Structure of 180092-32-4
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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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CAS No. : | 180092-32-4 |
Formula : | C10H12O |
M.W : | 148.20 |
SMILES Code : | OCC1=CC=CC=C1C(C)=C |
MDL No. : | MFCD30161178 |
InChI Key : | JTKILVMMBUMPQG-UHFFFAOYSA-N |
Pubchem ID : | 22172409 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 |
* 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 |
---|---|---|
95% | With thionyl chloride; In dichloromethane; at 0 - 5℃; for 1.0h; | Step 4: 1-(chloromethyl)-2-(prop-1-en-2-yl)benzene To a solution of <strong>[180092-32-4](2-(prop-1-en-2-yl)phenyl)methanol</strong> (obtained from step 3) (7.0 g, 47.2 mmol) in DCM (70 mL) was added thionyl chloride (6.2 g, 52.3 mmol) dropwise at 0˜5 C. The resulted mixture was stirred at the same temperature for 1 h and then diluted with saturated NaHCO3 aqueous solution (20 mL), the aqueous layer was extracted with DCM (50 mL*3). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford 1-(chloromethyl)-2-(prop-1-en-2-yl)benzene (7.5 g, yield: 95%) as light yellow oil. |
With pyridine; thionyl chloride; In dichloromethane; at 0 - 20℃; for 4.0h; | General procedure: To a stirred solution of 3a (0.55 g,2.6 mmol) in CH2Cl2 (8 mL) containing pyridine (0.21 g, 2.6 mmol) at 0 C was added SOCl2 (0.31 g, 2.6mmol) dropwise and temperature was raised to rt. After 4 h, the mixture was diluted by adding CH2Cl2(20 mL) and treated with H2O (20 mL). The layers were separated and the aqueous layer was extractedwith CH2Cl2 (2 × 15 mL). The combined organic layers were washed with brine (15 mL), dried (Na2SO4)and concentrated by evaporation. The crude product 4a (0.46 g) was used in the next reaction withoutpurification. Thus, to a stirred suspension of NaH (60% in mineral oil; 88 mg, 2.2 mmol) in DMF (3 mL)at 0 C was added t-BuSH (0.20 g, 2.2 mmol) dropwise. After evolution of H2 gas had ceased, a DMF (2mL) solution of the above 4a was added. After 5 min, saturated aqueous NH4Cl (20 mL) was added andthe mixture was extracted with AcOEt (3 × 15 mL). The combined extracts were washed with brine (20mL), dried (Na2SO4), and concentrated by evaporation. The residue was purified by columnchromatography on SiO2 (CH2Cl2/hexane 1:3) to give 5a (0.47 g, 64%); |