No renderable structure data available
C(CCCCBr)CCCC=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 9-bromononanal |
|---|---|
| IUPAC Name | — |
| CAS Number | 124388-97-2 |
| Database ID | 543330 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
9-bromononanal (CAS 124388-97-2) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 543330
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3cbd664d118e4cc8ac9bfbfd5a7cadc6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1ddba2a47293470eb7c1d5b64cb5a5e0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 9-Bromononanal (28.0 g, assumed 120 mmol), ethylene glycol (33.6 mL, 600 mmol) and para-toluenesulphonic acid (2.7 g, 13 mmol) in toluene (210 mL) were heated at reflux for 20 hours. The reaction was cooled to RT and quenched with saturated aqueous sodium bicarbonate solution (300 mL). The resulting mixture was extracted with diethyl ether (2×500 mL). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (300 mL), water (300 mL), brine (100 mL), dried (magnesium sulfate), filtered and evaporated under reduced pressure to afford the title compound (25.2 g, 79%). at reflux for 20 hours quenched with saturated aqueous sodium bicarbonate solution (300 mL) The resulting mixture was extracted with diethyl ether (2×500 mL) The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution (300 mL), water (300 mL), brine (100 mL) dried (magnesium sulfate) filtered evaporated under reduced pressure
Source ID: ord-a4c714a186604d398b6b4ba90372980cConditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 9-Bromononan-1-ol (3 g. 13.4 mmol) was dissolved in dichloromethane (70 mL, 0.2M) and to this solution were added dimethyl sulfoxide (2.9 mL, 40.3 mmol) and diisopropylethylamine (7.0 mL, 40.3 mmol). The flask was then sealed under nitrogen and cooled to −15° C. Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes and the resulting mixture was stirred at temperature between −10° C. and −20° C. for 30 minutes. The reaction was then quenched by adding water and the layers were separated. The organic layer was washed with aqueous sodium bisulfate (1M×3) and brine (×1), and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as an amber oil (2.4 g 81% yield). 1H NMR (CDCl3, δ): 9.78 (s, 1H), 3.40 (t, 2H), 2.43 (t, 2H), 1.85 (m, 2H), 1.63 (m, 2H), 1.5-1.25 (m, 8H). The flask was then sealed under nitrogen Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes The reaction was then quenched by adding water the layers were separated The organic layer was washed with aqueous sodium bisulfate (1M×3) and brine (×1) dried over magnesium sulfate filtered concentrated under reduced pressure
Source ID: ord-f981e7d826c84ab7b4ab3daec3799c16Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 9-Bromononan-1-ol (3 g. 13.4 mmol) was dissolved in dichloromethane (70 mL, 0.2M) and to this solution were added dimethyl sulfoxide (2.9 mL, 40.3 mmol) and diisopropylethylamine (7.0 mL, 40.3 mmol). The flask was then sealed under nitrogen and cooled to −15° C. Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes and the resulting mixture was stirred at temperature between −10° C. and −20° C. for 30 minutes. The reaction was then quenched by adding water and the layers were separated. The organic layer was washed with aqueous sodium bisulfate (1M×3) and brine (×1), and then dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as an amber oil (2.4 g 81% yield). 1H NMR (CDCl3, δ): 9.78 (s, 1H), 3.40 (t, 2H), 2.43 (t, 2H), 1.85 (m, 2H), 1.63 (m, 2H), 1.5-1.25 (m, 8H). The flask was then sealed under nitrogen Pyridine sulfur trioxide complex (6.4 g, 40.3 mmol) was added in two equal portions over 2 minutes The reaction was then quenched by adding water the layers were separated The organic layer was washed with aqueous sodium bisulfate (1M×3) and brine (×1) dried over magnesium sulfate filtered concentrated under reduced pressure
Source ID: ord-f981e7d826c84ab7b4ab3daec3799c16Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100 mL round-bottomed flask was added 9-bromononanal (7.2 g, 32.5 mmol), methanol (30 mL) and trimethylorthoformate (4 mL, 36.5 mmol). A solution of 4 N hydrochloric acid in dioxane (0.2 mL, 0.8 mmol) was added and the resulting mixture was refluxed for 3 h. The reaction mixture was then cooled to room temperature and solid sodium bicarbonate (100 mg, 1.2 mmol) was added. The resulting mixture was concentrated to one-fourth its original volume under reduced pressure and then ethyl acetate (50 mL) was added. The organic layer was washed with water (2×40 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.44 g, (97% yield)) as a liquid, which as used in the next step without further purification. the resulting mixture was refluxed for 3 h The resulting mixture was concentrated to one-fourth its original volume under reduced pressure ethyl acetate (50 mL) was added The organic layer was washed with water (2×40 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-f03ea079a8854ccca2f87edb5f97e2f2Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel and temperature controller, under nitrogen, was added 9-bromononanol (8.92 g, 40 mmol) and dichloromethane (30 mL). The resulting mixture was cooled to 5° C. and a solution of sodium bicarbonate (0.47 g, 5.6 mmol) and potassium bromide (0.48 g, 4 mmol) in water (10 mL) was added. 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added and then a 10 to 13% bleach solution (27 mL) was added dropwise through the addition funnel at a rate such that the temperature was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.). After addition of the bleach was complete, the mixture was stirred for 30 min. while maintaining the temperature at about 0° C. A solution of sodium bisulfite (1.54 g) in water (10 mL) was added and the resulting mixture was stirred at room temperature for 30 min. The layers of the mixture were then separated, and the milky aqueous layer was extracted with dichloromethane (1×20 mL). The combined dichloromethane layers were then washed with water (1×30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.3 g, 94% yield), which was used without further purification in the next step. To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.) After addition of the bleach while maintaining the temperature at about 0° C the resulting mixture was stirred at room temperature for 30 min The layers of the mixture were then separated the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-dcd62555c8c1432793f063de8e6efa8fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100 mL round-bottomed flask was added 9-bromononanal (7.2 g, 32.5 mmol), methanol (30 mL) and trimethylorthoformate (4 mL, 36.5 mmol). A solution of 4 N hydrochloric acid in dioxane (0.2 mL, 0.8 mmol) was added and the resulting mixture was refluxed for 3 h. The reaction mixture was then cooled to room temperature and solid sodium bicarbonate (100 mg, 1.2 mmol) was added. The resulting mixture was concentrated to one-fourth its original volume under reduced pressure and then ethyl acetate (50 mL) was added. The organic layer was washed with water (2×40 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.44 g, (97% yield)) as a liquid, which as used in the next step without further purification. the resulting mixture was refluxed for 3 h The resulting mixture was concentrated to one-fourth its original volume under reduced pressure ethyl acetate (50 mL) was added The organic layer was washed with water (2×40 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-ecfc9eeeacea4b7e9feae7cfb94007ebConditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel and temperature controller, under nitrogen, was added 9-bromononanol (8.92 g, 40 mmol) and dichloromethane (30 mL). The resulting mixture was cooled to 5° C. and a solution of sodium bicarbonate (0.47 g, 5.6 mmol) and potassium bromide (0.48 g, 4 mmol) in water (10 mL) was added. 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added and then a 10 to 13% bleach solution (27 mL) was added dropwise through the addition funnel at a rate such that the temperature was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.). After addition of the bleach was complete, the mixture was stirred for 30 min. while maintaining the temperature at about 0° C. A solution of sodium bisulfite (1.54 g) in water (10 mL) was added and the resulting mixture was stirred at room temperature for 30 min. The layers of the mixture were then separated, and the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.3 g, 94% yield), which was used without further purification in the next step. To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.) After addition of the bleach while maintaining the temperature at about 0° C the resulting mixture was stirred at room temperature for 30 min The layers of the mixture were then separated the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-d2d8754b4f3c4ff997f08246a9ce4dd2Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel and temperature controller, under nitrogen, was added 9-bromononanol (8.92 g, 40 mmol) and dichloromethane (30 mL). The resulting mixture was cooled to 5° C. and a solution of sodium bicarbonate (0.47 g, 5.6 mmol) and potassium bromide (0.48 g, 4 mmol) in water (10 mL) was added. 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added and then a 10 to 13% bleach solution (27 mL) was added dropwise through the addition funnel at a rate such that the temperature was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.). After addition of the bleach was complete, the mixture was stirred for 30 min. while maintaining the temperature at about 0° C. A solution of sodium bisulfite (1.54 g) in water (10 mL) was added and the resulting mixture was stirred at room temperature for 30 min. The layers of the mixture were then separated, and the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.3 g, 94% yield), which was used without further purification in the next step. To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.) After addition of the bleach while maintaining the temperature at about 0° C the resulting mixture was stirred at room temperature for 30 min The layers of the mixture were then separated the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-d2d8754b4f3c4ff997f08246a9ce4dd2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100 mL round-bottomed flask was added 9-bromononanal (7.2 g, 32.5 mmol), methanol (30 mL) and trimethylorthoformate (4 mL, 36.5 mmol). A solution of 4 N hydrochloric acid in dioxane (0.2 mL, 0.8 mmol) was added and the resulting mixture was refluxed for 3 h. The reaction mixture was then cooled to room temperature and solid sodium bicarbonate (100 mg, 1.2 mmol) was added. The resulting mixture was concentrated to one-fourth its original volume under reduced pressure and then ethyl acetate (50 mL) was added. The organic layer was washed with water (2×40 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.44 g, (97% yield)) as a liquid, which as used in the next step without further purification. the resulting mixture was refluxed for 3 h The resulting mixture was concentrated to one-fourth its original volume under reduced pressure ethyl acetate (50 mL) was added The organic layer was washed with water (2×40 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-b6e63bd2602e49e692f6a4c954b9e3e0Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel and temperature controller, under nitrogen, was added 9-bromononanol (8.92 g, 40 mmol) and dichloromethane (30 mL). The resulting mixture was cooled to 5° C. and a solution of sodium bicarbonate (0.47 g, 5.6 mmol) and potassium bromide (0.48 g, 4 mmol) in water (10 mL) was added. 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added and then a 10 to 13% bleach solution (27 mL) was added dropwise through the addition funnel at a rate such that the temperature was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.). After addition of the bleach was complete, the mixture was stirred for 30 min. while maintaining the temperature at about 0° C. A solution of sodium bisulfite (1.54 g) in water (10 mL) was added and the resulting mixture was stirred at room temperature for 30 min. The layers of the mixture were then separated, and the milky aqueous layer was extracted with dichloromethane (1×20 mL). The combined dichloromethane layers were then washed with water (1×30 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford the title intermediate (8.3 g, 94% yield), which was used without further purification in the next step. To a 100-mL round-bottomed flask equipped with a magnetic stirrer, addition funnel 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (TEMPO) (63 mg, 0.4 mmol) was added was maintained at about 8° C. (+/−2° C.) with an ice cold bath (over about 40 min.) After addition of the bleach while maintaining the temperature at about 0° C the resulting mixture was stirred at room temperature for 30 min The layers of the mixture were then separated the milky aqueous layer was extracted with dichloromethane (1×20 mL) The combined dichloromethane layers were then washed with water (1×30 mL) dried (MgSO4) filtered concentrated under reduced pressure
Source ID: ord-b738d5ea462d484cb5a8b6dc64d80dd2PubChem References
These sources are listed in the compound's public database record.
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