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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.
1-Hexanol is a primary alcohol with surfactant properties, used in industrial processes to enhance interfacial performance. It uncouples mitochondrial respiration via a non-protonic mechanism.
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CAS No. : | 111-27-3 |
Formula : | C6H14O |
M.W : | 102.17 |
SMILES Code : | CCCCCCO |
MDL No. : | MFCD00002982 |
InChI Key : | ZSIAUFGUXNUGDI-UHFFFAOYSA-N |
Pubchem ID : | 8103 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H225-H302+H312-H319-H412 |
Precautionary Statements: | P210-P233-P240-P241-P242-P243-P264-P270-P273-P280-P301+P312+P330-P303+P361+P353-P305+P351+P338-P337+P313-P363-P370+P378-P403+P235-P501 |
Class: | 3 |
UN#: | 2282 |
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 |
---|---|---|
99% | With triethylamine In dichloromethane at 0 - 20℃; | General procedure: Alcohols (50 mmol, 1 equiv.) and 11.08 mL Et3N (80 mmol, 1.6 equiv.) was dissolved in 60 mL CH2Cl2, and the solution was cooleddown to 0 °C, then 4.33 mL methanesulfonyl chloride (56 mmol, 1.12 equiv.) was introduced by syringe successively. The mixture is stirredfor 30 min at 0 °C, and then stirred overnight at room temperature. The organic layer is washed successively with 1M hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and brine. The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by column chromatography with silica gel (EtOAc: petroleum=1: 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.0% | With pyridine; | Step v) Production of n-hexyl p-toluenesulfonate 20 ml of pyridine was added to 5.02 g (49.2 mM) of n-hexanol, followed by stirring below 0 C. To the mixture, 11.24 g (59.0 mM) of p-toluenesulfonyl chloride was added. The mixture was stirred for 6 hours below 0 C. After the reaction, the reaction mixture was poured into iced water and acidified with conc. HCl, followed by two times of extraction with dichloromethane, two times of washing with water, drying with sodium sulfate and distilling-off of the solvent to obtain 12.0 g (46.8 mM) of an objective product (yield: 95.0%). |
95% | With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h; | To a solution of Tscl (2.86 g, 15 mmol) and DMAP (166 mg,1 mmol) in DCM (30 mL), triethylamine (2.1 mL, 15 mmol) and hexyl alcohol (1.58 mL, 10 mmol) in DCM (20 mL) was addeddropwise at 0 C, and the mixture was allowed warm to rt andstirred for 1 h, the solvent was evaporated in vacuo, the residuewasdissolved by ethyl acetate (EA) and washed with satd aq NaHCO3,the organic layer was dried with Na2SO4, filtered, concentrated, andpurified by column chromatography to afford 11 as yellow solid(2.7 g, 95%). 1H NMR (400 MHz, CDCl3): d 7.78 (d, J8.4 Hz, 2H), 7.34(d, J8.0 Hz, 2H), 4.02 (t, J6.4 Hz, 2H), 2.44 (s, 3H), 1.66e1.59 (m,2H), 1.33e1.17 (m, 6H), 0.84 (t, J7.0 Hz, 3H) ppm. |
95% | With dmap; In dichloromethane; for 1h; | The toluene sulfonyl chloride (compound 29, 2.86g, 15mmol) and DMAP (166 mg, 1mmol) dissolved in anhydrous dichloromethane (30 ml), add triethylamine (2.1 ml, 15mmol), compound 29 (1.58 ml, 10mmol) dissolved in dichloromethane (20 ml) is dropped into the, mixing 1h, decompression turns on lathe methylene chloride, the residue is dissolved in ethyl acetate (150 ml) is dissolved, the organic phase with saturated sodium bicarbonate solution and saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain compound 30 (2.7g, 95 |
93.2% | With triethylamine; In dichloromethane; at 10℃; for 6h;Large scale; | 1-hexanol (1.2 kg, 11.70 mol), TsCl (2.7 kg, 14.0 mol), methylene chloride (12.0 L) are stirred,Triethylamine (2.4 kg, 23.40 mol) was added dropwise while maintaining an internal temperature of 10 C. or lower.After completion of dropwise addition, the internal temperature was maintained at 10 C. or lower and stirred for 6 hours.After 5 L of purified water was added, the separated organic layer was concentrated under reduced pressure to obtain the title compound (2.8 kg, 93.2%). |
With pyridine; at 10 - 20℃; for 3h; | General procedure: 4-Methylbenzenesulphonyl chloride (55 mmol) was added slowly to a mixture of a primary alcohol (50 mmol) and 20 ml of pyridine at 10 C. The reaction mixture was stirred for 3 h at 20 C. After that 120 ml of 25 % hydrochloric acid was slowly added. The reaction mixture was then extracted with chloroform, organic layer dried with Na2SO4 and evaporated to yield alkyl 4-methylbenzenesulphonate as colourless oily liquid or white solid, which was used without further purification. Ethyl 4-methylbenzenesulphonate was purchased from Fluka. | |
With pyridine; for 6h;Cooling with ice; | 100 Ml reaction flask by adding the magnetic coil, is provided with a thermometer, adding 9.5 g of toluene sulfonyl chloride (0.05 µM), dissolved in 20 ml of pyridine in, the reaction bottle is located in the ice water bath and stirring, by way instillment hexyl alcohol, is hexanol adding amount is 5.1 g (0.05 µM), reaction time is 6 h, inverted ice water in the reaction liquid, adding concentrated hydrochloric acid until its [...], extraction, water vapor direct distillation, is paratoluene sulfonic acid hexyl pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In di-isopropyl ether; | EXAMPLE 4 In a 500 ml flask fitted with thermometer, mechanical stirrer, addition funnel, and a Dean-Stark trap, with attached condenser is placed 110g of resorcinol and 71.4g of 1-hexanol. The reaction mixture was heated at 160-200 C for 4 hours with no apparent reaction taking place. Alumina (15g) was added and the mixture heated gradually to 255 C over a period of 4 hours, 1.8 ml of water having been produced. Hexanol was removed from the reaction by drawing off through the Dean-Stark trap to allow the temperature to reach 255 C. Refluxing was continued at 240-255 C with the reflux temperature being controlled by the periodic addition of hexanol (that which had been removed) back to the reaction mixture. This procedure was continued over a period of about 8 hours, during which time all of the original hexanol had been added back to the reaction mixture, and during which 16.7 ml of produced water had been collected in the Dean-Stark trap. The reaction mixture was analyzed at this point (using o-cresol as an external standard) and was found to have the following composition, as determined by area under a gas chromatograph curve. A part of the crude reaction product (ca 90g was taken up in 500 ml of diisopropyl ether and washed with one 300 ml portion of 1N sulfuric acid and then with five 300 ml portions of water. The combined aqueous phases were back-extracted with 100 ml of diisopropyl ether, and this was combined with the other organic phase. Isopropyl ether was mostly removed from the organic material on a rotary evaporator. The residue 142.g was charged to a 4-foot spinning band fractional distillation column and distilled, the results shown in Table 1. The individual cuts were analyzed by gas chromatography. Cut 1 was essentially pure diisopropyl ether with about 8 percent hexenes. The compositions of the other cuts are listed in Table 2. The isolated yield of 4-n-hexylresorcinol amounts to about 24 wt %. A portion of cut 4, 5g. was recrystallized from petroleum ether to yield light yellow platelets, m.p. 57 C (m.p. of 4-n-hexylresorcinol is 61 C). The proton magnetic resonance spectrum of the recrystallized material was identical with that of a known sample of 4-n-hexylresorcinol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
platinum on carbon; In water; for 3h;Direct aqueous phase reforming; | Direct aqueous phase reforming (APR) experiments were conducted in 100-ml stirred reactors with draft-tube gas-induction impeller (Parr Series 4590). Reaction tests for direct bio-based feedstock aqueous phase reforming (APR) entailed filling the reactor with 60-grams of solvent (deionized water, or a mixture of DI water and isopropanol (IPA), and 3-3.5 grams of bio-based feedstock comprising biomass (bagasse, or pine sawdust)). One (1) gram of acetic acid was optionally charged to facilitate biomass hydrolysis.[0098] Bagasse was milled via a 1-mm grate. Dry, debarked Loblolly pine was ground via blender (Thomas Scientific of Swedesboro, NJ) and sieved to less than 30 mesh. Dry solids fraction was determined by vacuum drying at 80 °C to 82 °C. One gram of aqueous phase reforming catalyst (reduced 5percent Pt/C catalyst at 50percent moisture, or powdered 1.9percent Pt/A1203) was charged to the reactor, which was charged with 4200 kPa of hydrogen or nitrogen. To minimize degradation of hydrolysate to heavy ends, each reactor was typically heated with a staged temperature sequence of one hour at, 160 °C, 190 °C, 225 °C, and finally 250 °C, before leaving overnight at the final setpoint.[0099] Comparison tests were also conducted with glucose or sorbitol fed directly to the reaction in place of biomass, to simulate and quantify conversion of model hydrolysate to APR intermediates. Glucose is one of the sugars readily leached from biomass in hot water, while sorbitol is readily formed via hydrogenation of glucose, where platinum or other catalysts capable of hydrogenation are present.[00100] A batch reaction time of 20 hours under these conditions corresponds to a weight hourly space velocity (g-feed/g-catalyst/h) of about 3, for a comparable continuous flow reactor. A 0.5-micron sintered metal filter attached to a dip tube allowed liquid samples to be taken throughout the course of reaction, without loss of biomass or catalyst. Samples were analyzed by an HPLC method based on combined size and ion exclusionchromatography, to determine unreacted sorbitol, and amount of C3 and smaller polyols formed: glycerol (Gly), ethylene glycol (EG), and 1,2-propylene glycol (PG). Additional GC analysis via a moderate polarity DB-5 column were conducted to assess formation of C6 and lighter oxygenates (e.g., ketones, aldehydes, alcohols), as well as alkane and alkene products. A separate GC equipped with thermal conductivity and flame ionization (FID) detectors for refinery gas analysis, were used for detection of H2, C02, and light alkanes C1-C5. GC-mass spec was used to characterize select APR reaction product mixtures. Examples 1-3[00101] Batch APR reactions with sugar cane bagasse as biomass feed, and with a comparison of 25percent sorbitol as feed, were performed as described above. 1.7percent acetic acid was added to simulate catalysis of hydrolysis by recycle acid. Products formed from this concentration of acetic acid were subtracted from total product formation, to calculate the net production of liquid fuels from bagasse. This result shown in Table 1 shows the critical importance of concerted APR reaction with hydrolysis of biomass. In the absence of concerted aqueous phase reforming, the hydrolysate undergoes irreversible degradation (presumably to heavy ends), and cannot be reverted to liquid fuels upon subsequent APR and condensation. Converted reaction may be effected by direct inclusion of APR catalyst in the hydrolysis reactor, or via a pump around loop to recirculate liquid between a biomass contactor, and an APR catalytic reactor. Table 1: Direct APR of Biomass |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;Inert atmosphere; | Preparation of 4-{5-[Bis-(chloroethyl)-amino]-l-methyl-lH-benzimidazol-2-yl}butyric acid hexyl ester (<strong>[3543-75-7]bendamustine</strong> Ce ester): Method A: A 250 mL three neck round bottom flask was equipped with an overhead stirrer, thermocouple, temperature controller and nitrogen sweep then charged with 10.0 g (25.34 mmol) of <strong>[3543-75-7]<strong>[3543-75-7]bendamustine</strong> hydrochloride</strong>, 2.62 g (3.22 mL, 25.6 mmol, 1.01 eq) of 1-hexanol, 5.3 g (25.6 mmol, 1.01 eq) of dicyclohexylcarbodiimide (DCC), 100 mL of MDC and 0.31 g (2.54 mmol, 0.1 eq) of DMAP. The reaction was stirred at room temperature overnight at which time an in process analysis indicated the reaction was complete. Solids were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was washed with saturated aqueous sodium bicarbonate solution (2 X 100 mL), DI water (1 X 100 mL) and brine (1 X 100 mL) before drying over sodium sulfate, filtering and concentrating to dryness in vacuo to a brown oil. The oil was triturated with 25 mL of MDC and the solid impurities were removed by vacuum filtration and washed with 25 mL of MDC. The filtrate was concentrated to dryness in vacuo to yield 8.91 g (20.1 mmol, 79%) of the product as a clear light brown oil with an HPLC purity of 91.9A%. NMR (400 MHz, CDC13) delta 7.17 (d, J= 8.76 Hz, 1H), 7.08 (d, J= 2.32 Hz, 1H), 6.77 (dd, J= 2.36, 8.8 Hz, 1H), 4.05 (t, J= 6.76 Hz, 2 H), 3.72 (m, 4H), 3.69 (s, 3H), 3.63 (m, 4H), 2.91 (t, J= 7.4 Hz, 2H), 2.49 (t, J= 7.1 Hz, 2H), 2.18 (m, 2H), 1.60 (m, 2H), 1.32 (m, 6H), 0.89 (t, J= 4.56 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Appropriate ROH (3.00 mmol) was added topotassium tert-butoxide (3.00 mmol) solution in toluene (7 ml).1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 3ml)was added to the mixture and stirred for 30 min at 80 C. Aftercooled down to ambient temperature of the reaction mixture,2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) in toluenewas dropwise and stirred for 3 h at 80 C. The reaction wasquenched by adding water and extracted with EtOAc twice. Thecombined organic extracts were dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:7) eluantcondition. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | General procedure: To a stirred suspension of NaH (60% in mineral oil, 440 mg, 11 mmol, prewashed with hexane) in anhydrous THF (20 mL) was added the appropriate alcohol (15 mmol) at r.t. and the reaction mixture was stirred for 0.5 h. Next, <strong>[3356-89-6]5-chloro-3-phenylisoxazole</strong> (2) (1.0 g, 5.6mmol) was introduced as a solid and the mixture was refluxed for 1 h. After cooling to r.t., the mixture was quenched with H2O (20 mL). For 4a and 4b, the resulting precipitate was collected, washed with H2O and recrystallized from hexane-Et2O mixture. For 3a, the reaction mixture was extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give isoxazole 3a. 5-tert-Butoxy-3-phenylisoxazole (4c) was synthesized analogously using commercially available potassium tert-butoxide. |
Tags: 111-27-3 synthesis path| 111-27-3 SDS| 111-27-3 COA| 111-27-3 purity| 111-27-3 application| 111-27-3 NMR| 111-27-3 COA| 111-27-3 structure
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H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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The concentration of the dissolution solution you need to prepare is mg/mL