran (1 ml) with p-methoxybenzyl chloride added at -10C183 μl, 1.35 mmol), the reaction was carried out for 8 hours, and the reaction was terminated with the addition of water.The ester was extracted and the yield calculated by gas chromatography was 90%.
	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate; In 1,4-dioxane; for 18h;Inert atmosphere; Reflux;	Preparation of 2b is representative. A two-necked round-bottomed flask containing 2.07 g (15 mmol) of K2CO3, 1.52 g (6.0 mmol) of bis(pinacolato)diboron and 0.29 g (0.25 mmol) of tetrakis(triphenylphosphine)palladium was equipped with a reflux condenser, filled with nitrogen, and charged with dry 1,4-dioxane (30 mL) and 0.78 g of 4-methoxybenzyl chloride 5b (5.0 mmol). The mixture was refluxed with stirring for 18 h, and then the insoluble materials were filtered off after cooling. The filtrate was condensed under reduced pressure to give the crude benzylboron 6b, which was purified by short column chromatography on silica gel using hexane/ethyl acetate (9/1) as an eluent. The above product (0.79 g, 3.2 mmol) was dissolved in 8 mL of methanol. An aqueous solution (4 mL) of KHF2 (1.5 g, 19 mmol) was added drop-by-drop with vigorous stirring, and then the mixture was stirred for 24 h at room temperature. The solvents were removed under reduced pressure below 60 C to give a solid residue, which was suspended in hot acetone, stirred vigorously, and filtered with suction to extract the benzyltrifluoroborate. This treatment was repeated two more times. The combined filtrate was evaporated, and the residue was recrystallized from acetonitrile/ether to afford pure 2b in 56 % yield (0.41 g, 1.8 mmol).[i] 1H NMR (CD3CN): 6.98-6.68 (m, 4H, ArH), 3.70 (s, 3H, OCH3), 1.47 (br s, 2H, CH2Ar). [i] (a) P. Jain, S. Yi, P. T. Flaherty, J. Heterocycl. Chem. 2013, 50, E166. (b) J. C. Tellis, D. N. Primer, G. A. Molander, Science 2014, 345, 433.

References: [1]Tetrahedron Letters,2003,vol. 44,p. 233 - 235.
[2]Patent: CN107903281,2018,A .Location in patent: Paragraph 0022.
[3]Organic Letters,2022,vol. 24,p. 2931 - 2934.
[4]Chemistry Letters,2002,p. 780 - 781.
[5]Journal of the American Chemical Society,2014,vol. 136,p. 9521 - 9523.
[6]Chemistry Letters,2002,p. 780 - 781.
[7]Chemistry Letters,2020,vol. 49,p. 118 - 120.

3
[ 824-94-2 ]
[ 25015-63-8 ]
[ 475250-52-3 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 8031 - 8033.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827.
[3]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827.

4
[ 104-93-8 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 6Zr(4+)6C20H12O4(2-)8O(2-)4Cl(1-)4Co(2+); sodium triethylborohydride; In n-heptane; at 103℃; for 60h;Schlenk technique; Inert atmosphere; Glovebox;	General procedure: In a glovebox, UiO-68-MOF-CoCl (1.0 mg, 0.2 mol % Co) was charged into a small vial and 0.5 mL THF was added. Then, 15 μL NaBEt3H (1.0 M in THF) was added to the vial and the mixture was stirred slowly for 1 h in the glovebox. The solid was centrifuged out of suspension and washed with THF two times and with heptane two times. B2pin2 (43.0 mg, 0.169 mmol) and p-xylene (41.8 μL, 0.34 mmol) in 2.0 mL heptane was added to the vial and the resultant mixture was transferred to a Schlenk tube. The tube was heated under nitrogen at 103 C. for 2.5 d to obtain the alkyl boronate ester in 94% yield as determined by GC analysis. Upon treatment of NaEt3BH, UiO-68-Co became an active catalyst for undirected dehydrogenative borylation of benzylic C-H bonds using B2(pin)2 (pin=pinacolate) or HBpin as the borylating agents. Borylation of alkyl C-H bonds provides alkyl boronates, which are versatile reagents in organic synthesis. The UiO-68-Co catalyzed borylation reactions were first screened for optimized conditions such as temperature, solvents, and in neat arenes (without using a solvent) to obtain better results. The screening experiments revealed that high turnover frequencies as well as regioselectivities were observed when the borylation reactions were performed using B2(pin)2 in neat arene or refluxed in n-heptane for solid substrates at 103 C. See Table 1, below. The catalytic activity and regioselectivity of UiO-68-Co was higher compared to those of analogous UiO-MOFs having smaller pore sizes such as UiO-67-Co and UiO-66-Co. See Table 2, below. Under optimized reaction conditions, primary benzylic boronate esters were afforded in excellent yields from a range of methylarenes with 0.2 mol % UiO-68-Co. See Table 1. Impressively, UiO-68-Co catalyzed borylation occurred not only at primary benzylic C-H bonds, but also at secondary and tertiary benzylic C-H bonds. See entries 12 and 13, Table 1.

References: [1]Chemistry Letters,2001,p. 1082 - 1083.
[2]Patent: US2018/361370,2018,A1 .Location in patent: Paragraph 0238; 0243.
[3]Angewandte Chemie - International Edition,2022,vol. 61.
Angew. Chem.,2022,vol. 134.

5
[ 2746-25-0 ]
[ 25015-63-8 ]
[ 475250-52-3 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 11825 - 11827.

6
[ 104-92-7 ]
[ 78782-17-9 ]
[ 475250-52-3 ]

References: [1]Chemistry Letters,2013,vol. 42,p. 1363 - 1365.
[2]Organic Letters,2011,vol. 13,p. 3368 - 3371.

7
[ 100-61-8 ]
[ 475250-52-3 ]
[ 37931-52-5 ]

References: [1]Organic Letters,2013,vol. 15,p. 1544 - 1547.

8
[ 475250-52-3 ]
[ 74-88-4 ]
[ 1515-95-3 ]

References: [1]RSC Advances,2013,vol. 3,p. 9391 - 9401.

9
[ 37675-31-3 ]
[ 475250-52-3 ]
[ 42238-20-0 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 9526 - 9531.

10
[ 40775-69-7 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 1593 - 1600.

11
[ 911847-39-7 ]
[ 475250-52-3 ]
C₂₂H₂₇NO₄ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 2726 - 2744.

12
C₂₂H₃₈O₃Sn [ No CAS ]
[ 475250-52-3 ]
(R)-2-(1-(4-methoxyphenyl)propan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 4398 - 4403.

13
[ 104-93-8 ]
[ 745783-97-5 ]
[ 475250-52-3 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 8633 - 8643.

14
[ 73183-34-3 ]
[ 475250-52-3 ]

References: [1]Journal of the American Chemical Society,2022,vol. 144,p. 2460 - 2467.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 8633 - 8643.

15
[ 104-93-8 ]
[ 73183-34-3 ]
[ 123-11-5 ]
[ 475250-52-3 ]

References: [1]Journal of the American Chemical Society,2016,vol. 138,p. 766 - 769.

16
[ 66107-29-7 ]
[ 78782-17-9 ]
[ 475250-52-3 ]

References: [1]RSC Advances,2016,vol. 6,p. 51932 - 51935.

17
[ 105-13-5 ]
[ 73183-34-3 ]
[ 475250-52-3 ]

References: [1]ACS Catalysis,2021,vol. 11,p. 758 - 766.
[2]Organic Letters,2017,vol. 19,p. 1204 - 1207.

18
[ 76-09-5 ]
[ 5720-07-0 ]
[ 18107-18-1 ]
[ 475250-52-3 ]

Yield	Reaction Conditions	Operation in experiment
71%		To a 10 mL reaction tube equipped with a magnet, 0.4 mL (0.8 mmol) of trimethylsilyl diazomethane (2M n-hexane solution) was added to a solution of 1 mL of 4-methoxybenzeneboronic acid (0.4 mmol) 1,4-dioxane, plug the rubber stopper and react for 5 hours at 60 C on an electromagnetic heating stirrer.Followed by the addition of 71 mg (0.6 mmol) of pinacol (dissolved in 1 mL of 1,4-dioxane), 0.6 mL of tetrabutylammonium fluoride (1 M solution in tetrahydrofuran) and 200 uL of water at 60 C in an electromagnetic heating stirrer Continue to react for 5 hours.After the completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography to give 4-methoxybenzylboronic acid pinacol ester, whose structure was as follows:The compound was a colorless liquid in a yield of 71% and its NMR data were as follows:

References: [1]Patent: CN105884808,2016,A .Location in patent: Paragraph 0058; 0059; 0060; 0061; 0062; 0063.
[2]Chemical Science,2017,vol. 8,p. 6071 - 6075.

19
[ 15260-65-8 ]
[ 475250-52-3 ]
2-(3-(4-methoxyphenyl)-1-phenylpropyl)pyridine [ No CAS ]