2,6-DIMETHYL-4-NITROPHENOL Chemical Properties

Melting point:

168 °C (dec.)(lit.)

Boiling point:

285.73°C (rough estimate)

Density 

1.1820 (estimate)

refractive index 

1.5774 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

pK1:7.190 (25°C)

color 

Dark Yellow to Very Dark Yellow

Water Solubility 

Insoluble in water.

BRN 

1873275

CAS DataBase Reference

2423-71-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

ZE8225000

Hazard Note 

Irritant

HS Code 

29089990

Toxicity

mouse,LDLo,intraperitoneal,500mg/kg (500mg/kg),"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 64, 1954.

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,6-DIMETHYL-4-NITROPHENOL Usage And Synthesis

Chemical Properties

orange crystalline powder

Uses

2,6-Dimethyl-4-nitrophenol is a useful compound for the production and characterization of bio-?oil from hardwood and softwood lignin.

Uses

2,6-Dimethyl-4-nitrophenol was used to study the disposition requirement for binding of p-nitrophenol and sodium p-nitrophenolate like substrates with cyclohexaamylaose. It was used as internal standard in determination of 4-nitrophenol and 3-methyl-4-nitrophenol in human urine by liquid chromatography combined with tandem mass spectrometry .

Synthesis Reference(s)

Synthetic Communications, 16, p. 63, 1986 DOI: 10.1080/00397918608057689

Synthesis

General method: A solid mixture of 2,6-dimethylphenol (1-3 eq.) and Bi(NO3)3-3H2O (1 eq.) or Fe(NO3)3-9H2O (1 eq.) was mixed with acetone (10 mL/mmol). The reaction mixture was stirred in air at room temperature or under reflux conditions for 2-24 hours (see Tables 1 and 2). Upon completion of the reaction, the insoluble material was removed by filtration through a diatomaceous earth pad and the residue was washed with acetone (~5 mL/mmol). The filtrate was treated with NaHCO3 (0.1 g/mmol) until CO2 release ceased. The insoluble material was removed by filtration again, followed by concentration under reduced pressure in a water bath at 25-35°C to remove the solvent. The nitration products were separated or purified by silica gel column chromatography to give pure phenolic compounds. All products were characterized by 1H NMR, 13C NMR and IR and identified by comparison with spectral data and melting points reported in the literature.

References

[1] Synthetic Communications, 2015, vol. 45, # 1, p. 143 - 150

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