No renderable structure data available
CC1=CC(=CC(=C1C=O)C)NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-amino-2,6-dimethylbenzaldehyde |
|---|---|
| IUPAC Name | — |
| CAS Number | 63405-90-3 |
| Database ID | 12381235 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-amino-2,6-dimethylbenzaldehyde (CAS 63405-90-3) 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 12381235
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-0d4b48b5436e45cf96e18f0b1d32cdf6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6a1f74ecdd334732bec7f3ba2964cda5Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-72c7af8f7f1a4c1ca09edac089a5d2c7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dd381233f88441b2aa6ffa5e9c7c4aeaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5642a7c43a924ce1962d183154cb0ca1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0d4b48b5436e45cf96e18f0b1d32cdf6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6a1f74ecdd334732bec7f3ba2964cda5Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-72c7af8f7f1a4c1ca09edac089a5d2c7Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-dd381233f88441b2aa6ffa5e9c7c4aeaConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Amino-2,6-dimethylbenzaldehyde (3.0 g, 20.1 mmol) was taken up in enough 42% HBF4 until the suspension stirred well and then was cooled to 0° C. To this was added a solution of NaNO2 (1.39 g, 20.1 mmol) in water (10 mL) slowly. After 30 min at 0° C., MeOH (50 mL) was added followed by Pd(OAc)2 (677 mg) and diethyl allylphosphonate (5.38 g, 30.2 mmol). The reaction mixture was heated to 80° C. for 30 min and the suspension was filtered through Celite, washed with CH2Cl2, and the filtrate was extracted with CH2Cl2. The combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using a gradient of heptane/EtOAc (10:1 to 5:1 then followed by 100% EtOAc) to give [(E)-3-(4-formyl-3,5-dimethylphenyl)-allyl]-phosphonic acid diethyl ester as a light yellow oil. The reaction mixture was heated to 80° C. for 30 min the suspension was filtered through Celite washed with CH2Cl2 the filtrate was extracted with CH2Cl2 The combined organic layers were washed with water, brine dried with MgSO4 filtered The solvent was removed under reduced pressure the residue was purified by flash chromatography
Source ID: ord-daf75626f57b4616bfac6bb36bbc315bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Amino-2,6-dimethylbenzaldehyde (149 mg, 1.0 mmol)) was taken up in enough 42% HBF4 until the suspension stirred well and then was cooled to 0° C. To this was added a solution of NaNO2 (69 mg, 1.0 mmol) in water (0.5 mL) slowly. After 30 minutes at 0° C., MeOH (3 mL) was added and followed by Pd(OAc)2 (7.5 mg) and vinylphosphonic acid diethyl ester (197 mg, 1.2 mmol). The reaction mixture was heated at 80° C. for 30 min and the suspension was filtered through Celite, washed with CH2Cl2, and the filtrate was extracted with CH2Cl2. The organic layer was washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (4:1 then followed by 100% EtOAc) to give [(E)-2-(4-formyl-3,5-dimethylphenyl)-vinyl]-phosphonic acid diethyl ester as a colorless oil. The reaction mixture was heated at 80° C. for 30 min the suspension was filtered through Celite washed with CH2Cl2 the filtrate was extracted with CH2Cl2 The organic layer was washed with water, brine dried with MgSO4 filtered The solvent was removed under reduced pressure the residue was purified by flash chromatography
Source ID: ord-34f2fbabe198464291ff124aaba10a63Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The above 4-amino-2,6-dimethylbenzaldehyde (1.0 g, 6.71 mmol) was taken up in enough 42% HBF4 until the suspension stirred well and then was cooled to 0° C. A solution of NaNO2 (463 mg, 6.71 mmol) in water (5 mL) was added slowly and after 30 min at 0° C., MeOH (20 mL) was added followed by Pd(OAc)2 (229 mg) and methyl acrylate (1.16 g, 13.42 mmol). The reaction mixture was heated at 80° C. for 30 min then the suspension was filtered through Celite and washed with CH2Cl2. The combined organic layers were washed with water, brine, dried with MgSO4, and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using a 10/1 to 5/1 gradient of heptane/EtOAc to give 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester as a light yellow solid. The reaction mixture was heated at 80° C. for 30 min the suspension was filtered through Celite washed with CH2Cl2 The combined organic layers were washed with water, brine dried with MgSO4 filtered The solvent was removed under reduced pressure the residue was purified by flash chromatography
Source ID: ord-27ce6b507a7749ec95df1b07cd2f05b4PubChem References
These sources are listed in the compound's public database record.
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