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CAS No. : | 5350-41-4 | MDL No. : | MFCD00011780 |
Formula : | C10H16BrN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UUZYBYIOAZTMGC-UHFFFAOYSA-M |
M.W : | 230.15 | Pubchem ID : | 21449 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
48.1% | With acetic acid In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water | EXAMPLE II-18 (Synthesis of Ex. Comp. No. (II-15)) In a 5 liter-three necked flask, 169.5 g (1.28 M) of 1,2,3,4-tetrahydronaphthalene and 3 liters of acetic acid were placed and stirred at room temperature. Under stirring, to the mixture, 650 g (1.67 M) of benzyltrimethylammonium bromide and 244.8 g (1.80 M) of zinc chloride were successively added, followed by stirring for 5.5 hours at 70° C. After the reaction, the reaction mixture was cooled to room temperature and poured into 3 liters of ice water, followed by extraction with methyl t-butyl ether. The organic layer was successively washed with 5percent-NaHSO3 aqueous solution, 5percent-NaOH aqueous solution and distilled water, followed by distilling-off of the solvent under reduced pressure to obtain 243.2 g of a dark brown liquid. The liquid was subjected to vacuum distillation (distillation under reduced pressure) (boiling point=108-110° C. at 667 Pa) to obtain 130.2 g of 6-bromo-1,2,3,4-tetrahydronaphthalene (Yield: 48.1percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | at 25℃; for 24 h; Inert atmosphere | General procedure: In analogy to literature4, to a solution of benzyl halide 9 (1 equiv.) in THF (50 ml/g benzyl halide) were added 1.5 equiv. of trimethylamine 10 (33 wtpercent in EtOH).The resulting solution was stirred at RT for 24 hours, during which the product precipitated asa white solid. The resulting suspension was cooled to 0 °C, filtrated, washed with ice-cold Et2O and dried in vacuo to yield benzyl ammonium salts 6 in the reported yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 3-chloro-benzenecarboperoxoic acid; potassium bromide; In water; for 0.1h; | 6. Synthesis of Benzyltrimethylammonium tribromides, BTMATB: 1 equiv of benzyltrimethylammonium bromide (1 mmol, 0.120 g), 2 equiv of KBr (2 mmol, 0.238 g) and 2 equiv of MCPBA (2mmol, 0.346 g) were mixed together in 10 mL of water and stirred for ca. 6 min. The orange colouredproduct formed was washed with NaHCO3 solution (10 percent solution) for several times to remove unreactedsubstrate. After that the crude product was again washed with water to remove by-products. Thecompound was dried in vacuo and recrystallized with EtOAc; mp: 99oC. Yield: 0.346 g; 89 percent. |
82.04% | With sulfuric acid; dihydrogen peroxide; potassium bromide;molybdic acid; In water; at 0 - 20℃; for 0.916667h; | Molybdic acid monohydrate, H2MOO4. H20 (0.13mmol, 0.023g), potassium bromide, KBr (26. 06MMOL, 3.1g) and benzyltrimethylammonium bromide, BTMAB (13.03mmol, 3. 0g) were powdered separately, mixed together smoothly and thoroughly. The whole was transferred to a boat kept on ice-water bath and 30percent hydrogen peroxide, H202 (13. 23MMOL, 1. 5ML) was added drop wise with continuous grinding for 15 min, followed by drop wise addition of 10M H2SO4 (13. 0MMOL, 1. 3mL) leading to the formation of a yellow colored solution. It was stirred smoothly with glass rod for 10 min and then at room temperature for 30MIN. An exothermic reaction set in to form orange-yellow crystalline compound of <strong>[5350-41-4]benzyltrimethylammonium tribromide</strong>, BTMATB. The compound was dried over fused CaCl2 and extracted with ethyl acetate by dissolving in minimum amount of solvent followed by filtration through Whatman No. 42 filter paper. Aqueous phase, if present, could be separated using anhydrous sodium sulphate. The organic layer was concentrated to get yellow-orange <strong>[5350-41-4]benzyltrimethylammonium tribromide</strong>, BTMATB. Yield: 4.17g (82. 04percent) Mp: 98-101°C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature. Analytical data: The compound analyzed correctly COH, NBR3 : Calc. C, 30.8 ; H, 4.14 ; N, 3.59 ; Br, 61.47percent. Found. C, 30.7 ; H, 4.18 ; N, 3.62 ; Br, 61.53 percent. |
82% | With sodium hypochlorite; sulfuric acid; potassium bromide; for 0.166667h;Green chemistry; | A solution of 2.4 g (20 mmol) of KBr in 10 mL of 4N H2SO4 was added to 2.3 g (10 mmol) of benzyltrimethylammonium bromide. To the resulting solution was added 10 mL of 4 percent sodium hypochlorite. The solution was stirred for ca. 10 mins and then the bright orange-yellow colored crystalline benzytrimethylammonium tribromide, BTMATB which had separated out was isolated by suction filtration and washed with water (5 mL) three to four times and dried under vacuum over anhydrous CaCl2 to give 3.19 g of BTMATB as orange crystals(yield 82percent). Mp: 99 C. |
82% | With periodic acid; potassium bromide; In neat (no solvent); at 20℃; | General procedure: 1 equiv of tetraalkylammonium bromide (10 mmol), 2 equiv of KBr (20 mmol, 2.38 g)and 2 equiv of H5IO6 (20 mmol, 4.56 g) were mixed together and ground well in a mortar ca. 5-15 minutes. The orange coloured product formed was washed with water for several times to remove by-products. After that the crude product was extracted with ethyl acetate and the organic solvent was dried in vacuo to get pure product. Yield: 82-93 percent (0.3-0.4 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82.04% | With sulfuric acid; dihydrogen peroxide; potassium bromide;molybdic acid; In water; at 0 - 20℃; for 0.916667h;Product distribution / selectivity; | Molybdic acid monohydrate, H2MoO4.H2O (0.13 mmol, 0.023 g), potassium bromide, KBr (26.06 mmol, 3.1 g) and benzyltrimethylammonium bromide, BTMAB (13.03 mmol, 3.0 g) were powdered separately, mixed together smoothly and thoroughly. The whole was transferred to a boat kept on ice-water bath and 30percent hydrogen peroxide, H2O2 (13.23 mmol, 1.5 mL) was added drop wise with continuous grinding for 15 min, followed by drop wise addition of 10M H2SO4 (13.0 mmol, 1.3 mL) leading to the formation of a yellow colored solution. It was stirred smoothly with glass rod for 10 min and then at room temperature for 30 min. An exothermic reaction set in to form orange-yellow crystalline compound of <strong>[5350-41-4]benzyltrimethylammonium tribromide</strong>, BTMATB. The compound was dried over fused CaCl2 and extracted with ethyl acetate by dissolving in minimum amount of solvent followed by filtration through Whatman No. 42 filter paper. Aqueous phase, if present, could be separated using anhydrous sodium sulphate. The organic layer was concentrated to get yellow-orange <strong>[5350-41-4]benzyltrimethylammonium tribromide</strong>, BTMATB. Yield: 4.17 g (82.04percent) Mp: 98-101° C. The chemical analyses, IR and conductance of the compound match very well with those reported in literature.Analytical data: The compound analyzed correctly C10H16NBr3: Calc. C, 30.8; H, 4.14; N, 3.59; Br, 61.47percent. Found. C, 30.7; H, 4.18; N, 3.62; Br, 61.53percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.1% | With acetic acid;Zinc chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; | EXAMPLE II-18 (Synthesis of Ex. Comp. No. (II-15)) In a 5 liter-three necked flask, 169.5 g (1.28 M) of 1,2,3,4-tetrahydronaphthalene and 3 liters of acetic acid were placed and stirred at room temperature. Under stirring, to the mixture, 650 g (1.67 M) of benzyltrimethylammonium bromide and 244.8 g (1.80 M) of zinc chloride were successively added, followed by stirring for 5.5 hours at 70° C. After the reaction, the reaction mixture was cooled to room temperature and poured into 3 liters of ice water, followed by extraction with methyl t-butyl ether. The organic layer was successively washed with 5percent-NaHSO3 aqueous solution, 5percent-NaOH aqueous solution and distilled water, followed by distilling-off of the solvent under reduced pressure to obtain 243.2 g of a dark brown liquid. The liquid was subjected to vacuum distillation (distillation under reduced pressure) (boiling point=108-110° C. at 667 Pa) to obtain 130.2 g of 6-bromo-1,2,3,4-tetrahydronaphthalene (Yield: 48.1percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In dichloromethane; | EXAMPLE 3 The mixture of 50 parts of alpha-(4-biphenylyl)acetonitrile, 45.8 parts of 2-chloro-N,N-diisopropylethylamine, 80 parts by volume of 50percent sodium hydroxide, 250 parts by volume of methylene chloride and 1 part of benzyltrimethylammonium bromide is stirred at room temperature with slight cooling in an icy water bath for about 24 hours. The mixture is then poured into water and to this mixture additional quantity of methylene chloride is added. The organic layer is separated, washed with water, dried over anhydrous sodium sulfate and concentrated to afford alpha-(4-biphenylyl)-alpha-[2-(diisopropylamino)ethyl]acetonitrile, as a solid. This compound is identical to that of Example 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform-d1; at 25℃; | [Method A (cations)] Titrationcurves were obtained in CDCl3 at 25 oC, by adding stocksolution of host 1 to a constantconcentration (2 mM) of a guest. Up-field shift of the guest cation, especiallyCH3 or CH2, was observed. Plots of the variations of thechemical shift of the guest upon addition of the titration were registered.[Method B (anions)] Similarly,titration curves were obtained in CDCl3 at 25 oC, byadding stock solution of a guest to a constant concentration (2 mM) of host 1. Since down-field shift of amideprotons of the host 1 was observed,plots of the variations of the chemical shift of the guest upon addition of thetitration were registered.[Estimation of Ka]Titration data were then treated according to a standard binding isotherm forthe case of 1:1 association.2 Non-linear curve fitting usingKaleidaGraph 4.1 (Synergy Software) software package afforded Ka and Ddmax. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium carbonate; | Example 5 8H,9H-8a-Azabenzo[fg]naphthacene 55.3 g (158 mmol) of 5-(2-bromobenzyl)-5,6-dihydrophenanthridine are dissolved in 500 ml of dimethylformamide under protective-gas atmosphere. 17.3 g (75 mmol) of benzyltrimethylammonium bromide and 31.28 g (226 mmol) of potassium carbonate are added to this solution. 5.08 g (22 mmol) of Pd(OAC)2 is subsequently added under protective gas, and the mixture is stirred at 120° C. for 9 h. After this time, the reaction mixture is cooled to room temperature and extracted with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is recrystallised from n-heptane. The yield is 34 g (81percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium tert-butylate; In tetrahydrofuran; at 25℃; for 3h;Inert atmosphere; | General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.08 M) and stirred at RT. 3 equiv. of t-BuOK were added and the mixture was stirred vigorously. 2 equiv.of aldehyde 2 were dissolved in dry THF (0.25 M) and added to the reaction mixture over 2 hours via syringe pump. After stirring for another hour, the reaction was quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by column chromatography (gradient of heptanes andEtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With potassium phosphate; (NC5H3(N2C7H4(CH2)3CH3)2)NiBr(1+)*Br(1-)=Ni(NC5H3(N2C7H4(CH2)3CH3)2)Br2; triphenylphosphine; In 1,4-dioxane; at 80℃; for 24h;Schlenk technique; | General procedure: To a 50mL Schlenk tube containing benzylic ammonium iodide (0.5mmol), arylboronic acid (2.0mmol), K3PO4 (2.25mmol), castalyst (5molpercent) and PPh3 (20molpercent) were added and the tube was purged with N2 for 3 times. Then 1,4-dioxane (2.0mL), subsequently, was introduced to the tube. The resulted mixture was allowed to stir for 24h at 80°C under atmosphere of N2. After the completion of the reaction, the resulting mixture was filtered through a Celite pad and concentrated under the vacuum and directly purified by flash chromatography to give the desired product. |
82% | With potassium phosphate; palladium diacetate; XPhos; In tetrahydrofuran; at 50℃; for 14h;Sealed tube; Inert atmosphere; | General procedure: The desired amount of substrate, boronic acid (3 equiv), base (3equiv), Pd(OAc)2 (2.5 molpercent) and ligand (5 molpercent) were weighed out as solids, the vial was sealed and purged with argon, then solvent was added and the vial was purged again. The reactions were run for 14 h at the specified temperature. The crude material was filtered through a pad of Celite and washed three times with CHCl3. The solvent was removed under reduced pressure, an internal standard was added and the reaction was analysed by 1H NMR spectroscopy. For purification, the analysed mixture was concentrated, the product extracted with Et2O and filtered through anhydrous MgSO4 and further purified by flash column chromatography. |
Tags: 5350-41-4 synthesis path| 5350-41-4 SDS| 5350-41-4 COA| 5350-41-4 purity| 5350-41-4 application| 5350-41-4 NMR| 5350-41-4 COA| 5350-41-4 structure
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H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
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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