3-CHLORO-2-METHYLPHENOL Chemical Properties

Melting point:

86 °C

Boiling point:

225 °C

Density 

1.1104 (rough estimate)

refractive index 

1.5449 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder

pka

9.35±0.10(Predicted)

color 

Brown

Sensitive 

Stench

CAS DataBase Reference

3260-87-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

21/22-41-43-50-38-36

Safety Statements 

26-36/37/39-28

RIDADR 

3437

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29081990

3-CHLORO-2-METHYLPHENOL Usage And Synthesis

Synthesis

1. In a 1000 mL three-necked flask equipped with a thermometer, a mechanical stirrer and a dropping funnel, 700 mL of 22% sulfuric acid solution was pre-filled and heated to 70 °C. 2. 8 g of 3-chloro-2-methylaniline was added to the above solution in batches, maintaining the temperature at 70 °C until completely dissolved. 3. The reaction mixture was heated to 90 °C and then cooled to 10-12 °C to form a suspension. 4. the diazotization reaction was carried out by slowly adding 88.4 g of 40% sodium nitrite solution dropwise under stirring, maintaining the temperature at 10-12 °C. 5. the resulting diazonium salt mixture was heated to 90 °C and then slowly added to a mixture containing 200 mL of methyl isobutyl ketone and 2 g of 96% sulfuric acid under vigorous stirring. 6. The reaction was held at 90 °C for about 15 minutes to complete, after which the emulsion was cooled to 70 °C for phase separation. 7. The organic phase was washed with 50 mL of water to remove inorganic impurities. 8. The selectivity of the thermal decomposition step was 99.1% (a/a) by gas chromatography (GC) analysis. 9. The organic phase was purified by distillation to give 66.9 g of 3-chloro-2-methylphenol with a GC purity of 99.2% (a/a). 10. The distillation residue was 2.3 g. The yield of the target product was calculated to be 93.1%.

References

[1] Patent: CN105392764, 2016, A. Location in patent: Paragraph 0026
[2] Patent: WO2007/39563, 2007, A1. Location in patent: Page/Page column 23-24
[3] Patent: US2007/112019, 2007, A1. Location in patent: Page/Page column 12/2
[4] Justus Liebigs Annalen der Chemie, 1906, vol. 350, p. 113
[5] Chemische Berichte, 1904, vol. 37, p. 1021

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