Structure of 120870-47-5
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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'.
Search for reports by entering the product batch number.
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CAS No. : | 120870-47-5 |
Formula : | C13H14O2 |
M.W : | 202.25 |
SMILES Code : | O=C(C1=C(C#CCCCC)C=CC=C1)O |
MDL No. : | N/A |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
78% | With oxone; tetrabutylammomium bromide; In water; at 80℃; for 8h; | General procedure: 2-alkynylbenzoic acid 1 (0.2 mmol), TBAB (0.1 equiv), and Oxone(2.0 equiv) were added to a test tube, and then H2O (2.0 mL) wasadded. The mixture was stirred at 80 C for 8 h, under air. After thedisappearance of the substrate as indicated by TLC, the mixture wasfiltered and the resulting filtrate was extracted with DCM (3*2 mL).The organic layers were combined and dried over Na2SO4. Filtration,evaporation of the solvent and purification by flash column chromatography provided the desired product 2. |
77% | With rhenium(I) pentacarbonyl chloride; In hexane; at 80℃; for 10h;Inert atmosphere; | General procedure: A hexane (2.0 mL)solution of 2-ethynylbenzoic acid (0.3 mmol) and ReCl(CO)5 (5 mol%) was stirred under an atmosphereof nitrogen at 80 C for 10 h. After the reaction was complete, H2O was added to the reaction mixture andextracted with EtOAc. The organic layer was dried with MgSO4. The resulting mixture was filtered, andthe filtrate was concentrated. Purification of the residue by silica gel column chromatography affordedisocoumarins. The structures of the products were assigned by their 1H and 13C-NMR, and mass spectra.The products were characterized by comparing its spectral data with those of authentic samples orprevious reports 2a,3e 2b,3e 2c,3e 2d,3e 2e,10 2f,3e 2g,7b 2h,3e 2i,7b,11 2j,3e 2k,12 2l,13 3a,14 3b,14 3d,15 and3g.7b The structures of the products (3e and 3f) were assigned by their 1H and 13C NMR, IR and massspectrum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; | General procedure: ReBr(CO)5, ReCl(CO)5, (C5H5)ReO3, Re2(CO)10, and ReCl5 were commercially available andwere used without further purification. 2-(Arylethynyl)benzoic acids were prepared by the hydoration ofcorresponding methyl esters, which were prepared by the Sonogashira coupling of methyl 2-iodobenzoateand arylethyny, 1-pentyne, 1-hexyne, ethynylcyclohexane or 3,3-dimethyl-1-butyne. Other chemicalagents were obtained commercially and were purified if necessary by distillation. |