No renderable structure data available
B(CCCCBr)(O)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromobutylboronic acid |
|---|---|
| IUPAC Name | — |
| CAS Number | 61632-72-2 |
| Database ID | 14316432 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromobutylboronic acid (CAS 61632-72-2) 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 14316432
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-a8cbffe51f4e47c3925e86153d31f612Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6d54e51498ea441cb9d97463ce74921aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a8cbffe51f4e47c3925e86153d31f612Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).
Source ID: ord-0a945f79499b45f9b4a81bbacd2711e1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).
Source ID: ord-0a945f79499b45f9b4a81bbacd2711e1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium hydride (0.22 g, 7.2 mmol) was added to a solution of 6-chloropurine (0.93 g, 6.0 mmol) in dimethylformamide (20 mL) and stirred for 10 minutes. 4-Bromobutyl boronic acid (1.1 g, 6.0 mmol) in dimethylformamide (5 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. After the removal of the dimethylformamide under high vacuum, the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1) to yield 0.78 g of pure product. Yield 51%; mp 135°-138° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.78-1.91 (m, B CH2 CH2 CH2), 4.26-4.32 (t, CH2 CH2 N), 7.40-7.42 (s, (HO)2 B), 8.68-8.70 (s, H C8 purine), 8.80-8.81 (s, H C2 purine). Elemental Analysis. (C9H12BO2N4Cl); Calcd. C, 42.47%; H, 4.75%; N, 22.02%; Found C, 42.48%; H, 4.80%; N, 22.06%. stirred at room temperature for 16 hours After the removal of the dimethylformamide under high vacuum the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1)
Source ID: ord-a5eee8e304634e63a7a308323039aeccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated
Source ID: ord-81601c1a2c9d49b898d2b95a1b731986Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated
Source ID: ord-81601c1a2c9d49b898d2b95a1b731986Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was synthesized in a similar manner as the compound of Example 1 with 2-amino-6-chloropurine (1.36 g, 8 mmol), 4-bromobutyl boronic acid (1.45 g, 8 mmol), and potassium carbonate (1.66 g, 12 mmol) in dimethylformamide (20 mL). Yield 56%; Wt. 1.2 g; mp 154°-156° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.20-1.32 (m, B CH2 CH2), 1.68-1.77 (m, B CH2 CH2 CH2), 4.00-4.08 (t, CH2 CH2 N), 6.85-6.92 (s, H2N C2 purine), 7.40-7.42 (s, (HO)2 B), 8.10-8.12 (s, H C8 purine). Electrospray Mass Spectrum (MH)+ (low resolution); Calcd. 270.09 (C9H13O2N5BCl); Found 270.10 (37 ppm).
Source ID: ord-0a945f79499b45f9b4a81bbacd2711e1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium hydride (0.22 g, 7.2 mmol) was added to a solution of 6-chloropurine (0.93 g, 6.0 mmol) in dimethylformamide (20 mL) and stirred for 10 minutes. 4-Bromobutyl boronic acid (1.1 g, 6.0 mmol) in dimethylformamide (5 mL) was added to the reaction mixture and stirred at room temperature for 16 hours. After the removal of the dimethylformamide under high vacuum, the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1) to yield 0.78 g of pure product. Yield 51%; mp 135°-138° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.78-1.91 (m, B CH2 CH2 CH2), 4.26-4.32 (t, CH2 CH2 N), 7.40-7.42 (s, (HO)2 B), 8.68-8.70 (s, H C8 purine), 8.80-8.81 (s, H C2 purine). Elemental Analysis. (C9H12BO2N4Cl); Calcd. C, 42.47%; H, 4.75%; N, 22.02%; Found C, 42.48%; H, 4.80%; N, 22.06%. stirred at room temperature for 16 hours After the removal of the dimethylformamide under high vacuum the residue was purified by column chromatography (chloroform/methanol discontinuous gradient 95:5, 9:1)
Source ID: ord-a5eee8e304634e63a7a308323039aeccConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Potassium carbonate (0.6 g, 4.4 mmol) was added to a solution of thymine (0.56 g, 4.4 mmol) in dimethylformamide (15 mL) and stirred for 30 minutes. To this reaction mixture, 4-bromobutyl boronic acid (0.4 g, 2.2 mmol) dissolved in dimethylformamide (5 mL) was added dropwise, and stirring was continued 2 days at room temperature. After the potassium carbonate was filtered, the dimethylformamide was evaporated under high vacuum. The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15). The appropriate TLC-homogenous fractions were pooled and evaporated to give 0.22 g of pure product. Yield 44%; mp 130°-132° C.; 1H NMR (DMSO-d6) 0.55-0.68 (t, B CH2), 1.22-1.35 (m, B CH2 CH2), 1.42-1.60 (m, B CH2 CH2 CH2), 1.72-1.78 (s, CH3 C5 thymine), 3.52-3.63 (CH2 CH2 N), 7.40-7.43 (s, (HO)2 B), 7.48-7.51 (s, H C6 thymine), 11.12-11.18 (s, HN thymine). Elemental Analysis (C9H15BO4N2); Calcd. C, 47.82%; H, 6.69%; N, 12.40%; Found C, 47.71%; H, 6.72%; N, 12.35%. was added dropwise stirring was continued 2 days at room temperature After the potassium carbonate was filtered the dimethylformamide was evaporated under high vacuum The residue was purified on a silica gel column eluting with a discontinuous gradient of chloroform/methanol (95:5, 85:15) evaporated
Source ID: ord-81601c1a2c9d49b898d2b95a1b731986Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6d54e51498ea441cb9d97463ce74921aPubChem References
These sources are listed in the compound's public database record.
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