Structure of 629-27-6
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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.
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Batch number can be found on the product's label following the word 'Batch'.
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 629-27-6 |
Formula : | C8H17I |
M.W : | 240.13 |
SMILES Code : | CCCCCCCCI |
MDL No. : | MFCD00001105 |
InChI Key : | UWLHSHAHTBJTBA-UHFFFAOYSA-N |
Pubchem ID : | 12380 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
* 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 |
---|---|---|
90% | With potassium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux; | 6-bromo-2-naphthylamine (2.5 g, 11.26 mmol), 1-iodooctane (5.02 mL, 33.77 mmol), and K2CO3 (3.89 g, 28.14 mmol) were added to 15 mL of anhydrous dimethylformamide, and then the resulting mixture was refluxed and stirred for 24 hours.The reaction product was extracted with dichloromethane (CH2Cl2) three times and isolated using a column (eluting solvent=hexane) in a yield of 90percent (4.5 g); 1H NMR (300 MHz, CDCl3, ppm) delta 7.77 (J=1.5 Hz, d, 1H), 7.57 (J=9.0 Hz, d, 1H), 7.47 (J=9.0 Hz, d, 1H), 7.38 (J=9.0 Hz, J=2.1 Hz, dd, 1H), 7.07 (9.3 Hz, J=2.7 Hz, dd, 1H), 6.74 (J=2.4 Hz, d, 1H), 3.33 (t, 4H), 1.61 (m, 4H), 1.23-1.42 (m, 20H), 0.89 (t, 6H); 13C NMR (75 MHz, CDCl3, ppm) delta 146.19, 133.62, 129.12, 129.06, 127.76, 127.39, 126.87, 116.37, 114.07, 104.60, 51.14, 31.92, 29.58, 29.43, 27.37, 27.24, 22.75, 14.22 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With lithium tert-butylate; In methanol; water monomer; at 50℃; for 48h;Glovebox; | In a glove box, t-BuOLi (0.75 mmol, 1.5 equivalents, 60.1 mg), B2pin2 (1.5 mmol, 3 equivalents, 380.9 mg), 0.85 mL of solvent methanol, 10 μL of H2O were added to the vial containing the stirrer in turn.Iodo-n-octane (0.5 mmol). The capped vial was removed from the glove box and the reaction mixture was stirred at 50 C for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a 100 mL flask by methanol, and then a small amount of silica gel was added thereto. After removing the solvent in vacuo, the residue was poured onto a silica gel column.And purified by column chromatography, the developing solvent is a mixed solution of petroleum ether / ethyl acetate in a volume ratio of 50:1 to 30:1 to obtain the desired product n-octylboronic acid pinacol ester, the yield is 83%. The reaction was carried out in the same procedure using 0.5 mmol of bromo n-octane in a yield of 66%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In the dried reaction tube, add B2cat2 (4.0eq., 576mg), nBu4NBF4 (50mol%, 99mg), and add the electrode material to the above reaction tube, seal the reaction system, and replace it with inert gas (Ar) three times. A syringe was used to inject 1-iodooctane (0.6 mmol, 144 mg) and DMF (6 mL) into the above three-port reaction tube, and the reaction was conducted for 12 minutes at 25 C. with a current of 200 mA. After the reaction, pinacol (8.0eq., 567mg) and Et3N (1.5mL) were injected into the reaction system and stirred for 1h. The reaction was terminated, and the reaction solution was quenched with 15 mL of saturated sodium chloride solution, and then extracted with ethyl acetate (15 mL×3) for multiple times. The organic phases were combined, and the solvent was removed on the rotary evaporator. Finally, it is separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:150) to obtain 4,4,5,5-tetramethyl-2-octyl-1,3,2-di Oxaborane (116 mg, isolated yield: 80%), the compound is a colorless liquid. |