| Identification | Back Directory | [Name]
2-Amino-4-chlorobenzaldehyde | [CAS]
59236-37-2 | [Synonyms]
2-Amino-4-chlorobenzaldehyde
Benzaldehyde, 2-amino-4-chloro-
Benzo[i]dipyrido[3,2-a:2',5'-c]phenazine | [Molecular Formula]
C7H6ClNO | [MDL Number]
MFCD10696881 | [MOL File]
59236-37-2.mol | [Molecular Weight]
155.58 |
| Chemical Properties | Back Directory | [Boiling point ]
297.0±25.0 °C(Predicted) | [density ]
1.348±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
-0.70±0.10(Predicted) | [Appearance]
Off-white to light yellow Solid |
| Hazard Information | Back Directory | [Uses]
2-Amino-4-chlorobenzaldehyde is a reagent used in the synthesis of pharmaceuticals such as robenidine analogues which are active against MRSA and VRE. | [Synthesis]
General procedure for the synthesis of 2-amino-4-chlorobenzaldehyde from (2-amino-4-chlorophenyl)methanol: In a 2L three-necked round-bottomed flask, (2-amino-4-chlorophenyl)methanol (32 g, 203.82 mmol) was dissolved in dichloromethane (765 mL), and manganese dioxide (150 g, 1.724 mol) was slowly added under stirring. The reaction mixture was stirred continuously for 40 hours at room temperature and under argon protection. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the solid residue was washed well with dichloromethane (1000 mL). The filtrates were combined and concentrated under reduced pressure to give 2-amino-4-chlorobenzaldehyde as an orange solid. Yield: 24 g (76.2% yield). | [References]
[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 19, p. 5810 - 5831
[2] ChemistryOpen, 2015, vol. 4, # 2, p. 107 - 110
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 35, p. 10573 - 10576
[4] Angew. Chem., 2017, vol. 129, # 35, p. 10709 - 10712,4
[5] Synlett, 2017, vol. 28, # 14, p. 1724 - 1728 |
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