No renderable structure data available
C(CBr)C=C(F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromo-1,1-difluorobut-1-ene |
|---|---|
| IUPAC Name | — |
| CAS Number | 147804-02-2 |
| Database ID | 2782240 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromo-1,1-difluorobut-1-ene (CAS 147804-02-2) 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 2782240
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-e3d722003afb4649930f1d7ce45c427bConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5e62af371cc249539c6e4f1c399f0378Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-e3d722003afb4649930f1d7ce45c427bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of acetone oxime (0.365 g) in dry tetrahydrofuran (20 cm3) at 0° C. under nitrogen was added n-butyl lithium (4.6 cm3 of a 2.5M solution in hexanes) resulting in formation of a pale yellow precipitate. After stirring at 0° C. for 30 minutes, carbon disulfide (0.3 cm3) was added producing a bright orange solution. After a further 10 minutes, 3M HCl (20 cm3) was added and the reaction was heated under reflux for 3 hours and then cooled. The layers were separated and the aqueous layer was extracted with chloroform. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. The oil was then taken up in acetone (11 cm3) and 1-bromo-4,4-difluorobut-3-ene (0.77 g) and potassium carbonate (0.87 g) were added and the reaction heated under reflux for 3.5 hours and then cooled. The mixture was then poured into ethyl acetate and 2M HCl and the layers separated. The aqueous layer was extracted with ethyl acetate and the combined organic phases were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. Purification by column chromatography on silica gel using 1:9 ethyl acetate:hexane as eluant gave 2-(4,4-difluorobut-3-enylthio)-3-methylisoxazole (0.105 g). M+ =205; 1H NMR: δ 2.30(3H,s); 2.40(2H,m); 3.05(2H,t); 4.25(1H,m); 6.00(1H,s); (oil). resulting in formation of a pale yellow precipitate producing a bright orange solution After a further 10 minutes the reaction was heated under reflux for 3 hours cooled The layers were separated the aqueous layer was extracted with chloroform The combined organic layers were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil the reaction heated under reflux for 3.5 hours cooled the layers separated The aqueous layer was extracted with ethyl acetate the combined organic phases were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil Purification by column chromatography on silica gel using 1:9 ethyl acetate
Source ID: ord-ca58d9cdf08941bba012a495151c9912Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium disulfide (previously prepared from sodium sulfide nonahydrate (53 g) and sulfur (7.0 g) in ethanol (250 cm3)) was added to 1-bromo4,4-difluorobut-3-ene (50 g) in ethanol (100 cm3). The mixture was gradually heated and stirred under reflux for 2 hours, then cooled and evaporated under reduced pressure. The residue was extracted with diethyl ether, the organic phase filtered to remove sodium bromide and the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C. to give the bis-(4,4-difluorobut-3-enyl)disulfide (24 g) as a colourless liquid. The mixture was gradually heated under reflux for 2 hours cooled evaporated under reduced pressure The residue was extracted with diethyl ether the organic phase filtered to remove sodium bromide the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C.
Source ID: ord-407cb9abcd5e4c0e96152872eb36a75eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium thioacetate (1.98 g), 4-bromo-1,1-difluorobut-1-ene (3.0 g) and tetra-n-butylammonium bromide (0.3 g, catalyst) were stirred at the ambient temperature under nitrogen for 5 hours and stored for 18 hours. The mixture was distilled using a Kugelrohr apparatus to give 4,4-difluorobut-3-enyl thioacetate as a colourless liquid (1.12 g); 1H NMR δ 2.25(2H,m); 2.30(3H,s); 2.90(2H,t); 4.20(1H,m); (bp 115° C. at 120 mmHg). The mixture was distilled
Source ID: ord-1befadaa56fc4f8abe6fd1b59c888580Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium disulfide (previously prepared from sodium sulfide nonahydrate (53 g) and sulfur (7.0 g) in ethanol (250 cm3)) was added to 1-bromo4,4-difluorobut-3-ene (50 g) in ethanol (100 cm3). The mixture was gradually heated and stirred under reflux for 2 hours, then cooled and evaporated under reduced pressure. The residue was extracted with diethyl ether, the organic phase filtered to remove sodium bromide and the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C. to give the bis-(4,4-difluorobut-3-enyl)disulfide (24 g) as a colourless liquid. The mixture was gradually heated under reflux for 2 hours cooled evaporated under reduced pressure The residue was extracted with diethyl ether the organic phase filtered to remove sodium bromide the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C.
Source ID: ord-3475dfc603334e56b64100cc5912dc74Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium disulfide (previously prepared from sodium sulfide nonahydrate (53 g) and sulfur (7.0 g) in ethanol (250 cm3)) was added to 1-bromo4,4-difluorobut-3-ene (50 g) in ethanol (100 cm3). The mixture was gradually heated and stirred under reflux for 2 hours, then cooled and evaporated under reduced pressure. The residue was extracted with diethyl ether, the organic phase filtered to remove sodium bromide and the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C. to give the bis-(4,4-difluorobut-3-enyl)disulfide (24 g) as a colourless liquid. The mixture was gradually heated under reflux for 2 hours cooled evaporated under reduced pressure The residue was extracted with diethyl ether the organic phase filtered to remove sodium bromide the ether evaporated under reduced pressure to give a liquid which was distilled at 16 mm Hg, bp 120° C.
Source ID: ord-3475dfc603334e56b64100cc5912dc74Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of acetone oxime (0.365 g) in dry tetrahydrofuran (20 cm3) at 0° C. under nitrogen was added n-butyl lithium (4.6 cm3 of a 2.5M solution in hexanes) resulting in formation of a pale yellow precipitate. After stirring at 0° C. for 30 minutes, carbon disulfide (0.3 cm3) was added producing a bright orange solution. After a further 10 minutes, 3M HCl (20 cm3) was added and the reaction was heated under reflux for 3 hours and then cooled. The layers were separated and the aqueous layer was extracted with chloroform. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. The oil was then taken up in acetone (11 cm3) and 1-bromo-4,4-difluorobut-3-ene (0.77 g) and potassium carbonate (0,87 g) were added and the reaction heated under reflux for 3.5 hours and then cooled. The mixture was then poured into ethyl acetate and 2M HCl and the layers separated. The aqueous layer was extracted with ethyl acetate and the combined organic phases were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. Purification by column chromatography on silica gel using 1:9 ethyl acetate : hexane as eluant gave 2-(4,4-difluorobut-3-enylthio)-3-methylisoxazole (0.105 g). M+ =205; 1H NMR; δ2.30(3H,s); 2.40(2H,m); 3.05(2H,t); 4.25(1H,m); 6.00(1H,s); (oil). resulting in formation of a pale yellow precipitate producing a bright orange solution After a further 10 minutes the reaction was heated under reflux for 3 hours cooled The layers were separated the aqueous layer was extracted with chloroform The combined organic layers were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil the reaction heated under reflux for 3.5 hours cooled the layers separated The aqueous layer was extracted with ethyl acetate the combined organic phases were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil Purification by column chromatography on silica gel using 1:9 ethyl acetate
Source ID: ord-46aed94b4bea4930b53709550344fef5Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of acetone oxime (0.365 g) in dry tetrahydrofuran (20 cm3) at 0° C. under nitrogen was added n-butyl lithium (4.6 cm3 of a 2.5M solution in hexanes) resulting in formation of a pale yellow precipitate. After stirring at 0° C. for 30 minutes, carbon disulfide (0.3 cm3) was added producing a bright orange solution. After a further 10 minutes, 3M HCl (20 cm3) was added and the reaction was heated under reflux for 3 hours and then cooled. The layers were separated and the aqueous layer was extracted with chloroform. The combined organic layers were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. The oil was then taken up in acetone (11 cm3) and 1-bromo-4,4-difluorobut-3-ene (0.77 g) and potassium carbonate (0,87 g) were added and the reaction heated under reflux for 3.5 hours and then cooled. The mixture was then poured into ethyl acetate and 2M HCl and the layers separated. The aqueous layer was extracted with ethyl acetate and the combined organic phases were dried (MgSO4), filtered and evaporated under reduced pressure to give a brown oil. Purification by column chromatography on silica gel using 1:9 ethyl acetate : hexane as eluant gave 2-(4,4-difluorobut-3-enylthio)-3-methylisoxazole (0.105 g). M+ =205; 1H NMR; δ2.30(3H,s); 2.40(2H,m); 3.05(2H,t); 4.25(1H,m); 6.00(1H,s); (oil). resulting in formation of a pale yellow precipitate producing a bright orange solution After a further 10 minutes the reaction was heated under reflux for 3 hours cooled The layers were separated the aqueous layer was extracted with chloroform The combined organic layers were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil the reaction heated under reflux for 3.5 hours cooled the layers separated The aqueous layer was extracted with ethyl acetate the combined organic phases were dried (MgSO4) filtered evaporated under reduced pressure to give a brown oil Purification by column chromatography on silica gel using 1:9 ethyl acetate
Source ID: ord-46aed94b4bea4930b53709550344fef5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium thioacetate (1.98 g), 4-bromo-1,1-difluorobut-1-ene (3.0 g) and tetra-n-butylammonium bromide (0.3 g, catalyst) were stirred at the ambient temperature under nitrogen for 5 hours and stored for 18 hours. The mixture was distilled using a Kugelrohr apparatus to give 4,4-difluorobut-3-enyl thioacetate as a colourless liquid (1.12 g); 1H NMR; δ 2.25(2H,m); 2.30(3H,s); 2.90(2H,t); 4.20(1H,m); (bp 115° C. at 120 mmHg). The mixture was distilled
Source ID: ord-558c03d7f31842ddaf8c340c0ad0e533Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium thioacetate (1.98 g), 4-bromo-1,1-difluorobut-1-ene (3.0 g) and tetra-n-butylammonium bromide (0.3 g, catalyst) were stirred at the ambient temperature under nitrogen for 5 hours and stored for 18 hours. The mixture was distilled using a Kugelrohr apparatus to give 4,4-difluorobut-3-enyl thioacetate as a colourless liquid (1.12 g); 1H NMR; δ 2.25(2H,m); 2.30(3H,s); 2.90(2H,t); 4.20(1H,m); (bp 115° C. at 120 mmHg). The mixture was distilled
Source ID: ord-558c03d7f31842ddaf8c340c0ad0e533PubChem References
These sources are listed in the compound's public database record.
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