2-Amino-4-chlorobenzaldehyde

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2-Amino-4-chlorobenzaldehyde Basic information
Product Name:2-Amino-4-chlorobenzaldehyde
Synonyms:2-Amino-4-chlorobenzaldehyde;Benzaldehyde, 2-amino-4-chloro-;Benzo[i]dipyrido[3,2-a:2',5'-c]phenazine
CAS:59236-37-2
MF:C7H6ClNO
MW:155.58
EINECS:
Product Categories:
Mol File:59236-37-2.mol
2-Amino-4-chlorobenzaldehyde Structure
2-Amino-4-chlorobenzaldehyde Chemical Properties
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)
AppearanceOff-white to light yellow Solid
Safety Information
HS Code 2922390090
MSDS Information
2-Amino-4-chlorobenzaldehyde Usage And Synthesis
Uses2-Amino-4-chlorobenzaldehyde is a reagent used in the synthesis of pharmaceuticals such as robenidine analogues which are active against MRSA and VRE.
Synthesis
2-AMINO-4-CHLORO-BENZENEMETHANOL

37585-16-3

2-Amino-4-chlorobenzaldehyde

59236-37-2

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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