4-isopropylresorcinol Chemical Properties

Melting point:

105 °C

Boiling point:

114 °C(Press: 0.2 Torr)

Density 

1.116±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly)

pka

10.03±0.18(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C9H12O2/c1-6(2)8-4-3-7(10)5-9(8)11/h3-6,10-11H,1-2H3

InChIKey

LNFVQIGQENWZQN-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2907290090

4-isopropylresorcinol Usage And Synthesis

Uses

4-Isopropylbenzene-1,3-diol acts as a reagent in the synthesis of 3,5-disubstituted-4-alkynylisoxozales as HSP90 inhibitors against various human cancer cell lines.

Uses

4-Isopropylbenzene-1,3-diol acts as a reagent in the synthesis of 3,5-disubstituted-4-alkynylisoxozales as HSP90 inhibitors against various human cancer cell lines.

Synthesis

The general procedure for the synthesis of 4-isopropylresorcinol from (((4-(1-propen-2-yl)-1,3-phenylene)bis(oxy))bis(methylene))bis(benzene))diphenyl was as follows: a mixture of compound 17 (3 g, 9.08 mmol) with 10% Pd/C (30 wt%) in ethanol (48 mL) was placed in a hydrogen atmosphere and stirred for 18 hours at room temperature. Upon completion of the reaction, the solid catalyst was removed by filtration through a diatomaceous earth pad and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel fast column chromatography (eluent ratio: ethyl acetate:hexane=1:1) to afford compound 18 as a white crystalline solid (1.35 g, 98% yield). The physical and spectral data of the compound were consistent with those reported in the literature: melting point 87~89 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.02 (s, 1H), 8.90 (s, 1H), 6.85 (d, J=8.2 Hz, 1H), 6.26 (d, J=2.7 Hz, 1H), 6.16 (dd, J=8.2,2.3 Hz , 1H), 3.16-2.98 (m, 1H), 1.18-1.04 (s, 6H); 13C NMR (100 MHz, DMSO-d6) δ 155.59,154.78,125.87,124.56,105.67,102.11,25.52,22.64. ESI-MS: m/z = 170 (M +H2O)+.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 23-24, p. 3658 - 3664
[2] Patent: US2009/76006, 2009, A1. Location in patent: Page/Page column 32; 41
[3] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 16, p. 3129 - 3134
[4] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 765 - 781
[5] Patent: CN103724269, 2016, B. Location in patent: Paragraph 0388; 0389; 0399; 0400; 0401; 0402

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