4-Methyl-3-nitrophenol Chemical Properties

Melting point:

78-81 °C (lit.)

Boiling point:

266.03°C (rough estimate)

Density 

1.2744 (estimate)

vapor pressure 

0.084Pa at 25℃

refractive index 

1.5744 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Ethyl Acetate, Methanol

form 

Powder

pka

8.66±0.10(Predicted)

color 

Pale Yellow Crystalline

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C7H7NO3/c1-5-2-3-6(9)4-7(5)8(10)11/h2-4,9H,1H3

InChIKey

BQEXDUKMTVYBRK-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(C)C([N+]([O-])=O)=C1

LogP

2.18 at 25℃

CAS DataBase Reference

2042-14-0(CAS DataBase Reference)

NIST Chemistry Reference

4-Methyl-3-nitrophenol(2042-14-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

RIDADR 

2446

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29089990

MSDS

• Language:English Provider:4-Methyl-3-nitrophenol
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4-Methyl-3-nitrophenol Usage And Synthesis

Chemical Properties

Pale Yellow Crystalline Solid

Uses

3-Nitro-4-methylphenol (cas# 2042-14-0) is a compound useful in organic synthesis.

Synthesis Reference(s)

Synthesis, p. 735, 1986 DOI: 10.1055/s-1986-31759

Synthesis

General procedure for the synthesis of 4-methyl-3-nitrophenol from 4-methyl-3-nitroaniline: 4-methyl-3-nitroaniline (200 mg, 1.31 mmol) was dissolved in a 3:1 mixture of H2SO4-H2O. The resulting mixture was heated to 100 °C and kept for 30 min. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and NaNO2 solution was added slowly and dropwise. After the dropwise addition was completed, the reaction was continued for 1 hour, after which the mixture was heated to reflux. After the reaction was complete, the reaction mixture was extracted several times with EtOAc, the organic phases were combined and dried with anhydrous Na2SO4, and subsequently concentrated. The crude product was purified by fast column chromatography (eluent ratio: petroleum ether-ethyl acetate 9:1) to give a yellow solid in 70% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.48 (s, 1H), 7.17 (d, J = 8.4 Hz, 1H), 7.01 (dd, J = 8.4, 2.4 Hz, 1H), 5.84 (s, 1H), 2.48 (s, 3H) ppm.

References

[1] Chemistry - A European Journal, 2009, vol. 15, # 12, p. 2742 - 2746
[2] Patent: WO2016/128541, 2016, A1. Location in patent: Page/Page column 92; 93
[3] Patent: WO2017/162834, 2017, A1. Location in patent: Page/Page column 85
[4] Justus Liebigs Annalen der Chemie, 1882, vol. 215, p. 83
[5] Chemische Berichte, 1882, vol. 15, p. 2992

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