NISTC5651478 Chemical Properties

Melting point:

51.55°C

Boiling point:

288.61°C (estimate)

Density 

1.0670 (estimate)

refractive index 

1.5198 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

4.24±0.10(Predicted)

color 

Off white

Safety Information

HS Code 

2916399090

NISTC5651478 Usage And Synthesis

Synthesis

Synthesis of 3-isopropylbenzoic acid (Method A): 1. In a dry reaction flask, 1-bromo-3-isopropylbenzene (1.24 g, 6.23 mmol) and anhydrous THF (18 mL) were added. 2. add magnesium filament (0.151 g, 6.23 mmol, 1 eq.) and heat the mixture to 50-60°C until the magnesium is completely dissolved to form Grignard reagent. 3. An excess of solid carbon dioxide (CO2) was added to the reaction system and the reaction was continued for 40 minutes. 4. Upon completion of the reaction, the reaction mixture was acidified with 1 M aqueous hydrochloric acid to pH<3. 5. The products were extracted with dichloromethane (DCM) and the organic phases were combined. 6. The organic phase was dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to afford the target product 3-isopropylbenzoic acid as a white solid (1.07 g, quantitative yield). 7. The product was characterized by 1H-NMR (CDCl3) δ (ppm) 8.00 (s, 1H), 7.95 (d, 1H), 7.49 (d, 1H), 7.41 (t, 1H), 3.00 (m, 1H), 1.30 (d, 6H).

References

[1] Patent: WO2007/75896, 2007, A2. Location in patent: Page/Page column 125-126
[2] Patent: WO2006/40568, 2006, A1. Location in patent: Page/Page column 73
[3] Journal of Organic Chemistry, 1972, vol. 37, # 1, p. 126 - 131
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797

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