2-Chloro-5-methoxyaniline Chemical Properties

Melting point:

207 °C (dec.)(lit.)

Boiling point:

135-137°C 12mm

Density 

1.261 g/mL at 25 °C

refractive index 

1.5848

Flash point:

135-137°C/12mm

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump to clear liquid

pka

2.23±0.10(Predicted)

color 

White or Colorless to Yellow to Orange

Water Solubility 

Slightly soluble in water.

BRN 

2082193

InChI

InChI=1S/C7H8ClNO/c1-10-5-2-3-6(8)7(9)4-5/h2-4H,9H2,1H3

InChIKey

GBOUQGUQUUPGLO-UHFFFAOYSA-N

SMILES

C1(N)=CC(OC)=CC=C1Cl

CAS DataBase Reference

2401-24-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36-36/37

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2922290090

MSDS

• Language:English Provider:2-Chloro-5-methoxyaniline
• Language:English Provider:ALFA

2-Chloro-5-methoxyaniline Usage And Synthesis

Uses

2-Chloro-5-methoxyaniline is used in the preparation of 4-amino-5-chloro-2-methoxyphenyl thiocyanate.

Synthesis

General procedure for the synthesis of 2-chloro-5-methoxyaniline from 4-chloro-3-nitroanisole: nitro compounds (0.6 mmol) and ethanol (2 mL) were added to a sealed tube, followed by hydrazine hydrate (2.6-6.0 mmol, cf. Table 2) and an Au/TiO2 catalyst (100 mg, 1 wt%, with 0.8 mol% [Au]). The reaction mixture was heated at 60 °C for an appropriate time under an inert atmosphere (see Table 2). The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction slurry was filtered under pressure through a short pad of diatomaceous earth and silica gel and washed using ethanol or methanol (~5 mL) to recover the loaded catalyst. The filtrate was evaporated under vacuum to give pure 2-chloro-5-methoxyaniline. The nuclear magnetic resonance hydrogen (1H NMR) and carbon (13C NMR) spectral data of the products 1a-20a were in agreement with those reported in the literature [28,30,31] and most of the products were commercially available chemicals. The Au/TiO2, Au/Al2O3 and Au/ZnO catalysts used (~1 wt% Au content) were purchased from Strem Chemicals and the average size of their Au microcrystals was about 2-3 nm.

References

[1] Chemistry - A European Journal, 2017, vol. 23, # 42, p. 9996 - 10000
[2] New Journal of Chemistry, 2015, vol. 39, # 7, p. 5360 - 5365
[3] Chemistry - A European Journal, 2016, vol. 22, # 13, p. 4600 - 4607
[4] Catalysis Communications, 2013, vol. 36, p. 48 - 51
[5] ACS Catalysis, 2014, vol. 4, # 10, p. 3504 - 3511

2-Chloro-5-methoxyaniline(2401-24-3)Related Product Information

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