METHYL 4-[(Z)-AMINO(HYDROXYIMINO)METHYL]BENZOATE Chemical Properties

Melting point:

172-174

Boiling point:

327.2±44.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

13.88±0.50(Predicted)

form 

solid

color 

White

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

HazardClass 

IRRITANT

HS Code 

2921490090

METHYL 4-[(Z)-AMINO(HYDROXYIMINO)METHYL]BENZOATE Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 4-(N-hydroxyformamidinyl)benzoate (IV) from methyl 4-cyanobenzoate (III): methyl 4-cyanobenzoate (III) (2.50kg, 1wt) was dissolved in methanol (7.5L, 3vol) and diluted with methyl tert-butyl ether (9.3kg, 3.7wt). Aqueous hydroxylamine (50% solution; 1.23 kg, 0.5 wt, 1.2 eq.) was added slowly over about 0.5 h at 20-25 °C. The dosing line was flushed with methanol (1 kg, 0.4 wt) and the reaction was kept at 20-25 °C for about 12 hours. Upon completion of the reaction, the reaction mixture was cooled to 5±5°C and aged at this temperature for 3 hours. The product, methyl 4-(N'-hydroxyformamidinyl)benzoate (IV), was isolated by filtration, washed with methyl tert-butyl ether (2 x 5.5 kg, 2 x 2.2 wt) and dried under a stream of nitrogen for about 4 h to give the product (2.38 kg, 93% yield).

References

[1] Patent: WO2017/220446, 2017, A1. Location in patent: Page/Page column 26
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2012, vol. 55, # 2, p. 71 - 79
[3] Organic Letters, 2017, vol. 19, # 11, p. 2885 - 2888

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