4-Amino-3,5-xylenol Chemical Properties

Melting point:

181 °C

Boiling point:

296.5±28.0 °C(Predicted)

Density 

1.118±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

10.47±0.23(Predicted)

color 

White to Gray to Brown

InChI

InChI=1S/C8H11NO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,9H2,1-2H3

InChIKey

GCWYXRHXGLFVFE-UHFFFAOYSA-N

SMILES

C1(O)=CC(C)=C(N)C(C)=C1

CAS DataBase Reference

3096-70-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

61

RTECS 

ZE6740000

HS Code 

2922290090

4-Amino-3,5-xylenol Usage And Synthesis

Chemical Properties

Brown Solid

Uses

A major Lidocaine metabolite.

Definition

ChEBI: A substituted aniline in which the aniline ring carries 4-hydroxy and 2,6-dimethyl substituents; a urinary metabolite of lidocaine.

Synthesis

1. An aqueous solution (4 ml) of sodium nitrite (1.90 g, 27.5 mmol) was slowly added dropwise to an aqueous solution (20 ml) of sodium sulfate dihydrate (5.78 g, 25.0 mmol) under the condition of an ice bath and mixed with stirring. 2. The above mixed solution was prepared as solution A by dropping it into a beaker pre-filled with concentrated hydrochloric acid (5.1 ml) and ice (30 g) and continued to cool in an ice bath for 20 minutes. 3. In another vessel, sodium hydroxide (5.50 g, 138 mmol) and ice (20 g) were added to an aqueous solution (30 ml) of 3,5-dimethylphenol (3.05 g, 25.0 mmol) and stirred until completely dissolved. 4. Solution A was slowly added dropwise to the above 3,5-dimethylphenol solution under ice bath conditions, and after completion of the dropwise addition, stirring was continued in the ice bath for 1 hour. 5. The reaction mixture was heated to 65 °C to 75 °C and sodium lienodisulfate (16.8 g, 96.5 mmol) was added in batches until the solution was completely discolored. 6. After completion of the reaction, the solution was cooled to room temperature and stirring was continued for 30 minutes. 7. The reaction mixture was filtered and the solid product was collected and dried to give 4-amino-3,5-dimethylphenol (2.46 g, 72% yield).

References

[1] Patent: EP1403255, 2004, A1. Location in patent: Page 170

4-Amino-3,5-xylenol(3096-70-6)Related Product Information

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