No renderable structure data available
C1=CC(=C(C(=C1)Cl)C(=O)CC#N)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(2,6-dichlorophenyl)-3-oxopropanenitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 71463-50-8 |
| Database ID | 3018140 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(2,6-dichlorophenyl)-3-oxopropanenitrile (CAS 71463-50-8) 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 3018140
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
10 reactions · 10 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7372fd2d0a834e61a15613d617f06cd3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-44ce46c022be4bc49f4470eb12a790aeConditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-(2,6-dichlorophenyl)-3-oxopropanenitrile (0.200 g, 0.93 mmol), acetic anhydride (0.22 g, 2.20 mmol), and triethyl orthoformate (0.21 g, 1.40 mmol) was stirred at 150° C. for 1 hr. The solution was then concentrated and the residue redissolved in ethanol (5 mL). 4-heptylamine (0.16 g, 1.4 mmol) in 1 mL of tetrahydrofuran was added to the reaction mixture at 0° C. The reaction stirred for 30 minutes and was then concentrated. Flash chromatography (20% Ethyl acetate/hexanes) gave the desired compound (0.033 g, 10%). The solution was then concentrated the residue redissolved in ethanol (5 mL) The reaction stirred for 30 minutes was then concentrated
Source ID: ord-c02c2c1bc69342f3afc648452bc0ea63Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: n-Butyl lithium (20.1 mL, 32.2 mmol, 1.6M in hexanes) was added to THF (30 mL) and the solution was cooled to −78° C. Acetonitrile (1.7 mL, 32 mmol) was added dropwise and the reaction stirred at the temperature for 45 minutes. Methyl 2,6-dichlorobenzoate (1.00 g, 4.88 mmol) was dissolved in 2 mL THF and added to the reaction mixture. The reaction stirred at −78° C. for 0.5 hr. The solution was quenched with methanol and warmed to room temperature. The material was diluted with water and 1N HCl. The solution was then extracted with Ethyl acetate, dried, and concentrated to give 1.08 g of desired product at 85% purity. Material used as is in the next step. added to the reaction mixture The reaction stirred at −78° C. for 0.5 hr The solution was quenched with methanol warmed to room temperature The material was diluted with water and 1N HCl The solution was then extracted with Ethyl acetate dried concentrated
Source ID: ord-77175a3bf88e461f971e10ca09d4c908Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: n-Butyl lithium (20.1 mL, 32.2 mmol, 1.6M in hexanes) was added to THF (30 mL) and the solution was cooled to −78° C. Acetonitrile (1.7 mL, 32 mmol) was added dropwise and the reaction stirred at the temperature for 45 minutes. Methyl 2,6-dichlorobenzoate (1.00 g, 4.88 mmol) was dissolved in 2 mL THF and added to the reaction mixture. The reaction stirred at −78° C. for 0.5 hr. The solution was quenched with methanol and warmed to room temperature. The material was diluted with water and 1N HCl. The solution was then extracted with Ethyl acetate, dried, and concentrated to give 1.08 g of desired product at 85% purity. Material used as is in the next step. added to the reaction mixture The reaction stirred at −78° C. for 0.5 hr The solution was quenched with methanol warmed to room temperature The material was diluted with water and 1N HCl The solution was then extracted with Ethyl acetate dried concentrated
Source ID: ord-77175a3bf88e461f971e10ca09d4c908Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7372fd2d0a834e61a15613d617f06cd3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-44ce46c022be4bc49f4470eb12a790aeConditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 3-(2,6-dichlorophenyl)-3-oxopropanenitrile (0.200 g, 0.93 mmol), acetic anhydride (0.22 g, 2.20 mmol), and triethyl orthoformate (0.21 g, 1.40 mmol) was stirred at 150° C. for 1 hr. The solution was then concentrated and the residue redissolved in ethanol (5 mL). 4-heptylamine (0.16 g, 1.4 mmol) in 1 mL of tetrahydrofuran was added to the reaction mixture at 0° C. The reaction stirred for 30 minutes and was then concentrated. Flash chromatography (20% Ethyl acetate/hexanes) gave the desired compound (0.033 g, 10%). The solution was then concentrated the residue redissolved in ethanol (5 mL) The reaction stirred for 30 minutes was then concentrated
Source ID: ord-c02c2c1bc69342f3afc648452bc0ea63Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: n-Butyl lithium (20.1 mL, 32.2 mmol, 1.6M in hexanes) was added to THF (30 mL) and the solution was cooled to −78° C. Acetonitrile (1.7 mL, 32 mmol) was added dropwise and the reaction stirred at the temperature for 45 minutes. Methyl 2,6-dichlorobenzoate (1.00 g, 4.88 mmol) was dissolved in 2 mL THF and added to the reaction mixture. The reaction stirred at −78° C. for 0.5 hr. The solution was quenched with methanol and warmed to room temperature. The material was diluted with water and 1N HCl. The solution was then extracted with Ethyl acetate, dried, and concentrated to give 1.08 g of desired product at 85% purity. Material used as is in the next step. added to the reaction mixture The reaction stirred at −78° C. for 0.5 hr The solution was quenched with methanol warmed to room temperature The material was diluted with water and 1N HCl The solution was then extracted with Ethyl acetate dried concentrated
Source ID: ord-77175a3bf88e461f971e10ca09d4c908Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-44ce46c022be4bc49f4470eb12a790aePubChem References
These sources are listed in the compound's public database record.
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