Structure of 14447-15-5
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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'.
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CAS No. : | 14447-15-5 |
Formula : | C6H9NO2 |
M.W : | 127.14 |
SMILES Code : | O=C(OCCC)CC#N |
MDL No. : | MFCD00015784 |
InChI Key : | NLFIMXLLXGTDME-UHFFFAOYSA-N |
Pubchem ID : | 84444 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302+H312+H332-H315-H319 |
Precautionary Statements: | P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 |
* 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 |
---|---|---|
91% | With sulfur; diethylamine; In methanol; ethanol; at 20℃;Sonication; | General procedure: Compound C was synthesized following to the procedure ofGewald et al. [22], as already reported with some minor modifications[21]. The mixture of ketone D (1 mmol), alkyl cyanoacetateE (1.1 mmol), sulfur (1.1 mmol), and diethylamine (1.1 mmol) inethanol/methanol (10 mL) was kept at room temperature in anultrasonic cleaner for 1-3 h. After completion of the reaction, thesolvent was evaporated to dryness under reduced pressure. Thecrude product was purified by flash column chromatography onsilica gel (petroleum ether/ethyl acetate elute) to provide theproduct C. |
With sulfur; diethylamine; In DMF (N,N-dimethyl-formamide); at 60℃; for 2h; | To n-<strong>[14447-15-5]propyl cyanoacetate</strong> (2.54 g, 20 mmol) and sulfur (0.64 g) in DMF (4 mL), diethylamine (1.6 mL) is added under stirring. To this solution cyclohexanone (2.03 g, 20 mmol) is added dropwise. The mixture is heated to [60 C] for 2 hours and it is poured into water (30 mL), which is extracted with diethyl ether (30 mL). The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (2.85 g). Physical characteristics: MS (ES+) [FOR M/Z] 240. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium acetate; In ethanol; | 25 parts of the compound (Ma) are suspended in 314 parts of ethanol and stirred for 30 min. 5.5 parts of anhydrous sodium acetate and 21.85 parts of propyl <n="11"/>cyanoacetate are added. The mixture is subsequently stirred overnight. Completeness of reaction is tested by means of thin layer chromatography. After the reaction is complete, the solids are filtered off with suction and washed with ethanol and water to leave, after drying, 18.55 parts of the dye of the following formula, which corresponds to 60% of theory:λmax = 604 nm (DMF) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With trimethylsilylazide; dibutyltin diacetate; In benzene; at 30℃; for 60h; | General procedure: TMSN3 (0.52 mL, 4 mmol) and Bu2Sn(OAc)2 (0.56 mL, 2 mmol) were added to a solution of nitrile 1 (2 mmol) in benzene (2 mL). After stirring for 60 h at 30 C, the benzene was evaporated to give a crude residue, which was purified by column chromatography to give tetrazole 2. |
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