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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: 4-Methoxytoluene
4.5
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 104-93-8 |
Formula : | C8H10O |
M.W : | 122.16 |
SMILES Code : | CC1=CC=C(OC)C=C1 |
Synonyms : |
4-Methoxytoluene
|
MDL No. : | MFCD00008413 |
InChI Key : | CHLICZRVGGXEOD-UHFFFAOYSA-N |
Pubchem ID : | 7731 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H302-H315-H361-H412 |
Precautionary Statements: | P273-P280 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 3h; | l-(2-Metho l)-ethanoneI -(2-M elhoxy-5-methy]-pheny])-ethanoncLambda solution of acetyl chloride (6.79 ml, 95.1 mmol). l-Methoxy-4-methyl-benzene (intermediate LXXXVII) (9.69 g, 79.4 mmol) in 50 ml of dichloromethane was added dropwise to a suspension of aluminium chloride (12.69 g, 95.1 mmol) in 50 ml of dichloromethane at 0 C. rPhen the reaction mixture was stirred at room temperature for 3 hours. Then the reaction mixture was quenched with 1.5 N hydrochloric acid solution and extracted with dichloromethane. The combined organic extract was washed with water. brine, dried over anhydrous sodium sulphate and evaporated. The crude material was purified using column chromatography (silica gel 100-200 mesh, 15:85 ethylacetate:hexane) to afford l-(2-Methoxy-5-methyl-phenyl)-ethanone in 69 % yield. ?-Iota NMR (400 MHz, CDCI3): 7.528 (s, JH), 7.247 (bs, lH), 6.852-6.873 (d, 111, J=8.4 Hz), 3.881 (s, 3H), 2.601 (s, 3H), 2.299 (s, 3H). |
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. |