4-hydroxy-3,5-dimethyl-benzenecarbonitrile Chemical Properties

Melting point:

123-127 °C

Boiling point:

267.28°C (rough estimate)

Density 

1.1135 (rough estimate)

vapor pressure 

0.005Pa at 25℃

refractive index 

1.5290 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder

pka

pK1:8.27 (25°C)

color 

White to beige

Water Solubility 

320mg/L at 20℃

InChI

InChI=1S/C9H9NO/c1-6-3-8(5-10)4-7(2)9(6)11/h3-4,11H,1-2H3

InChIKey

WFYGXOWFEIOHCZ-UHFFFAOYSA-N

SMILES

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

LogP

1.6 at 20℃

CAS DataBase Reference

4198-90-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,Xn,Xi

Risk Statements 

25-36-32-20/21/22-36/37/38

Safety Statements 

26-45-36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DI4359000

Hazard Note 

Toxic

HazardClass 

IRRITANT

HS Code 

29269095

Toxicity

mouse,LD50,intraperitoneal,650mg/kg (650mg/kg),Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 201, 1960.

MSDS

• Language:English Provider:ACROS

4-hydroxy-3,5-dimethyl-benzenecarbonitrile Usage And Synthesis

Chemical Properties

White to beige crystalline powder

Uses

Intermediate in the preparation of HIV replication inhibitors.

Definition

ChEBI: 4-Hydroxy-3,5-dimethylbenzonitrile is a hydroxytoluene.

Flammability and Explosibility

Not classified

Synthesis

GENERAL STEPS: Under nitrogen protection, 4-bromo-2,6-dimethylphenol (0.250 mmol), malononitrile (0.500 mmol), palladium catalyst (0.005 mmol), CuI (0.125 mmol), 1,10-phenanthroline (0.063 mmol), t-BuONa (0.500 mmol) and KF ( 0.500 mmol) were dissolved in DMF or NMP (1 mL). The reaction mixture was stirred at 130 °C for 24 hours. After the reaction was completed, the reaction mixture was diluted with EtOAc (4.0 mL), filtered through the diatomite layer and the diatomite layer was washed with EtOAc. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent to give the crude product. The reaction conversion was determined by GC analysis. The crude product was purified by silica gel column chromatography to give pure 3,5-dimethyl-4-hydroxybenzonitrile.

References

[1] Synlett, 2014, vol. 25, # 4, p. 547 - 550

4-hydroxy-3,5-dimethyl-benzenecarbonitrile(4198-90-7)Related Product Information

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