No renderable structure data available
C(CCC(=O)Cl)CCN=[N+]=[N-]Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 6-azidohexanoyl chloride |
|---|---|
| IUPAC Name | — |
| CAS Number | 5515-02-6 |
| Database ID | 14580383 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
6-azidohexanoyl chloride (CAS 5515-02-6) 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 14580383
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-3eceee271e2141c2ae6ae761953e8058Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-9d7892c749c04a87bebad39e52fe2f58Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-f9456a51145648c587ad706293bc377aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled
Source ID: ord-9642e2d5bd604a5ba19a36594c8fb2dcConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-60425537d9854f0c8e2429c1e77528b6Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-45d5137b5186465bae09a01efb52c75fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-9d7892c749c04a87bebad39e52fe2f58Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-9d7892c749c04a87bebad39e52fe2f58Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-f9456a51145648c587ad706293bc377aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent
Source ID: ord-f9456a51145648c587ad706293bc377aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled
Source ID: ord-9642e2d5bd604a5ba19a36594c8fb2dcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled
Source ID: ord-9642e2d5bd604a5ba19a36594c8fb2dcPubChem References
These sources are listed in the compound's public database record.
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